tilidine

Term ID

CHEBI:77823

Synonyms

• ethyl trans-2-(dimethylamino)-1-phenylcyclohex-3-ene-1-carboxylate
• rac-ethyl (1R,2S)-2-(dimethylamino)-1-phenylcyclohex-3-ene-1-carboxylate
• rac-ethyl (1S,2R)-2-(dimethylamino)-1-phenylcyclohex-3-ene-1-carboxylate
• tilidina
• tilidine
• tilidinum

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.

References

• cas:51931-66-9
• kegg.drug:D08597
• patent:GB1120186
• patent:US3557127
• pubmed:11144998
• pubmed:21140136
• pubmed:212687
• pubmed:22381043
• pubmed:23844964
• pubmed:2610722
• pubmed:3803198
• pubmed:6852098
• pubmed:720208
• reaxys:2813935
• wikipedia.en:Tilidine

Ontology

ChEBI  ( EBI )