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Revision as of 09:51, 21 November 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{drugbox}} taken from revid 461633075 of page Hyoscyamine for the Chem/Drugbox validation project (updated: 'ChEMBL').  Latest revision as of 03:19, 20 December 2024 edit Citation bot (talk | contribs)Bots5,430,954 edits Added bibcode. | Use this bot. Report bugs. | Suggested by Whoop whoop pull up | #UCB_webform 107/662 
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{{Distinguish||text=], another name for the drug scopolamine}}{{Short description|Tropane alkaloid}}
{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid of page ] with values updated to verified values.}}
{{Use dmy dates|date=January 2024}}
⚫ {{Drugbox| Verifiedfields = changed
{{cs1 config |name-list-style=vanc |display-authors=6}}
⚫ | verifiedrevid = 407250174
{{Infobox drug
⚫ | IUPAC_name = (8-methyl-8-azabicyclooct-3-yl) 3-hydroxy-2-phenylpropanoate
⚫ | Verifiedfields = changed
| Watchedfields =
⚫ | verifiedrevid = 461742575
| image = Hyoscyamine.svg | image = Hyoscyamine.svg
| width = 200px | width = 200
| alt =
| image2 = Hyoscyamine-from-xtal-3D-balls.png | image2 = Hyoscyamine-from-xtal-3D-balls.png
| alt2 =


<!--Clinical data--> <!-- Clinical data -->
| tradename = Anaspaz, Levbid, Levsin | tradename = Anaspaz, Levbid, Levsin
| Drugs.com = {{drugs.com|monograph|hyoscyamine}} | Drugs.com = {{drugs.com|monograph|hyoscyamine}}
| MedlinePlus = a684010 | MedlinePlus = a684010
| pregnancy_category = C | pregnancy_category =
⚫ | routes_of_administration = ], Injection
| legal_status = Prescription only (US)
⚫ | ATC_prefix = A03
⚫ | routes_of_administration = Oral, Injection
⚫ | ATC_suffix = BA03

| legal_AU = S4
| legal_US = Rx only


<!--Pharmacokinetic data--> <!-- Pharmaeecokinetic data -->
| bioavailability = 50% Protein binding | bioavailability = 50% protein binding
| metabolism = Hepatic | metabolism = ]
| elimination_half-life = 3–5 hrs. | elimination_half-life = 3–5 hrs.
| excretion = Urine | excretion = ]


<!--Identifiers--> <!-- Identifiers -->
| CAS_number_Ref = {{cascite|correct|??}} | CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 101-31-5 | CAS_number = 101-31-5
⚫ | ATC_prefix = A03
⚫ | ATC_suffix = BA03
| PubChem = 154417 | PubChem = 154417
| PubChem_Ref = {{pubchemcite|correct}}
| DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB00424 | DrugBank = DB00424
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| UNII_Ref = {{fdacite|correct|FDA}} | UNII_Ref = {{fdacite|correct|FDA}}
| UNII = PX44XO846X | UNII = PX44XO846X
| KEGG = D00147
| ChEBI_Ref = {{ebicite|changed|EBI}} | ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 17486 | ChEBI = 17486
| ChEMBL_Ref = {{ebicite|changed|EBI}} | ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = <!-- blanked - oldvalue: 1697729 --> | ChEMBL = 1697729

