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Showing drug card for Levallorphan (DB00504)

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Creation Date 2005-06-13 13:24:05
Update Date 2009-04-16 16:47:45
Primary Accession Number DB00504
Secondary Accession Number
  • APRD00733
Name Levallorphan
Drug Type
  • Approved
  • Small Molecule
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)
Synonyms Not Available
Brand Names
  1. Levallofano [Dcit]
  2. Levallorphane [INN-French]
  3. Levallorphanum [INN-Latin]
  4. Levalorfano [INN-Spanish]
  5. Lorfan
  6. Naloxiphan
Brand Mixtures Not Available
Chemical IUPAC Name adamantan-1-amine
Chemical Formula C19H25NO
Chemical Structure Structure
CAS Registry Number 152-02-3
InChI Identifier InChI=1/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
InChI Key OZYUPQUCAUTOBP-WDSOQIARBF
KEGG Drug Not Available
KEGG Compound C07069 Link Image
PubChem Compound 5359371 Link Image
PubChem Substance 152219 Link Image
ChEBI ID Not Available
PharmGKB ID Not Available
HET ID Not Available
GenBank ID Not Available
Drug ID Number [DIN] Not Available
RxList Link Not Available
PDRhealth Link Not Available
Wikipedia Link Not Available
FDA Label Not Available
Material Safety Data Sheet (MSDS) Not Available
Synthesis Reference Schnider, et al., Helv. Chim. Acta. 34, 2211 (1951)
Average Molecular Weight 283.4079
Monoisotopic Molecular Weight 283.1936
State Solid
Melting Point 181 oC
Experimental Water Solubility 633 mg/L Source: PhysProp
Predicted Water Solubility 2.52e-02 mg/mL Calculated using ALOGPS
Experimental LogP/Hydrophobicity 3.9 Source: PhysProp
Predicted LogP 3.92 Calculated using ALOGPS
Experimental LogS Not Available
Predicted LogS -4.05 Calculated using ALOGPS
Experimental Caco2 Permeability Not Available
pKa/Isoelectric Point Not Available
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 OC1=CC2=C(C[C@@H]3[C@@H]4CCCC[C@]24CCN3CC=C)C=C1
Canonical SMILES OC1=CC2=C(CC3C4CCCCC24CCN3CC=C)C=C1
Drug Category
  • Analgesic Antagonists
  • Antinarcotic Agents
  • Morphine Antidotes
  • Narcotic Antagonists
ATC Codes Not Available
AHFS Codes Not Available
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.
Mechanism of Action Levallorphan antagonizes opioid effects by competing for the same receptor sites. It binds to the opioid mu receptor and the nicotinic acetylcholine receptor alpha2/alpha3.
Absorption Rapidly absorbed.
Toxicity Oral, rat LD50: 109±4 mg/kg
Protein Binding Not Available
Biotransformation Hepatic.
Half Life 1 hour
Dosage Forms Not Available
Patient Information Not Available
Contraindications Show Link Image
Interactions Not Available
Drug Interactions Not Available
Food Interactions Not Available
Pathways Not Available
General References Not Available
Organisms Affected
  • Humans and other mammals
Targets
  1. Neuronal acetylcholine receptor subunit alpha-2
  2. Mu-type opioid receptor
Drug Target 1 [top]
Target 1 ID 813
Target 1 Name Neuronal acetylcholine receptor subunit alpha-2
Target 1 Synonyms
  1. Neuronal acetylcholine receptor subunit alpha-2 precursor
Target 1 Gene Name CHRNA2
Target 1 Protein Sequence >Neuronal acetylcholine receptor protein subunit alpha-2 precursor 
MGPSCPVFLSFTKLSLWWLLLTPAGGEEAKRPPPRAPGDPLSSPSPTALPQGGSHTETED
RLFKHLFRGYNRWARPVPNTSDVVIVRFGLSIAQLIDVDEKNQMMTTNVWLKQEWSDYKL
RWNPADFGNITSLRVPSEMIWIPDIVLYNNADGEFAVTHMTKAHLFSTGTVHWVPPAIYK
SSCSIDVTFFPFDQQNCKMKFGSWTYDKAKIDLEQMEQTVDLKDYWESGEWAIVNATGTY
NSKKYDCCAEIYPDVTYAFVIRRLPLFYTINLIIPCLLISCLTVLVFYLPSDCGEKITLC
ISVLLSLTVFLLLITEIIPSTSLVIPLIGEYLLFTMIFVTLSIVITVFVLNVHHRSPSTH
