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Camazepam

HCID 37367
NotesReactions
Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
36104-80-0
Standard SMILES
CN(C)C(=O)OC1N=C(c2ccccc2)c2cc(Cl)ccc2N(C)C1=O
InChIKey
PXBVEXGRHZFEOF-UHFFFAOYSA-N
Molecular formula
C19H18ClN3O3
Average molar mass
371.8 g/mol
Monoisotopic mass
371.1036691

Overview

Camazepam is a benzodiazepine.

Names & identifiers

Preferred name
Camazepam
IUPAC
(7-chloro-1-methyl-2-oxo-5-phenyl-3H-1,4-benzodiazepin-3-yl) N,N-dimethylcarbamate
English name
camazepam
Molecular formula
C19H18ClN3O3
Molecular weight
371.82

Names & synonyms

CamazepamAlbegoPaxorLimpidonCamazepamumPanevrilNebolan36104-80-0SB 5833HZ3XRH03C3Carbamic acid, dimethyl-, 7-chloro-2,3-dihydro-1-methyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl ester3-N,N-Dimethylcarbamoyloxy-7-chloro-5-phenyl-1-methyl-1,3-dihydro-2H-1,4-benzodiazepin-2-one
Show more names
B-5333SB-5833KTH-497dl-CaMazepaMRaceMic CaMazepaMcamazepam USP/EP/BPPXBVEXGRHZFEOF-UHFFFAOYSA-NDimethylcarbamic acid 7-chloro-2,3-dihydro-1-methyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl ester
DTXSID50865803(+-)-CamazepamRefChem:573665DTXCID10814170N05BA157-chloro-1-methyl-2-oxo-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-3-yl N,N-dimethylcarbamateB-5833S-58-33

Database identifiers

CAS
36104-80-0

Properties

Computed structural properties

XLogP
2.8
Topological polar surface area
62.2 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
4
Rotatable bonds
3
Heavy atoms
26
Formal charge
0
Complexity
574

Experimental & physicochemical properties

Drugs · 2 items

DEA NFLIS-Drug Category -> Benzodiazepines

DEA Schedule IV Controlled Substance -> Depressants

Human DrugsPharmaceuticals
Melting Point173-174

Physicochemical properties

Melting point
173 · 173-174°
Boiling point
568.3 · 568.3±50.0 °C(Predicted)
Density
1.2902 · 1.2902 (rough estimate)
refractive index
1.647 · 1.6470 (estimate)
solubility
Chloroform (Slightly), Methanol (Slightly)
form
Solid
pka
2.21 · 2.21±0.50(Predicted)
color
White to Off-White
Stability
Light Sensitive
FDA UNII
3 XRH03C3 · HZ3XRH03C3

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

Hazard information

Regulatory InformationDEA schedule IV controlled substance

Toxicology

Treatment · 1 item

General supportive measures should be employed, along with intravenous fluids, and an adequate airway maintained. Hypotension may be combated by the use of norepinephrine or metaraminol. Dialysis is of limited value. Flumazenil (Anexate) is a competitive benzodiazepine receptor antagonist that can be used as an antidote for benzodiazepine overdose. In particular, flumazenil is very effective at reversing the CNS depression associated with benzodiazepines but is less effective at reversing respiratory depression. Its use, however, is controversial as it has numerous contraindications. It is contraindicated in patients who are on long-term benzodiazepines, those who have ingested a substance that lowers the seizure threshold, or in patients who have tachycardia or a history of seizures. As a general rule, medical observation and supportive care are the mainstay of treatment of benzodiazepine overdose. Although benzodiazepines are absorbed by activated charcoal, gastric decontamination with activated charcoal is not beneficial in pure benzodiazepine overdose as the risk of adverse effects often outweigh any potential benefit from the procedure. It is recommended only if benzodiazepines have been taken in combination with other drugs that may benefit from decontamination. Gastric lavage (stomach pumping) or whole bowel irrigation are also not recommended.

Exposure RoutesAlmost completely absorbed into the bloodstream after oral administration. 90% bioavailability can be achieved in humans.
Toxicity Summary · 1 item

Camazepam has been shown to bind competitively to benzodiazepine receptors in the brain with a relatively low affinity in animal models. This binding of benzodiazepine receptors by camazepam and its active metabolites is responsible for its anticonvulsant effects. Notably, only three metabolites were shown to exert anticonvulsant activity, temazepam, oxazepam, and hydroxy camazepam. The anxiolytic properties of camazepam are also attributed to their ability to bind benzodiazepine receptors, also known as GABA receptors. When benzodiazepines bind to GABA receptors they increase the efficiency with which the inhibitory neurotransmitter GABA binds.

Chemistry & industry

Pharmacology

ATC Code · 2 items

N - Nervous system

QN - Nervous system

Mechanism of Action · 1 item

Camazepam has been shown to bind competitively to benzodiazepine receptors in the brain with a relatively low affinity in animal models. This binding of benzodiazepine receptors by camazepam and its active metabolites is responsible for its anticonvulsant effects. Notably, only three metabolites were shown to exert anticonvulsant activity, temazepam, oxazepam, and hydroxy camazepam. The anxiolytic properties of camazepam are also attributed to their ability to bind benzodiazepine receptors, also known as GABA receptors. When benzodiazepines bind to GABA receptors they increase the efficiency with which the inhibitory neurotransmitter GABA binds.

Metabolism/Metabolites · 2 items

Metabolized by the liver into more than 10 metabolites, some of which are also active and posses anticonvulsant properties. [3] One active metabolite of note is temazepam which has roughly equal in effectiveness as an anxiolytic, but is less anticonvulsant, sedating, and motor-impairing. Camazepam undergoes enantioselective metabolism by human liver microsomes. [1]

Metabolized by the liver into more than 10 metabolites, some of which are also active and posses anticonvulsant properties. [3] One active metabolite of note is temazepam which has roughly equal in effectiveness as an anxiolytic, but is less anticonvulsant, sedating, and motor-impairing. Camazepam undergoes enantioselective metabolism by human liver microsomes. [1] Route of Elimination: Renally eliminated.

Absorption, Distribution and Excretion · 2 items

Almost completely absorbed into the bloodstream after oral administration. 90% bioavailability can be achieved in humans.

Renally eliminated.

Uses & manufacturing

UsesCamazepam has been used in placebo controlled studies for the treatment of patients suffering from anxiety and depression.

Related reactions

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
PubChem CID
37367
DTXSID
DTXSID50865803
ChEMBL
CHEMBL1095282
ChEBI
CHEBI:135570
UNII
HZ3XRH03C3
EC Number
252-866-6
Nikkaji
J19.779C
ATC code
5 BA15 · N05BA15
RIDADR
3249 · 3249
HazardClass
6.1 · 6.1(b)
PackingGroup
III
Toxicity
50 in · LD50 in mice, rats (mg/kg): 970, >4000 orally (Ferrini)
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).

Safety data

ridadr
3249
Toxicity
LD50 in mice, rats (mg/kg): 970, >4000 orally (Ferrini)
hazard_class
6.1(b)
packing_group
III
Use ClassificationPharmaceuticals

Applications

UsesAnxiolytic. Controlled substance (depressant).

Upstream & downstream products

Upstream raw materials

Phenyl chloroformateAzaDimethylamine4-Benzodiazepine-2-One

Additional notes

DefinitionChEBI: Camazepam is a benzodiazepine.