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Version 2.5
Creation Date 2005-06-13 13:24:05
Update Date 2009-04-16 16:48:04
Primary Accession Number DB00854
Secondary Accession Number
  • APRD00764
Name Levorphanol
Drug Type
  • Approved
  • Small Molecule
Description A narcotic analgesic that may be habit-forming. It is nearly as effective orally as by injection. [PubChem]
Synonyms
  1. Dea No. 9220
  2. Dea No. 9733
  3. Levorfanol [INN-Spanish]
  4. Levorfanolo [Dcit]
  5. Levorphan
  6. Levorphanal
  7. Levorphanol Dl-Form
  8. Levorphanol Tartrate
  9. Levorphanolum [INN-Latin]
  10. Methorfinan [Czech]
  11. Methorphinan
  12. Racemethorphanum
  13. Racemorfano [INN-Spanish]
Brand Names
  1. Antalgin
  2. Aromarone
  3. Cetarin
  4. Dromoran
  5. Lemoran
  6. Levo-Dromoran
  7. Racemic Dromoran
Brand Mixtures Not Available
Chemical IUPAC Name Not Available
Chemical Formula C17H23NO
Chemical Structure Structure
CAS Registry Number 77-07-6
InChI Identifier InChI=1/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
InChI Key JAQUASYNZVUNQP-XIRDDKMYBC
KEGG Drug Not Available
KEGG Compound C08014 Link Image
PubChem Compound 5359272 Link Image
PubChem Substance 10214 Link Image
ChEBI ID Not Available
PharmGKB ID PA450219 Link Image
HET ID Not Available
GenBank ID Not Available
Drug ID Number [DIN] Not Available
RxList Link http://www.rxlist.com/cgi/generic2/levorphanol.htm Link Image
PDRhealth Link Not Available
Wikipedia Link http://en.wikipedia.org/wiki/Levorphanol Link Image
FDA Label Not Available
Material Safety Data Sheet (MSDS)
Synthesis Reference Woods LA, et al. J Pharmacol Exp Ther. 1958 Sep;124(1):1-8.
Average Molecular Weight 257.3706
Monoisotopic Molecular Weight 257.1780
State Solid
Melting Point 198-199 oC
Experimental Water Solubility 1840 mg/L Source: PhysProp
Predicted Water Solubility 1.73e-01 mg/mL Calculated using ALOGPS
Experimental LogP/Hydrophobicity 3.3 Source: PhysProp
Predicted LogP 3.29 Calculated using ALOGPS
Experimental LogS Not Available
Predicted LogS -3.17 Calculated using ALOGPS
Experimental Caco2 Permeability Not Available
pKa/Isoelectric Point 9.58
Mass Spectrum Not Available
MOL File Show Link Image | Download Link Image
SDF File Show Link Image | Download Link Image
PDB File Show Link Image | Download Link Image
2D Structure
3D Structure
Experimental PDB ID Not Available
Isomeric SMILES CN1CC[C@]23CCCC[C@H]2[C@H]1CC1=C3C=C(O)C=C1
Canonical SMILES CN1CCC23CCCCC2C1CC1=C3C=C(O)C=C1
Drug Category
  • Analgesics, Opioid
  • Narcotics
ATC Codes Not Available
AHFS Codes Not Available
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.
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.
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.
Protein Binding 40%
Biotransformation Levorphanol is extensively metabolized in the liver and is eliminated as the glucuronide metabolite.
Half Life 11-16 hours
Dosage Forms
Form Route
Injection, solution Intramuscular
Injection, solution Intravenous
Injection, solution Subcutaneous
Tablet Oral
Patient Information Not Available
Contraindications Show Link Image
Interactions Show Link Image
Drug Interactions
Drug Interaction
Cimetidine Cimetidine increases the effect of the narcotic
Naltrexone Naltrexone may precipitate a withdrawal syndrome in opioid-dependent individual
Food Interactions
  • Take without regard to meals. Avoid alcohol.
