LOFENTANIL OXALATE

Details

Stereochemistry	UNKNOWN
Molecular Formula	C25H32N2O3.C2H2O4
Molecular Weight	498.5681
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC(=O)C(O)=O.CCC(=O)N(C1=CC=CC=C1)[C@@]2(CCN(CCC3=CC=CC=C3)C[C@@H]2C)C(=O)OC

InChI

InChIKey=CBKLICUQYUTWQL-XWGBWKJCSA-N

InChI=1S/C25H32N2O3.C2H2O4/c1-4-23(28)27(22-13-9-6-10-14-22)25(24(29)30-3)16-18-26(19-20(25)2)17-15-21-11-7-5-8-12-21;3-1(4)2(5)6/h5-14,20H,4,15-19H2,1-3H3;(H,3,4)(H,5,6)/t20-,25+;/m0./s1

HIDE SMILES / InChI

Molecular Formula	C25H32N2O3
Molecular Weight	408.5332
Charge	0
Count

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

Molecular Formula	C2H2O4
Molecular Weight	90.0349
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/6133403 | Stanley, T.H., Petty, W.C. (2012) Anesthesiology: Today and Tomorrow, retrieved from: https://books.google.ru/books?id=Dp3dBgAAQBAJ | Castro, de J. et al. (2012) Regional Opioid Analgesia, page 162, retrieved from: https://books.google.ru/books?id=b9HyCAAAQBAJ

Lofentanil is a pure mu-opioid receptor agonist derived from fentanyl. It is the most potent opioid to be administered to humans, about 500-1000 times more potent than morphine. Lofentanil provides a higher affinity quotient with longer dissociation times for the mu-receptors than fentanyl. The clinical study of the compound is difficult because there is a very individual sensibility. The appropriate doses are not easy to evaluate. Reversal of the loventanil depression needs very high and repeated naloxone dose. Practical use of lofentanil is limited. Lofentanil side effects are: nausea, vomiting and sedation.

Approval Year

PubMed

Title	Date	PubMed
The fentanyl/etomidate-anaesthetised beagle (FEAB) dog: a versatile in vivo model in cardiovascular safety research.	2009-03-24	19422925
In vivo mechanisms precipitating torsades de pointes in a canine model of drug-induced long-QT1 syndrome.	2007-11-01	17669388
Oral transmucosal fentanyl citrate in cancer pain management: a practical application of nanotechnology.	2007	17722512
Development of an enzyme-linked immunosorbent assay for fentanyl and applications of fentanyl antibody-coated nanoparticles for sample preparation.	2006-06-16	16621415
Pharmacological profiles of opioid ligands at kappa opioid receptors.	2006-01-25	16433932
Ligand-regulated internalization of the opioid receptor-like 1: a confocal study.	2004-06	15016723
Activity of opioid ligands in cells expressing cloned mu opioid receptors.	2003-01-04	12513698
Activation profiles of opioid ligands in HEK cells expressing delta opioid receptors.	2002-11-18	12437765

Patents

Sample Use Guides

In Vivo Use Guide

Single doses: 0.25 ug, 0.50 ug and 0.75 ug

Route of Administration: Intramuscular

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:23:07 GMT 2025` Edited by `admin` on `Mon Mar 31 18:23:07 GMT 2025`
Record UNII	6C1599T3OQ
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

LOFENTANIL OXALATE

Official Name

English

R 34,995

Preferred Name

English

LOFENTANIL OXALATE [USAN]

Common Name

English

LOFENTANIL OXALATE [MI]

Common Name

English

R-34995

Code

English

4-PIPERIDINECARBOXYLIC ACID, 3-METHYL-4-((1-OXOPROPYL)PHENYLAMINO)-1-(2-PHENYLETHYL)-, METHYL ESTER, CIS, (-)-, ETHANEDIOATE (1:1)

Common Name

English

(-)-METHYL CIS-3-METHYL-1-PHENETHYL-4-(N-PHENYLPROPIONAMIDO)ISONIPECOTATE OXALATE (1:1)

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C67413