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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 of LOFENTANIL OXALATE

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 C2H2O4
Molecular Weight 90.0349
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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

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

PubMed

TitleDatePubMed
Activation profiles of opioid ligands in HEK cells expressing delta opioid receptors.
2002 Nov 18
Activity of opioid ligands in cells expressing cloned mu opioid receptors.
2003 Jan 4
Ligand-regulated internalization of the opioid receptor-like 1: a confocal study.
2004 Jun
Pharmacological profiles of opioid ligands at kappa opioid receptors.
2006 Jan 25
Development of an enzyme-linked immunosorbent assay for fentanyl and applications of fentanyl antibody-coated nanoparticles for sample preparation.
2006 Jun 16
Oral transmucosal fentanyl citrate in cancer pain management: a practical application of nanotechnology.
2007
In vivo mechanisms precipitating torsades de pointes in a canine model of drug-induced long-QT1 syndrome.
2007 Nov 1
The fentanyl/etomidate-anaesthetised beagle (FEAB) dog: a versatile in vivo model in cardiovascular safety research.
2009 Jul-Aug
Patents

Sample Use Guides

Single doses: 0.25 ug, 0.50 ug and 0.75 ug
Route of Administration: Intramuscular
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:15:18 UTC 2023
Edited
by admin
on Fri Dec 15 16:15:18 UTC 2023
Record UNII
6C1599T3OQ
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LOFENTANIL OXALATE
MI   USAN  
USAN  
Official 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
R 34,995
Code English
Classification Tree Code System Code
NCI_THESAURUS C67413
Created by admin on Fri Dec 15 16:15:18 UTC 2023 , Edited by admin on Fri Dec 15 16:15:18 UTC 2023
Code System Code Type Description
MERCK INDEX
m1205
Created by admin on Fri Dec 15 16:15:18 UTC 2023 , Edited by admin on Fri Dec 15 16:15:18 UTC 2023
PRIMARY Merck Index
MESH
C034846
Created by admin on Fri Dec 15 16:15:18 UTC 2023 , Edited by admin on Fri Dec 15 16:15:18 UTC 2023
PRIMARY
ChEMBL
CHEMBL28198
Created by admin on Fri Dec 15 16:15:18 UTC 2023 , Edited by admin on Fri Dec 15 16:15:18 UTC 2023
PRIMARY
CAS
61380-41-4
Created by admin on Fri Dec 15 16:15:18 UTC 2023 , Edited by admin on Fri Dec 15 16:15:18 UTC 2023
PRIMARY
ECHA (EC/EINECS)
262-750-7
Created by admin on Fri Dec 15 16:15:18 UTC 2023 , Edited by admin on Fri Dec 15 16:15:18 UTC 2023
PRIMARY
EPA CompTox
DTXSID10976924
Created by admin on Fri Dec 15 16:15:18 UTC 2023 , Edited by admin on Fri Dec 15 16:15:18 UTC 2023
PRIMARY
FDA UNII
6C1599T3OQ
Created by admin on Fri Dec 15 16:15:18 UTC 2023 , Edited by admin on Fri Dec 15 16:15:18 UTC 2023
PRIMARY
PUBCHEM
65498
Created by admin on Fri Dec 15 16:15:18 UTC 2023 , Edited by admin on Fri Dec 15 16:15:18 UTC 2023
PRIMARY
NCI_THESAURUS
C80584
Created by admin on Fri Dec 15 16:15:18 UTC 2023 , Edited by admin on Fri Dec 15 16:15:18 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY