(1S,5R,13R,17S)-17-hydroxy-10-methoxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.01,13.05,17.07,18]octadeca-7,9,11(18)-trien-14-one

• ChemBase ID: 130370
• Molecular Formular: C18H21NO4
• Molecular Mass: 315.36364
• Monoisotopic Mass: 315.14705816
• SMILES: O=C1[C@@H]2Oc3c4c(ccc3OC)C[C@H]3N(CC[C@@]24[C@@]3(O)CC1)C
• Canonical SMILES: COc1ccc2c3c1O[C@@H]1[C@@]43CCN([C@H](C2)[C@]4(O)CCC1=O)C
• InChI: InChI=1S/C18H21NO4/c1-19-8-7-17-14-10-3-4-12(22-2)15(14)23-16(17)11(20)5-6-18(17,21)13(19)9-10/h3-4,13,16,21H,5-9H2,1-2H3/t13-,16+,17+,18-/m1/s1
• InChIKey: BRUQQQPBMZOVGD-XFKAJCMBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,5R,13R,17S)-17-hydroxy-10-methoxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0^1,^1^3.0^5,^1^7.0^7,^1^8]octadeca-7,9,11(18)-trien-14-one
• IUPAC Traditional name: oxycodone
• Brand Name: Oxycodone
• Synonyms: dihydrohydroxycodeinone; 14-hydroxydihydrocodeinone; 6-deoxy-7,8-dihydro-14-hydroxy-3-O-methyl-6-oxomorphine; Oxycodone

Database IDs

• CAS Number: 76-42-6
• PubChem SID: 162224649
• PubChem CID: 5284603
• CHEBI ID: 7852
• ATC CODE: N02AA05; N02AA55
• CHEMBL: 656
• Chemspider ID: 4447649
• DrugBank ID: DB00497
• KEGG ID: D05312
• Unique Ingredient Identifier: CD35PMG570
• Wikipedia Title: Oxycodone
• Medline Plus: a682132

CALCULATED PROPERTIES

• Acid pKa: 13.562788
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): -1.6110451
• LogD (pH = 7.4): 0.16306217
• Log P: 1.0348654
• Molar Refractivity: 84.0418 cm^3
• Polarizability: 33.020885 Å^3
• Polar Surface Area: 59.0 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: HCl: 166 mg/mL (20°C)

Pharmacology Properties

• Admin Routes: oral, intramuscular, intravenous, intranasal, subcutaneous, transdermal, rectal, epidural
• Bioavailability: 100% (IV); Up to 87% (oral)
• Dependency Liability: Moderate–High
• Excretion: Urine (19% unchanged)
• Half Life: 3–4.5 h
• Metabolism: Hepatic: primarily CYP3A, secondarily CYP2D6
• Protein Bound: 45%
• Legal Status: Class A (CD)Schedule II (UK); Schedule 8 (Australia); Schedule I (Canada); Schedule II (US)
• Pregnancy Category: B/D (prolonged use or in high doses at term)