|Systematic (IUPAC) name|
A 1 to 1 mixture of (1R,2S)- and (1S,2R)-Ethyl 2-(N,N-dimethylamino)- 1-phenylcyclohex- 3-enecarboxylate
|Biological half-life||4 - 6 hours|
|ATC code||N02AX01 (WHO)|
|Molar mass||273.37[[Script error: No such module "String".]]|
Tilidine (INN, USAN), or tilidate (BAN) (Valoron, Valtran, Tilidin) is a synthetic opioid analgesic, used mainly in Germany, Switzerland and Belgium for treatment of moderate to severe pain, both acute and chronic.
Considered a low- to medium-potency opioid, tilidine has the oral potency of about 0.2, i.e., a dose of 100 mg p.o. is equianalgesic to approximately 20 mg morphine sulfate orally. It is administered orally (by mouth), rectally (by a suppository), or by injection (s.c., i.m. or slowly i.v.) with single doses of 50 to 100 mg, the maximal daily dose being up to 600 mg.
Tilidine is used in the form of hydrochloride or phosphate salt. In Germany, tilidine is available in a fixed combination with naloxone for oral administration (Valoron N and generics); the admixture of naloxone is claimed to lower the abuse liability of the opioid analgesic. In Switzerland the original Valoron brand with only tilidine and no naloxone is also available.
It is manufactured by a Diels-Alder reaction of 1-N,N-dimethylaminobuta-1,3-diene with ethyl atropate, yielding a mixture of isomers, of which only the (E)-(trans)-isomers are active and is separated subsequently from the mixture by precipitation of the inactive (Z)-(cis)-isomers as zinc complex.
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- Martindale: The Complete Drug Reference
- Waldvogel: Analgetika, Antinozizeptiva, Adjuvanzien. (in german)
- Buschmann: Analgesics.
- Schulz R, Bläsig J, Wüster M, Herz A. The opiate-like action of tilidine is mediated by metabolites. Naunyn Schmiedebergs Archives of Pharmacology. 1978 Sep 12;304(2):89-93.
- Fachinfo (SPC) for Valoron N (in german)
- Tings T, Trenkwalder C. When L-Dopa preparations, dopamine agonists or opioids? Therapy of restless legs syndrome. (German) MMW Fortschritte der Medizin. 2003 Mar 6;145(10):48-9. PMID 12688028
- Robert M. Novack. Process for producing substituted cyclohexene compounds. US Patent 3649628