TREFENTANIL HYDROCHLORIDE

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 Search

SMILES

Cl.CCN1N=NN(CCN2CCC(CC2)(N(C(=O)CC)C3=CC=CC=C3F)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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/7924121 | https://www.ncbi.nlm.nih.gov/pubmed/15927477 | https://www.ncbi.nlm.nih.gov/pubmed/8466023

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.

Originator

Approval Year

PubMed

Title	Date	PubMed
Mu opiate active substances trefentanil and naloxonazine: tritiation at high specific activity.	2005-08	15927477
New opioid analgesics: an update.	1997	9246581
Pharmacokinetic-pharmacodynamic relationships for opioids in balanced anaesthesia.	1995-10	8549025
Validation of the alfentanil canonical univariate parameter as a measure of opioid effect on the electroencephalogram.	1995-10	7574054
Pharmacokinetic-pharmacodynamic modeling in drug development: application to the investigational opioid trefentanil.	1994-09	7924121
A-3665, a new short-acting opioid: a comparison with alfentanil.	1993-04	8466023

Patents

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:00:42 GMT 2025` Edited by `admin` on `Mon Mar 31 18:00:42 GMT 2025`
Record UNII	20742ZOB3G
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

A-3665 HYDROCHLORIDE

Preferred Name

English

TREFENTANIL HYDROCHLORIDE

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

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