Pathways Not Available
General References
  1. Drugs.com Link Image
  2. Wikipedia Link Image
  3. RxList Link Image
Organisms Affected
  • Humans and other mammals
Targets
  1. Mu-type opioid receptor
Drug Target 1 [top]
Target 1 ID 847
Target 1 Name Mu-type opioid receptor
Target 1 Synonyms
  1. MOR-1
Target 1 Gene Name OPRM1
Target 1 Protein Sequence >Mu-type opioid receptor 
MDSSAAPTNASNCTDALAYSSCSPAPSPGSWVNLSHLDGNLSDPCGPNRTDLGGRDSLCP
PTGSPSMITAITIMALYSIVCVVGLFGNFLVMYVIVRYTKMKTATNIYIFNLALADALAT
STLPFQSVNYLMGTWPFGTILCKIVISIDYYNMFTSIFTLCTMSVDRYIAVCHPVKALDF
RTPRNAKIINVCNWILSSAIGLPVMFMATTKYRQGSIDCTLTFSHPTWYWENLLKICVFI
FAFIMPVLIITVCYGLMILRLKSVRMLSGSKEKDRNLRRITRMVLVVVAVFIVCWTPIHI
YVIIKALVTIPETTFQTVSWHFCIALGYTNSCLNPVLYAFLDENFKRCFREFCIPTSSNI
EQQNSTRIRQNTRDHPSTANTVDRTNHQLENLEAETAPLP
Target 1 Number of Residues 406
Target 1 Molecular Weight 44780
Target 1 Theoretical pI 8.29
Target 1 GO Classification
Function
peptide receptor activity, G-protein coupled
opioid receptor activity
mu-opioid receptor activity
signal transducer activity
receptor activity
transmembrane receptor activity
G-protein coupled receptor activity
rhodopsin-like receptor activity
Process
cellular process
cell communication
signal transduction
cell surface receptor linked signal transduction
G-protein coupled receptor protein signaling pathway
Component
cell
membrane
intrinsic to membrane
integral to membrane
Target 1 General Function Involved in rhodopsin-like receptor activity
Target 1 Specific Function Inhibits neurotransmitter release by reducing calcium ion currents and increasing potassium ion conductance. Receptor for beta-endorphin
Target 1 Pathways Not Available
Target 1 Reactions Not Available
Target 1 Pfam Domain Function
Target 1 Signals
  • None
Target 1 Transmembrane Regions
  • 67-96
  • 106-123
  • 146-165
  • 196-211
  • 237-259
  • 283-305
  • 314-330
Target 1 Essentiality Non-Essential
Target 1 GenBank ID Protein 452073 Link Image
Target 1 UniProtKB/Swiss-Prot ID P35372 Link Image
Target 1 UniProtKB/Swiss-Prot Entry Name OPRM_HUMAN Link Image
Target 1 PDB ID Not Available
Target 1 Cellular Location
  • Membrane
  • multi-pass membrane protein
Target 1 Gene Sequence >1203 bp 
ATGGACAGCAGCGCTGCCCCCACGAACGCCAGCAATTGCACTGATGCCTTGGCGTACTCA
AGTTGCTCCCCAGCACCCAGCCCCGGTTCCTGGGTCAACTTGTCCCACTTAGATGGCAAC
CTGTCCGACCCATGCGGTCCGAACCGCACCAACCTGGGCGGGAGAGACAGCCTGTGCCCT
CCGACCGGCAGTCCCTCCATGATCACGGCCATCACGATCATGGCCCTCTACTCCATCGTG
TGCGTGGTGGGGCTCTTCGGAAACTTCCTGGTCATGTATGTGATTGTCAGATACACCAAG
ATGAAGACTGCCACCAACATCTACATTTTCAACCTTGCTCTGGCAGATGCCTTAGCCACC
AGTACCCTGCCCTTCCAGAGTGTGAATTACCTAATGGGAACATGGCCATTTGGAACCATC
CTTTGCAAGATAGTGATCTCCATAGATTACTATAACATGTTCACCAGCATATTCACCCTC
TGCACCATGAGTGTTGATCGATACATTGCAGTCTGCCACCCTGTCAAGGCCTTAGATTTC
CGTACTCCCCGAAATGCCAAAATTATCAATGTCTGCAACTGGATCCTCTCTTCAGCCATT
