7-bromo-5-(pyridin-2-yl)-2,3-dihydro-1H-1,4-benzodiazepin-2-one

• ChemBase ID: 1342
• Molecular Formular: C14H10BrN3O
• Molecular Mass: 316.1527
• Monoisotopic Mass: 315.00072396
• SMILES: Brc1cc2c(NC(=O)CN=C2c2ncccc2)cc1
• Canonical SMILES: O=C1CN=C(c2c(N1)ccc(c2)Br)c1ccccn1
• InChI: InChI=1S/C14H10BrN3O/c15-9-4-5-11-10(7-9)14(17-8-13(19)18-11)12-3-1-2-6-16-12/h1-7H,8H2,(H,18,19)
• InChIKey: VMIYHDSEFNYJSL-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 7-bromo-5-(pyridin-2-yl)-2,3-dihydro-1H-1,4-benzodiazepin-2-one
• IUPAC Traditional name: bromazepam
• Brand Name: Apo-Bromazepam; Calmepam; Compedium; Compendium; Creosedin; Durazanil; Gen-Bromazepam; Lectopam; Lekotam; Lexaurin; Lexilium; Lexomil; Lexotan; Lexotanil; Normoc; Novo-bromazepam; Nu-Bromazepam; Ultramidol; Somalium; Lexotan, Lexotanil
• Synonyms: Bromazepam; 7-Bromo-1,3-dihydro-5-(2-pyridinyl)-2H-1,4-benzodiazepin-2-one; Compendium; Creosedin; Durazanil; Lexilium; Lexomil; Lexotan; Lexotanil; NSC 140669; Normoc; Ro 5-3350; Bromazepam; 7-Bromo-5-(2-pyridyl)-3H-1,4-benzodiaxepin-2(1H)-one; 7-Bromo-5-(2-pyridyl)-3H-1,4-benzodiazepin-2(1H)-one; Bromazepamum [inn-latin]; 7-溴-5-(2-吡啶基)-3H-1,4-苯并二氮杂卓-2(1H)-酮; 溴西泮

Database IDs

• CAS Number: 1812-30-2
• EC Number: 217-322-4; 200-659-6
• MDL Number: MFCD00057902
• PubChem SID: 46505694; 24891754; 160964802
• PubChem CID: 2441
• ATC CODE: N05BA08
• CHEMBL: 277062
• Chemspider ID: 2347
• DrugBank ID: DB01558
• KEGG ID: D01245
• Unique Ingredient Identifier: X015L14V0O
• Wikipedia Title: Bromazepam

CALCULATED PROPERTIES

JChem

• Acid pKa: 12.238634
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 2.5442781
• LogD (pH = 7.4): 2.5448925
• Log P: 2.5449064
• Molar Refractivity: 76.9851 cm^3
• Polarizability: 28.506214 Å^3
• Polar Surface Area: 54.35 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.09
• LOG S: -3.9
• Solubility (Water): 3.99e-02 g/l

PROPERTIES

Physical Property

• Apperance: Crystalline Solid
• Melting Point: 205-210°C (dec.)
• Flash Point: 11 °C; 51.8 °F
• Hydrophobicity(logP): 2.05 [SANGSTER (1994)]

Safety Information

• RTECS: DE9800000
• European Hazard Symbols: Flammable (F); Toxic (T); Harmful (Xn)
• UN Number: 1230
• German water hazard class: 1; 3
• Hazard Class: 3
• Packing Group: 2
• Risk Statements: 11-23/24/25-39/23/24/25; 22-36/37/38
• Safety Statements: 26-36; 7-16-36/37-45
• GHS Pictograms: GHS02; GHS06; GHS07; GHS08
• GHS Signal Word: Danger; Warning
• GHS Hazard statements: H225-H301-H311-H331-H370; H302-H315-H319-H335
• GHS Precautionary statements: P210-P260-P280-P301 + P310-P311; P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves; Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US)
• RID/ADR: UN 1230 3/PG 2
• Drug Control: USDEA Schedule IV; Home Office Schedule 4.1; psychotrope; kontrollierte Droge in Deutschland; regulated under CDSA - not available from Sigma-Aldrich Canada
• Storage Temperature: 2-8°C

