Camazepam

Title: Camazepam
CAS Registry Number: 36104-80-0
CAS Name: Dimethylcarbamic acid 7-chloro-2,3-dihydro-1-methyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl ester
Additional Names: 7-chloro-1,3-dihydro-3-hydroxy-1-methyl-5-phenyl-2H-1,4-benzodiazepin-2-one dimethylcarbamate (ester); 7-chloro-1,3-dihydro-3-(N,N-dimethylcarbamoyl)-1-methyl-5-phenyl-2H-1,4-benzodiazepin-2-one
Manufacturers' Codes: SB-5833
Trademarks: Albego (Boehringer, Ing.)
Molecular Formula: C19H18ClN3O3
Molecular Weight: 371.82
Percent Composition: C 61.37%, H 4.88%, Cl 9.53%, N 11.30%, O 12.91%
Literature References: Prepn: G. Ferrari, C. Casagrande, DE 2142181; eidem, US 3799920 (1972, 1974 both to Siphar). Metabolism: F. Marcucci et al., J. Pharm. Sci. 67, 1470 (1978). Pharmacology: L. Merlo et al., Arzneim.-Forsch. 24, 1759 (1974); R. Ferrini et al., ibid. 2029. Clinical studies: A. Tammaro et al., ibid. 27, 2177 (1978); S. Carrara et al., Eur. J. Clin. Pharmacol. 13, 335 (1978).
Properties: White crystalline powder from ethyl acetate, mp 173-174°. Sol in alcohol, moderately sol in water. LD50 in mice, rats (mg/kg): 970, >4000 orally (Ferrini).
Melting point: mp 173-174°
Toxicity data: LD50 in mice, rats (mg/kg): 970, >4000 orally (Ferrini)
NOTE: This is a controlled substance (depressant): 21 CFR, 1308.14.
Therap-Cat: Anxiolytic.
Keywords: Anxiolytic; Benzodiazepine Derivatives.
Cambendazole Cameleons Camostat Camphene Camphoric Acid

Camazepam
Camazepam.svg
Camazepam3d.png
Systematic (IUPAC) name
(9-Chloro-2-methyl-3-oxo-6-phenyl-2,5-diazabicyclo[5.4.0]undeca-5,8,10,12-tetraen-4-yl)-N,N-dimethylcarbamate
Clinical data
Pregnancy cat.  ?
Legal status Schedule IV(US)
Routes Oral
Pharmacokinetic data
Bioavailability  ?
Metabolism Hepatic
Half-life  ?
Excretion Renal
Identifiers
CAS number 36104-80-0 YesY
ATC code N05BA15
PubChem CID 37367
DrugBank DB01489
ChemSpider 34285 YesY
UNII HZ3XRH03C3 YesY
KEGG D07315 YesY
ChEMBL CHEMBL1095282 YesY
Chemical data
Formula C19H18ClN3O3 
Mol. mass 371.8
 YesY (what is this?)  (verify)

Camazepam[1] is a benzodiazepine psychoactive drug, marketed under the brand names Albego, Limpidon and Paxor. It is the dimethyl carbamate ester of temazepam, a metabolite of diazepam.[2] While it possesses anxiolytic, anticonvulsant, skeletal muscle relaxant and hypnotic properties[3] it differs from other benzodiazepines in that its anxiolytic properties are particularly prominent but has comparatively limited anticonvulsant, hypnotic and skeletal muscle relaxant properties.

Compared to other benzodiazepines, it has reduced side effects such as impaired cognition, reaction times and coordination.[4][5][6][7][8] which makes it best suited as an anxiolytic because of these reduced sides effects. With higher doses such as 40 mg of camazepam, impairments similar to those caused by other benzodiazepines manifest as disrupted sleep patterns and impaired cognitive performance.[9] Animal studies have shown camazepam and its active metabolites possess anticonvulsant properties.[10] Skin disorders have been reported with use of camazepam however.[11] Camazepam is believed to increase attention.[12] Unlike other benzodiazepines it does not disrupt normal sleep patterns.[13] Camazepam has been shown in animal experiments to have a very low affinity for benzodiazepine receptors compared to other benzodiazepines.[14] It is almost completely absorbed into the bloodstream after oral administration with, 90 percent bioavailability achieved in humans.[15] Camazepam is metabolised into the active metabolite temazepam.[16] Compared to temazepam, camazepam has shown roughly equal anxiolytic properties, and less anticonvulsant, sedative and motor-impairing properties.