Cyprazepam

Cyprazepam
Clinical data
Routes of; administration	Oral
ATC code	none;
Legal status
Legal status	US: Unscheduled;
Pharmacokinetic data
Metabolism	Hepatic
Excretion	Renal
Identifiers
	IUPAC name 10-chloro-N-(cyclopropylmethyl)-3-hydroxy-2-phenyl-3,6-diazabicyclo[5.4.0]undeca-1,6,8,10-tetraen-5-imine;
CAS Number	15687-07-7 ;
PubChem CID	27452;
ChemSpider	16736916 ;
UNII	933N61G4SL;
KEGG	D03631 ;
ChEMBL	ChEMBL2104165 ;
CompTox Dashboard (EPA)	DTXSID70897505 ;
Chemical and physical data
Formula	C19H18ClN3O
Molar mass	339.82 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES ClC1=CC2=C(N/C(C[N+]([O-])=C2C3=CC=CC=C3)=N/CC4CC4)C=C1;
	InChI InChI=1S/C19H18ClN3O/c20-15-8-9-17-16(10-15)19(14-4-2-1-3-5-14)23(24)12-18(22-17)21-11-13-6-7-13/h1-5,8-10,13H,6-7,11-12H2,(H,21,22) ; Key:UKFDTMNJMKWWNK-UHFFFAOYSA-N ;
	(what is this?) (verify)

Cyprazepam^[1] is a drug which is a sedative-hypnotic benzodiazepine derivative.^[2]^[3]^[4]^[5] It has anxiolytic properties,^[6] and presumably also has hypnotic, skeletal muscle relaxant, anticonvulsant and amnestic properties.

Synthesis

The lactam moiety in benzodiazepams is active towards nucleophiles and numerous analogues have been made by exploiting this fact.

Cyprazepam synthesis:^[1]

For example, heating demoxepam with N-cyclopropylmethylamine leads to amidine formation, the minor tranquilizer cyprazepam.

References

^ ^a ^b US 3138586, Wuest HM, "2-Cycloalkylamino Derivatives of 1,4-Benzodiazipines", issued 23 June 1964, assigned to Warner-Lambert Pharmaceutical Company ; Chem. Abstr., 61: 7,032f (1964).
^ Oelschläger H, Martienssen D, Belal F (22 September 2006). "Ring Contraction of 1,4-Benzodiazepines to 3,4-Dihydroquinazolines During Macro Scale Reduction (Example 5: Cyprazepam)". Archiv der Pharmazie. 325 (8). Wiley Interscience: 503–507. doi:10.1002/ardp.19923250810. ISSN 0365-6233. S2CID 96638676. Archived from the original on 5 January 2013.
^ EP 1466628, Matthews B, Victor S, Nigel, Swindell C, "DHA-pharmaceutical agent conjugates", published 13 October 2004, assigned to American Regent Inc.
^ "Harmonized Tariff Schedule of the United States (2009) - Supplement 1 - PHARMACEUTICAL APPENDIX TO THE HARMONIZED TARIFF SCHEDULE" (PDF). USA: United States International Trade Commission. 2009. Archived from the original (PDF) on 31 July 2009. Retrieved 19 September 2009.
^ Schafer EW, Bowles WA, Hurlbut J (May 1983). "The acute oral toxicity, repellency, and hazard potential of 998 chemicals to one or more species of wild and domestic birds". Archives of Environmental Contamination and Toxicology. 12 (3): 355–82. Bibcode:1983ArECT..12..355S. doi:10.1007/BF01059413. PMID 6882015. S2CID 32956594.
^ World Health Organization (2006). "The use of stems in the selection of International Nonproprietary Names (INN) for pharmaceutical substances" (PDF). USA: Ministry of health, Syria. Retrieved 19 September 2009. ^{[dead link‍]}

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[US3138586-1] US 3138586, Wuest HM, "2-Cycloalkylamino Derivatives of 1,4-Benzodiazipines", issued 23 June 1964, assigned to Warner-Lambert Pharmaceutical Company ; Chem. Abstr., 61: 7,032f (1964).

[2] Oelschläger H, Martienssen D, Belal F (22 September 2006). "Ring Contraction of 1,4-Benzodiazepines to 3,4-Dihydroquinazolines During Macro Scale Reduction (Example 5: Cyprazepam)". Archiv der Pharmazie. 325 (8). Wiley Interscience: 503–507. doi:10.1002/ardp.19923250810. ISSN 0365-6233. S2CID 96638676. Archived from the original on 5 January 2013.

[3] EP 1466628, Matthews B, Victor S, Nigel, Swindell C, "DHA-pharmaceutical agent conjugates", published 13 October 2004, assigned to American Regent Inc.

[4] "Harmonized Tariff Schedule of the United States (2009) - Supplement 1 - PHARMACEUTICAL APPENDIX TO THE HARMONIZED TARIFF SCHEDULE" (PDF). USA: United States International Trade Commission. 2009. Archived from the original (PDF) on 31 July 2009. Retrieved 19 September 2009.

[5] Schafer EW, Bowles WA, Hurlbut J (May 1983). "The acute oral toxicity, repellency, and hazard potential of 998 chemicals to one or more species of wild and domestic birds". Archives of Environmental Contamination and Toxicology. 12 (3): 355–82. Bibcode:1983ArECT..12..355S. doi:10.1007/BF01059413. PMID 6882015. S2CID 32956594.

[6] World Health Organization (2006). "The use of stems in the selection of International Nonproprietary Names (INN) for pharmaceutical substances" (PDF). USA: Ministry of health, Syria. Retrieved 19 September 2009. ^{[dead link‍]}

[1]

[2]

[3]

[4]

[5]

[6]

Cyprazepam

Synthesis

See also

References

zproxy.org

Clinical data


Routes of administration	Oral
ATC code	none
Legal status
Legal status	US: Unscheduled
Pharmacokinetic data
Metabolism	Hepatic
Excretion	Renal
Identifiers
IUPAC name 10-chloro-N-(cyclopropylmethyl)-3-hydroxy-2-phenyl-3,6-diazabicyclo[5.4.0]undeca-1,6,8,10-tetraen-5-imine
CAS Number	15687-07-7^Y
PubChem CID	27452
ChemSpider	16736916^Y
UNII	933N61G4SL
KEGG	D03631^Y
ChEMBL	ChEMBL2104165^N
CompTox Dashboard (EPA)	DTXSID70897505
Chemical and physical data
Formula	C₁₉H₁₈ClN₃O
Molar mass	339.82 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES ClC1=CC2=C(N/C(C[N+]([O-])=C2C3=CC=CC=C3)=N/CC4CC4)C=C1
InChI InChI=1S/C19H18ClN3O/c20-15-8-9-17-16(10-15)19(14-4-2-1-3-5-14)23(24)12-18(22-17)21-11-13-6-7-13/h1-5,8-10,13H,6-7,11-12H2,(H,21,22)^Y Key:UKFDTMNJMKWWNK-UHFFFAOYSA-N^Y
^NY (what is this?) (verify)