Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C25H32N2O3 |
| Molecular Weight | 408.5332 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CCC(=O)N(C1=CC=CC=C1)[C@@]2(CCN(CCC3=CC=CC=C3)C[C@@H]2C)C(=O)OC
InChI
InChIKey=IMYHGORQCPYVBZ-NBGIEHNGSA-N
InChI=1S/C25H32N2O3/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/h5-14,20H,4,15-19H2,1-3H3/t20-,25+/m0/s1
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 |
|---|---|---|
| Activation profiles of opioid ligands in HEK cells expressing delta opioid receptors. | 2002 Nov 18 |
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| Activity of opioid ligands in cells expressing cloned mu opioid receptors. | 2003 Jan 4 |
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| Ligand-regulated internalization of the opioid receptor-like 1: a confocal study. | 2004 Jun |
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| Pharmacological profiles of opioid ligands at kappa opioid receptors. | 2006 Jan 25 |
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| Development of an enzyme-linked immunosorbent assay for fentanyl and applications of fentanyl antibody-coated nanoparticles for sample preparation. | 2006 Jun 16 |
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| Oral transmucosal fentanyl citrate in cancer pain management: a practical application of nanotechnology. | 2007 |
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| In vivo mechanisms precipitating torsades de pointes in a canine model of drug-induced long-QT1 syndrome. | 2007 Nov 1 |
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| The fentanyl/etomidate-anaesthetised beagle (FEAB) dog: a versatile in vivo model in cardiovascular safety research. | 2009 Jul-Aug |
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NCI_THESAURUS |
C67413
Created by
admin on Fri Dec 15 16:00:12 GMT 2023 , Edited by admin on Fri Dec 15 16:00:12 GMT 2023
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WIKIPEDIA |
List_of_fentanyl_analogues
Created by
admin on Fri Dec 15 16:00:12 GMT 2023 , Edited by admin on Fri Dec 15 16:00:12 GMT 2023
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DB09174
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C034846
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7H7YQ564XV
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4817
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65499
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LOFENTANIL
Created by
admin on Fri Dec 15 16:00:12 GMT 2023 , Edited by admin on Fri Dec 15 16:00:12 GMT 2023
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PRIMARY | Lofentanil is one of the most potent opioid analgesics known and is an analogue of fentanyl, which was developed in 1960. It is most similar to the highly potent opioid carfentanil (4-carbomethoxyfentanyl), only slightly more potent. Lofentanil can be described as 3-methylcarfentanil, or 3-methyl-4-carbomethoxyfentanyl. While 3-methylfentanyl is considerably more potent than fentanyl itself, lofentanil is only slightly stronger than carfentanil.(1)(2) This suggests that substitution at both the 3 and 4 positions of the piperidine ring introduces steric hindrance which prevents .MU.-opioid affinity from increasing much further. As with other 3-substituted fentanyl derivatives such as ohmefentanyl, the stereoisomerism of lofentanil is very important, with some stereoisomers being much more potent than | ||
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m1205
Created by
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PRIMARY | Merck Index | ||
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LOFENTANYL
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DTXSID201016402
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100000082019
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SUB08556MIG
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CHEMBL28198
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C83890
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61380-40-3
Created by
admin on Fri Dec 15 16:00:12 GMT 2023 , Edited by admin on Fri Dec 15 16:00:12 GMT 2023
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)
