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Revision as of 12:22, 18 January 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers from ChemSpider, CommonChemistry and FDA for the Chem/Drugbox validation project - Updated: ChEMBL.← Previous edit		Latest revision as of 23:35, 27 March 2024 edit undoKimen8 (talk | contribs)Extended confirmed users5,112 edits →See also: swap See also entry for one not already mentioned in article body
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			{{Short description|Benzodiazepine drug}}
⚫	{{Drugbox| Verifiedfields = changed
			{{Drugbox
⚫	| verifiedrevid = 400853047
		⚫	| Verifiedfields = changed
	|
		⚫	| verifiedrevid = 464206801
	|IUPAC_name = 7-chloro-5-phenyl-1-prop-2-yn-1-yl-1,3-dihydro-2''H''-1,4-benzodiazepin-2-one
	|synonyms = <small>9-chloro-6-phenyl-2-prop-2-ynyl-2,5-diazabicycloundeca-5,8,10,12-tetraen-3-one</small>		| IUPAC_name = 7-chloro-5-phenyl-1-prop-2-yn-1-yl-1,3-dihydro-2''H''-1,4-benzodiazepin-2-one
	| image = Pinazepam.svg		| image = Pinazepam.svg
	| width=150		| width = 175
	| image2 = Pinazepam3d.png		| image2 = Pinazepam3d.png
			| width2 = 160
			<!--Clinical data-->
			| tradename =
			| Drugs.com = {{drugs.com|international|pinazepam}}
		⚫	| pregnancy_category =
			| 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 = Anlage III
			| legal_US = Schedule IV
		⚫	| routes_of_administration = Oral
			<!--Pharmacokinetic data-->
		⚫	| bioavailability =
		⚫	| metabolism = ]
		⚫	| elimination_half-life =
		⚫	| excretion = ]
			<!--Identifiers-->
		⚫	| CAS_number_Ref = {{cascite|changed|??}}
		⚫	| CAS_number = 52463-83-9
		⚫	| ATC_prefix = N05
		⚫	| ATC_suffix = BA14
		⚫	| PubChem = 40391
			| DrugBank_Ref = {{drugbankcite|changed|drugbank}}
		⚫	| DrugBank = ?
	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}		| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
	| ChemSpiderID = 36899		| ChemSpiderID = 36899
			| UNII_Ref = {{fdacite|correct|FDA}}
	| InChI = 1/C18H13ClN2O/c1-2-10-21-16-9-8-14(19)11-15(16)18(20-12-17(21)22)13-6-4-3-5-7-13/h1,3-9,11H,10,12H2
			| UNII = 5286RBZ882
	| InChIKey = MFZOSKPPVCIFMT-UHFFFAOYAQ
			| KEGG_Ref = {{keggcite|correct|kegg}}
⚫	| smiles = Clc3cc\1c(N(C(=O)C/N=C/1c2ccccc2)CC#C)cc3
		⚫	| KEGG = D07314
			| ChEMBL_Ref = {{ebicite|correct|EBI}}
	| ChEMBL = 1213352		| ChEMBL = 1213352
			<!--Chemical data-->
		⚫	| C=18 | H=13 | Cl=1 | N=2 | O=1
		⚫	| smiles = Clc3cc\1c(N(C(=O)C/N=C/1c2ccccc2)CC#C)cc3
	| StdInChI_Ref = {{stdinchicite|correct|chemspider}}		| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
	| StdInChI = 1S/C18H13ClN2O/c1-2-10-21-16-9-8-14(19)11-15(16)18(20-12-17(21)22)13-6-4-3-5-7-13/h1,3-9,11H,10,12H2		| StdInChI = 1S/C18H13ClN2O/c1-2-10-21-16-9-8-14(19)11-15(16)18(20-12-17(21)22)13-6-4-3-5-7-13/h1,3-9,11H,10,12H2
	| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}		| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
	| StdInChIKey = MFZOSKPPVCIFMT-UHFFFAOYSA-N		| StdInChIKey = MFZOSKPPVCIFMT-UHFFFAOYSA-N
			| synonyms = <small>9-chloro-6-phenyl-2-prop-2-ynyl-2,5-diazabicycloundeca-5,8,10,12-tetraen-3-one</small>
⚫	| CAS_number=52463-83-9
⚫	| ATC_prefix=N05
⚫	| ATC_suffix=BA14
	| ATC_supplemental=
⚫	| PubChem=40391
⚫	| DrugBank=?
⚫	| KEGG_Ref = {{keggcite|changed|kegg}}
⚫	| KEGG = D07314
⚫	|C=18|H=13|Cl=1|N=2|O=1
	| molecular_weight = 308.8
⚫	| bioavailability= ?
