U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C19H25NO
Molecular Weight 283.4079
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LEVALLORPHAN

SMILES

[H][C@@]12CCCC[C@@]13CCN(CC=C)[C@@H]2CC4=C3C=C(O)C=C4

InChI

InChIKey=OZYUPQUCAUTOBP-QXAKKESOSA-N
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

HIDE SMILES / InChI
Levallorphan (brand name Lorfan), is an opiate antagonist of morphine family. Levallorphan was formerly used in general anesthesia, mainly to reverse the respiratory depression produced by opioid analgesics and barbiturates used for induction of surgical anaesthesia whilst maintaining a degree of analgesia. Levallorphan was also used in combination with opioid analgesics to reduce their side effects, mainly in obstetrics. The combination of levallorphan with pethidine was used so frequently, a standardized formulation was made available, known as Pethilorfan, by Roche Products Ltd in later 1950s. Is known to be used for narcotic overdose. Levallorphan is similar to naloxone but differs from naloxone in that it also possesses some agonist properties. It acts as an antagonist and partial agonist of the mu opioid receptor (MOR). Levallorphan can produce severe mental reactions at sufficient doses including hallucinations, dissociation, and other psychotomimetic effects, dysphoria, anxiety, confusion, dizziness, disorientation, derealization, feelings of drunkenness, and bizarre, unusual, or disturbing dreams.

Approval Year

Overview

Overview

OverviewOther

Other InhibitorOther SubstrateOther Inducer
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
yes [IC50 0.65 uM]
yes [IC50 >50 uM]
Drug as victim

Drug as victim

PubMed

PubMed

TitleDatePubMed
Mechanism of morphine-induced miosis in the dog.
1975 Feb
Serotonin and norepinephrine uptake inhibiting activity of centrally acting analgesics: structural determinants and role in antinociception.
1995 Sep
Evidence for a peripheral mechanism in cardiac opioid withdrawal.
2001 Sep
Development and validation of a chemical hydrolysis method for dextromethorphan and dextrophan determination in urine samples: application to the assessment of CYP2D6 activity in fibromyalgia patients.
2008 Jan 1
A validated SIM GC/MS method for the simultaneous determination of dextromethorphan and its metabolites dextrorphan, 3-methoxymorphinan and 3-hydroxymorphinan in biological matrices and its application to in vitro CYP2D6 and CYP3A4 inhibition study.
2009 Nov
Adverse drug effects in hospitalized elderly: data from the healthcare cost and utilization project.
2010
Patents

Sample Use Guides

A dose of 2 mg levallorphan in combination with 100 mg pethidine repeated in an hour administered to women in labor
Route of Administration: Intramuscular
In Vitro Use Guide
Efficacy and potency of Levallorphan for stimulation of [35S]GTPγS binding to mMOR-CHO membranes was studied. Membranes were incubated incubated for 1 hr at 30° with various concentrations of levallorphan in the presence of 0.05 nm [35S]GTPγS and 10 uM GDP. EC50 of levallorphan was 2.7 nM. It was a partial agonist in these cells, producing ∼12% of the stimulation observed with DAMGO.
Name Type Language
LEVALLORPHAN
HSDB   INN   MI   WHO-DD  
INN  
Official Name English
levallorphan [INN]
Common Name English
Levallorphan [WHO-DD]
Common Name English
LEVALLORPHAN [HSDB]
Common Name English
17-ALLYLMORPHINAN-3-OL
Systematic Name English
LEVALLORPHAN [MI]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C681
Created by admin on Sat Dec 16 16:59:52 GMT 2023 , Edited by admin on Sat Dec 16 16:59:52 GMT 2023
Code System Code Type Description
DRUG BANK
DB00504
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PRIMARY
PUBCHEM
5359371
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CAS
152-02-3
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ECHA (EC/EINECS)
205-799-1
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DRUG CENTRAL
1560
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FDA UNII
353613BU4U
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EPA CompTox
DTXSID9023205
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SMS_ID
100000082820
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MERCK INDEX
m6780
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PRIMARY Merck Index
NCI_THESAURUS
C66004
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IUPHAR
7209
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INN
264
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HSDB
2148
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ChEMBL
CHEMBL1254682
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MESH
D007977
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RXCUI
6370
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PRIMARY RxNorm
EVMPD
SUB08452MIG
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PRIMARY
WIKIPEDIA
LEVALLORPHAN
Created by admin on Sat Dec 16 16:59:52 GMT 2023 , Edited by admin on Sat Dec 16 16:59:52 GMT 2023
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