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23887-31-2 molecular structure
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7-chloro-2-oxo-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepine-3-carboxylic acid

ChemBase ID: 510
Molecular Formular: C16H11ClN2O3
Molecular Mass: 314.72314
Monoisotopic Mass: 314.0458199
SMILES and InChIs

SMILES:
Clc1cc2C(=NC(C(=O)Nc2cc1)C(=O)O)c1ccccc1
Canonical SMILES:
OC(=O)C1N=C(c2ccccc2)c2c(NC1=O)ccc(c2)Cl
InChI:
InChI=1S/C16H11ClN2O3/c17-10-6-7-12-11(8-10)13(9-4-2-1-3-5-9)19-14(16(21)22)15(20)18-12/h1-8,14H,(H,18,20)(H,21,22)
InChIKey:
XDDJGVMJFWAHJX-UHFFFAOYSA-N

Cite this record

CBID:510 http://www.chembase.cn/molecule-510.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
7-chloro-2-oxo-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepine-3-carboxylic acid
IUPAC Traditional name
clorazepic acid
Brand Name
Chlorazepate
Chlorazepic acid
Clorazepate dipotassium
Clorazepic acid
Clorazepic acid [BAN]
Gen-xene
Tranxene
Novo-Clopate
Synonyms
Clorazepate
CAS Number
23887-31-2
PubChem SID
46506595
160963973
PubChem CID
2809

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID
DrugBank DB00628 external link
PubChem 2809 external link
Data Source Data ID Price

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 3.3205173  H Acceptors
H Donor LogD (pH = 5.5) 1.0428067 
LogD (pH = 7.4) -0.21537913  Log P 3.2063386 
Molar Refractivity 82.6761 cm3 Polarizability 30.881063 Å3
Polar Surface Area 78.76 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 2.68  LOG S -4.1 
Solubility (Water) 2.48e-02 g/l 

PROPERTIES

PROPERTIES

Physical Property Bioassay(PubChem)
Solubility
Very soluble expand Show data source
Hydrophobicity(logP)
3 expand Show data source

DETAILS

DETAILS

DrugBank DrugBank
DrugBank - DB00628 external link
Item Information
Drug Groups illicit; approved
Description A water-soluble benzodiazepine derivative effective in the treatment of anxiety. It has also muscle relaxant and anticonvulsant actions. [PubChem]
Indication For the management of anxiety disorders or for the short-term relief of the symptoms of anxiety. Also used as adjunctive therapy in the management of partial seizures and for the symptomatic relief of acute alcohol withdrawal.
Pharmacology Clorazepate is a member of the group of drugs called benzodiazepines. Pharmacologically, clorazepate has the characteristics of the benzodiazepines. It has depressant effects on the central nervous system. The primary metabolite, nordiazepam, quickly appears in the blood stream. Studies in healthy men have shown that clorazenate has depressant effects on the central nervous system. Since orally administered clorazepate dipotassium is rapidly decarboxylated to form nordiazepam, there is essentially no circulating parent drug.
Toxicity Oral LD50 in rats is 1320 mg/kg. In monkeys, oral LD50 exceed 1600 mg/kg. Symptoms of overdose include confusion, coma, impaired coordination, sleepiness, and slowed reaction time.
Affected Organisms
Humans and other mammals
Biotransformation The drug is metabolized in the liver and excreted primarily in the urine. The primary metabolite, nordiazepam, is further metabolized by hydroxylation. The major urinary metabolite is conjugated oxazepam (3-hydroxynordiazepam), and smaller amounts of conjugated p-hydroxynordiazepam and nordiazepam are also found in the urine.
Absorption Rapidly absorbed following oral administration (bioavailability is 91%).
Half Life The serum half-life is about 2 days. Nordiazepam, the primary metabolite, quickly appears in the blood and is eliminated from the plasma with an apparent half-life of about 40 to 50 hours.
Protein Binding The protein binding of nordiazepam in plasma is high (97-98%).
Elimination The drug is metabolized in the liver and excreted primarily in the urine.
References
: Systematic review of the benzodiazepines. Guidelines for data sheets on diazepam, chlordiazepoxide, medazepam, clorazepate, lorazepam, oxazepam, temazepam, triazolam, nitrazepam, and flurazepam. Committee on the Review of Medicines. Br Med J. 1980 Mar 29;280(6218):910-2. [Pubmed]
McElhatton PR: The effects of benzodiazepine use during pregnancy and lactation. Reprod Toxicol. 1994 Nov-Dec;8(6):461-75. [Pubmed]
External Links
Wikipedia
RxList
Drugs.com

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • : Systematic review of the benzodiazepines. Guidelines for data sheets on diazepam, chlordiazepoxide, medazepam, clorazepate, lorazepam, oxazepam, temazepam, triazolam, nitrazepam, and flurazepam. Committee on the Review of Medicines. Br Med J. 1980 Mar 29;280(6218):910-2. Pubmed
  • • McElhatton PR: The effects of benzodiazepine use during pregnancy and lactation. Reprod Toxicol. 1994 Nov-Dec;8(6):461-75. Pubmed
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PATENTS

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