TMPHWVRGALLGCVPRWLLMNRPPPPVELCHPLRLKLSPSYHWLESNVDAEEREVVVEEE
DRWACAGHVAPSVGTLCSHGHLHSGASGPKAEALLQEGELLLSPHMQKALEGVHYIADHL
RSEDADSSVKEDWKYVAMVIDRIFLWLFIIVCFLGTIGLFLPPFLAGMI
Target 1 Number of Residues 537
Target 1 Molecular Weight 59736
Target 1 Theoretical pI 6.02
Target 1 GO Classification
Function
excitatory extracellular ligand-gated ion channel activity
nicotinic acetylcholine-activated cation-selective channel activity
transporter activity
ion transporter activity
ion channel activity
ligand-gated ion channel activity
extracellular ligand-gated ion channel activity
signal transducer activity
receptor activity
neurotransmitter receptor activity
Process
physiological process
cellular physiological process
transport
ion transport
Component
postsynaptic membrane
intrinsic to membrane
integral to membrane
cell
membrane
Target 1 General Function Involved in neurotransmitter receptor activity
Target 1 Specific Function After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane
Target 1 Pathways Not Available
Target 1 Reactions Not Available
Target 1 Pfam Domain Function
Target 1 Signals
  • 1-26
Target 1 Transmembrane Regions
  • 265-289
  • 297-315
  • 331-352
  • 503-521
Target 1 Essentiality Non-Essential
Target 1 GenBank ID Protein 1458110 Link Image
Target 1 UniProtKB/Swiss-Prot ID Q15822 Link Image
Target 1 UniProtKB/Swiss-Prot Entry Name ACHA2_HUMAN Link Image
Target 1 PDB ID Not Available
Target 1 Cellular Location
  • Membrane
  • multi-pass membrane protein
Target 1 Gene Sequence >1590 bp 
ATGGGCCCCTCCTGTCCTGTGTTCCTGTCCTTCACAAAGCTCAGCCTGTGGTGGCTCCTT
CTGACCCCAGCAGGTGGAGAGGAAGCTAAGCGCCCACCTCCCAGGGCTCCTGGAGACCCA
CTCTCCTCTCCCAGTCCCACGGCATTGCCGCAGGGAGGCTCGCATACCGAGACTGAGGAC
CGGCTCTTCAAACACCTCTTCCGGGGCTACAACCGCTGGGCGCGCCCGGTGCCCAACACT
TCAGACGTGGTGATTGTGCGCTTTGGACTGTCCATCGCTCAGCTCATCGATGTGGATGAG
AAGAACCAAATGATGACCACCAACGTCTGGCTAAAACAGGAGTGGAGCGACTACAAACTG
CGCTGGAACCCCGCTGATTTTGGCAACATCACATCTCTCAGGGTCCCTTCTGAGATGATC
TGGATCCCCGACATTGTTCTCTACAACAATGCAGATGGGGAGTTTGCAGTGACCCACATG
ACCAAGGCCCACCTCTTCTCCACGGGCACTGTGCACTGGGTGCCCCCGGCCATCTACAAG
AGCTCCTGCAGCATCGACGTCACCTTCTTCCCCTTCGACCAGCAGAACTGCAAGATGAAG
TTTGGCTCCTGGACTTATGACAAGGCCAAGATCGACCTGGAGCAGATGGAGCAGACTGTG
GACCTGAAGGACTACTGGGAGAGCGGCGAGTGGGCCATCGTCAATGCCACGGGCACCTAC
AACAGCAAGAAGTACGACTGCTGCGCCGAGATCTACCCCGACGTCACCTACGCCTTCGTC
ATCCGGCGGCTGCCGCTCTTCTACACCATCAACCTCATCATCCCCTGCCTGCTCATCTCC
TGCCTCACTGTGCTGGTCTTCTACCTGCCCTCCGACTGCGGCGAGAAGATCACGCTGTGC
ATTTCGGTGCTGCTGTCACTCACCGTCTTCCTGCTGCTCATCACTGAGATCATCCCGTCC
ACCTCGCTGGTCATCCCGCTCATCGGCGAGTACCTGCTGTTCACCATGATCTTCGTCACC
CTGTCCATCGTCATCACCGTCTTCGTGCTCAATGTGCACCACCGCTCCCCCAGCACCCAC
ACCATGCCCCACTGGGTGCGGGGGGCCCTTCTGGGCTGTGTGCCCCGGTGGCTTCTGATG
AACCGGCCCCCACCACCCGTGGAGCTCTGCCACCCCCTACGCCTGAAGCTCAGCCCCTCT
TATCACTGGCTGGAGAGCAACGTGGATGCCGAGGAGAGGGAGGTGGTGGTGGAGGAGGAG
GACAGATGGGCATGTGCAGGTCATGTGGCCCCCTCTGTGGGCACCCTCTGCAGCCACGGC
CACCTGCACTCTGGGGCCTCAGGTCCCAAGGCTGAGGCTCTGCTGCAGGAGGGTGAGCTG
CTGCTATCACCCCACATGCAGAAGGCACTGGAAGGTGTGCACTACATTGCCGACCACCTG
CGGTCTGAGGATGCTGACTCTTCGGTGAAGGAGGACTGGAAGTATGTTGCCATGGTCATC
GACAGGATCTTCCTCTGGCTGTTTATCATCGTCTGCTTCCTGGGGACCATCGGCCTCTTT
CTGCCTCCGTTCCTAGCTGGAATGATCTGA
Target 1 GenBank Gene ID
Target 1 GeneCard ID CHRNA2 Link Image
Target 1 GenAtlas ID CHRNA2 Link Image
Target 1 HGNC ID HGNC:1956 Link Image
Target 1 Chromosome Location 8
Target 1 Locus 8p21
Target 1 SNPs SNPJam Report Link Image
Target 1 General References
  1. Elliott KJ, Ellis SB, Berckhan KJ, Urrutia A, Chavez-Noriega LE, Johnson EC, Velicelebi G, Harpold MM: Comparative structure of human neuronal alpha 2-alpha 7 and beta 2-beta 4 nicotinic acetylcholine receptor subunits and functional expression of the alpha 2, alpha 3, alpha 4, alpha 7, beta 2, and beta 4 subunits. J Mol Neurosci. 1996 Fall;7(3):217-28. [PubMed Link Image]
