LEVALLORPHAN TARTRATE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C19H25NO.C4H6O6
Molecular Weight	433.4947
Optical Activity	UNSPECIFIED
Defined Stereocenters	5 / 5
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=FWMLYVACGDQRFU-ZTMWJVNESA-N

InChI=1S/C19H25NO.C4H6O6/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;5-1(3(7)8)2(6)4(9)10/h2,6-7,13,16,18,21H,1,3-5,8-12H2;1-2,5-6H,(H,7,8)(H,9,10)/t16-,18+,19+;1-,2-/m01/s1

HIDE SMILES / InChI

Molecular Formula	C4H6O6
Molecular Weight	150.0868
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Molecular Formula	C19H25NO
Molecular Weight	283.4079
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	3 / 3
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/13805887 | https://www.ncbi.nlm.nih.gov/pubmed/14000851 | https://www.ncbi.nlm.nih.gov/pubmed/5664147 | https://www.ncbi.nlm.nih.gov/pubmed/9016350 | https://www.ncbi.nlm.nih.gov/pubmed/9918595 | https://www.ncbi.nlm.nih.gov/pubmed/8968334 | https://books.google.com/books?id=zHpRYbGaQFcC&pg=PA204&lpg=PA204&dq=LORFAN+discontinued&source=bl&ots=SUQPCChX4m&sig=rPDny0s3f-9OK_myckJJoyY0aNk&hl=en&sa=X&ved=0ahUKEwjhj7aipq_UAhVHWD4KHbC-Ch0Q6AEIQjAH#v=onepage&q=LORFAN%20discontinued&f=false | https://books.google.com/books?id=lSX2CAAAQBAJ&pg=PA364#v=onepage&q&f=falsehttps://www.ncbi.nlm.nih.gov/pubmed/7723747

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.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Mu-type opioid receptor 61 Target ID: P35372\|\|\|G8XRH8\|\|\|Q5TDA1\|\|\|Q9UN57 Gene ID: 4988.0 Gene Symbol: OPRM1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/5664147 \| https://www.ncbi.nlm.nih.gov/pubmed/9016350 \| https://www.ncbi.nlm.nih.gov/pubmed/8819494 \| https://www.ncbi.nlm.nih.gov/pubmed/8968334	Antagonist 2778		1.12 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Respiratory depression, induced by opioids 2 Sources: https://www.ncbi.nlm.nih.gov/pubmed/13805887 https://www.ncbi.nlm.nih.gov/pubmed/13278165 https://www.ncbi.nlm.nih.gov/pubmed/13314010	Secondary		Approved 8429	Lorfan Approved Use Unknown
Narcotic overdose 2 Sources: Zerwekh, J. (2012) Illustrated Study Guide for the NCLEX-RN® Exam8, page 204, retrieved from: https://books.google.ru/books?id=zHpRYbGaQFcC	Secondary		Approved 8429	Lorfan Approved Use Unknown

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1737 inhibitor 1587		substrate 1217 inhibitor 1852

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
CYP2D6 1891	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/19797609/	yes [IC50 0.65 uM]
CYP3A4 1925	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/19797609/	yes [IC50 >50 uM]

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
CYP2D6 1217	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/19797609/	yes
CYP3A4 1737	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/19797609/	yes

Sourcing

Vendor/Aggregator	ID	URL
ChemTik	CTK5J4760
Chemieliva Pharmaceutical Co., Ltd	PBCM1195733
Compound Cloud	5359371
Compound Cloud	5464111
HongKong Chemhere	SCA54097
MolPort	MolPort-003-942-989
MuseChem	M070189	https://www.musechem.com/product/M070189.html
NovoSeek	6916182
Parchem	59741	https://www.parchem.com/chemical-supplier-distributor/Levallorphan-059741.aspx
Sigma Aldrich	L121
Sigma Aldrich	L121\|SIGMA
Smolecule	S532904	http://www.smolecule.com/products/s532904
THE BioTek	bt-273302	https://www.thebiotek.com/product/inhibitors/bt-273302
ZINC	ZINC000003875992	http://zinc15.docking.org/substances/ZINC000003875992
eMolecules	110005368
eMolecules	300866060

PubMed

Title	Date	PubMed
Effects of Innovar and innovar plus nitrous oxide on muscle tone and "H" reflex.	1971 Sep-Oct	5165426
Suppression of the drug-induced morphine withdrawal syndrome by cyproheptadine.	1973 Jan 1	4735135
Mechanism of morphine-induced miosis in the dog.	1975 Feb	1117427
Serotonin and norepinephrine uptake inhibiting activity of centrally acting analgesics: structural determinants and role in antinociception.	1995 Sep	7562497
Three-choice discrimination in pigeons is based on relative efficacy differences among opioids.	2001 Jun	11441428
Evidence for a peripheral mechanism in cardiac opioid withdrawal.	2001 Sep	11521160
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	12604679
Effects of opioids in morphine-treated pigeons trained to discriminate among morphine, the low-efficacy agonist nalbuphine, and saline.	2004 Jul	15044559
Determination of dextromethorphan and its metabolite dextrorphan in human urine using high performance liquid chromatography with atmospheric pressure chemical ionization tandem mass spectrometry: a study of selectivity of a tandem mass spectrometric assay.	2005 Feb 25	15664362
Electron ionization mass spectra of ephedrines in a doping confirmatory procedure: a curious migration of the trimethylsilyl group in the N-acetyl-O-trimethylsilyl derivatives.	2007	17523214
Adverse drug effects in hospitalized elderly: data from the healthcare cost and utilization project.	2010	22291486
Exploration of catalytic properties of CYP2D6 and CYP3A4 through metabolic studies of levorphanol and levallorphan.	2010 Jan	19797609
Generation of novel radiolabeled opiates through site-selective iodination.	2011 Jul 1	21621410

Patents

Sample Use Guides

In Vivo Use Guide

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.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:16:37 UTC 2023` Edited by `admin` on `Fri Dec 15 16:16:37 UTC 2023`
Record UNII	U0VSF7HTN0
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

LEVALLORPHAN TARTRATE

Common Name

English

LEVALLORPHAN TARTRATE [JAN]

Common Name

English

MORPHINAN-3-OL, 17-(2-PROPENYL)-, (R-(R*,R*))-2,3-DIHYDROXYBUTANEDIOATE (1:1) (SALT)

Common Name

English

17-Allylmorphinan-3-ol tartrate (1:1) (salt)

Common Name

English

Levallorphan tartrate [WHO-DD]

Common Name

English

LEVALLORPHAN TARTRATE [ORANGE BOOK]

Common Name

English

LEVALLORPHAN TARTRATE [MART.]

Common Name

English

LORFAN

Brand Name

English

LEVALLORPHAN TARTRATE [MI]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C681