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{{short description|Chemical compound}}
{{Drugbox
{{Drugbox
| Watchedfields = changed
| Watchedfields = changed
| verifiedrevid = 447995075
| verifiedrevid = 447995075
| IUPAC_name = 7-Chloro-1-methyl-5-phenyl-1,3-dihydro- 2''H''- 1,4-benzodiazepine-2-thione
| IUPAC_name = 7-Chloro-1-methyl-5-phenyl-1,3-dihydro- 2''H''-1,4-benzodiazepine-2-thione
| image = Sulazepam.svg
| image = Sulazepam.svg
| width = 180
| width = 200

<!------- Clinical data-->
<!------- Clinical data-->
| tradename =
| tradename =
| legal_status =
| legal_CA = Schedule IV
| legal_status =

<!------- Pharmacokinetic data-->
<!------- Pharmacokinetic data-->
| bioavailability =
| bioavailability =
| metabolism =
| metabolism =
| elimination_half-life =
| elimination_half-life =
| excretion =
| excretion =

<!------- Identifiers-->
<!------- Identifiers-->
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number_Ref = {{cascite|correct|??}}
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| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D05942
| KEGG = D05942

<!------- Chemical data-->
<!------- Chemical data-->
| C=16 | H=13 | Cl=1 | N=2 | S=1
| C=16 | H=13 | Cl=1 | N=2 | S=1
| molecular_weight = 300.81 g/mol
| smiles = ClC1=CC=C(N(C)C(CN=C2C3=CC=CC=C3)=S)C2=C1
| smiles = ClC1=CC=C(N(C)C(CN=C2C3=CC=CC=C3)=S)C2=C1
| InChI = 1/C16H13ClN2S/c1-19-14-8-7-12(17)9-13(14)16(18-10-15(19)20)11-5-3-2-4-6-11/h2-9H,10H2,1H3
| InChIKey = MWGWTOPCKLQYEU-UHFFFAOYAA
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C16H13ClN2S/c1-19-14-8-7-12(17)9-13(14)16(18-10-15(19)20)11-5-3-2-4-6-11/h2-9H,10H2,1H3
| StdInChI = 1S/C16H13ClN2S/c1-19-14-8-7-12(17)9-13(14)16(18-10-15(19)20)11-5-3-2-4-6-11/h2-9H,10H2,1H3
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}}
}}


'''Sulazepam''' is a [[benzodiazepine]] derivative. It is the [[thioamide]] derivative of [[diazepam]]. It is metabolised into [[diazepam]], [[desmethyldiazepam]] and [[temazepam|oxydiazepam]]. It has [[sedative]], [[muscle relaxant]], [[hypnotic]], [[anticonvulsant]] and [[anxiolytic]] properties like those of other benzodiazepines.<ref>{{Cite web | url = http://www.psychotropics.dk/moleculeView/default.aspx?ID=1444&Catalogtype=A&ChapterID=1&Thissortorder=41 | title = sulazepam | accessdate = 29 December 2008 | year = 2003 | publisher = psychotropics.dk }}</ref><ref>{{cite journal |author=Golovenko NIa, Zin'kovskii VG |title=(title in Russian) |trans_title=Analysis of the structure of the components of the convulsive action of corazole following administration of sulazepam and its metabolites to mice |language=Russian |journal=Biull Eksp Biol Med |volume=82 |issue=9 |pages=1078–1081 |date=September 1976 |pmid=11012 |doi= |url=}}</ref> It was never marketed.
'''Sulazepam''' is a [[benzodiazepine]] derivative. It is the [[thioamide]] derivative of [[diazepam]]. It is metabolised into [[diazepam]], [[desmethyldiazepam]] and [[temazepam|oxydiazepam]]{{Citation needed|date=June 2018}}. It has [[sedative]], [[muscle relaxant]], [[hypnotic]], [[anticonvulsant]] and [[anxiolytic]] properties like those of other benzodiazepines.<ref>{{Cite web | url = http://www.psychotropics.dk/moleculeView/default.aspx?ID=1444&Catalogtype=A&ChapterID=1&Thissortorder=41 | title = sulazepam | access-date = 29 December 2008 | year = 2003 | publisher = psychotropics.dk }}</ref><ref>{{cite journal | vauthors = Golovenko NI, Zin'kovskii VG | title = [Analysis of the structure of the components of the convulsive action of corazole following administration of sulazepam and its metabolites to mice] | language = ru | journal = Biulleten' Eksperimental'noi Biologii I Meditsiny | volume = 82 | issue = 9 | pages = 1078–81 | date = September 1976 | pmid = 11012 | trans-title = Analysis of the structure of the components of the convulsive action of corazole following administration of sulazepam and its metabolites to mice }}</ref> It was never marketed.

