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{{Short description|Benzodiazepine medication}}
{{Chembox
{{Drugbox
| ImageFileL1 = Oxazepam Structural Formulae.png
| verifiedrevid = 460765704
| ImageFileL1_Ref = {{chemboximage|correct|??}}
| class = ]
| ImageSizeL1 = 121
| IUPAC_name = (''RS'')-7-Chloro-3-hydroxy-5-phenyl-1,3-dihydro-1,4-benzodiazepin-2-one<ref>{{PubChem|4616}}</ref>
| ImageNameL1 = Kekulé, skeletal formula of a minor tautomer of oxazepam
| image = Oxazepam.svg
| ImageFileR1 = Oxazepam3d.png
| width = 190
| ImageFileR1_Ref = {{chemboximage|correct|??}}
| image2 = Oxazepam3d.png
| ImageSizeR1 = 121
| width2 = 150
| ImageNameR1 = Spacefill model of a minor tautomer of oxazepam ((3S)-3-hydroxy)
| IUPACNAme = 7-Chloro-3-hydroxy-5-phenyl-1,3-dihydro-1,4-benzodiazepin-2-one<ref>{{PubChem|4616}}</ref>
| Section1 = {{Chembox Identifiers
| CASNo = 604-75-1
| CASNo_Ref = {{cascite|correct|CAS}}
| PubChem = 4616
| PubChem_Ref = {{Pubchemcite|correct|Pubchem}}
| PubChem1 = 921299
| PubChem1_Ref = {{Pubchemcite|correct|Pubchem}}
| PubChem1_Comment = <small>(''R'')</small>
| PubChem2 = 667436
| PubChem2_Ref = {{Pubchemcite|correct|Pubchem}}
| PubChem2_Comment = <small>(''S'')</small>
| ChemSpiderID = 4455
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID1 = 804298
| ChemSpiderID1_Ref = {{chemspidercite|correct|chemspider}}
| ChemPSiderID1_Comment = <small>(''R'')</small>
| UNII = 6GOW6DWN2A
| UNII_Ref = {{fdacite|correct|FDA}}
| EINECS = 210-076-9
| DrugBank = DB00842
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| KEGG = D00464
| KEGG_Ref = {{keggcite|correct|kegg}}
| MeSHName = Oxazepam
| ChEBI = 7823
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 568
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| RTECS = DF1400000
| ATCCode_prefix = N05
| ATCCode_suffix = BA04
| SMILES = OC1NC(c2ccccc2)=c2cc(Cl)ccc2=NC1=O
| StdInChI = 1S/C15H11ClN2O2/c16-10-6-7-12-11(8-10)13(9-4-2-1-3-5-9)18-15(20)14(19)17-12/h1-8,15,20H,(H,17,19)
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = ADIMAYPTOBDMTL-UHFFFAOYSA-N
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
}}
| Section2 = {{Chembox Properties
| C=15|H=11|N=2|O=2|Cl=1
| ExactMass = 286.050905313 g mol<sup>-1</sup>
| MeltingPtCL = 205
| MeltingPtCH = 206
| Solubility = 179 mg L<sup>-1</sup>
| LogP = 2.216
| pKa = 10.939
| pKb = 3.058
}}
| Section3 = {{Chembox Pharmacology
| Bioavail = 95.5%
| AdminRoutes = Oral
| Metabolism = Hepatic
| HalfLife = 5-15 h
| Excretion = Renal
| Legal_AU = S4
| Legal_US = Schedule IV
}}
| Section4 = {{Chembox Hazards
| GHSPictograms = {{GHS health hazard}}
| GHSSignalWord = '''WARNING'''
| HPhrases = {{H-phrases|351}}
| PPhrases = {{P-phrases|281}}
| EUClass = {{Hazchem Xn}}
| RPhrases = {{R40}}
| SPhrases = {{S36/37}}
}}
}}


<!-- Clinical data -->| pronounce = {{IPAc-en|ɒ|k|ˈ|s|æ|z|ɪ|p|æ|m}}<br />{{respell|ok|SAZ|i|pam}}
'''Oxazepam''' (marketed in English speaking countries under the following brand names '''Alepam''', '''Medopam''', '''Murelax''', '''Noripam''', '''Opamox''', '''Ox-Pam''', '''Purata''', '''Serax''' and '''Serepax''', as '''Vaben''' in Israel, and as '''Sobril''' and '''Oxascand''' in Sweden), is a drug which is a short to intermediate acting 3-hydroxy ] derivative.<ref>{{cite web| url= http://www.non-benzodiazepines.org.uk/benzodiazepine-names.html| title=Benzodiazepine Names| accessdate=2008-12-29| publisher=non-benzodiazepines.org.uk}}</ref><ref>{{cite web| url=http://www.fass.se/LIF/produktfakta/substance_products.jsp?substanceId=IDE4POCGU9ITHVERT1| title=FASS| accessdate=2011-02-03| publisher=Läkemedelsindustriföreningens Service AB}}</ref> Oxazepam is a benzodiazepine used extensively since the 1960s for the treatment of anxiety and insomnia and in the control of symptoms of alcohol withdrawal. It is a metabolite of ], ] and ].<ref>{{cite web| url=http://www.inchem.org/documents/iarc/vol66/oxazepam.html|title=Oxazepam (IARC Summary & Evaluation, Volume 66, 1996)| accessdate=2009-03-12| publisher=IARC}}</ref> Oxazepam has moderate ], ], ], ], ] and ] properties compared to other benzodiazepines.<ref>{{cite journal |author=Mandrioli R, Mercolini L, Raggi MA |title=Benzodiazepine metabolism: an analytical perspective |journal=Curr. Drug Metab. |volume=9 |issue=8 |pages=827–44 |year=2008 |month=October |pmid=18855614 |doi= 10.2174/138920008786049258|url=http://www.benthamdirect.org/pages/content.php?CDM/2008/00000009/00000008/0009F.SGM}}</ref>
| tradename = Serax, Alepam, Serepax, others
| pregnancy_US =
| legal_AU = S4
| legal_BR = B1
| legal_BR_comment = <ref>{{Cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=2023-03-31 |title=RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |url-status=live |archive-url=https://web.archive.org/web/20230803143925/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |archive-date=2023-08-03 |access-date=2023-08-16 |publisher=] |language=pt-BR |publication-date=2023-04-04}}</ref>
| legal_CA = Schedule IV
| legal_DE = Rx-only/Anlage III
| legal_US = Schedule IV


