(1S,5R,13R,17S)-10,17-dihydroxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.01,13.05,17.07,18]octadeca-7(18),8,10-trien-14-one

• ChemBase ID: 130354
• Molecular Formular: C17H19NO4
• Molecular Mass: 301.33706
• Monoisotopic Mass: 301.13140809
• SMILES: O=C1[C@@H]2Oc3c(O)ccc4c3[C@@]32[C@](CC1)(O)[C@H](N(CC3)C)C4
• Canonical SMILES: O=C1CC[C@@]2([C@@]34[C@H]1Oc1c4c(C[C@H]2N(CC3)C)ccc1O)O
• InChI: InChI=1S/C17H19NO4/c1-18-7-6-16-13-9-2-3-10(19)14(13)22-15(16)11(20)4-5-17(16,21)12(18)8-9/h2-3,12,15,19,21H,4-8H2,1H3/t12-,15+,16+,17-/m1/s1
• InChIKey: UQCNKQCJZOAFTQ-ISWURRPUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,5R,13R,17S)-10,17-dihydroxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0^1,^1^3.0^5,^1^7.0^7,^1^8]octadeca-7(18),8,10-trien-14-one
• IUPAC Traditional name: oxymorphone
• Brand Name: Opana
• Synonyms: 14-Hydroxydihydromorphinone; Oxymorphone

Database IDs

• CAS Number: 76-41-5
• PubChem SID: 162224633
• PubChem CID: 5284604
• ATC CODE: N02A
• CHEMBL: 963
• Chemspider ID: 4447650
• DrugBank ID: DB01192
• KEGG ID: D08323
• Unique Ingredient Identifier: 9VXA968E0C
• Wikipedia Title: Oxymorphone
• Medline Plus: a610022

CALCULATED PROPERTIES

• Acid pKa: 7.3428044
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): -1.6811097
• LogD (pH = 7.4): -0.15812743
• Log P: 0.10033912
• Molar Refractivity: 79.5595 cm^3
• Polarizability: 31.115646 Å^3
• Polar Surface Area: 70.0 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Pharmacology Properties

• Admin Routes: intravenous, intramusucular, subcutaneous, oral, rectal, intranasal.
• Bioavailability: 10% (oral) 40% (Intranasal) 100% (IV, IM)
• Dependency Liability: High
• Excretion: 35% urine, 65% feces
• Half Life: 1.3 +/- 0.7 hrs (with parenteral admin); 7.25-9.43 hr (with oral admin)
• Metabolism: hepatic
• Legal Status: Class A (UK); Schedule I (Canada); Schedule II (US)
• Pregnancy Category: C (US)