CHEBI:77823 - tilidine

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ChEBI Name tilidine
ChEBI ID CHEBI:77823
Definition A racemate that is an equimolar mixture of the two trans diastereoisomers of ethyl 2-(dimethylamino)-1-phenylcyclohex-3-ene-1-carboxylate, namely dextilidine and ent-dextilidine. It is used (commonly as the hydrochloride hemihydrate) as an opioid analgesic for the management of moderate to severe pain. A prodrug, it is metabolised in the body to nortilidine, which is responsible for the analgesic activity; virtually all of the opioid activity resides in the (1S,2R) isomer.
Stars This entity has been manually annotated by the ChEBI Team.
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Roles Classification
Biological Role(s): opioid analgesic
A narcotic or opioid substance, synthetic or semisynthetic agent producing profound analgesia, drowsiness, and changes in mood.
Application(s): opioid analgesic
A narcotic or opioid substance, synthetic or semisynthetic agent producing profound analgesia, drowsiness, and changes in mood.
prodrug
A compound that, on administration, must undergo chemical conversion by metabolic processes before becoming the pharmacologically active drug for which it is a prodrug.
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ChEBI Ontology
Outgoing tilidine (CHEBI:77823) has part ent-dextilidine (CHEBI:77821)
tilidine (CHEBI:77823) has part dextilidine (CHEBI:77822)
tilidine (CHEBI:77823) has role opioid analgesic (CHEBI:35482)
tilidine (CHEBI:77823) has role prodrug (CHEBI:50266)
tilidine (CHEBI:77823) is a racemate (CHEBI:60911)
IUPAC Names
rac-ethyl (1R,2S)-2-(dimethylamino)-1-phenylcyclohex-3-ene-1-carboxylate
rac-ethyl (1S,2R)-2-(dimethylamino)-1-phenylcyclohex-3-ene-1-carboxylate
INNs Sources
tilidina WHO MedNet
tilidine WHO MedNet
tilidine WHO MedNet
tilidinum WHO MedNet
Synonym Source
ethyl trans-2-(dimethylamino)-1-phenylcyclohex-3-ene-1-carboxylate ChemIDplus
Manual Xrefs Databases
D08597 KEGG DRUG
GB1120186 Patent
Tilidine Wikipedia
US3557127 Patent
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Registry Numbers Types Sources
2813935 Reaxys Registry Number Reaxys
51931-66-9 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
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Last Modified
22 February 2017