<!-- Chemical data -->
⚫ | IUPAC_name = (''S'')-(1''R'',3''r'',5''S'')-8-methyl-8-azabicyclooctan-3-yl 3-hydroxy-2-phenylpropanoate
| C=17 | H=23 | N=1 | O=3 | C=17 | H=23 | N=1 | O=3
| molecular_weight = 289.375 g/mol
| smiles = CN31CC3C(C1)OC(=O)(CO)c2ccccc2 | smiles = CN31CC3C(C1)OC(=O)(CO)c2ccccc2
| InChI = 1/C17H23NO3/c1-18-13-7-8-14(18)10-15(9-13)21-17(20)16(11-19)12-5-3-2-4-6-12/h2-6,13-16,19H,7-11H2,1H3/t13-,14+,15+,16-/m1/s1
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C17H23NO3/c1-18-13-7-8-14(18)10-15(9-13)21-17(20)16(11-19)12-5-3-2-4-6-12/h2-6,13-16,19H,7-11H2,1H3/t13-,14+,15+,16-/m1/s1 | StdInChI = 1S/C17H23NO3/c1-18-13-7-8-14(18)10-15(9-13)21-17(20)16(11-19)12-5-3-2-4-6-12/h2-6,13-16,19H,7-11H2,1H3/t13-,14+,15+,16-/m1/s1
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| StdInChIKey = RKUNBYITZUJHSG-FXUDXRNXSA-N | StdInChIKey = RKUNBYITZUJHSG-FXUDXRNXSA-N
}} }}

'''Hyoscyamine''' (also known as '''daturine''' or '''duboisine''') is a naturally occurring ] and plant toxin. It is a ] found in certain plants of the family ], including ], ], ], ], ], and ] (deadly nightshade). It is the ] ] of ] (third of the three major nightshade alkaloids) and thus sometimes known as levo-atropine.<ref>{{cite journal | vauthors = Ushimaru R, Ruszczycky MW, Liu HW | title = Changes in Regioselectivity of H Atom Abstraction during the Hydroxylation and Cyclization Reactions Catalyzed by Hyoscyamine 6β-Hydroxylase | journal = Journal of the American Chemical Society | volume = 141 | issue = 2 | pages = 1062–1066 | date = January 2019 | pmid = 30545219 | pmc = 6488026 | doi = 10.1021/jacs.8b11585 | bibcode = 2019JAChS.141.1062U }}</ref>

In 2021, it was the 272nd most commonly prescribed medication in the United States, with more than 900,000 prescriptions.<ref>{{cite web | title=The Top 300 of 2021 | url=https://clincalc.com/DrugStats/Top300Drugs.aspx | website=ClinCalc | access-date=14 January 2024 | archive-date=15 January 2024 | archive-url=https://web.archive.org/web/20240115223848/https://clincalc.com/DrugStats/Top300Drugs.aspx | url-status=live }}</ref><ref>{{cite web | title = Hyoscyamine - Drug Usage Statistics | website = ClinCalc | url = https://clincalc.com/DrugStats/Drugs/Hyoscyamine | access-date = 14 January 2024}}</ref>

==Medical uses==
Hyoscyamine is used to provide symptomatic relief of spasms caused by various lower abdominal and bladder disorders including ]s, ], ], ], ], and ].<ref>{{Cite book | author = National Clinical Guideline Centre (UK) |url=https://www.ncbi.nlm.nih.gov/books/NBK132836/ |title=Treatment to improve bladder storage |publisher=] |year=2012 |edition=8th |series=NBK132836 |location= United Kingdom |pages=83 |language=en |via=]}}</ref><ref name=":0">{{Cite web |title=Hyoscyamine Uses, Side Effects & Warnings |url=https://www.drugs.com/mtm/hyoscyamine.html |url-status=live |archive-url=https://web.archive.org/web/20220820204721/https://www.drugs.com/mtm/hyoscyamine.html |archive-date=20 August 2022 |access-date=20 August 2022 |website=] |language=en}}</ref><ref>{{Cite web |title=Bladder Control Medicines {{!}} NIDDK |url=https://www.niddk.nih.gov/health-information/urologic-diseases/bladder-control-medicines |url-status=live |archive-url=https://web.archive.org/web/20220820204616/https://www.niddk.nih.gov/health-information/urologic-diseases/bladder-control-medicines |archive-date=20 August 2022 |access-date=20 August 2022 |website=] |language=en-US}}</ref> It has also been used to relieve some heart problems, control some of the symptoms of ], as well as for control of abnormal respiratory symptoms and "hyper-mucus secretions" in patients with lung disease.<ref>{{Cite web |title=Hyoscyamine: MedlinePlus Drug Information |url=https://medlineplus.gov/druginfo/meds/a684010.html |url-status=live |archive-url=https://web.archive.org/web/20220820211337/https://medlineplus.gov/druginfo/meds/a684010.html |archive-date=20 August 2022 |access-date=20 August 2022 |website=] |language=en}}</ref>

] Mixture are sodium citrate, sodium bicarbonate, liquid extract of hyoscyamine and chloroform dissolved in water.]]

