TILIDINE

U.S. Department of Health & Human Services Divider Arrow

National Institutes of Health Divider Arrow

NCATS

Possibly Marketed Outside US

Details

Stereochemistry	RACEMIC
Molecular Formula	C17H23NO2
Molecular Weight	273.37
Optical Activity	( + / - )
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of TILIDINE

Structure Search

SMILES

CCOC(=O)[C@@]1(CCC=C[C@H]1N(C)C)C2=CC=CC=C2

InChI

InChIKey=WDEFBBTXULIOBB-WBVHZDCISA-N

InChI=1S/C17H23NO2/c1-4-20-16(19)17(14-10-6-5-7-11-14)13-9-8-12-15(17)18(2)3/h5-8,10-12,15H,4,9,13H2,1-3H3/t15-,17+/m1/s1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/212687 | https://www.ncbi.nlm.nih.gov/mesh/68013993 | https://www.ncbi.nlm.nih.gov/pubmed/15627429

TILIDINE is a low to medium potency opioid analgesic. It is metabolized to its active metabolites, nortilidine and bisnortilidine. Its analgesic activity is largely exerted through nortilidine which is a potent agonist at Mu opioid receptors.

Approval Year

PubMed

PubMed

Title	Date	PubMed
The opiate-like action of tilidine is mediated by metabolites.	1978 Sep	212687
Antagonism between tilidine and naloxone on cerebral potentials and pain ratings in man.	1983 Mar 4	6852098
[Erroneous intravenous injection of adrenaline].	1998 May 29	9645186
Actions of tilidine and nortilidine on cloned opioid receptors.	2005 Jan 4	15627429

Sample Use Guides

In Vitro Use Guide

The selectivity of tilidine and nortilidine for human opioid and opioid-like receptors stably expressed in CHO-K1 cells, using the inhibition of the forskolin (FK)-induced accumulation of cAMP as the endpoint was measured. In cells expressing the Mu opioid receptor, tilidine and nortilidine inhibited cAMP accumulation with IC50 of 11 microM and 110 nM, respectively.

Name

Type

Language

TILIDINE

Official Name

English

3-CYCLOHEXENE-1-CARBOXYLIC ACID, 2-(DIMETHYLAMINO)-1-PHENYL-, ETHYL ESTER, (TRANS)-(±)-

Common Name

English

TILIDATE

Common Name

English

TILIDINE [MI]

Common Name

English

TRANS-TILIDINE

Common Name

English

DL-TRANS-TILIDINE

Common Name

English

3-CYCLOHEXENE-1-CARBOXYLIC ACID, 2-(DIMETHYLAMINO)-1-PHENYL-, ETHYL ESTER, (1R,2S)-REL-

Systematic Name

English

tilidine [INN]

Common Name

English

IDS-NT-003

Code

English

Tilidine [WHO-DD]

Common Name

English

(±)-ETHYL TRANS-2-(DIMETHYLAMINO)-1-PHENYL-3-CYCLOHEXENE-1-CARBOXYLATE

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C67413

Created by admin on Fri Dec 16 15:51:24 UTC 2022 , Edited by admin on Fri Dec 16 15:51:24 UTC 2022

WHO-VATC

QN02AX01

Created by admin on Fri Dec 16 15:51:24 UTC 2022 , Edited by admin on Fri Dec 16 15:51:24 UTC 2022

NCI_THESAURUS

C241

Created by admin on Fri Dec 16 15:51:24 UTC 2022 , Edited by admin on Fri Dec 16 15:51:24 UTC 2022

DEA NO.

9750

Created by admin on Fri Dec 16 15:51:24 UTC 2022 , Edited by admin on Fri Dec 16 15:51:24 UTC 2022

WHO-ATC

N02AX01

Created by admin on Fri Dec 16 15:51:24 UTC 2022 , Edited by admin on Fri Dec 16 15:51:24 UTC 2022

Code System Code Type Description

DRUG CENTRAL

2663

Created by admin on Fri Dec 16 15:51:24 UTC 2022 , Edited by admin on Fri Dec 16 15:51:24 UTC 2022

PRIMARY

DRUG BANK

DB13787

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PRIMARY

MESH

D013993

Created by admin on Fri Dec 16 15:51:24 UTC 2022 , Edited by admin on Fri Dec 16 15:51:24 UTC 2022

PRIMARY

ECHA (EC/EINECS)

243-774-7

Created by admin on Fri Dec 16 15:51:24 UTC 2022 , Edited by admin on Fri Dec 16 15:51:24 UTC 2022

ALTERNATIVE

RXCUI

10597

Created by admin on Fri Dec 16 15:51:24 UTC 2022 , Edited by admin on Fri Dec 16 15:51:24 UTC 2022

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RxNorm

FDA UNII

GY33N31E9Y

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MERCK INDEX

M10864

Created by admin on Fri Dec 16 15:51:24 UTC 2022 , Edited by admin on Fri Dec 16 15:51:24 UTC 2022

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Merck Index

ECHA (EC/EINECS)

257-522-9

Created by admin on Fri Dec 16 15:51:24 UTC 2022 , Edited by admin on Fri Dec 16 15:51:24 UTC 2022

PRIMARY

WIKIPEDIA

TILIDINE

Created by admin on Fri Dec 16 15:51:24 UTC 2022 , Edited by admin on Fri Dec 16 15:51:24 UTC 2022

PRIMARY

CAS

20380-58-9

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SUPERSEDED

CAS

51931-66-9

Created by admin on Fri Dec 16 15:51:24 UTC 2022 , Edited by admin on Fri Dec 16 15:51:24 UTC 2022

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NCI_THESAURUS

C152628

Created by admin on Fri Dec 16 15:51:24 UTC 2022 , Edited by admin on Fri Dec 16 15:51:24 UTC 2022

PRIMARY

EVMPD

SUB11051MIG

Created by admin on Fri Dec 16 15:51:24 UTC 2022 , Edited by admin on Fri Dec 16 15:51:24 UTC 2022

PRIMARY

INN

2510

Created by admin on Fri Dec 16 15:51:24 UTC 2022 , Edited by admin on Fri Dec 16 15:51:24 UTC 2022

PRIMARY

CHEBI

77823

Created by admin on Fri Dec 16 15:51:24 UTC 2022 , Edited by admin on Fri Dec 16 15:51:24 UTC 2022

PRIMARY

ChEMBL

CHEMBL2220384

Created by admin on Fri Dec 16 15:51:24 UTC 2022 , Edited by admin on Fri Dec 16 15:51:24 UTC 2022

PRIMARY

ACTIVE MOIETY


					GY33N31E9Y

TILIDINE

METABOLITE ACTIVE (PRODRUG)


					58NDD17NUF

METABOLITE ACTIVE (PRODRUG)


					7145G6817J

SALT/SOLVATE (PARENT)


					DXT828600R

TILIDINE FUMARATE

SALT/SOLVATE (PARENT)


					4YI72J28N9

TILIDINE HYDROCHLORIDE

SALT/SOLVATE (PARENT)


					PJ7Z0WL915

TILIDINE PHOSPHATE

SALT/SOLVATE (PARENT)


					Y757T3419R

TILIDINE HYDROCHLORIDE HEMIHYDRATE