Pharmacology Properties

• Admin Routes: Oral
• Bioavailability: 84%
• Excretion: Renal
• Half Life: 12-20 hours
• Metabolism: Hepatic
• Legal Status: Schedule IV(US)
• Pregnancy Category: D (USA)

Product Information

• Purity: ≥98%
• Concentration: 1.0 mg/mL±5% in methanol
• Grade: analytical standard, for drug analysis; drug standard

DETAILS

DrugBank - DB01558

• Drug Groups: illicit; approved
• Description: One of the benzodiazepines that is used in the treatment of anxiety disorders. [PubChem] It is a Schedule IV drug in the U.S. and Canada and under the Convention on Psychotropic Substances.
• Indication: For the short-term treatment of insomnia, short-term treatment of anxiety or panic attacks, if a benzodiazepine is required, and the alleviation of the symptoms of alcohol- and opiate-withdrawal.
• Pharmacology: Bromazepam is a lipophilic, long-acting benzodiazepine and with sedative, hypnotic, anxiolytic and skeletal muscle relaxant properties. It does not possess any antidepressant qualities. Bromazepam shares with other benzodiazepines the risk of abuse, misuse, psychological and/or physical dependence. According to many psychiatric experts Bromazepam has a greater abuse potential than other benzodiazepines because of fast resorption and rapid onset of action.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatically, via oxidative pathways (via an enzyme belonging to the Cytochrome P450 family of enzymes).
• Absorption: Bioavailability is 84% following oral administration.
• Half Life: 10-20 hours
• References: Oelschlager H: [Chemical and pharmacologic aspects of benzodiazepines] Schweiz Rundsch Med Prax. 1989 Jul 4;78(27-28):766-72. [Pubmed] ; Oda M, Kotegawa T, Tsutsumi K, Ohtani Y, Kuwatani K, Nakano S: The effect of itraconazole on the pharmacokinetics and pharmacodynamics of bromazepam in healthy volunteers. Eur J Clin Pharmacol. 2003 Nov;59(8-9):615-9. Epub 2003 Sep 27. [Pubmed] ; van Harten J: Overview of the pharmacokinetics of fluvoxamine. Clin Pharmacokinet. 1995;29 Suppl 1:1-9. [Pubmed] ; Ochs HR, Greenblatt DJ, Friedman H, Burstein ES, Locniskar A, Harmatz JS, Shader RI: Bromazepam pharmacokinetics: influence of age, gender, oral contraceptives, cimetidine, and propranolol. Clin Pharmacol Ther. 1987 May;41(5):562-70. [Pubmed]
• External Links: Wikipedia

Sigma Aldrich - B4144

Biochem/physiol Actions
抗焦虑药

Toronto Research Chemicals - B678500

Controlled substance (depressant). Anxiolytic.

REFERENCES

• Oelschlager H: [Chemical and pharmacologic aspects of benzodiazepines] Schweiz Rundsch Med Prax. 1989 Jul 4;78(27-28):766-72. Pubmed
• Oda M, Kotegawa T, Tsutsumi K, Ohtani Y, Kuwatani K, Nakano S: The effect of itraconazole on the pharmacokinetics and pharmacodynamics of bromazepam in healthy volunteers. Eur J Clin Pharmacol. 2003 Nov;59(8-9):615-9. Epub 2003 Sep 27. Pubmed
• van Harten J: Overview of the pharmacokinetics of fluvoxamine. Clin Pharmacokinet. 1995;29 Suppl 1:1-9. Pubmed
• Ochs HR, Greenblatt DJ, Friedman H, Burstein ES, Locniskar A, Harmatz JS, Shader RI: Bromazepam pharmacokinetics: influence of age, gender, oral contraceptives, cimetidine, and propranolol. Clin Pharmacol Ther. 1987 May;41(5):562-70. Pubmed
• Schwartz, M.A., et al.: J. Pharm. Sci., 62, 1776 (1973)
• Chalmers, P., et al.: Anesthesia, 39, 370 (1973)
• Hassan, M.M., et al.: Anal. Profiles Drug Subs., 16, 1 (1973)