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Tilidine
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| 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 | |
| ATC code | N02 |
| PubChem | ? |
| 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) |
| Routes | ? |
Tilidine (INN, USAN), or tilidate (BAN) (Valoron, Valtran, Tilidin) is a synthetic opioid analgesic, used for treatment of moderate to severe pain, both acute and chronic.[1] Considered a low- to medium-potency opioid, it 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] It is manufactured by a Diels-Alder reaction of 1-N,N-dimethylaminobuta-1,3-diene with ethyl atropate, yielding a mixture of isomers,[5] of which only the (E)-(trans)-isomer is active and is separated subsequently from the mixture by precipitation of the inactive (Z)-(cis)-isomer as zinc complex.[3] 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.[6]
Authorities in Germany have recently reported increased cases of Tilidine abuse.[7] It remains unclear if this is empirically true.
Notes
- ^ Martindale: The Complete Drug Reference
- ^ Waldvogel: Analgetika, Antinozizeptiva, Adjuvanzien. (in german)
- ^ a b 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.
- ^ Robert M. Novack. Process for producing substituted cyclohexene compounds. US Patent 3649628
- ^ Fachinfo (SPC) for Valoron N (in german)
- ^ Tilidin: Modedroge macht super aggressiv - Nachrichten Wissenschaft - Medizin - WELT ONLINE
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Wikipedia content modification information:
- This page was last modified on 13 August 2008, at 06:28.
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