<!-- Chemical data -->| C = 15
==Indications==
| H = 11
It is an intermediate acting benzodiazepine with a slow onset of action,<ref>{{cite book |last1=Galanter |first1=Marc |last2=Kleber |first2=Herbert D. |title=The American Psychiatric Publishing Textbook of Substance Abuse Treatment |url=http://books.google.com/?id=6wdJgejlQzYC&pg=PA216 |edition=4th |date=1 July 2008 |publisher=American Psychiatric Publishing Inc |location=United States of America |isbn=978-1585622764 |page=216 |chapter= |chapterurl= }}</ref> so it is usually prescribed to individuals who have trouble staying asleep, rather than falling asleep. It is commonly prescribed for anxiety disorders with associated tension, irritability, and agitation. It is also prescribed for drug and ], and for anxiety associated with ]. Physicians may use Oxazepam outside its approved indications to treat ], ], ], ], and other conditions.<ref>http://www.psychatlanta.com/documents/serax.pdf</ref>
| N = 2
]
| O = 2
| Cl = 1
| melting_point = 205
| melting_high = 206


<!-- Identifiers -->| IUPHAR_ligand = 7253
==Dosage==
| CAS_number = 604-75-1
{{Unreferenced-section|date=November 2011}}
| PubChem = 4616
* Mild/moderate anxiety - 10 to 15&nbsp;mg, 3 to 4 times daily
| ChemSpiderID = 4455
* Severe anxiety - 15 to 30&nbsp;mg, 3 to 4 times daily
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
* Symptoms related to alcohol withdrawal - 15 to 30&nbsp;mg, 3 to 4 times daily
| UNII = 6GOW6DWN2A
| UNII_Ref = {{fdacite|correct|FDA}}
| DrugBank = DB00842
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| KEGG = D00464
| KEGG_Ref = {{keggcite|correct|kegg}}
| ChEBI = 7823
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 568
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ATC_prefix = N05
| ATC_suffix = BA04
| smiles = O=C1Nc2ccc(Cl)cc2C(c2ccccc2)=NC1O
| StdInChI = 1S/C15H11ClN2O2/c16-10-6-7-12-11(8-10)13(9-4-2-1-3-5-9)18-15(20)14(19)17-12/h1-8,15,18,20H
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = IMAUTQQURLXUGJ-UHFFFAOYSA-N
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}


<!-- Pharmacokinetic data -->| bioavailability = 92.8%
==Availability==
| legal_status = Prescription drug
In the United Kingdom, oxazepam is available generically in the form of 10&nbsp;mg, 15&nbsp;mg and 30&nbsp;mg tablets.
| addiction_liability = Low–moderate
In Finland, oxazepam is available generically in the form of 15&nbsp;mg, 30&nbsp;mg and 50&nbsp;mg tablets.
| routes_of_administration = ]
In France, oxazepam is available in the form of 10&nbsp;mg and 50&nbsp;mg tablets.
| metabolism = Hepatic (glucuronidation)
In Australia, oxazepam is available in the form of 5&nbsp;mg, 7.5&nbsp;mg, 10&nbsp;mg, 15&nbsp;mg and 30&nbsp;mg tablets.
| onset = 30 - 120 minutes
| elimination_half-life = 6–9 hours<ref></ref><ref name=pmid3197746>{{cite journal | vauthors = Sonne J, Loft S, Døssing M, Vollmer-Larsen A, Olesen KL, Victor M, Andreasen F, Andreasen PB | display-authors = 6 | title = Bioavailability and pharmacokinetics of oxazepam | journal = European Journal of Clinical Pharmacology | volume = 35 | issue = 4 | pages = 385–389 | date = 1988 | pmid = 3197746 | doi = 10.1007/bf00561369 | s2cid = 31007311 }}</ref><ref name="Pharmacokinetics and pharmacodynami">{{cite journal | vauthors = Sonne J, Boesgaard S, Poulsen HE, Loft S, Hansen JM, Døssing M, Andreasen F | title = Pharmacokinetics and pharmacodynamics of oxazepam and metabolism of paracetamol in severe hypothyroidism | journal = British Journal of Clinical Pharmacology | volume = 30 | issue = 5 | pages = 737–742 | date = November 1990 | pmid = 2271373 | pmc = 1368175 | doi = 10.1111/j.1365-2125.1990.tb03844.x }}</ref>
| duration_of_action = 6 - 12 hours
| excretion = ]
}}

'''Oxazepam''' is a short-to-intermediate-acting ].<ref>{{cite web| url=http://www.non-benzodiazepines.org.uk/benzodiazepine-names.html| title=Benzodiazepine Names| access-date=2008-12-29| publisher=non-benzodiazepines.org.uk| url-status=dead| archive-url=https://web.archive.org/web/20081208054743/http://www.non-benzodiazepines.org.uk/benzodiazepine-names.html| archive-date=2008-12-08}}</ref><ref>{{cite web| url=http://www.fass.se/LIF/produktfakta/substance_products.jsp?substanceId=IDE4POCGU9ITHVERT1| title=FASS| access-date=2011-02-03| publisher=Läkemedelsindustriföreningens Service AB| url-status=live| archive-url=https://web.archive.org/web/20111001011224/http://www.fass.se/LIF/produktfakta/substance_products.jsp?substanceId=IDE4POCGU9ITHVERT1| archive-date=2011-10-01}}</ref> Oxazepam is used for the treatment of ],<ref>{{cite journal | vauthors = Janecek J, Vestre ND, Schiele BC, Zimmermann R | title = Oxazepam in the treatment of anxiety states: a controlled study | journal = Journal of Psychiatric Research | volume = 4 | issue = 3 | pages = 199–206 | date = December 1966 | pmid = 20034170 | doi = 10.1016/0022-3956(66)90007-0 }}</ref><ref>{{cite journal | vauthors = Sarris J, Scholey A, Schweitzer I, Bousman C, Laporte E, Ng C, Murray G, Stough C | display-authors = 6 | title = The acute effects of kava and oxazepam on anxiety, mood, neurocognition; and genetic correlates: a randomized, placebo-controlled, double-blind study | journal = Human Psychopharmacology | volume = 27 | issue = 3 | pages = 262–269 | date = May 2012 | pmid = 22311378 | doi = 10.1002/hup.2216 | s2cid = 44801451 }}</ref> ], and to control symptoms of ].

