Tifluadom

Details

Stereochemistry	RACEMIC
Molecular Formula	C22H20FN3OS
Molecular Weight	393.477
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CN1C(CNC(=O)C2=CSC=C2)CN=C(C3=CC=CC=C3F)C4=CC=CC=C14

InChI

InChIKey=NPGABYHTDVGGJK-UHFFFAOYSA-N

InChI=1S/C22H20FN3OS/c1-26-16(13-25-22(27)15-10-11-28-14-15)12-24-21(17-6-2-4-8-19(17)23)18-7-3-5-9-20(18)26/h2-11,14,16H,12-13H2,1H3,(H,25,27)

HIDE SMILES / InChI

Molecular Formula	C22H20FN3OS
Molecular Weight	393.477
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/6287271 | https://www.ncbi.nlm.nih.gov/pubmed/3084201 | https://www.ncbi.nlm.nih.gov/pubmed/3034631

Tifluadom is an opioid benzodiazepine with potent analgesic activity. Studies using antagonists for κ-, δ-, and μ-opiate receptors in guinea pig myenteric plexus-longitudinal muscle preparation and mouse and rabbit vasa deferentia showed that Tifluadom is an opioid analgesic with a preference for opiate κ-receptors. In rat brain homogenates, tifluadom displaced kappa-antagonist naloxone from its binding sites with an IC50 of 12nM but had no effect on flunitrazepam binding. Tifluadom produced a dose-related diuresis in normally hydrated rats and the diuretic effect was antagonized by naloxone and blocked by morphine administration.

Originator

Approval Year

PubMed

Title	Date	PubMed
Synthesis, biological evaluation, and receptor docking simulations of 2-[(acylamino)ethyl]-1,4-benzodiazepines as kappa-opioid receptor agonists endowed with antinociceptive and antiamnesic activity.	2003-08-28	12930147
Enantiomers of 2-[(Acylamino)ethyl]-1,4-benzodiazepines, potent ligands of kappa-opioid receptor: chiral chromatographic resolution, configurational assignment and biological activity.	2001	11579457
Activation of the cloned human kappa opioid receptor by agonists enhances [35S]GTPgammaS binding to membranes: determination of potencies and efficacies of ligands.	1997-08	9262330
Differential effects of fedotozine compared to other kappa agonists on diuresis in rats.	1996-12	8968362
Studies on the adrenomedullary dependence of kappa-opioid agonist-induced diuresis in conscious rats.	1989-12	2558758
Unexpected opioid activity in a known class of drug.	1982-09-20	6292610
An opioid benzodiazepine.	1982-08-19	6287271

Patents

Sample Use Guides

In Vivo Use Guide

Dog: 5, 10, 20, 40, 80 micrograms/kg

Route of Administration: Oral

Substance Class	Chemical Created by `admin` on `Wed Apr 02 08:20:56 GMT 2025` Edited by `admin` on `Wed Apr 02 08:20:56 GMT 2025`
Record UNII	TF8X866L0I
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

Tifluadom

Official Name

English

KC-5103

Preferred Name

English

(±)-N-((5-(O-FLUOROPHENYL)-2,3-DIHYDRO-1-METHYL-1H-1,4-BENZODIAZEPIN-2-YL)METHYL)-3-THIOPHENECARBOXAMIDE

Common Name

English

tifluadom [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C67413