It is also useful in pain control for neuropathic pain, chronic pain and palliative care — "comfort care" — for those with intractable pain from treatment resistant, untreatable, and incurable diseases. When combined with opioids it increases the level of analgesia (pain relief) obtained.<ref>{{cite journal | vauthors = Harden RN | title = Chronic neuropathic pain. Mechanisms, diagnosis, and treatment | journal = The Neurologist | volume = 11 | issue = 2 | pages = 111–122 | date = March 2005 | pmid = 15733333 | doi = 10.1097/01.nrl.0000155180.60057.8e | s2cid = 12602416 }}</ref> Several mechanisms are thought to contribute to this effect. The closely related drugs atropine and ] and other members of the anticholinergic drug group like ], ], and ] are also used for this purpose.<ref>{{cite journal | vauthors = Ali-Melkkilä T, Kanto J, Iisalo E | title = Pharmacokinetics and related pharmacodynamics of anticholinergic drugs | journal = Acta Anaesthesiologica Scandinavica | volume = 37 | issue = 7 | pages = 633–642 | date = October 1993 | pmid = 8249551 | doi = 10.1111/j.1399-6576.1993.tb03780.x | s2cid = 22808654 }}</ref> When hyoscyamine is used along with opioids or other anti-peristaltic agents, measures to prevent constipation are especially important given the risk of paralytic ].<ref name="Kamimura_2020">{{cite journal | vauthors = Kamimura A, Howard S, Weaver S, Panahi S, Ashby J | title = The Use of Complementary and Alternative Medicine Strategies, Opioids, and Nonsteroidal Anti-Inflammatory Drugs (NSAIDS) Among Patients Attending a Free Clinic | journal = Journal of Patient Experience | volume = 7 | issue = 6 | pages = 1701–1707 | date = December 2020 | pmid = 33457633 | pmc = 7786764 | doi = 10.1177/2374373520937514 }}</ref>

==Adverse effects==
Side effects include dry mouth and throat, increased appetite leading to weight gain, eye pain, blurred vision, restlessness, dizziness, ], flushing, and faintness.<ref name=":0" /> An overdose will cause headache, nausea, vomiting, and central nervous system symptoms including disorientation, hallucinations, euphoria, sexual arousal, short-term memory loss, and possible coma in extreme cases. The euphoric and sexual effects are stronger than those of atropine but weaker than those of ], as well as ], ], ], ], and ethanolamine antihistamines like ].<ref>{{cite book | vauthors = Kang M, Galuska MA, Ghassemzadeh S | chapter = Benzodiazepine Toxicity |date=2022 | chapter-url=http://www.ncbi.nlm.nih.gov/books/NBK482238/ | title = StatPearls |archive-url= https://web.archive.org/web/20220820213407/https://www.ncbi.nlm.nih.gov/books/NBK482238/ |place=Treasure Island (FL) |publisher=StatPearls Publishing |pmid=29489152 | archive-date=20 August 2022 }}</ref><ref>{{Cite web |title=Hyoscyamine Sulfate Sublingual Tablets, 0.125 mgRx Only |url=https://www.dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=ec5a3a71-54b7-428f-9017-51848a588c97 |url-status=live |archive-url=https://web.archive.org/web/20220820213627/https://www.dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=ec5a3a71-54b7-428f-9017-51848a588c97 |archive-date=20 August 2022 |access-date=20 August 2022 |website=www.dailymed.nlm.nih.gov}}</ref>