⚫	| metabolism = ]
⚫	| elimination_half-life= ?
⚫	| excretion = ]
⚫	| pregnancy_category = ?
	| legal_status = ](US)
⚫	| routes_of_administration= Oral
	}}		}}
⚫	'''Pinazepam''' (marketed under the brand name '''Domar''' and '''Duna''') is a drug which is a ] derivative.<ref>{{cite journal |pmid=3146986 |year=1988 |month=Sep |last1=Schütz |first1=H |last2=Holland |last3=Kazemian-Erdmann |last4=Schölermann |title=Screening of the new benzodiazepine derivative, pinazepan, and its major metabolites |volume=38 |issue=9 |pages=1372–5 |issn=0004-4172 |journal=Arzneimittel-Forschung |first2=EM |first3=F |first4=K }}</ref> It possesses ], ], ] and ] properties.
		⚫	'''Pinazepam''' (marketed under the brand name '''Domar''' and '''Duna''') is a ] drug.<ref>{{cite journal | vauthors = Schütz H, Holland EM, Kazemian-Erdmann F, Schölermann K | title = | journal = Arzneimittel-Forschung | volume = 38 | issue = 9 | pages = 1372–5 | date = September 1988 | pmid = 3146986 }}</ref> It possesses ], ], ] and ] properties.<ref>{{Cite journal|last=Janbroers|first=J. M.|date=1984|title=Pinazepam: review of pharmacological properties and therapeutic efficacy|url=https://pubmed.ncbi.nlm.nih.gov/6147192/|journal=Clinical Therapeutics|volume=6|issue=4|pages=434–450|issn=0149-2918|pmid=6147192}}</ref>
⚫	Pinazepam and its metabolite N-desmethyldiazepam (nordiazepam, ]) are transferred to the developing fetus ''in utero'', but the plasma drug level in the mother is usually significantly higher than in the fetus.<ref>{{cite journal |pmid=6150857 |year=1984 |last1=Pacifici |first1=GM |last2=Cuoci |last3=Guarneri |last4=Fornaro |last5=Arcidiacono |last6=Cappelli |last7=Moggi |last8=Placidi |title=Placental transfer of pinazepam and its metabolite N-desmethyldiazepam in women at term |volume=27 |issue=3 |pages=307–10 |issn=0031-6970 |journal=European journal of clinical pharmacology |doi=10.1007/BF00542165 |first2=L |first3=M |first4=P |first5=G |first6=N |first7=G |first8=GF }}</ref>
		⚫	Pinazepam and its metabolite ] are transferred to the developing fetus ''in ]'', but the plasma drug level in the mother is usually significantly higher than in the fetus.<ref>{{cite journal | vauthors = Pacifici GM, Cuoci L, Guarneri M, Fornaro P, Arcidiacono G, Cappelli N, Moggi G, Placidi GF | display-authors = 6 | title = Placental transfer of pinazepam and its metabolite N-desmethyldiazepam in women at term | journal = European Journal of Clinical Pharmacology | volume = 27 | issue = 3 | pages = 307–10 | year = 1984 | pmid = 6150857 | doi = 10.1007/BF00542165 | s2cid = 1389302 }}</ref>
⚫	Pinazepam differs from other benzodiazepines in that it has a propargyl group at the N-1 position of the benzodiazepine structure. It is less toxic than diazepam and in animal studies it appears to produce anxiolytic and anti-agitation properties with limited ] and motor coordination impairing properties. Pinazepam is rapidly absorbed after oral administration. The main active metabolites of pinazepam are depropargylpinazepam (N-desmethyldiazepam, ]) and ]. In humans pinazepam acts as a pure anxiolytic agent in that it does not possess to any significant degree the other pharmacological characteristics of benzodiazepines. Its lack of intellectual, motor and hypnotic impairing effects makes it more appropriate than other benzodiazepines for day time use.<ref>{{cite journal |pmid=6147192 |year=1984 |last1=Janbroers |first1=JM |title=Pinazepam: review of pharmacological properties and therapeutic efficacy |volume=6 |issue=4 |pages=434–50 |issn=0149-2918 |journal=Clinical therapeutics |url= |format= }}</ref><ref>{{cite journal |pmid=6147314 |year=1983 |last1=Pacifici |first1=GM |last2=Placidi |last3=Fornaro |last4=Gomeni |title=Pharmacokinetics of pinazepam in healthy volunteers |volume=3 |issue=5 |pages=331–7 |issn=0251-1649 |journal=International journal of clinical pharmacology research |first2=GF |first3=P |first4=R }}</ref><ref>{{cite journal |pmid=6809477 |year=1982 |last1=Pacifici |first1=GM |last2=Placidi |last3=Fornaro |last4=Gomeni |title=Pinazepam: a precursor of N-desmethyldiazepam |volume=22 |issue=3 |pages=225–8 |issn=0031-6970 |journal=European journal of clinical pharmacology |doi=10.1007/BF00545219 |first2=GF |first3=P |first4=R }}</ref> The elimination half-life is longer in the elderly.