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Tilidine
Systematic (IUPAC) name
A 1 to 1 mixture of (1R,2S)- and (1S,2R)-Ethyl 2-(N,N-dimethylamino)- 1-phenylcyclohex- 3-enecarboxylate
Identifiers
CAS number 51931-66-9
ATC code N02AX01
Chemical data
Formula C17H23NO2 
Mol. mass 273.37
Pharmacokinetic data
Bioavailability Oral: >90%
Metabolism Hepatic demethylation
Half life 4 - 6 hours
Excretion Renal, 90%
Therapeutic considerations
Pregnancy cat.  ?
Legal status Schedule I (US); BtM Anlage III (Germany)

Tilidine (INN, USAN), or tilidate (BAN) (Valoron, Valtran, Tilidin) is a synthetic opioid analgesic, used mainly in Germany and Switzerland for treatment of moderate to severe pain, both acute and chronic.[1]

Contents

Pharmacology

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.[2]

Tilidine itself is only a weak opioid, but is rapidly metabolised in the liver and gut to its active metabolites nortilidine and bisnortilidine, which are fairly potent, µ-selective agonists.[3][4]

Indications

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.[5] In Switzerland the original Valoron brand with only tilidine and no naloxone is also available.

As well as its use as an analgesic, tilidine is also commonly used in Germany for treatment of restless legs syndrome.[6]

Synthesis

It is manufactured by a Diels-Alder reaction of 1-N,N-dimethylaminobuta-1,3-diene with ethyl atropate, yielding a mixture of isomers,[7] 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.[3]

Tilidine synthesis.PNG

References

  1. ^ Martindale: The Complete Drug Reference
  2. ^ Waldvogel: Analgetika, Antinozizeptiva, Adjuvanzien. (in german)
  3. ^ a b Buschmann: Analgesics.
  4. ^ 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.
  5. ^ Fachinfo (SPC) for Valoron N (in german)
  6. ^ 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
  7. ^ Robert M. Novack. Process for producing substituted cyclohexene compounds. US Patent 3649628







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