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Details

Stereochemistry ACHIRAL
Molecular Formula C25H31FN6O2.ClH
Molecular Weight 503.012
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TREFENTANIL HYDROCHLORIDE

SMILES

Cl.CCN1N=NN(CCN2CCC(CC2)(N(C(=O)CC)C3=C(F)C=CC=C3)C4=CC=CC=C4)C1=O

InChI

InChIKey=YMRJQYDWCFOMRR-UHFFFAOYSA-N
InChI=1S/C25H31FN6O2.ClH/c1-3-23(33)32(22-13-9-8-12-21(22)26)25(20-10-6-5-7-11-20)14-16-29(17-15-25)18-19-31-24(34)30(4-2)27-28-31;/h5-13H,3-4,14-19H2,1-2H3;1H

HIDE SMILES / InChI

Molecular Formula C25H31FN6O2
Molecular Weight 466.551
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Trefentanil is a short-acting synthetic opioid of the piperidine class. The drug caused potent analgesia with the peak effect occurring 3 min after injection. There was no significant difference in analgesic potency of trefentanil and alfentanil as measured by tolerance to tibial pressure at 3 min. Trefentanil had a pharmacokinetic and pharmacodynamic profile similar to alfentanil, with a small extent of tissue distribution and a rapid blood/brain equilibration. Trefentanil caused significant respiratory depression at doses of 32 ug/kg and 64 ug/kg. It is a mu-opioid receptor agonist. Trefentanil produced naloxone reversible anti-nociception equi-efficacious to that of fentanyl.

Approval Year

PubMed

PubMed

TitleDatePubMed
A-3665, a new short-acting opioid: a comparison with alfentanil.
1993 Apr
Pharmacokinetic-pharmacodynamic modeling in drug development: application to the investigational opioid trefentanil.
1994 Sep
Pharmacokinetic-pharmacodynamic relationships for opioids in balanced anaesthesia.
1995 Oct
Validation of the alfentanil canonical univariate parameter as a measure of opioid effect on the electroencephalogram.
1995 Oct
New opioid analgesics: an update.
1997 Spring
Mu opiate active substances trefentanil and naloxonazine: tritiation at high specific activity.
2005 Aug
Patents

Patents

Substance Class Chemical
Created
by admin
on Fri Dec 15 15:32:44 UTC 2023
Edited
by admin
on Fri Dec 15 15:32:44 UTC 2023
Record UNII
20742ZOB3G
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TREFENTANIL HYDROCHLORIDE
USAN   WHO-DD  
USAN  
Official Name English
1-(2-(4-ETHYL-4,5-DIHYDRO-5-OXO-1H-TETRAZOL-1-YL)ETHYL)-4-PHENYL-4-(N-(2-FLUOROPHENYL)PROPIONAMIDO)PIPERIDINE HYDROCHLORIDE
Systematic Name English
A-3665 HYDROCHLORIDE
Code English
Trefentanil hydrochloride [WHO-DD]
Common Name English
A-3665.HCL
Code English
TREFENTANIL HYDROCHLORIDE [USAN]
Common Name English
PROPANAMIDE, N-(1-(2-(4-ETHYL-4,5-DIHYDRO-5-OXO-1H-TETRAZOL-1-YL)ETHYL)-4-PHENYL-4-PIPERIDINYL)-N-(2-FLUOROPHENYL)-, HYDROCHLORIDE (1:1)
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C241
Created by admin on Fri Dec 15 15:32:44 UTC 2023 , Edited by admin on Fri Dec 15 15:32:44 UTC 2023
NCI_THESAURUS C67413
Created by admin on Fri Dec 15 15:32:44 UTC 2023 , Edited by admin on Fri Dec 15 15:32:44 UTC 2023
Code System Code Type Description
USAN
DD-40
Created by admin on Fri Dec 15 15:32:44 UTC 2023 , Edited by admin on Fri Dec 15 15:32:44 UTC 2023
PRIMARY
DRUG BANK
DBSALT001793
Created by admin on Fri Dec 15 15:32:44 UTC 2023 , Edited by admin on Fri Dec 15 15:32:44 UTC 2023
PRIMARY
NCI_THESAURUS
C152721
Created by admin on Fri Dec 15 15:32:44 UTC 2023 , Edited by admin on Fri Dec 15 15:32:44 UTC 2023
PRIMARY
EPA CompTox
DTXSID40152956
Created by admin on Fri Dec 15 15:32:44 UTC 2023 , Edited by admin on Fri Dec 15 15:32:44 UTC 2023
PRIMARY
PUBCHEM
60727
Created by admin on Fri Dec 15 15:32:44 UTC 2023 , Edited by admin on Fri Dec 15 15:32:44 UTC 2023
PRIMARY
ChEMBL
CHEMBL84617
Created by admin on Fri Dec 15 15:32:44 UTC 2023 , Edited by admin on Fri Dec 15 15:32:44 UTC 2023
PRIMARY
FDA UNII
20742ZOB3G
Created by admin on Fri Dec 15 15:32:44 UTC 2023 , Edited by admin on Fri Dec 15 15:32:44 UTC 2023
PRIMARY
CAS
120656-93-1
Created by admin on Fri Dec 15 15:32:44 UTC 2023 , Edited by admin on Fri Dec 15 15:32:44 UTC 2023
PRIMARY
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