13-bromo-2-(2-fluorophenyl)-3-oxa-6,9-diazatricyclo[8.4.0.02,6]tetradeca-1(10),11,13-trien-8-one

• ChemBase ID: 1274
• Molecular Formular: C17H14BrFN2O2
• Molecular Mass: 377.2076632
• Monoisotopic Mass: 376.02226792
• SMILES: Brc1cc2C3(OCCN3CC(=O)Nc2cc1)c1c(F)cccc1
• Canonical SMILES: O=C1Nc2ccc(cc2C2(N(C1)CCO2)c1ccccc1F)Br
• InChI: InChI=1S/C17H14BrFN2O2/c18-11-5-6-15-13(9-11)17(12-3-1-2-4-14(12)19)21(7-8-23-17)10-16(22)20-15/h1-6,9H,7-8,10H2,(H,20,22)
• InChIKey: XDKCGKQHVBOOHC-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 13-bromo-2-(2-fluorophenyl)-3-oxa-6,9-diazatricyclo[8.4.0.0^2,^6]tetradeca-1(10),11,13-trien-8-one; 13-bromo-2-(2-fluorophenyl)-3-oxa-6,9-diazatricyclo[8.4.0.0^{2,6}]tetradeca-1(10),11,13-trien-8-one; 13-bromo-2-(2-fluorophenyl)-3-oxa-6,9-diazatricyclo[8.4.0.0^2,^6]tetradeca-1(14),10,12-trien-8-one
• IUPAC Traditional name: haloxazolam
• Brand Name: Somelin
• Synonyms: Haloxazolam; 10-Bromo-11b-(2-fluorophenyl)-2,3,7,11b-tetrahydrooxazolo[3,2-d][1,4]benzodiazepin-6(5H)-one; CS 430; Somelin

Database IDs

• CAS Number: 59128-97-1
• PubChem SID: 160964734; 46508327
• PubChem CID: 3563
• Chemspider ID: 3442
• DrugBank ID: DB01476
• KEGG ID: D01758
• Unique Ingredient Identifier: M448L2V8XP verifiedrevid = 461766568
• Wikipedia Title: Haloxazolam

CALCULATED PROPERTIES

JChem

• Acid pKa: 12.679916
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 3.8310661
• LogD (pH = 7.4): 3.8312893
• Log P: 3.8312943
• Molar Refractivity: 89.2761 cm^3
• Polarizability: 33.58441 Å^3
• Polar Surface Area: 41.57 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.98
• LOG S: -4.09
• Solubility (Water): 3.08e-02 g/l

PROPERTIES

Pharmacology Properties

• Admin Routes: Oral
• Excretion: Renal
• Metabolism: Hepatic
• Legal Status: Schedule IV(US)

DETAILS

DrugBank - DB01476

• Drug Groups: illicit; experimental
• External Links: Wikipedia

Toronto Research Chemicals - H104000

Sleep-inducing agent, related structurally to Oxazolam and Cloxazolam (C587475). Sedative, hypnotic. Controlled substance (depressant).

REFERENCES

• Miyadera, T., et al.: J. Med. Chem., 14, 520, (1971)
• Yoshimoto, M., et al.: Chem. Pharm. Bull., 25, 1378 (1971)