GGTCTTCCTGTAATGTTCATGGCTACAACAAAATACAGGCAAGGTTCCATAGATTGTACA
CTAACATTCTCTCATCCAACCTGGTACTGGGAAAACCTCGTGAAGATCTGTGTTTTCATC
TTCGCCTTCATTATGCCAGTGCTCATCATTACCGTGTGCTATGGACTGATGATCTTGCGC
CTCAAGAGTGTCCGCATGCTCTCTGGCTCCAAAGAAAAGGACAGGAATCTTCGAAGGATC
ACCAGGATGGTGCTGGTGGTGGTGGCTGTGTTCATCGTCTGCTGGACTCCCATTCACATT
TACGTCATCATTAAAGCCTTGGTTACAATCCCAGAAACTACGTTCCAGACTGTTTCTTGG
CACTTCTGCATTGCTCTAGGTTACACAAACAGCTGCCTCAACCCAGTCCTTTATGCATTT
CTGGATGAAAACTTCAAACGATGCTTCAGAGAGTTCTGTATCCCAACCTCTTCCAACATT
GAGCAACAAAACTCCACTCGAATTCGTCAGAACACTAGAGACCACCCCTCCACGGCCAAT
ACAGTGGATAGAACTAATCATCAGCTAGAAAATCTGGAAGCAGAAACTGCTCCGTTGCCC
TAA
Target 1 GenBank Gene ID
Target 1 GeneCard ID OPRM1 Link Image
Target 1 GenAtlas ID OPRM1 Link Image
Target 1 HGNC ID HGNC:8156 Link Image
Target 1 Chromosome Location 6
Target 1 Locus 6q24-q25
Target 1 SNPs SNPJam Report Link Image
Target 1 General References
  1. Uhl GR, Sora I, Wang Z: The mu opiate receptor as a candidate gene for pain: polymorphisms, variations in expression, nociception, and opiate responses. Proc Natl Acad Sci U S A. 1999 Jul 6;96(14):7752-5. [PubMed Link Image]
  2. Chuang TK, Killam KF Jr, Chuang LF, Kung HF, Sheng WS, Chao CC, Yu L, Chuang RY: Mu opioid receptor gene expression in immune cells. Biochem Biophys Res Commun. 1995 Nov 22;216(3):922-30. [PubMed Link Image]
  3. Mestek A, Hurley JH, Bye LS, Campbell AD, Chen Y, Tian M, Liu J, Schulman H, Yu L: The human mu opioid receptor: modulation of functional desensitization by calcium/calmodulin-dependent protein kinase and protein kinase C. J Neurosci. 1995 Mar;15(3 Pt 2):2396-406. [PubMed Link Image]
  4. Wang JB, Johnson PS, Persico AM, Hawkins AL, Griffin CA, Uhl GR: Human mu opiate receptor. cDNA and genomic clones, pharmacologic characterization and chromosomal assignment. FEBS Lett. 1994 Jan 31;338(2):217-22. [PubMed Link Image]
  5. Bare LA, Mansson E, Yang D: Expression of two variants of the human mu opioid receptor mRNA in SK-N-SH cells and human brain. FEBS Lett. 1994 Nov 7;354(2):213-6. [PubMed Link Image]
  6. Bergen AW, Kokoszka J, Peterson R, Long JC, Virkkunen M, Linnoila M, Goldman D: Mu opioid receptor gene variants: lack of association with alcohol dependence. Mol Psychiatry. 1997 Oct-Nov;2(6):490-4. [PubMed Link Image]
  7. Bond C, LaForge KS, Tian M, Melia D, Zhang S, Borg L, Gong J, Schluger J, Strong JA, Leal SM, Tischfield JA, Kreek MJ, Yu L: Single-nucleotide polymorphism in the human mu opioid receptor gene alters beta-endorphin binding and activity: possible implications for opiate addiction. Proc Natl Acad Sci U S A. 1998 Aug 4;95(16):9608-13. [PubMed Link Image]
Target 1 Drug 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 Link Image]

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.