TILIDINE

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National Institutes of Health Divider Arrow

NCATS

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

Molecular Formula	C17H23NO2
Molecular Weight	273.37
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

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

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.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 14:59:30 GMT 2023` Edited by `admin` on `Fri Dec 15 14:59:30 GMT 2023`
Record UNII	GY33N31E9Y
Record Status	`Validated (UNII)`
Record Version

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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 15 14:59:30 GMT 2023 , Edited by admin on Fri Dec 15 14:59:30 GMT 2023

WHO-VATC

QN02AX01

Created by admin on Fri Dec 15 14:59:30 GMT 2023 , Edited by admin on Fri Dec 15 14:59:30 GMT 2023

NCI_THESAURUS

C241

Created by admin on Fri Dec 15 14:59:30 GMT 2023 , Edited by admin on Fri Dec 15 14:59:30 GMT 2023

DEA NO.

9750

Created by admin on Fri Dec 15 14:59:30 GMT 2023 , Edited by admin on Fri Dec 15 14:59:30 GMT 2023

WHO-ATC

N02AX01

Created by admin on Fri Dec 15 14:59:30 GMT 2023 , Edited by admin on Fri Dec 15 14:59:30 GMT 2023

Code System Code Type Description

DRUG CENTRAL

2663

Created by admin on Fri Dec 15 14:59:30 GMT 2023 , Edited by admin on Fri Dec 15 14:59:30 GMT 2023

PRIMARY

DRUG BANK

DB13787

Created by admin on Fri Dec 15 14:59:30 GMT 2023 , Edited by admin on Fri Dec 15 14:59:30 GMT 2023

PRIMARY

MESH

D013993

Created by admin on Fri Dec 15 14:59:30 GMT 2023 , Edited by admin on Fri Dec 15 14:59:30 GMT 2023

PRIMARY

ECHA (EC/EINECS)

243-774-7

Created by admin on Fri Dec 15 14:59:30 GMT 2023 , Edited by admin on Fri Dec 15 14:59:30 GMT 2023

ALTERNATIVE

RXCUI

10597

Created by admin on Fri Dec 15 14:59:30 GMT 2023 , Edited by admin on Fri Dec 15 14:59:30 GMT 2023

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RxNorm

FDA UNII

GY33N31E9Y

Created by admin on Fri Dec 15 14:59:30 GMT 2023 , Edited by admin on Fri Dec 15 14:59:30 GMT 2023

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MERCK INDEX

m10864

Created by admin on Fri Dec 15 14:59:30 GMT 2023 , Edited by admin on Fri Dec 15 14:59:30 GMT 2023

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Merck Index

ECHA (EC/EINECS)

257-522-9

Created by admin on Fri Dec 15 14:59:30 GMT 2023 , Edited by admin on Fri Dec 15 14:59:30 GMT 2023

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SMS_ID

100000082696

Created by admin on Fri Dec 15 14:59:30 GMT 2023 , Edited by admin on Fri Dec 15 14:59:30 GMT 2023

PRIMARY

WIKIPEDIA

TILIDINE

Created by admin on Fri Dec 15 14:59:30 GMT 2023 , Edited by admin on Fri Dec 15 14:59:30 GMT 2023

PRIMARY

CAS

20380-58-9

Created by admin on Fri Dec 15 14:59:30 GMT 2023 , Edited by admin on Fri Dec 15 14:59:30 GMT 2023

SUPERSEDED

CAS

51931-66-9

Created by admin on Fri Dec 15 14:59:30 GMT 2023 , Edited by admin on Fri Dec 15 14:59:30 GMT 2023

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NCI_THESAURUS

C152628

Created by admin on Fri Dec 15 14:59:30 GMT 2023 , Edited by admin on Fri Dec 15 14:59:30 GMT 2023

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EVMPD

SUB11051MIG

Created by admin on Fri Dec 15 14:59:30 GMT 2023 , Edited by admin on Fri Dec 15 14:59:30 GMT 2023

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INN

2510

Created by admin on Fri Dec 15 14:59:30 GMT 2023 , Edited by admin on Fri Dec 15 14:59:30 GMT 2023

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CHEBI

77823

Created by admin on Fri Dec 15 14:59:30 GMT 2023 , Edited by admin on Fri Dec 15 14:59:30 GMT 2023

PRIMARY

ChEMBL

CHEMBL2220384

Created by admin on Fri Dec 15 14:59:30 GMT 2023 , Edited by admin on Fri Dec 15 14:59:30 GMT 2023

PRIMARY

PUBCHEM

30131

Created by admin on Fri Dec 15 14:59:30 GMT 2023 , Edited by admin on Fri Dec 15 14:59:30 GMT 2023

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Related Record Type Details


					DXT828600R

TILIDINE FUMARATE

SALT/SOLVATE -> PARENT

Amount:


					4YI72J28N9

TILIDINE HYDROCHLORIDE

SALT/SOLVATE -> PARENT

Comments:

APPROXIMATE PURE ANHYDROUS DRUG CONTENT (IN PERCENT)

Amount:


					PUO0521HZV

CYTOCHROME P450 3A4

METABOLIC ENZYME -> SUBSTRATE

Amount:


					PJ7Z0WL915

TILIDINE PHOSPHATE

SALT/SOLVATE -> PARENT

Comments:

APPROXIMATE PURE ANHYDROUS DRUG CONTENT (IN PERCENT)

Amount:


					1PE72K8X46

MU-TYPE OPIOID RECEPTOR

TARGET->WEAK AGONIST

Comments:

Inhibition of forskolin-induced cAMP accumulation

Qualification:

IC50

Amount:


					2728MV084C

ACTIVE ENANTIOMER->RACEMATE

Amount:


					Y757T3419R

TILIDINE HYDROCHLORIDE HEMIHYDRATE

SALT/SOLVATE -> PARENT

Comments:

APPROXIMATE PURE ANHYDROUS DRUG CONTENT (IN PERCENT)

Amount:


					081I12ZA58

CYTOCHROME P450 2C19

METABOLIC ENZYME -> SUBSTRATE

Amount:


					0UY97CSG1T

CYTOCHROME P450 2B6

METABOLIC ENZYME -> SUBSTRATE

Amount:

Related Record Type Details


					58NDD17NUF

METABOLITE ACTIVE -> PRODRUG

Amount:


					7145G6817J

METABOLITE ACTIVE -> PRODRUG

Comments:

After oral intake tilidine is completely absorbed and rapidly metabolised to nortilidine, bisnortilidine. 100 fold more active than Tilidine.

Amount:

Related Record Type Details


					GY33N31E9Y

TILIDINE

ACTIVE MOIETY

Amount: