(1R,9R,10R)-17-methyl-17-azatetracyclo[7.5.3.0^{1,10}.0^{2,7}]heptadeca-2(7),3,5-trien-4-ol

• ChemBase ID: 732
• Molecular Formular: C17H23NO
• Molecular Mass: 257.37062
• Monoisotopic Mass: 257.17796436
• SMILES: Oc1cc2[C@@]34[C@H]([C@@H](N(CC3)C)Cc2cc1)CCCC4
• Canonical SMILES: Oc1ccc2c(c1)[C@]13CCCC[C@H]3[C@H](C2)N(CC1)C
• InChI: InChI=1S/C17H23NO/c1-18-9-8-17-7-3-2-4-14(17)16(18)10-12-5-6-13(19)11-15(12)17/h5-6,11,14,16,19H,2-4,7-10H2,1H3/t14-,16+,17+/m0/s1
• InChIKey: JAQUASYNZVUNQP-USXIJHARSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,9R,10R)-17-methyl-17-azatetracyclo[7.5.3.0^{1,10}.0^{2,7}]heptadeca-2(7),3,5-trien-4-ol; (1R,9R,10R)-17-methyl-17-azatetracyclo[7.5.3.0^1,^1^0.0^2,^7]heptadeca-2(7),3,5-trien-4-ol
• IUPAC Traditional name: levorphanol
• Brand Name: Antalgin; Aromarone; Cetarin; Dromoran; Lemoran; Levo-Dromoran; Racemic Dromoran
• Synonyms: Dea No. 9220; Dea No. 9733; Levorfanol [INN-Spanish]; Levorfanolo [Dcit]; Levorphanol Dl-Form; Levorphanol Tartrate; Levorphanolum [INN-Latin]; Methorfinan [Czech]; Methorphinan; Racemethorphanum; Racemorfano [INN-Spanish]; Levorphanal; Levorphan; Levorphanol

Database IDs

• CAS Number: 77-07-6
• PubChem SID: 160964195
• PubChem CID: 5359272
• CHEMBL: 651
• Chemspider ID: 16736212
• DrugBank ID: DB00854
• KEGG ID: D08123
• Unique Ingredient Identifier: 27618J1N2X
• Wikipedia Title: Levorphanol
• Medline Plus: a682020

CALCULATED PROPERTIES

JChem

• Rotatable Bonds: 0
• Lipinski's Rule of Five: true
• Acid pKa: 10.461597
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): -0.095644645
• LogD (pH = 7.4): 0.9349801
• Log P: 2.9030437
• Molar Refractivity: 78.0809 cm^3
• Polarizability: 30.3868 Å^3
• Polar Surface Area: 23.47 Å^2

ALOGPS 2.1

• Solubility (Water): 1.73e-01 g/l
• Log P: 3.29
• LOG S: -3.17

PROPERTIES

Physical Property

• Solubility: 1840 mg/L
• Hydrophobicity(logP): 3.3

Pharmacology Properties

• Admin Routes: oral, intravenous, subcutaneous, intramuscular
• Bioavailability: 70% (oral); 100% (IV)
• Dependency Liability: High
• Half Life: 11-16 hours
• Metabolism: Hepatic
• Protein Bound: 40%
• Legal Status: Class A (UK); S8 (Australia); Schedule I (Canada); Schedule II (US)
• Pregnancy Category: C

DETAILS

DrugBank - DB00854

• Drug Groups: approved
• Description: A narcotic analgesic that may be habit-forming. It is nearly as effective orally as by injection. [PubChem]
• Indication: For the management of moderate to severe pain or as a preoperative medication where an opioid analgesic is appropriate
• Pharmacology: Levorphanol is a potent synthetic opioid analgesic indicated for the management of moderate to severe pain or as a preoperative medication where an opioid analgesic is appropriate. Levorphanol is similar to morphine in its actions, however it is up to 8 times more potent than morphine. Levorphanol produces a degree of respiratory depression similar to that produced by morphine at equianalgesic doses, and like many mu-opioid drugs, levorphanol produces euphoria or has a positive effect on mood in many individuals.
• Toxicity: LD₅₀=150 mg/kg (orally in rats). Signs of overdose include nausea, emesis, dizziness, respiratory depression, hypotension, urinary retention, cardiac arrhythmias, allergic reactions, skin rash, and uticaria.
• Affected Organisms: Humans and other mammals
• Biotransformation: Levorphanol is extensively metabolized in the liver and is eliminated as the glucuronide metabolite.
• Absorption: Levorphanol is well absorbed after PO administration with peak plasma concentrations occurring approximately 1 hour after dosing.
• Half Life: 11-16 hours
• Protein Binding: 40%
• Distribution: * 10 to 13 L/kg
• Clearance: * 0.78 to 1.1 L/kg/hr
• External Links: Wikipedia; RxList; Drugs.com