==Synthesis==
==Synthesis==
[[File:Sulazepam synthesis.svg|thumb|center|400px|Sulazepam synthesis:<ref>{{Cite DOI|10.1021/jo01024a511}}</ref> {{US Patent|3141890}}]]
[[File:Sulazepam synthesis.svg|thumb|center|400px|Sulazepam synthesis:<ref>{{cite journal|doi=10.1021/jo01024a511|title=Quinazolines and 1,4-Benzodiazepines. XVI. Synthesis and Transformations of 5-Phenyl-1,4-benzodiazepine-2-thiones |journal=The Journal of Organic Chemistry |volume=29 |pages=231 |year=1964| vauthors = Archer GA, Sternbach LH }}</ref> {{US Patent|3141890}}]]
Treatment of diazepam with [[phosphorus pentasulfide]] produces the corresponding [[thionamide]], sulazepam.
Treatment of diazepam with [[phosphorus pentasulfide]] produces the corresponding [[thionamide]], sulazepam.
==References==
== See also ==
*[[Uldazepam]]

== References ==
{{Reflist}}
{{Reflist}}



{{Benzodiazepines}}
{{Benzodiazepines}}
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[[Category:Benzodiazepines]]
[[Category:Benzodiazepines]]
[[Category:Organochlorides]]
[[Category:Chloroarenes]]
[[Category:Thioamides]]
[[Category:Thioamides]]
[[Category:GABAA receptor positive allosteric modulators]]



{{drug-stub}}
{{sedative-stub}}

Latest revision as of 07:39, 7 December 2023

Sulazepam
Clinical data
ATC code
  • none
Legal status
Legal status
Identifiers
  • 7-Chloro-1-methyl-5-phenyl-1,3-dihydro- 2H-1,4-benzodiazepine-2-thione
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC16H13ClN2S
Molar mass300.80 g·mol−1
3D model (JSmol)
  • ClC1=CC=C(N(C)C(CN=C2C3=CC=CC=C3)=S)C2=C1
  • InChI=1S/C16H13ClN2S/c1-19-14-8-7-12(17)9-13(14)16(18-10-15(19)20)11-5-3-2-4-6-11/h2-9H,10H2,1H3 checkY
  • Key:MWGWTOPCKLQYEU-UHFFFAOYSA-N checkY
  (verify)

Sulazepam is a benzodiazepine derivative. It is the thioamide derivative of diazepam. It is metabolised into diazepam, desmethyldiazepam and oxydiazepam[citation needed]. It has sedative, muscle relaxant, hypnotic, anticonvulsant and anxiolytic properties like those of other benzodiazepines.[1][2] It was never marketed.

Synthesis

[edit]
Sulazepam synthesis:[3] U.S. patent 3,141,890

Treatment of diazepam with phosphorus pentasulfide produces the corresponding thionamide, sulazepam.

See also

[edit]

References

[edit]
  1. ^ "sulazepam". psychotropics.dk. 2003. Retrieved 29 December 2008.
  2. ^ Golovenko NI, Zin'kovskii VG (September 1976). "[Analysis of the structure of the components of the convulsive action of corazole following administration of sulazepam and its metabolites to mice]" [Analysis of the structure of the components of the convulsive action of corazole following administration of sulazepam and its metabolites to mice]. Biulleten' Eksperimental'noi Biologii I Meditsiny (in Russian). 82 (9): 1078–81. PMID 11012.
  3. ^ Archer GA, Sternbach LH (1964). "Quinazolines and 1,4-Benzodiazepines. XVI. Synthesis and Transformations of 5-Phenyl-1,4-benzodiazepine-2-thiones". The Journal of Organic Chemistry. 29: 231. doi:10.1021/jo01024a511.
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