It is a metabolite of ], ], and ],<ref>{{cite web| url=http://www.inchem.org/documents/iarc/vol66/oxazepam.html| title=Oxazepam (IARC Summary & Evaluation, Volume 66, 1996)| access-date=2009-03-12| publisher=IARC| url-status=live| archive-url=https://web.archive.org/web/20080907155723/http://www.inchem.org/documents/iarc/vol66/oxazepam.html| archive-date=2008-09-07}}</ref> and has moderate ], ], ], ], ], and ] properties compared to other benzodiazepines.<ref>{{cite journal | vauthors = Mandrioli R, Mercolini L, Raggi MA | title = Benzodiazepine metabolism: an analytical perspective | journal = Current Drug Metabolism | volume = 9 | issue = 8 | pages = 827–844 | date = October 2008 | pmid = 18855614 | doi = 10.2174/138920008786049258 | url = http://www.benthamdirect.org/pages/content.php?CDM/2008/00000009/00000008/0009F.SGM | url-status = dead | archive-url = https://web.archive.org/web/20090317092123/http://www.benthamdirect.org/pages/content.php?CDM%2F2008%2F00000009%2F00000008%2F0009F.SGM | archive-date = 2009-03-17 }}</ref>

<!-- Society and culture -->
It was patented in 1962 and approved for medical use in 1964.<ref name=Fis2006>{{cite book | vauthors = Fischer J, Ganellin CR |title=Analogue-based Drug Discovery |date=2006 |publisher=John Wiley & Sons |isbn=9783527607495 |page=536 |url=https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA536 |language=en}}</ref>


==Usage== ==Medical uses==
It is an intermediate-acting benzodiazepine with a slow onset of action,<ref>{{cite book | vauthors = Galanter M, Kleber HD |title=The American Psychiatric Publishing Textbook of Substance Abuse Treatment |url=https://books.google.com/books?id=6wdJgejlQzYC&pg=PA216 |edition=4th |date=1 July 2008 |publisher=American Psychiatric Publishing Inc |location=United States of America |isbn=978-1-58562-276-4 |page=216 }}</ref> so it is usually prescribed to individuals who have trouble staying asleep, rather than falling asleep. It is commonly prescribed for anxiety disorders with associated tension, irritability, and agitation. It is also prescribed for drug and alcohol ], and for anxiety associated with ]. Oxazepam is sometimes prescribed ] to treat ], ], ], ], and other conditions.<ref>{{cite web |url=http://www.psychatlanta.com/documents/serax.pdf |title=Serax (oxazepam) |access-date=2009-04-22 |url-status=dead |archive-url=https://web.archive.org/web/20110715125737/http://www.psychatlanta.com/documents/serax.pdf |archive-date=2011-07-15 }}</ref>
Oxazepam along with diazepam, nitrazepam and temazepam, were the four benzodiazepines listed on the pharmaceutical benefits scheme and represented 82% of the benzodiazepine prescriptions in Australia in 1990-1991.<ref>{{cite journal | doi = 10.1111/j.1753-6405.1993.tb00167.x | author = Mant A | coauthors = Whicker SD, McManus P, Birkett DJ, Edmonds D, Dumbrell D. | title =Benzodiazepine utilisation in Australia: report from a new pharmacoepidemiological database | journal = Aust J Public Health. | volume =17 | issue =4 | pages=345–9 | month =December | year=1993 | pmid = 7911332 }}</ref>
]


==Side effects== ==Side effects==
The side effects of oxazepam are similar in nature to those of other benzodiazepines and may include dizziness, drowsiness, headache, memory impairment, ], ].{{cn|date=November 2011}} Side effects due to rapid decrease in dose or abrupt withdrawal from oxazepam may include abdominal and muscle cramps, convulsions, depression, inability to fall asleep or stay asleep, sweating, tremors, or vomiting.<ref></ref> The side effects of oxazepam are similar to those of other benzodiazepines, and may include dizziness, drowsiness, headache, memory impairment, ], and ], but does not affect ].{{Citation needed|date=November 2011}} Withdrawal effects due to rapid decreases in dosage or abrupt discontinuation of oxazepam may include abdominal and muscle ], ], ], ], ], ], or ] and ].<ref>{{cite web|url=https://www.drugs.com/pdr/oxazepam.html|title=Oxazepam Uses, Side Effects & Warnings - Drugs.com|website=drugs.com|url-status=live|archive-url=https://web.archive.org/web/20090604161605/http://www.drugs.com/pdr/oxazepam.html|archive-date=2009-06-04}}</ref>

In September 2020, the U.S. ] (FDA) required the ] be updated for all benzodiazepine medicines to describe the risks of abuse, misuse, ], ], and withdrawal reactions consistently across all the medicines in the class.<ref>{{cite web | title=FDA expands Boxed Warning to improve safe use of benzodiazepine drug | website=U.S. ] (FDA) | date=23 September 2020 | url=https://www.fda.gov/drugs/drug-safety-and-availability/fda-requiring-boxed-warning-updated-improve-safe-use-benzodiazepine-drug-class | access-date=23 September 2020}} {{PD-notice}}</ref>

===Tolerance, dependence and withdrawal===
Oxazepam, as with other benzodiazepine drugs, can cause ], ], ], and ]. Withdrawal from oxazepam or other benzodiazepines often leads to withdrawal symptoms which are similar to those seen during alcohol and ] withdrawal. The higher the dose and the longer the drug is taken, the greater the risk of experiencing unpleasant withdrawal symptoms. Withdrawal symptoms can occur, though, at standard dosages and also after short-term use. Benzodiazepine treatment should be discontinued as soon as possible by a slow and gradual dose reduction regimen.<ref>{{cite journal | vauthors = MacKinnon GL, Parker WA | title = Benzodiazepine withdrawal syndrome: a literature review and evaluation | journal = The American Journal of Drug and Alcohol Abuse | volume = 9 | issue = 1 | pages = 19–33 | year = 1982 | pmid = 6133446 | doi = 10.3109/00952998209002608 }}</ref>


==Contraindications== ==Contraindications==
Oxazepam is contraindicated in ], ] and limited pulmonary reserve, as well as severe ]. Oxazepam is contraindicated in ], ], and limited pulmonary reserve, as well as severe ].


