DT-Web

DB00504 - Levallorphan


Identification
Name Levallorphan
Accession Number DB00504 (APRD00733)
Type 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)
Structure
MOL SDF PDB SMILES InChI
Categories (*)
Molecular Weight 283.4079
Groups approved
Monoisotopic Weight 283.193614427
Pharmacology
Indication For the complete or partial reversal of narcotic depression, including respiratory depression, induced by opioids.
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.
Protein binding Not Available
Biotransformation Hepatic.
Route of elimination Not Available
Toxicity Oral, rat LD50: 109±4 mg/kg
Affected organisms
  • Humans and other mammals
Interactions
Drug Interactions Not Available
Food Interactions Not Available

Targets


Mu-type opioid receptor
Name Mu-type opioid receptor
Gene Name OPRM1
Pharmacological action yes
Actions partial agonist
References
  • 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
  • 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
  • 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
  • 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
  • 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
DTHybrid score 0.44

Predictions


Id Partner name Gene Name Score
467 Delta-type opioid receptor OPRD1 0.2329
696 Kappa-type opioid receptor OPRK1 0.2156
4512 Cytochrome P450 3A4 CYP3A4 0.0398
4119 Cytochrome P450 2D6 CYP2D6 0.0383
1716 Tripartite motif-containing protein 13 TRIM13 0.0335
6107 Cytochrome P450 3A7 CYP3A7 0.0261
1262 Corticotropin-lipotropin POMC 0.0243
4118 Cytochrome P450 3A5 CYP3A5 0.0184
1588 Multidrug resistance protein 1 ABCB1 0.0157
174 Sigma 1-type opioid receptor SIGMAR1 0.0153
4137 Nociceptin receptor OPRL1 0.0113
4924 Cytochrome P450 2C8 CYP2C8 0.0106
4757 Cytochrome P450 2C9 CYP2C9 0.0104
319 Opioid receptor, sigma 1 OPRS1 0.01
6030 Cytochrome P450 2B6 CYP2B6 0.009
6018 UDP-glucuronosyltransferase 1-9 UGT1A9 0.0085
6180 UDP-glucuronosyltransferase 2B4 UGT2B4 0.0084
6178 UDP-glucuronosyltransferase 2B7 UGT2B7 0.0081
6022 UDP-glucuronosyltransferase 1-1 UGT1A1 0.0072
6078 Neuronal acetylcholine receptor subunit beta-4 CHRNB4 0.0065
4120 NADPH--cytochrome P450 reductase POR 0.006
3811 Cytochrome P450 19A1 CYP19A1 0.0058
6079 Neuronal acetylcholine receptor subunit alpha-3 CHRNA3 0.0058
341 5-hydroxytryptamine 3 receptor HTR3A 0.0057
587 Serum albumin ALB 0.0051
824 Sodium-dependent serotonin transporter SLC6A4 0.0049
1291 cAMP response element-binding protein CREB1 0.0049
540 Sodium-dependent noradrenaline transporter SLC6A2 0.0048
706 Glutamate [NMDA] receptor subunit 3A GRIN3A 0.0048
4210 Toll-like receptor 4 TLR4 0.0044
6016 Cytochrome P450 2C19 CYP2C19 0.0043
4200 Cytochrome P450 1A2 CYP1A2 0.0041
392 Voltage-dependent P/Q-type calcium channel subunit alpha-1A CACNA1A 0.004
1181 Alpha-1-acid glycoprotein 1 ORM1 0.004
6106 Cytochrome P450 2C18 CYP2C18 0.0038
5878 Alpha-7 nicotinic cholinergic receptor subunit CHRFAM7A 0.0037
94 5-hydroxytryptamine 4 receptor HTR4 0.0035
6181 UDP-glucuronosyltransferase 1-8 UGT1A8 0.0035
20 Prostaglandin G/H synthase 1 PTGS1 0.0029
465 Calmodulin CALM1 0.0028
6176 UDP-glucuronosyltransferase 1-3 UGT1A3 0.0026
885 5-hydroxytryptamine 1B receptor HTR1B 0.0025
458 Neuronal acetylcholine receptor subunit alpha-10 CHRNA10 0.0025
6145 Solute carrier family 22 member 1 SLC22A1 0.0025
590 5-hydroxytryptamine 2C receptor HTR2C 0.0024
136 Estrogen receptor ESR1 0.0024
6139 Solute carrier organic anion transporter family member 1A2 SLCO1A2 0.0023
320 5-hydroxytryptamine 1A receptor HTR1A 0.0023
51 Muscarinic acetylcholine receptor M3 CHRM3 0.0022
6013 Cytochrome P450 2E1 CYP2E1 0.0018
5718 Cytochrome P450 2A6 CYP2A6 0.0015
1732 ATP-binding cassette sub-family G member 2 ABCG2 0.0015
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