(1S,9R,10S)-17-(cyclobutylmethyl)-10-methoxy-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5-trien-4-ol

• ChemBase ID: 126290
• Molecular Formular: C22H31NO2
• Molecular Mass: 341.48704
• Monoisotopic Mass: 341.23547924
• SMILES: Oc1cc2c(C[C@H]3N(CC4CCC4)CC[C@]42CCCC[C@@]34OC)cc1
• Canonical SMILES: CO[C@]12CCCC[C@]32CCN([C@@H]1Cc1c3cc(cc1)O)CC1CCC1
• InChI: InChI=1S/C22H31NO2/c1-25-22-10-3-2-9-21(22)11-12-23(15-16-5-4-6-16)20(22)13-17-7-8-18(24)14-19(17)21/h7-8,14,16,20,24H,2-6,9-13,15H2,1H3/t20-,21+,22-/m1/s1
• InChIKey: AVDWHTCJIXKWKF-BHIFYINESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,9R,10S)-17-(cyclobutylmethyl)-10-methoxy-17-azatetracyclo[7.5.3.0^1,^1^0.0^2,^7]heptadeca-2(7),3,5-trien-4-ol
• IUPAC Traditional name: (1S,9R,10S)-17-(cyclobutylmethyl)-10-methoxy-17-azatetracyclo[7.5.3.0^1,^1^0.0^2,^7]heptadeca-2(7),3,5-trien-4-ol
• Brand Name: Stadol
• Synonyms: Butorphanol

Database IDs

• CAS Number: 42408-82-2
• PubChem SID: 162220629
• PubChem CID: 54584882; 5361092
• CHEBI ID: 3242
• ATC CODE: N02AX02; QR05DA90
• CHEMBL: 33986
• Chemspider ID: 16735714
• DrugBank ID: DB00611
• KEGG ID: D00837
• Unique Ingredient Identifier: QV897JC36D
• Wikipedia Title: Butorphanol
• Medline Plus: a682667

CALCULATED PROPERTIES

• Acid pKa: 10.206664
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 1.7366108
• LogD (pH = 7.4): 3.507372
• Log P: 4.2907143
• Molar Refractivity: 100.6722 cm^3
• Polarizability: 39.54722 Å^3
• Polar Surface Area: 32.7 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Pharmacology Properties

• Admin Routes: IV, intranasal
• Bioavailability: Nasal: 60-70%
• Excretion: Renal, 75%; Biliary, 11-14%; Fecal, 15%
• Half Life: 4-7 hours
• Metabolism: Hepatic hydroxylated & glucuronidated
• Legal Status: Schedule IV (US)
• Pregnancy Category: C/D (United States)