Target 1 Drug References
  1. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed Link Image]
  2. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed Link Image]
Drug Target 2 [top]
Target 2 ID 847
Target 2 Name Mu-type opioid receptor
Target 2 Synonyms
  1. MOR-1
Target 2 Gene Name OPRM1
Target 2 Protein Sequence >Mu-type opioid receptor 
MDSSAAPTNASNCTDALAYSSCSPAPSPGSWVNLSHLDGNLSDPCGPNRTDLGGRDSLCP
PTGSPSMITAITIMALYSIVCVVGLFGNFLVMYVIVRYTKMKTATNIYIFNLALADALAT
STLPFQSVNYLMGTWPFGTILCKIVISIDYYNMFTSIFTLCTMSVDRYIAVCHPVKALDF
RTPRNAKIINVCNWILSSAIGLPVMFMATTKYRQGSIDCTLTFSHPTWYWENLLKICVFI
FAFIMPVLIITVCYGLMILRLKSVRMLSGSKEKDRNLRRITRMVLVVVAVFIVCWTPIHI
YVIIKALVTIPETTFQTVSWHFCIALGYTNSCLNPVLYAFLDENFKRCFREFCIPTSSNI
EQQNSTRIRQNTRDHPSTANTVDRTNHQLENLEAETAPLP
Target 2 Number of Residues 406
Target 2 Molecular Weight 44780
Target 2 Theoretical pI 8.29
Target 2 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 2 General Function Involved in rhodopsin-like receptor activity
Target 2 Specific Function Inhibits neurotransmitter release by reducing calcium ion currents and increasing potassium ion conductance. Receptor for beta-endorphin
Target 2 Pathways Not Available
Target 2 Reactions Not Available
Target 2 Pfam Domain Function
Target 2 Signals
  • None
Target 2 Transmembrane Regions
  • 67-96
  • 106-123
  • 146-165
  • 196-211
  • 237-259
  • 283-305
  • 314-330
Target 2 Essentiality Non-Essential
Target 2 GenBank ID Protein 452073 Link Image
Target 2 UniProtKB/Swiss-Prot ID P35372 Link Image
Target 2 UniProtKB/Swiss-Prot Entry Name OPRM_HUMAN Link Image
Target 2 PDB ID Not Available
Target 2 Cellular Location
  • Membrane
  • multi-pass membrane protein
Target 2 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 2 GenBank Gene ID
Target 2 GeneCard ID OPRM1 Link Image
Target 2 GenAtlas ID OPRM1 Link Image
Target 2 HGNC ID HGNC:8156 Link Image
Target 2 Chromosome Location 6
Target 2 Locus 6q24-q25
Target 2 SNPs SNPJam Report Link Image
Target 2 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 2 Drug References
  1. Traynor JR, Nahorski SR: Modulation by mu-opioid agonists of guanosine-5'-O-(3-[35S]thio)triphosphate binding to membranes from human neuroblastoma SH-SY5Y cells. Mol Pharmacol. 1995 Apr;47(4):848-54. [PubMed Link Image]
  2. Emmerson PJ, Clark MJ, Mansour A, Akil H, Woods JH, Medzihradsky F: Characterization of opioid agonist efficacy in a C6 glioma cell line expressing the mu opioid receptor. J Pharmacol Exp Ther. 1996 Sep;278(3):1121-7. [PubMed Link Image]
  3. Picker MJ, Benyas S, Horwitz JA, Thompson K, Mathewson C, Smith MA: Discriminative stimulus effects of butorphanol: influence of training dose on the substitution patterns produced by Mu, Kappa and Delta opioid agonists. J Pharmacol Exp Ther. 1996 Dec;279(3):1130-41. [PubMed Link Image]
  4. Selley DE, Sim LJ, Xiao R, Liu Q, Childers SR: mu-Opioid receptor-stimulated guanosine-5'-O-(gamma-thio)-triphosphate binding in rat thalamus and cultured cell lines: signal transduction mechanisms underlying agonist efficacy. Mol Pharmacol. 1997 Jan;51(1):87-96. [PubMed Link Image]
  5. Morgan D, Picker MJ: The mu opioid irreversible antagonist beta-funaltrexamine differentiates the discriminative stimulus effects of opioids with high and low efficacy at the mu opioid receptor. Psychopharmacology (Berl). 1998 Nov;140(1):20-8. [PubMed Link Image]

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