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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

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

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

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

Sample Use Guides

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 Wed Jul 05 22:31:32 UTC 2023
Edited
by admin
on Wed Jul 05 22:31:32 UTC 2023
Record UNII
GY33N31E9Y
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TILIDINE
INN   MI   WHO-DD  
INN  
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 Wed Jul 05 22:31:32 UTC 2023 , Edited by admin on Wed Jul 05 22:31:32 UTC 2023
WHO-VATC QN02AX01
Created by admin on Wed Jul 05 22:31:33 UTC 2023 , Edited by admin on Wed Jul 05 22:31:33 UTC 2023
NCI_THESAURUS C241
Created by admin on Wed Jul 05 22:31:32 UTC 2023 , Edited by admin on Wed Jul 05 22:31:32 UTC 2023
DEA NO. 9750
Created by admin on Wed Jul 05 22:31:32 UTC 2023 , Edited by admin on Wed Jul 05 22:31:32 UTC 2023
WHO-ATC N02AX01
Created by admin on Wed Jul 05 22:31:32 UTC 2023 , Edited by admin on Wed Jul 05 22:31:32 UTC 2023
Code System Code Type Description
DRUG CENTRAL
2663
Created by admin on Wed Jul 05 22:31:32 UTC 2023 , Edited by admin on Wed Jul 05 22:31:32 UTC 2023
PRIMARY
DRUG BANK
DB13787
Created by admin on Wed Jul 05 22:31:32 UTC 2023 , Edited by admin on Wed Jul 05 22:31:32 UTC 2023
PRIMARY
MESH
D013993
Created by admin on Wed Jul 05 22:31:32 UTC 2023 , Edited by admin on Wed Jul 05 22:31:32 UTC 2023
PRIMARY
ECHA (EC/EINECS)
243-774-7
Created by admin on Wed Jul 05 22:31:32 UTC 2023 , Edited by admin on Wed Jul 05 22:31:32 UTC 2023
ALTERNATIVE
RXCUI
10597
Created by admin on Wed Jul 05 22:31:32 UTC 2023 , Edited by admin on Wed Jul 05 22:31:32 UTC 2023
PRIMARY RxNorm
FDA UNII
GY33N31E9Y
Created by admin on Wed Jul 05 22:31:32 UTC 2023 , Edited by admin on Wed Jul 05 22:31:32 UTC 2023
PRIMARY
MERCK INDEX
M10864
Created by admin on Wed Jul 05 22:31:32 UTC 2023 , Edited by admin on Wed Jul 05 22:31:32 UTC 2023
PRIMARY Merck Index
ECHA (EC/EINECS)
257-522-9
Created by admin on Wed Jul 05 22:31:32 UTC 2023 , Edited by admin on Wed Jul 05 22:31:32 UTC 2023
PRIMARY
SMS_ID
100000082696
Created by admin on Wed Jul 05 22:31:33 UTC 2023 , Edited by admin on Wed Jul 05 22:31:33 UTC 2023
PRIMARY
WIKIPEDIA
TILIDINE
Created by admin on Wed Jul 05 22:31:33 UTC 2023 , Edited by admin on Wed Jul 05 22:31:33 UTC 2023
PRIMARY
CAS
20380-58-9
Created by admin on Wed Jul 05 22:31:32 UTC 2023 , Edited by admin on Wed Jul 05 22:31:32 UTC 2023
SUPERSEDED
CAS
51931-66-9
Created by admin on Wed Jul 05 22:31:32 UTC 2023 , Edited by admin on Wed Jul 05 22:31:32 UTC 2023
PRIMARY
NCI_THESAURUS
C152628
Created by admin on Wed Jul 05 22:31:32 UTC 2023 , Edited by admin on Wed Jul 05 22:31:32 UTC 2023
PRIMARY
EVMPD
SUB11051MIG
Created by admin on Wed Jul 05 22:31:32 UTC 2023 , Edited by admin on Wed Jul 05 22:31:32 UTC 2023
PRIMARY
INN
2510
Created by admin on Wed Jul 05 22:31:32 UTC 2023 , Edited by admin on Wed Jul 05 22:31:32 UTC 2023
PRIMARY
CHEBI
77823
Created by admin on Wed Jul 05 22:31:32 UTC 2023 , Edited by admin on Wed Jul 05 22:31:32 UTC 2023
PRIMARY
ChEMBL
CHEMBL2220384
Created by admin on Wed Jul 05 22:31:32 UTC 2023 , Edited by admin on Wed Jul 05 22:31:32 UTC 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
APPROXIMATE PURE ANHYDROUS DRUG CONTENT (IN PERCENT)
METABOLIC ENZYME -> SUBSTRATE
SALT/SOLVATE -> PARENT
APPROXIMATE PURE ANHYDROUS DRUG CONTENT (IN PERCENT)
TARGET->WEAK AGONIST
Inhibition of forskolin-induced cAMP accumulation
IC50
ACTIVE ENANTIOMER->RACEMATE
SALT/SOLVATE -> PARENT
APPROXIMATE PURE ANHYDROUS DRUG CONTENT (IN PERCENT)
METABOLIC ENZYME -> SUBSTRATE
METABOLIC ENZYME -> SUBSTRATE
Related Record Type Details
METABOLITE ACTIVE -> PRODRUG
METABOLITE ACTIVE -> PRODRUG
After oral intake tilidine is completely absorbed and rapidly metabolised to nortilidine, bisnortilidine. 100 fold more active than Tilidine.
Related Record Type Details
ACTIVE MOIETY