Tilidine

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Tilidine
Systematic (IUPAC) name
(1RS,2SR)-Ethyl 2-(N,N-dimethylamino)-1-phenylcyclohex-3-enecarboxylate
Identifiers
CAS number	51931-66-9
ATC code	N02AX01
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, 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^[5]. 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].

[edit] Notes

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