==Special precautions== ==Special precautions==
Benzodiazepines require special precaution if used in the elderly, during pregnancy, in children, alcohol- or drug-dependent individuals and individuals with ] ].<ref>{{Cite journal | last1 = Authier | first1 = N. | last2 = Balayssac | first2 = D. | last3 = Sautereau | first3 = M. | last4 = Zangarelli | first4 = A. | last5 = Courty | first5 = P. | last6 = Somogyi | first6 = AA. | last7 = Vennat | first7 = B. | last8 = Llorca | first8 = PM. | last9 = Eschalier | first9 = A. | title = Benzodiazepine dependence: focus on withdrawal syndrome | journal = Ann Pharm Fr | volume = 67 | issue = 6 | pages = 408–13 | month= November| year = 2009 | doi = 10.1016/j.pharma.2009.07.001 | pmid = 19900604 }}</ref> Benzodiazepines including oxazepam are lipophilic drugs and rapidly penetrate membranes and therefore rapidly cross over into the placenta with significant uptake of the drug. Use of benzodiazepines in late pregnancy especially high doses may result in ].<ref>{{cite journal | author = Kanto JH. | coauthors = | year = 1982 | month = May | title = Use of benzodiazepines during pregnancy, labour and lactation, with particular reference to pharmacokinetic considerations | journal = Drugs. | volume = 23 | issue = 5 | pages = 354–80 | pmid = 6124415 | doi = 10.2165/00003495-198223050-00002 }}</ref> Benzodiazepines require special precautions if used in the elderly, during pregnancy, in children, alcohol- or drug-dependent individuals, and individuals with ] ].<ref>{{cite journal | vauthors = Authier N, Balayssac D, Sautereau M, Zangarelli A, Courty P, Somogyi AA, Vennat B, Llorca PM, Eschalier A | display-authors = 6 | title = Benzodiazepine dependence: focus on withdrawal syndrome | journal = Annales Pharmaceutiques Françaises | volume = 67 | issue = 6 | pages = 408–413 | date = November 2009 | pmid = 19900604 | doi = 10.1016/j.pharma.2009.07.001 }}</ref> Benzodiazepines including oxazepam are lipophilic drugs and rapidly penetrate membranes, so rapidly crosses over into the placenta with significant uptake of the drug. Use of benzodiazepines in late pregnancy, especially high doses, may result in ].<ref>{{cite journal | vauthors = Kanto JH | title = Use of benzodiazepines during pregnancy, labour and lactation, with particular reference to pharmacokinetic considerations | journal = Drugs | volume = 23 | issue = 5 | pages = 354–380 | date = May 1982 | pmid = 6124415 | doi = 10.2165/00003495-198223050-00002 | s2cid = 27014006 }}</ref>


===Pregnancy=== ===Pregnancy===
Oxazepam when taken during late in pregnancy, the ], causes a definite risk to the ] including a severe ] in the neonate with symptoms including ], and reluctance to suck, to ] spells, ], and impaired ] responses to cold stress. Floppy infant syndrome and sedation in the new born may also occur. Symptoms of floppy infant syndrome and the neonatal benzodiazepine withdrawal syndrome have been reported to persist from hours to months after birth.<ref>{{cite journal | author = McElhatton PR. | coauthors = | year = 1994 | month = Nov-Dec | title = The effects of benzodiazepine use during pregnancy and lactation | journal = Reprod Toxicol. | volume = 8 | issue = 6 | pages = 461–75 | pmid = 7881198 | doi = 10.1016/0890-6238(94)90029-9 }}</ref> Oxazepam, when taken during the ], causes a definite risk to the ], including a severe ] including ], reluctance to suck, ] spells, ], and impaired ] responses to cold stress. Floppy infant syndrome and sedation in the newborn may also occur. Symptoms of floppy infant syndrome and the neonatal benzodiazepine withdrawal syndrome have been reported to persist from hours to months after birth.<ref>{{cite journal | vauthors = McElhatton PR | title = The effects of benzodiazepine use during pregnancy and lactation | journal = Reproductive Toxicology | volume = 8 | issue = 6 | pages = 461–475 | date = Nov–Dec 1994 | pmid = 7881198 | doi = 10.1016/0890-6238(94)90029-9 | bibcode = 1994RepTx...8..461M }}</ref>


== Interactions ==
==Tolerance, dependence and withdrawal==
Oxazepam as with other ] drugs can cause ], ], ] and what is known as the ]. Withdrawal from oxazepam or other benzodiazepines often leads to withdrawal symptoms which are similar to those seen during alcohol and ] withdrawal. The higher the dose and the longer the drug is taken the greater the risk of experiencing unpleasant withdrawal symptoms. Withdrawal symptoms can however occur at standard dosages and also after short term use. Benzodiazepine treatment should be discontinued as soon as possible via a slow and gradual dose reduction regimen.<ref>{{cite journal | author = MacKinnon GL | coauthors = Parker WA. | year = 1982 | title = Benzodiazepine withdrawal syndrome: a literature review and evaluation | journal = The American journal of drug and alcohol abuse. | volume = 9 | issue = 1 | pages = 19–33 | pmid = 6133446| doi = 10.3109/00952998209002608 }}</ref>


