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

Details

Stereochemistry ABSOLUTE
Molecular Formula C19H25NO
Molecular Weight 283.4086
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LEVALLORPHAN

SMILES

C=CCN1CC[C@@]23CCCC[C@@]3([H])[C@@]1([H])Cc4ccc(cc42)O

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
Effects of Innovar and innovar plus nitrous oxide on muscle tone and "H" reflex.
1971 Sep-Oct
Suppression of the drug-induced morphine withdrawal syndrome by cyproheptadine.
1973 Jan 1
Serotonin and norepinephrine uptake inhibiting activity of centrally acting analgesics: structural determinants and role in antinociception.
1995 Sep
Three-choice discrimination in pigeons is based on relative efficacy differences among opioids.
2001 Jun
Discrimination of a single dose of morphine followed by naltrexone: substitution of other agonists for morphine and other antagonists for naltrexone in a rat model of acute dependence.
2003 Mar
Adverse drug effects in hospitalized elderly: data from the healthcare cost and utilization project.
2010
Exploration of catalytic properties of CYP2D6 and CYP3A4 through metabolic studies of levorphanol and levallorphan.
2010 Jan
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 [HSDB]
Common Name English
17-ALLYLMORPHINAN-3-OL
Systematic Name English
LEVALLORPHAN [WHO-DD]
Common Name English
LEVALLORPHAN [MI]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C681
Created by admin on Sat Jun 26 06:09:27 UTC 2021 , Edited by admin on Sat Jun 26 06:09:27 UTC 2021
Code System Code Type Description
DRUG BANK
DB00504
Created by admin on Sat Jun 26 06:09:27 UTC 2021 , Edited by admin on Sat Jun 26 06:09:27 UTC 2021
PRIMARY
PUBCHEM
5359371
Created by admin on Sat Jun 26 06:09:27 UTC 2021 , Edited by admin on Sat Jun 26 06:09:27 UTC 2021
PRIMARY
CAS
152-02-3
Created by admin on Sat Jun 26 06:09:27 UTC 2021 , Edited by admin on Sat Jun 26 06:09:27 UTC 2021
PRIMARY
ECHA (EC/EINECS)
205-799-1
Created by admin on Sat Jun 26 06:09:27 UTC 2021 , Edited by admin on Sat Jun 26 06:09:27 UTC 2021
PRIMARY
DRUG CENTRAL
1560
Created by admin on Sat Jun 26 06:09:27 UTC 2021 , Edited by admin on Sat Jun 26 06:09:27 UTC 2021
PRIMARY
FDA UNII
353613BU4U
Created by admin on Sat Jun 26 06:09:27 UTC 2021 , Edited by admin on Sat Jun 26 06:09:27 UTC 2021
PRIMARY
EPA CompTox
152-02-3
Created by admin on Sat Jun 26 06:09:27 UTC 2021 , Edited by admin on Sat Jun 26 06:09:27 UTC 2021
PRIMARY
MERCK INDEX
M6780
Created by admin on Sat Jun 26 06:09:27 UTC 2021 , Edited by admin on Sat Jun 26 06:09:27 UTC 2021
PRIMARY Merck Index
NCI_THESAURUS
C66004
Created by admin on Sat Jun 26 06:09:27 UTC 2021 , Edited by admin on Sat Jun 26 06:09:27 UTC 2021
PRIMARY
IUPHAR
7209
Created by admin on Sat Jun 26 06:09:27 UTC 2021 , Edited by admin on Sat Jun 26 06:09:27 UTC 2021
PRIMARY
INN
264
Created by admin on Sat Jun 26 06:09:27 UTC 2021 , Edited by admin on Sat Jun 26 06:09:27 UTC 2021
PRIMARY
HSDB
2148
Created by admin on Sat Jun 26 06:09:27 UTC 2021 , Edited by admin on Sat Jun 26 06:09:27 UTC 2021
PRIMARY
ChEMBL
CHEMBL1254682
Created by admin on Sat Jun 26 06:09:27 UTC 2021 , Edited by admin on Sat Jun 26 06:09:27 UTC 2021
PRIMARY
MESH
D007977
Created by admin on Sat Jun 26 06:09:27 UTC 2021 , Edited by admin on Sat Jun 26 06:09:27 UTC 2021
PRIMARY
RXCUI
6370
Created by admin on Sat Jun 26 06:09:27 UTC 2021 , Edited by admin on Sat Jun 26 06:09:27 UTC 2021
PRIMARY RxNorm
EVMPD
SUB08452MIG
Created by admin on Sat Jun 26 06:09:27 UTC 2021 , Edited by admin on Sat Jun 26 06:09:27 UTC 2021
PRIMARY
WIKIPEDIA
LEVALLORPHAN
Created by admin on Sat Jun 26 06:09:27 UTC 2021 , Edited by admin on Sat Jun 26 06:09:27 UTC 2021
PRIMARY