==Pharmacology==
===Pharmacodynamics===
Hyoscyamine is an ]; i.e., an antagonist of ]s. It blocks the action of ] at sweat glands (sympathetic) and at ] sites in salivary glands, stomach secretions, heart muscle, ], smooth muscle in the ], and the ]. It increases cardiac output and heart rate, lowers blood pressure and dries secretions.<ref name="nhl-hyo">{{cite web | author1 = Edwards Pharmaceuticals, Inc. | author2 = Belcher Pharmaceuticals, Inc. | title = DailyMed | publisher = U.S. National Library of Medicine | date = May 2010 | url = http://dailymed.nlm.nih.gov/dailymed/lookup.cfm?setid=f33a4774-9fbb-4782-a7e1-068e83b7504d | access-date = 13 January 2013}}</ref> It may antagonize ].<ref name="kapoor">{{cite book | vauthors = Kapoor AK, Raju SM |year=2013 |title= Illustrated Medical Pharmacology |page=131|url=https://books.google.com/books?id=Le28AQAAQBAJ&q=Hyoscyamine+serotonin&pg=PA131 |publisher=JP Medical Ltd |isbn=9789350906552 |access-date= 11 January 2014}}</ref> At comparable doses, hyoscyamine has 98 percent of the ] power of atropine. The other major ]-derived drug ] (known in the United States as Scopolamine) has 92 per cent of the antimuscarinic potency of atropine.<ref name="kapoor" />

Hyoscyamine has been described as a ] muscarinic acetylcholine ] ] without significant effects at the other muscarinic acetylcholine receptors.<ref name="LakstygalKolesnikovaKhatsko2019">{{cite journal | vauthors = Lakstygal AM, Kolesnikova TO, Khatsko SL, Zabegalov KN, Volgin AD, Demin KA, Shevyrin VA, Wappler-Guzzetta EA, Kalueff AV | title = DARK Classics in Chemical Neuroscience: Atropine, Scopolamine, and Other Anticholinergic Deliriant Hallucinogens | journal = ACS Chem Neurosci | volume = 10 | issue = 5 | pages = 2144–2159 | date = May 2019 | pmid = 30566832 | doi = 10.1021/acschemneuro.8b00615 | url = }}</ref><ref name="ShimKangSharma2022">{{cite journal | vauthors = Shim KH, Kang MJ, Sharma N, An SS | title = Beauty of the beast: anticholinergic tropane alkaloids in therapeutics | journal = Nat Prod Bioprospect | volume = 12 | issue = 1 | pages = 33 | date = September 2022 | pmid = 36109439 | pmc = 9478010 | doi = 10.1007/s13659-022-00357-w | url = | quote = Antagonism at M1 and M2 receptors have negative impact on memory and cognition . Atropine and scopolamine are non-selective competitive antagonist of muscarinic receptors. Atropine has the highest affinity for subtype M1, followed by M2 and M3 and weak affinity for M4 and M5 . On the other hand, scopolamine has strong affinity for M1-M4 compared to M5 while hyoscyamine binds to M2 only .}}</ref> This is in contrast to related antimuscarinics like ] and ], which are ] antagonists of all five muscarinic acetylcholine receptors.<ref name="LakstygalKolesnikovaKhatsko2019" /><ref name="ShimKangSharma2022" /> Antagonism of both the muscarinic acetylcholine ] and M<sub>2</sub> receptor has been implicated as having negative effects on ] and ].<ref name="ShimKangSharma2022" /> Hyoscyamine has been described as having ] effects similarly to scopolamine, atropine, and other antimuscarinics.<ref name="LakstygalKolesnikovaKhatsko2019" /> However, other sources have reported that hyoscyamine potently antagonizes all five muscarinic acetylcholine receptor subtypes.<ref name="LavradorCabralVeríssimo2023">{{cite journal | vauthors = Lavrador M, Cabral AC, Veríssimo MT, Fernandez-Llimos F, Figueiredo IV, Castel-Branco MM | title = A Universal Pharmacological-Based List of Drugs with Anticholinergic Activity | journal = Pharmaceutics | volume = 15 | issue = 1 | date = January 2023 | page = 230 | pmid = 36678858 | pmc = 9863833 | doi = 10.3390/pharmaceutics15010230 | doi-access = free | url = }}</ref>

==Biosynthesis in plants==
] are present and labeled in the diagram.]]

