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: 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

NAMES AND DATABASE IDS

Names

• 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

Database IDs

• CAS Number: 23887-31-2
• PubChem SID: 160963973; 46506595
• PubChem CID: 2809

CALCULATED PROPERTIES

JChem

• Acid pKa: 3.3205173
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 1.0428067
• LogD (pH = 7.4): -0.21537913
• Log P: 3.2063386
• Molar Refractivity: 82.6761 cm^3
• Polarizability: 30.881063 Å^3
• Polar Surface Area: 78.76 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.68
• LOG S: -4.1
• Solubility (Water): 2.48e-02 g/l

PROPERTIES

Physical Property

• Solubility: Very soluble
• Hydrophobicity(logP): 3

DETAILS

DrugBank - DB00628

• 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

• : 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