As oxazepam is an active metabolite of diazepam, an overlap in possible interactions is likely with other drugs or food, with exception of the pharmacokinetic ] interactions (e.g. with ]). Precautions and following the prescription are required when taking oxazepam (or other benzodiazepines) in combinations with ] or ]. Concurrent use of these medications can interact in a way that is difficult to predict. Drinking ] when taking oxazepam is not recommended. Concomitant use of oxazepam and alcohol can lead to increased ], memory impairment, ], decreased muscle tone, and, in severe cases or in predisposed patients, ] and ].
==Pharmacology==
Oxazepam is an intermediate acting benzodiazepine of the 3-hydroxy family. Oxazepam acts on ] resulting in increased effect of ] to the GABA<sub>A</sub> receptor which results in inhibitory effects on the ].<ref>{{cite journal | author = Skerritt JH | coauthors = Johnston GA. | date = May 6, 1983 | title = Enhancement of GABA binding by benzodiazepines and related anxiolytics | journal = Eur J Pharmacol. | volume = 89 | issue = 3–4 | pages = 193–8 | pmid = 6135616 | doi = 10.1016/0014-2999(83)90494-6 }}</ref><ref>{{cite journal | author = Oelschläger H. | coauthors = | date = July 4, 1989 | title = | journal = Schweiz Rundsch Med Prax. | volume = 78 | issue = 27–28 | pages = 766–72 | pmid = 2570451 | doi=}}</ref> The ] of oxazepam is 4–15 hours.<ref>{{cite web | url = http://www.bcnc.org.uk/equivalence.html | title = Benzodiazepine equivalency table | accessdate = September 23, 2007 | author = Professor heather Ashton | year = 2007 | month = April }}</ref> Oxazepam has been shown to suppress ] levels.<ref>{{cite journal | author = Christensen P | coauthors = Lolk A, Gram LF, Kragh-Sørensen P. | year = 1992 | title = Benzodiazepine-induced sedation and ] suppression. A placebo-controlled comparison of oxazepam and nitrazepam in healthy male volunteers | journal = Psychopharmacology. | volume = 106 | issue = 4 | pages = 511–6 | pmid = 1349754 | doi = 10.1007/BF02244823 }}</ref> Oxazepam is the most slowly absorbed benzodiazepine and has the slowest onset of action of all the common benzodiazepines according to one British study.<ref name="autogenerated386">{{cite journal |author=Serfaty M, Masterton G |title=Fatal poisonings attributed to benzodiazepines in Britain during the 1980s |journal=Br J Psychiatry |volume=163 |issue= 3|pages=386–93 |year=1993 |pmid=8104653 |doi=10.1192/bjp.163.3.386}}</ref>

Oxazepam is an active metabolite formed during the breakdown of ], ], and certain similar drugs. Oxazepam may be safer than many other benzodiazepines in patients with impaired liver function because it does not require hepatic oxidation, but rather it is simply metabolized via ]. This means that oxazepam is less likely to accumulate and cause adverse reactions in the elderly or people with liver disease. Oxazepam is similar to ] in this respect.
There is preferential storage of oxazepam in some organs including the heart of the neonate. Absorption by any administered route and the risk of accumulation is significantly increased in the neonate and it is recommended to withdraw oxazepam during pregnancy and breast feeding as oxazepam is excreted in breast milk.<ref>{{cite journal | author = Olive G | coauthors = Dreux C. | year = 1977 | month = January | title = Pharmacologic bases of use of benzodiazepines in peréinatal medicine | journal = Arch Fr Pediatr. | volume = 34 | pages = 74–89 | pmid = 851373 | issue = 1 }}</ref>

==Interactions==
As oxazepam is an active metabolite of ], there is likely an overlap in possible interactions with other drugs or food, with exception of the pharmacokinetic ] interactions (e.g. with ]). Take precautions, and follow closely the prescription of your doctor, when taking oxazepam (or other benozodiazepines) in combinations with antidepressant medication (]s such as ], ], and ], or multiple reuptake inhibitors such as ], ], or ]), potent ] (opioids, e.g. ], ] or ]). Concurrent use of these medicines (as well as other ]s) can interact in a way that is difficult to predict. Drinking alcohol when taking oxazepam is not recommended. Concomitant use of oxazepam and alcohol can lead to increased ], severe problems with ] (]e), decreased muscle tone and in severe cases or in predisposed patients even to life-threatening ]s with ], ] and ].
Concomitant use of alcohol and oxazepam (as well as other benzodiazepines) also increases the risk of an ]. {{Citation needed|date=July 2008}}


==Overdose== ==Overdose==
{{main|Benzodiazepine overdose}} {{main|Benzodiazepine overdose}}
Oxazepam is generally less toxic in overdose than other benzodiazepines.<ref>{{cite journal |author=Buckley NA, Dawson AH, Whyte IM, O'Connell DL |title=Relative toxicity of benzodiazepines in overdose |journal=BMJ |volume=310 |issue=6974 |pages=219–21 |date=28 January 1995|pmid=7866122 |url=http://www.bmj.com/cgi/content/full/310/6974/219 |pmc=2548618 |doi=10.1136/bmj.310.6974.219 }}</ref> Important factors which effect the severity of a benzodiazepine overdose include the dose ingested, the age of the patient, health status prior to overdose. Benzodiazepine overdoses can be much more dangerous if there has been a coingestion of other ] such as opiates or alcohol. Symptoms of an oxazepam overdose include:<ref>{{cite journal |author=Gaudreault P, Guay J, Thivierge RL, Verdy I |title=Benzodiazepine poisoning. Clinical and pharmacological considerations and treatment |journal=Drug Saf |volume=6 |issue=4 |pages=247–65 |year=1991 |pmid=1888441 |doi= 10.2165/00002018-199106040-00003|url=}}</ref><ref>{{cite journal |author=Perry HE, Shannon MW |title=Diagnosis and management of opioid- and benzodiazepine-induced comatose overdose in children |journal=Curr. Opin. Pediatr. |volume=8 |issue=3 |pages=243–7 |year=1996 |month=June |pmid=8814402 |doi= 10.1097/00008480-199606000-00010|url=}}</ref><ref>{{cite journal |author=Busto U, Kaplan HL, Sellers EM |title=Benzodiazepine-associated emergencies in Toronto |journal=Am J Psychiatry |volume=137 |issue=2 |pages=224–7 |year=1980 |month=February |pmid=6101526 |doi= |url=}}</ref> Oxazepam is generally less toxic in overdose than other benzodiazepines.<ref>{{cite journal | vauthors = Buckley NA, Dawson AH, Whyte IM, O'Connell DL | title = Relative toxicity of benzodiazepines in overdose | journal = BMJ | volume = 310 | issue = 6974 | pages = 219–221 | date = January 1995 | pmid = 7866122 | pmc = 2548618 | doi = 10.1136/bmj.310.6974.219 }}</ref> Important factors which affect the severity of a benzodiazepine overdose include the dose ingested, the age of the patient, and health status prior to overdose. Benzodiazepine overdoses can be much more dangerous if a coingestion of other ] such as opiates or alcohol has occurred. Symptoms of an oxazepam overdose include:<ref>{{cite journal | vauthors = Gaudreault P, Guay J, Thivierge RL, Verdy I | title = Benzodiazepine poisoning. Clinical and pharmacological considerations and treatment | journal = Drug Safety | volume = 6 | issue = 4 | pages = 247–265 | year = 1991 | pmid = 1888441 | doi = 10.2165/00002018-199106040-00003 | s2cid = 27619795 }}</ref><ref>{{cite journal | vauthors = Perry HE, Shannon MW | title = Diagnosis and management of opioid- and benzodiazepine-induced comatose overdose in children | journal = Current Opinion in Pediatrics | volume = 8 | issue = 3 | pages = 243–247 | date = June 1996 | pmid = 8814402 | doi = 10.1097/00008480-199606000-00010 | s2cid = 43105029 }}</ref><ref>{{cite journal | vauthors = Busto U, Kaplan HL, Sellers EM | title = Benzodiazepine-associated emergencies in Toronto | journal = The American Journal of Psychiatry | volume = 137 | issue = 2 | pages = 224–227 | date = February 1980 | pmid = 6101526 | doi = 10.1176/ajp.137.2.224 }}</ref>