<ref>{{cite journal |pmid=6802645 |year=1982 |month=Jan |last1=Pacifici |first1=GM |last2=Cuoci |last3=Placidi |last4=Fornaro |last5=Gomeni |title=Elimination kinetics of desmethyldiazepam in two young and two elderly subjects |volume=7 |issue=1 |pages=69–72 |issn=0398-7639 |journal=European journal of drug metabolism and pharmacokinetics |url= |format= |first2=L |first3=GF |first4=P |first5=R }}</ref>
		⚫	Pinazepam differs from other ] in that it has a ] at the ''N''-1 position of the benzodiazepine structure. It is less toxic than diazepam and in animal studies it appears to produce anxiolytic and anti-agitation properties with limited ] and motor coordination impairing properties.<ref>{{Cite web|title=Diazepam Injection BP - Summary of Product Characteristics (SmPC) - (emc)|url=https://www.medicines.org.uk/emc/product/6274/smpc#gref|access-date=2021-08-23|website=www.medicines.org.uk}}</ref> Pinazepam is rapidly absorbed after oral administration. The main active metabolites of pinazepam are depropargylpinazepam (''N''-desmethyldiazepam, ]) and ].<ref>{{Cite journal|last=Dinis-Oliveira|first=Ricardo Jorge|date= Sep 14, 2017|title=Metabolic profile of oxazepam and related benzodiazepines: clinical and forensic aspects|url=https://pubmed.ncbi.nlm.nih.gov/28903606/|journal=Drug Metabolism Reviews|volume=49|issue=4|pages=451–463|doi=10.1080/03602532.2017.1377223|issn=1097-9883|pmid=28903606|s2cid=4528255}}</ref> In humans pinazepam acts as a pure anxiolytic agent in that it does not possess to any significant degree the other pharmacological characteristics of benzodiazepines. Its lack of intellectual, motor and hypnotic impairing effects makes it more appropriate than other benzodiazepines for day time use.<ref>{{cite journal | vauthors = Janbroers JM | title = Pinazepam: review of pharmacological properties and therapeutic efficacy | journal = Clinical Therapeutics | volume = 6 | issue = 4 | pages = 434–50 | year = 1984 | pmid = 6147192 }}</ref><ref>{{cite journal | vauthors = Pacifici GM, Placidi GF, Fornaro P, Gomeni R | title = Pharmacokinetics of pinazepam in healthy volunteers | journal = International Journal of Clinical Pharmacology Research | volume = 3 | issue = 5 | pages = 331–7 | year = 1983 | pmid = 6147314 }}</ref><ref>{{cite journal | vauthors = Pacifici GM, Placidi GF, Fornaro P, Gomeni R | title = Pinazepam: a precursor of N-desmethyldiazepam | journal = European Journal of Clinical Pharmacology | volume = 22 | issue = 3 | pages = 225–8 | year = 1982 | pmid = 6809477 | doi = 10.1007/BF00545219 | s2cid = 1977572 }}</ref> The elimination half-life is longer in the elderly.<ref>{{cite journal | vauthors = Pacifici GM, Cuoci L, Placidi GF, Fornaro P, Gomeni R | title = Elimination kinetics of desmethyldiazepam in two young and two elderly subjects | journal = European Journal of Drug Metabolism and Pharmacokinetics | volume = 7 | issue = 1 | pages = 69–72 | date = Jan 1982 | pmid = 6802645 | doi = 10.1007/bf03189546 | s2cid = 21836038 }}</ref>
	==See also==
	*]
	==References==		== See also ==
			*]
			== References ==
	{{reflist}}		{{reflist}}
	==External links==		== External links ==
	*		*
	{{Benzodiazepines}}		{{Benzodiazepines}}
	{{Anxiolytics}}		{{Anxiolytics}}
			{{GABAAR PAMs}}
		⚫	]
	]		]
	]		]
	]		]
⚫	]
	{{Musculoskeletal-drug-stub}}
	{{Nervous-system-drug-stub}}
			{{sedative-stub}}
	]