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CHEBI:77823 - tilidine
| ChEBI ID | CHEBI:77823 |
| ChEBI Name | tilidine |
| Stars | |
| 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. |
| Last Modified | 22 February 2017 |
| Submitter | Gareth Owen |
| Wikipedia |
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| Roles Classification |
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| Biological Role: | opioid analgesic A narcotic or opioid substance, synthetic or semisynthetic agent producing profound analgesia, drowsiness, and changes in mood. |
| Applications: | 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. opioid analgesic A narcotic or opioid substance, synthetic or semisynthetic agent producing profound analgesia, drowsiness, and changes in mood. |
| ChEBI Ontology |
|---|
| Outgoing Relation(s) |
| 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 | Source |
|---|---|
| tilidinum | WHO MedNet |
| tilidine | WHO MedNet |
| tilidine | WHO MedNet |
| tilidina | WHO MedNet |
| Synonym | Source |
|---|---|
| ethyl trans-2-(dimethylamino)-1-phenylcyclohex-3-ene-1-carboxylate | ChemIDplus |
| Registry Numbers | Sources |
|---|---|
| Reaxys:2813935 | Reaxys |
| CAS:51931-66-9 | ChemIDplus |
| Citations |
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