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*Occasionally ] and ] *Occasionally ] and ]
*Rarely deep ] *Rarely, deep ]


==Abuse== ==Pharmacology==
{{See also|Benzodiazepine drug misuse}} {{Main|Benzodiazepine#Pharmacology}}
Oxazepam is an intermediate-acting benzodiazepine of the 3-hydroxy family; it acts on ], resulting in increased effect of ] to the GABA<sub>A</sub> receptor which results in inhibitory effects on the ].<ref>{{cite journal | vauthors = Skerritt JH, Johnston GA | title = Enhancement of GABA binding by benzodiazepines and related anxiolytics | journal = European Journal of Pharmacology | volume = 89 | issue = 3–4 | pages = 193–198 | date = May 1983 | pmid = 6135616 | doi = 10.1016/0014-2999(83)90494-6 }}</ref><ref>{{cite journal | vauthors = Oelschläger H | title = | journal = Schweizerische Rundschau für Medizin Praxis = Revue Suisse de Médecine Praxis | volume = 78 | issue = 27–28 | pages = 766–772 | date = July 1989 | pmid = 2570451 }}</ref> The ] of oxazepam is between 6 and 9 hours.<ref name="Pharmacokinetics and pharmacodynami">{{cite journal | vauthors = Sonne J, Boesgaard S, Poulsen HE, Loft S, Hansen JM, Døssing M, Andreasen F | title = Pharmacokinetics and pharmacodynamics of oxazepam and metabolism of paracetamol in severe hypothyroidism | journal = British Journal of Clinical Pharmacology | volume = 30 | issue = 5 | pages = 737–742 | date = November 1990 | pmid = 2271373 | pmc = 1368175 | doi = 10.1111/j.1365-2125.1990.tb03844.x }}</ref><ref name=pmid3197746/><ref>https://www.has-sante.fr/upload/docs/application/pdf/2011-11/mama_troubles_comportement_encadre_1_anxiolitiques.pdf{{full citation needed|date=January 2020}}</ref> It has been shown to suppress ] levels.<ref>{{cite journal | vauthors = Christensen P, Lolk A, Gram LF, Kragh-Sørensen P | title = Benzodiazepine-induced sedation and cortisol suppression. A placebo-controlled comparison of oxazepam and nitrazepam in healthy male volunteers | journal = Psychopharmacology | volume = 106 | issue = 4 | pages = 511–516 | year = 1992 | pmid = 1349754 | doi = 10.1007/BF02244823 | s2cid = 29331503 | title-link = cortisol }}</ref> Oxazepam is the most slowly absorbed and has the slowest onset of action of all the common benzodiazepines according to one British study.<ref name="autogenerated386">{{cite journal | vauthors = Serfaty M, Masterton G | title = Fatal poisonings attributed to benzodiazepines in Britain during the 1980s | journal = The British Journal of Psychiatry | volume = 163 | issue = 3 | pages = 386–393 | date = September 1993 | pmid = 8104653 | doi = 10.1192/bjp.163.3.386 | s2cid = 46001278 }}</ref>
Oxazepam is a drug with the potential for misuse. Drug misuse is defined as taking the drug to achieve a high, or continuing to take the drug in the long term against medical advice.<ref>{{cite journal |author=Griffiths RR, Johnson MW |title=Relative abuse liability of hypnotic drugs: a conceptual framework and algorithm for differentiating among compounds |journal=J Clin Psychiatry |volume=66 Suppl 9 |issue= |pages=31–41 |year=2005 |pmid=16336040 |doi= |url=}}</ref> Benzodiazepines, including ], oxazepam, ], and ], accounted for the largest volume of forged drug prescriptions in Sweden 1982-1986. During this time, a total of 52% of drug forgeries were for benzodiazepines, suggesting benzodiazepines were a major prescription drug class of abuse.<ref>{{cite journal | author = Bergman U | coauthors = Dahl-Puustinen ML. | year = 1989 | title = Use of prescription forgeries in a drug abuse surveillance network | volume = 36 | issue = 6 | pages = 621–3 | pmid = 2776820 | journal = Eur J Clin Pharmacol.| doi = 10.1007/BF00637747}}</ref>


However, due to its slow rate of absorption (the slowest of all benzodiazepines) and its slow onset of action,<ref name="autogenerated386"/> oxazepam has a relatively low potential for abuse compared to some other benzodiazepines like ], ], or ], which have a high potential for abuse that is similar to barbiturate abuse potential.<ref>{{cite journal |author=Griffiths RR, Wolf B |title=Relative abuse liability of different benzodiazepines in drug abusers |journal=J Clin Psychopharmacol |volume=10 |issue=4 |pages=237–43 |year=1990 |month=August |pmid=1981067 |doi= 10.1097/00004714-199008000-00002|url=}}</ref> Oxazepam is an active metabolite formed during the breakdown of ], ], and certain similar drugs. It may be safer than many other benzodiazepines in patients with impaired liver function because it does not require hepatic oxidation, but rather, it is simply metabolized by ], so oxazepam is less likely to accumulate and cause adverse reactions in the elderly or people with liver disease. Oxazepam is similar to ] in this respect.<ref>{{cite journal | vauthors = Sabath LD | title = Current status of treatment of pneumonia | journal = Southern Medical Journal | volume = 68 | issue = 12 | pages = 1507–1511 | date = December 1975 | pmid = 0792 | doi = 10.1097/00007611-197512000-00012 | s2cid = 20789345 }}</ref>
Preferential storage of oxazepam occurs in some organs, including the heart of the neonate. Absorption by any administered route and the risk of accumulation is significantly increased in the neonate, and withdrawal of oxazepam during pregnancy and breast feeding is recommended, as oxazepam is excreted in breast milk.<ref>{{cite journal | vauthors = Olive G, Dreux C | title = | journal = Archives Françaises de Pédiatrie | volume = 34 | issue = 1 | pages = 74–89 | date = January 1977 | pmid = 851373 }}</ref>


