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Cloxazolam

HCID 2816
NotesReactions
Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Substructure searchFind similar structures

Basic information

CAS
24166-13-0
Standard SMILES
O=C1CN2CCOC2(c2ccccc2Cl)c2cc(Cl)ccc2N1
InChIKey
ZIXNZOBDFKSQTC-UHFFFAOYSA-N
Molecular formula
C17H14Cl2N2O2
Average molar mass
349.2 g/mol
Monoisotopic mass
348.0432331

Overview

Cloxazolam is a hemiaminal ether and an oxazolobenzodiazepine.

Names & identifiers

Preferred name
Cloxazolam
IUPAC
10-chloro-11b-(2-chlorophenyl)-2,3,5,7-tetrahydro-[1,3]oxazolo[3,2-d][1,4]benzodiazepin-6-one
English name
CLOXAZOLAM
Molecular formula
C17H14Cl2N2O2
Molecular weight
349.21

Names & synonyms

cloxazolamCloxazolazepamSepazonEnadelOlcadil24166-13-0CloxazolamumTolestanBetavelCloxamCS 370DTXSID0022854
Show more names
cs370Lubalixmt14-411Sepazone
MT 14-411GYL649Z0HY10-chloro-11b-(2-chlorophenyl)-2,3,5,7-tetrahydro-[1,3]oxazolo[3,2-d][1,4]benzodiazepin-6-oneDTXCID902854CHEBI:3142610-Chloro-11b-(o-chlorophenyl)-2,3,7,11b-tetrahydro-oxazolo(3,2-d) (1,4)benzodiazepin-6(5H)-one10-Chloro-2,3,5,6,7,11b-hexahydro-11b-(o-chlorophenyl)benzo(6,7)-1,4-diazepino-(5,4-b)-oxazol-6-one10-chloro-11b-(2-chlorophenyl)-2,3,5,7-tetrahydro-(1,3)oxazolo(3,2-d)(1,4)benzodiazepin-6-one

Database identifiers

CAS
24166-13-0
PubChem CID
2816
DTXSID
DTXSID0022854
ChEMBL
CHEMBL2107254
ChEBI
CHEBI:31426
UNII
GYL649Z0HY
EC Number
815-874-6
Nikkaji
J3.158E

Properties

Computed structural properties

XLogP
3.2
Topological polar surface area
41.6 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
3
Rotatable bonds
1
Heavy atoms
23
Formal charge
0
Complexity
478

Experimental & physicochemical properties

Drugs · 3 items

DEA NFLIS-Drug Category -> Benzodiazepines

DEA Schedule IV Controlled Substance -> Depressants

Pharmaceuticals -> Synthetic Cannabinoids or Psychoactive Compounds

Melting Point202-204

Physicochemical properties

Melting point
202 · 202-204° (dec)
Boiling point
172 °C · 172°C (rough estimate)
Density
1.4125 · 1.4125 (rough estimate)
refractive index
1.61 · 1.6100 (estimate)
pka
12.7 · 12.70±0.40(Predicted)
CAS DataBase Reference
24166 · 24166-13-0
FDA UNII
649 Z0HY · GYL649Z0HY
ATC code
5 BA22 · N05BA22
Symbol(GHS)
7 · GHS07
Signal word
Warning

Safety & regulation

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

GHS classification

GHS Classification · 4 items

Warning

H302+H312+H332 (50%): Harmful if swallowed, in contact with skin or if inhaled [Warning Acute toxicity, oral; acute toxicity, dermal; acute toxicity, inhalation]

P203, P261, P264, P270, P271, P280, P301+P317, P302+P352, P304+P340, P317, P318, P319, P321, P330, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 2 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory InformationDEA schedule IV controlled substance
Hazard Classes and CategoriesAcute Tox. 4 (50%)

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.

Chemistry & industry

Pharmacology

ATC Code · 3 items

N05BA22

N - Nervous system

QN - Nervous system

Pharmacodynamics · 1 item

Studies have shown a superiority of 4mg/day of cloxazepam to 12mg/day of bromazepam in terms of anxiety, depressed mood, and sleep; an insignificant difference in terms of sedative effect; and less muscle relaxant effects. [3] Cloxazolam, administered as a single oral dose of 3mg, when compared to a single 5 mg dose of diazepam in one study, showed similar subjective measures; however, there cloxazolam caused more fatigue, and less mood improvement. Cloxazolam also induced a significant increase in heart rate in the control group of this study. [3]

Mechanism of ActionCloxazolam is a long acting benzodiazepine. It acts as a prodrug, with pharmacologically active metabolites, which bind to to the GABAa receptor, which other benzodiazepines bind to, to illicit a physiological response.
Biological Half-Life65 hours
Metabolism/Metabolites · 2 items

Cloxazolam is metabolised by the liver into the active metabolite chlordesmethyldiazepam (delorazepam). [5]

Cloxazolam is metabolised by the liver into the active metabolite chlordesmethyldiazepam (delorazepam). [5] Route of Elimination: Renal elimination. Half Life: 65 hours

Absorption, Distribution and ExcretionRenal elimination.

Uses & manufacturing

UsesUsed primarily as an anti-anxiety agent. Typically used short term, and may be given as a single dose of up to 100mcg/kg to reduce anxiety and tension experienced prior to surgery.

Applications

Related reactions

6 records
New reaction record
HRID 305735 reaction equation
HRID 305735As reactantTraining data from https://doi.org/10.1039/C8SC04228D (8/10)
HRID 328481 reaction equation
HRID 328481As reactantuspto-grants-1977_04
HRID 328493 reaction equation
HRID 328493As reactantuspto-grants-1977_04
HRID 597627 reaction equation
HRID 597627As reactantuspto-grants-1977_03
HRID 1658604 reaction equation
HRID 1658604As reactantuspto-grants-1976_06
HRID 1973528 reaction equation
HRID 1973528As reactantuspto-grants-1976_12

Compound notes

Loading…

On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Hazard statements
336 · H336-H302+H312+H332
Precautionary statements
261 · P261-P271-P304+P340-P312-P403+P233-P405-P501
RIDADR
3249 · 3249
HazardClass
6.1 · 6.1(b)
PackingGroup
III
Toxicity
50 in · LD50 in mice (g/kg): 3.3 orally; >2.0 i.p. (Kamioka)
Toxicity SummaryCloxazolam is a long acting benzodiazepine. It acts as a prodrug, with pharmacologically active metabolites, which bind to to the GABAa receptor, which other benzodiazepines bind to, to illicit a physiological response.
Signs and Symptoms · 1 item

Drowsiness and ataxia are dose related. Central nervous system toxicity may result in respiratory depression and loss of consciousness. As such, pre-existing central nervous system depression and severe hepatic impairment are two particular contraindications for use.

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).

Safety data

ridadr
3249
Toxicity
LD50 in mice (g/kg): 3.3 orally; >2.0 i.p. (Kamioka)
Signal word
Warning
Symbol(GHS)
GHS07
hazard_class
6.1(b)
packing_group
III
Hazard statements
H336-H302+H312+H332
Precautionary statements
P261-P271-P304+P340-P312-P403+P233-P405-P501

UsesCLOXAZOLAM is a benzodiazepine derivative with anxiolytic, hypnotic and antihypertensive properties used as an anti-anxiety drug. It is metabolized into the active metabolite Delorezepam (D230675). Controlled Subs tance.

Upstream & downstream products

Upstream raw materials

Monoethanolamine

Additional notes

DefinitionChEBI: Cloxazolam is an oxazolobenzodiazepine and a hemiaminal ether.