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targets (3)
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Identification
Name Levorphanol
Accession Number DB00854 (APRD00764)
Type small molecule
Groups approved
Description

A narcotic analgesic that may be habit-forming. It is nearly as effective orally as by injection. [PubChem]
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  • Dea No. 9220
  • Dea No. 9733
  • Levorfanol [INN-Spanish]
  • Levorfanolo [Dcit]
  • Levorphan
  • Levorphanal
  • Levorphanol Dl-Form
  • Levorphanol Tartrate
  • Levorphanolum [INN-Latin]
  • Methorfinan [Czech]
  • Methorphinan
  • Racemethorphanum
  • Racemorfano [INN-Spanish]
Brand names
  • Antalgin
  • Aromarone
  • Cetarin
  • Dromoran
  • Lemoran
  • Levo-Dromoran
  • Racemic Dromoran
Brand name mixtures Not Available
Categories
  • Narcotics
  • Analgesics, Opioid
CAS number 77-07-6
Weight Average: 257.3706
Monoisotopic: 257.177964363
Chemical Formula C17H23NO
InChI Key InChIKey=JAQUASYNZVUNQP-USXIJHARSA-N
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
Plain Text
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
SMILES
[H][C@@]12CCCC[C@@]11CCN(C)[C@@H]2CC2=C1C=C(O)C=C2
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Not Available
Classes Not Available
Substructures Not Available
Pharmacology
Indication For the management of moderate to severe pain or as a preoperative medication where an opioid analgesic is appropriate
Pharmacodynamics 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.
Mechanism of action Like other mu-agonist opioids it is believed to act at receptors in the periventricular and periaqueductal gray matter in both the brain and spinal cord to alter the transmission and perception of pain.
Absorption Levorphanol is well absorbed after PO administration with peak plasma concentrations occurring approximately 1 hour after dosing.
Volume of distribution
  • 10 to 13 L/kg
Protein binding 40%
Metabolism

Levorphanol is extensively metabolized in the liver and is eliminated as the glucuronide metabolite.
Route of elimination Not Available
Half life 11-16 hours
Clearance
  • 0.78 to 1.1 L/kg/hr
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
Pathways Not Available
Pharmacoeconomics
Manufacturers
  • Valeant pharmaceuticals international
  • Roxane laboratories inc
Packagers
Dosage forms
Form Route Strength
Injection, solution Intramuscular
Injection, solution Intravenous
Injection, solution Subcutaneous
Tablet Oral
Prices Not Available
Patents Not Available
Properties
State solid
Melting point 198-199 oC
Experimental Properties
Property Value Source
water solubility 1840 mg/L PhysProp
logP 3.3 PhysProp
pKa 9.58 Various sources
Predicted Properties
Property Value Source
water solubility 1.73e-01 g/l ALOGPS
logP 3.29 ALOGPS
logP 2.89 ChemAxon Molconvert
logS -3.17 ALOGPS
pKa ChemAxon Molconvert
hydrogen acceptor count 2 ChemAxon Molconvert
hydrogen donor count 1 ChemAxon Molconvert
polar surface area 23.47 ChemAxon Molconvert
rotatable bond count 0 ChemAxon Molconvert
refractivity 78.08 ChemAxon Molconvert
polarizability 29.84 ChemAxon Molconvert
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
KEGG Compound C08014 Link_out
BindingDB 50017233 Link_out
Therapeutic Targets Database DAP000268 Link_out
PharmGKB PA450219 Link_out
Drug Product Database 0 Link_out
RxList http://www.rxlist.com/cgi/generic2/levorphanol.htm Link_out
Drugs.com http://www.drugs.com/cdi/levorphanol.html Link_out
Wikipedia http://en.wikipedia.org/wiki/Levorphanol Link_out
ATC Codes Not Available
AHFS Codes Not Available
PDB Entries Not Available
FDA label Not Available
MSDS show (5.2 KB)
Interactions
Drug Interactions Not Available
Food Interactions
  • Take without regard to meals. Avoid alcohol.
Targets

1. Mu-type opioid receptor

Pharmacological action: yes
Actions: agonist

Inhibits neurotransmitter release by reducing calcium ion currents and increasing potassium ion conductance. Receptor for beta-endorphin

Organism class: human
UniProt ID: P35372 Link_out
Gene: OPRM1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Allen RM, Granger AL, Dykstra LA: The competitive N-methyl-D-aspartate receptor antagonist (-)-6-phosphonomethyl-deca-hydroisoquinoline-3-carboxylic acid (LY235959) potentiates the antinociceptive effects of opioids that vary in efficacy at the mu-opioid receptor. J Pharmacol Exp Ther. 2003 Nov;307(2):785-92. Epub 2003 Sep 15. Pubmed
  2. Prommer E: Levorphanol: the forgotten opioid. Support Care Cancer. 2007 Mar;15(3):259-64. Epub 2006 Oct 13. Pubmed

2. Delta-type opioid receptor

Pharmacological action: unknown
Actions: agonist

Inhibits neurotransmitter release by reducing calcium ion currents and increasing potassium ion conductance. Highly stereoselective. receptor for enkephalins

Organism class: human
UniProt ID: P41143 Link_out
Gene: OPRD1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Prommer E: Levorphanol: the forgotten opioid. Support Care Cancer. 2007 Mar;15(3):259-64. Epub 2006 Oct 13. Pubmed

3. Kappa-type opioid receptor

Pharmacological action: unknown
Actions: agonist

Inhibits neurotransmitter release by reducing calcium ion currents and increasing potassium ion conductance. Receptor for dynorphins. May play a role in arousal and regulation of autonomic and neuroendocrine functions

Organism class: human
UniProt ID: P41145 Link_out
Gene: OPRK1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Prommer E: Levorphanol: the forgotten opioid. Support Care Cancer. 2007 Mar;15(3):259-64. Epub 2006 Oct 13. Pubmed
Comments
Drug created on June 13, 2005 07:24 / Updated on November 19, 2010 08:07

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.