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

• ChemBase ID: 387
• Molecular Formular: C19H25NO
• Molecular Mass: 283.4079
• Monoisotopic Mass: 283.19361443
• SMILES: [C@@]123[C@H]([C@H](N(CC2)CC=C)Cc2c1cc(cc2)O)CCCC3
• Canonical SMILES: C=CCN1CC[C@@]23[C@H]([C@H]1Cc1c3cc(cc1)O)CCCC2
• InChI: InChI=1S/C19H25NO/c1-2-10-20-11-9-19-8-4-3-5-16(19)18(20)12-14-6-7-15(21)13-17(14)19/h2,6-7,13,16,18,21H,1,3-5,8-12H2/t16-,18+,19+/m0/s1
• InChIKey: OZYUPQUCAUTOBP-QXAKKESOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,9R,10R)-17-(prop-2-en-1-yl)-17-azatetracyclo[7.5.3.0^{1,10}.0^{2,7}]heptadeca-2(7),3,5-trien-4-ol; (1R,9R,10R)-17-(prop-2-en-1-yl)-17-azatetracyclo[7.5.3.0^1,^1^0.0^2,^7]heptadeca-2,4,6-trien-4-ol
• IUPAC Traditional name: levallorphan
• Brand Name: Levallofano [Dcit]; Levallorphane [INN-French]; Levallorphanum [INN-Latin]; Levalorfano [INN-Spanish]; Lorfan; Naloxiphan
• Synonyms: Levallorphan

Database IDs

• CAS Number: 152-02-3
• PubChem SID: 46505682; 160963850
• PubChem CID: 5359371
• CHEMBL: 1254682
• Chemspider ID: 4514267
• DrugBank ID: DB00504
• Unique Ingredient Identifier: 353613BU4U
• Wikipedia Title: Levallorphan

CALCULATED PROPERTIES

JChem

• Acid pKa: 10.3627615
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 0.6962585
• LogD (pH = 7.4): 1.9874055
• Log P: 3.7553673
• Molar Refractivity: 87.2436 cm^3
• Polarizability: 33.84198 Å^3
• Polar Surface Area: 23.47 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 3.91
• LOG S: -4.05
• Solubility (Water): 2.52e-02 g/l

PROPERTIES

Physical Property

• Solubility: 633 mg/L
• Hydrophobicity(logP): 3.9

Pharmacology Properties

• Admin Routes: Oral
• Legal Status: Rx-only

DETAILS

DrugBank - DB00504

• Drug Groups: approved
• Description: An opioid antagonist with properties similar to those of naloxone; in addition it also possesses some agonist properties. It should be used cautiously; levallorphan reverses severe opioid-induced respiratory depression but may exacerbate respiratory depression such as that induced by alcohol or other non-opioid central depressants. (From Martindale, The Extra Pharmacopoeia, 30th ed, p683)
• Indication: For the complete or partial reversal of narcotic depression, including respiratory depression, induced by opioids.
• Pharmacology: Levallorphan, an opioid antagonist similar to naloxone, is used to treat drug overdoses. Levallorphan differs from naloxone in that it also possesses some agonist properties. It is an analogue of levelorphanol that counteracts the actions of narcotic analgesics such as morphine. It is used especially in the treatment of respiratory depression due to narcotic overdoses. Levallorphan prevents or reverses the effects of opioids including respiratory depression, sedation and hypotension. Also, it can reverse the psychotomimetic and dysphoric effects of agonist-antagonists such as pentazocine.
• Toxicity: Oral, rat LD₅₀: 109±4 mg/kg
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic.
• Absorption: Rapidly absorbed.
• Half Life: 1 hour