2&nbsp;mg of oxazepam equates to 1&nbsp;mg of diazepam according to the benzodiazepine equivalency converter, therefore 20&nbsp;mg of oxazepam according to BZD equivalency equates to 10&nbsp;mg of diazepam and 15&nbsp;mg oxazepam to 7.5&nbsp;mg diazepam (rounded up to 8&nbsp;mg of diazepam).<ref>{{cite web |url=https://www.benzo.org.uk/bzequiv.htm |title = benzo.org.uk : Benzodiazepine Equivalence Table}}</ref> Some BZD equivalency converters use 3 to 1 (oxazepam to diazepam), 1 to 3 (diazepam to oxazepam) as the ratio (3:1 and 1:3), so 15&nbsp;mg of oxazepam would equate to 5&nbsp;mg of diazepam.<ref>{{Cite web|url=https://globalrph.com/medcalcs/benzodiazepine-converter-dosage-conversions/|title=Benzodiazepine equivalent dosage converter|website=GlobalRPH|language=en-US|access-date=2019-09-21}}</ref>
==Legal status==
Oxazepam is a ] drug under the ].<ref>http://www.incb.org/pdf/e/list/green.pdf</ref>


==Chemistry== ==Chemistry==
Oxazepam exists as a ].<ref>{{cite journal | vauthors = Aso Y, Yoshioka S, Shibazaki T, Uchiyama M | title = The kinetics of the racemization of oxazepam in aqueous solution | journal = Chemical & Pharmaceutical Bulletin | volume = 36 | issue = 5 | pages = 1834–1840 | date = May 1988 | pmid = 3203421 | doi = 10.1248/cpb.36.1834 | doi-access = free }}</ref> Early attempts to isolate ] were unsuccessful; the corresponding ] has been isolated as a single enantiomer. Given the different rates of ] that occur at different pH levels, it was determined that there would be no therapeutic benefit to the administration of a single enantiomer over the racemic mixture.<ref>{{cite book | vauthors = Crossley RJ |date=1995 |title=Chirality and Biological Activity of Drugs |url=https://books.google.com/books?id=N7zds_HN9r4C&q=oxazepam+racemate&pg=PA8 |publisher=CRC Press |isbn=978-0849391408}}</ref>
6-Chloro-2-chloromethyl-4-phenylquinazolin-3-oxide undergoes treatment with ], giving 7-chloro-5-phenyl-1,2-dihydro-3H-1,4-benzodiazepin-2-on-4-oxide. This undergoes an acetoxylation reaction of the third position of the benzodiazepine ring, using ], and which reminiscents the ], giving 7-chloro-1,3-dihydro-3-acetoxy-5-phenyl-2''H''-benzodiazepin-2-one. Subsequent hydrolysis of the product's acetyl group gives oxazepam.<ref>S.C. Bell, {{US Patent|3176009}} (1965)</ref><ref>S.C. Bell, {{US Patent|3296249}} (1967)</ref><ref>E. Reeder, L.H. Sternbach, {{US Patent|3109843}} (1963)</ref><ref>{{Cite doi|10.1021/jo01049a052}}</ref><ref>{{Cite doi|10.1021/jo01052a049}}</ref><ref>{{Cite doi|10.1021/jo01265a041}}</ref>
:]


==Frequency of use==
==Carcinogenicity==
Oxazepam, along with diazepam, nitrazepam, and temazepam, were the four benzodiazepines listed on the pharmaceutical benefits scheme and represented 82% of the benzodiazepine prescriptions in Australia in 1990–1991.<ref>{{cite journal | vauthors = Mant A, Whicker SD, McManus P, Birkett DJ, Edmonds D, Dumbrell D | title = Benzodiazepine utilisation in Australia: report from a new pharmacoepidemiological database | journal = Australian Journal of Public Health | volume = 17 | issue = 4 | pages = 345–349 | date = December 1993 | pmid = 7911332 | doi = 10.1111/j.1753-6405.1993.tb00167.x | doi-access = free }}</ref>
Oxazepam is listed as a possible ] (]) by the ].
It is in several countries the benzodiazepine of choice for novice users, due to a low chance of accumulation and a relatively slow absorption speed.<ref>{{Cite web|url=https://www.drugbank.ca/drugs/DB00842|title = Oxazepam}}</ref>


==See also== ==Society and culture==
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==References== ===Misuse===
{{See also|Benzodiazepine drug misuse}}
{{Reflist|2}}
Oxazepam has the potential for misuse, defined as taking the drug to achieve a high, or continuing to take the drug in the long term against medical advice.<ref>{{cite journal | vauthors = Griffiths RR, Johnson MW | title = Relative abuse liability of hypnotic drugs: a conceptual framework and algorithm for differentiating among compounds | journal = The Journal of Clinical Psychiatry | volume = 66 Suppl 9 | pages = 31–41 | year = 2005 | pmid = 16336040 }}</ref> Benzodiazepines, including diazepam, oxazepam, nitrazepam, and flunitrazepam, accounted for the largest volume of forged drug prescriptions in Sweden from 1982 to 1986. During this time, a total of 52% of drug forgeries were for benzodiazepines, suggesting they were a major prescription drug class of abuse.<ref>{{cite journal | vauthors = Bergman U, Dahl-Puustinen ML | title = Use of prescription forgeries in a drug abuse surveillance network | journal = European Journal of Clinical Pharmacology | volume = 36 | issue = 6 | pages = 621–623 | year = 1989 | pmid = 2776820 | doi = 10.1007/BF00637747 | s2cid = 19770310 }}</ref>