Hyoscyamine can be extracted from plants of the family ], notably '']''. As hyoscyamine is a direct ] in the ], it is produced via the same ].<ref name="Ziegler2008">{{cite journal | vauthors = Ziegler J, Facchini PJ | title = Alkaloid biosynthesis: metabolism and trafficking | journal = Annual Review of Plant Biology | volume = 59 | issue = 1 | pages = 735–769 | year = 2008 | pmid = 18251710 | doi = 10.1146/annurev.arplant.59.032607.092730 }}</ref>

The ] of hyoscine begins with the ] of ''L''-] to ] by ] (). Putrescine is ] to ''N''-methylputrescine by ] ().<ref name="Ziegler2008"/>

A ] () that specifically recognizes methylated putrescine catalyzes the ] of this compound to 4-methylaminobutanal which then undergoes a spontaneous ring formation to ''N''-methylpyrrolium cation. In the next step, the pyrrolium cation condenses with ] yielding ]. No enzymatic activity could be demonstrated that catalyzes this reaction. Hygrine further rearranges to ].<ref name="Ziegler2008" />

Subsequently, ] () converts tropinone to ] which condenses with ]-derived phenyllactate to littorine. A ] classified as Cyp80F1<ref>{{cite journal | vauthors = Li R, Reed DW, Liu E, Nowak J, Pelcher LE, Page JE, Covello PS | title = Functional genomic analysis of alkaloid biosynthesis in Hyoscyamus niger reveals a cytochrome P450 involved in littorine rearrangement | journal = Chemistry & Biology | volume = 13 | issue = 5 | pages = 513–520 | date = May 2006 | pmid = 16720272 | doi = 10.1016/j.chembiol.2006.03.005 | doi-access = free }}</ref> oxidizes and rearranges littorine to hyoscyamine ].

]
==Bush medicine basis==

A ] developed by ] of the ] from the soft ] tree, or '']'', was used by the ] in World War II to stop soldiers getting ] when they sailed across the ] during the ]. Later, it was found that the same substance could be used in the production of ] and hyoscyamine, which are used in ], and a multi-million dollar industry was built in ] based on this substance.<ref name=kc2019>{{cite web | title=Visitors to Art of Healing exhibition told how Australian Indigenous bush medicine was given to every allied soldier landing at Normandy on D-Day | website=King's College London | date=7 June 2019 | url=https://www.kcl.ac.uk/news/australian-indigenous-bush-medicine-was-given-to-allied-soldiers-on-d-day | access-date=2 June 2020}}</ref>

== Society and culture ==
=== Brand names ===
Brand names for hyoscyamine include Symax, HyoMax, Anaspaz, Egazil, Buwecon, Cystospaz, Levsin, Levbid, Levsinex, Donnamar, NuLev, Spacol T/S, and Neoquess.<ref>{{Cite web |title=Hyoscyamine - brand name list from Drugs.com |url=https://www.drugs.com/ingredient/hyoscyamine.html |url-status=live |archive-url=https://web.archive.org/web/20220820211121/https://www.drugs.com/ingredient/hyoscyamine.html |archive-date=20 August 2022 |access-date=20 August 2022 |website=] |language=en}}</ref>

== References ==
{{Reflist}}

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{{Drugs for functional gastrointestinal disorders}}
{{Hallucinogens}}
{{Muscarinic acetylcholine receptor modulators}}
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