However, due to its slow rate of absorption and its slow onset of action,<ref name="autogenerated386"/> oxazepam has a relatively low potential for abuse compared to some other benzodiazepines, such as temazepam, flunitrazepam, or ]. This is similar to the varied potential for abuse between different drugs of the ] class.<ref>{{cite journal | vauthors = Griffiths RR, Wolf B | title = Relative abuse liability of different benzodiazepines in drug abusers | journal = Journal of Clinical Psychopharmacology | volume = 10 | issue = 4 | pages = 237–243 | date = August 1990 | pmid = 1981067 | doi = 10.1097/00004714-199008000-00002 | s2cid = 28209526 }}</ref>

===Legal status===
Oxazepam is a ] drug under the ].<ref>{{cite web |url=http://www.incb.org/pdf/e/list/green.pdf |title=List of psychotropic substances under international control | date = August 2003 | location = Vienna Austria | publisher = International Narcotics Control Board |access-date=2005-11-19 |url-status=live |archive-url=https://web.archive.org/web/20051205125434/http://www.incb.org/pdf/e/list/green.pdf |archive-date=2005-12-05 }}</ref>

===Brand names===
It is marketed under many brand names worldwide, including: Alepam, Alepan, Anoxa, Anxiolit, Comedormir, durazepam, Murelax, Nozepam, Oksazepam, Opamox, Ox-Pam, Oxa-CT, Oxabenz, Oxamin, Oxapam, Oxapax, Oxascand, Oxaze, Oxazepam, Oxazépam, Oxazin, Oxepam, Praxiten, Purata, Selars, Serax, Serepax, Seresta, Séresta, Serpax, Sobril, Tazepam, Vaben, and Youfei.<ref name=brands>{{cite web|title=Oxazepam - International Brand Names|url=https://www.drugs.com/international/oxazepam.html|publisher=Drugs.com|access-date=4 January 2017|url-status=live|archive-url=https://web.archive.org/web/20170105085259/https://www.drugs.com/international/oxazepam.html|archive-date=5 January 2017}}</ref>

It is also marketed in combination with ] as Novalona and in combination with ] as Pausafrent T.<ref name=brands/>

== Environmental concerns ==

In 2013, a laboratory study which exposed ] to oxazepam concentrations equivalent to those present in ]s (1.8&nbsp;μg/L) found that they exhibited increased activity, reduced sociality, and higher feeding rate.<ref>{{cite journal | vauthors = Brodin T, Fick J, Jonsson M, Klaminder J | title = Dilute concentrations of a psychiatric drug alter behavior of fish from natural populations | journal = Science | volume = 339 | issue = 6121 | pages = 814–815 | date = February 2013 | pmid = 23413353 | doi = 10.1126/science.1226850 | s2cid = 38518537 | bibcode = 2013Sci...339..814B }}</ref> In 2016, a follow-up study which exposed ] ] to oxazepam for seven days before letting them migrate observed increased intensity of migratory behaviour compared to controls.<ref>{{cite journal | vauthors = Hellström G, Klaminder J, Finn F, Persson L, Alanärä A, Jonsson M, Fick J, Brodin T | display-authors = 6 | title = GABAergic anxiolytic drug in water increases migration behaviour in salmon | journal = Nature Communications | volume = 7 | issue = 13460 | pages = 13460 | date = December 2016 | pmid = 27922016 | pmc = 5155400 | doi = 10.1038/ncomms13460 | bibcode = 2016NatCo...713460H }}</ref> A 2019 study associated this faster, bolder behaviour in exposed smolt to increased mortality due to a higher likelihood of being ].<ref>{{cite journal | vauthors = Klaminder J, Jonsson M, Leander J, Fahlman J, Brodin T, Fick J, Hellström G | title = Less anxious salmon smolt become easy prey during downstream migration | journal = The Science of the Total Environment | volume = 687 | pages = 488–493 | date = October 2019 | pmid = 31212157 | doi = 10.1016/j.scitotenv.2019.05.488 | s2cid = 195065107 | bibcode = 2019ScTEn.687..488K }}</ref>

On the other hand, a 2018 study from the same authors, which kept 480 European perch and 12 ]s in 12 ponds over 70 days, half of them control and half spiked with oxazepam, found no significant difference in either perch growth or mortality. However, it suggested that the latter could be explained by the exposed perch and pike being equally hampered by oxazepam, rather than the lack of an overall effect.<ref>{{cite journal | vauthors = Lagesson A, Brodin T, Fahlman J, Fick J, Jonsson M, Persson J, Byström P, Klaminder J | display-authors = 6 | title = No evidence of increased growth or mortality in fish exposed to oxazepam in semi-natural ecosystems | journal = The Science of the Total Environment | volume = 615 | pages = 608–614 | date = February 2018 | pmid = 28988097 | doi = 10.1016/j.scitotenv.2017.09.070 | bibcode = 2018ScTEn.615..608L }}</ref> Lastly, a 2021 study built on these results by comparing two whole lakes filled with perch and pikes - one control while the other was exposed to oxazepam 11 days into experiment, at concentrations between 11 and 24&nbsp;μg/L, which is 200 times greater than the reported concentrations in the European rivers. Even so, there were no measurable effects on pike behaviour after the addition of oxazepam, while the effects on perch behaviour were found to be negligible. The authors concluded that the effects previously attributed to oxazepam were instead likely caused by a combination of fish being stressed by human handling and small aquaria, followed by being exposed to a novel environment.<ref>{{cite journal | vauthors = Fahlman J, Hellström G, Jonsson M, Fick JB, Rosvall M, Klaminder J | title = Impacts of Oxazepam on Perch (''Perca fluviatilis'') Behavior: Fish Familiarized to Lake Conditions Do Not Show Predicted Anti-anxiety Response | journal = Environmental Science & Technology | volume = 55 | issue = 6 | pages = 3624–3633 | date = March 2021 | pmid = 33663207 | pmc = 8031365 | doi = 10.1021/acs.est.0c05587 | bibcode = 2021EnST...55.3624F }}</ref>

== References ==
{{Reflist}}


==External links== == External links ==
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{{Benzodiazepines}} {{Benzodiazepines}}
{{Anxiolytics}} {{Anxiolytics}}
{{GABAAR PAMs}}


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