medicine: tilidine

tilidine description








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. 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.

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. 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.

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.

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

Notes

^ 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.
^ Robert M. Novack. Process for producing substituted cyclohexene compounds. US Patent 3649628
^ 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
v • d • eOpioids (N02A)Opium and
Poppy straw
derivativesCrude opiate
extracts

Compote/Kompot/Polish heroin · Diascordium · B & O Supprettes · Dover's powder · Laudanum · Mithridate · Opium · Paregoric · Poppy straw concentrate · Poppy tea · Smoking Opium · Theriac

Natural OpiatesOpium Alkaloids
see also: Components of Opium

Codeine · Morphine · Oripavine · Pseudomorphine · Thebaine

Alkaloid Salts Mixtures

Pantopon · Papaveretum (Omnopon) · Tetrapon

SemisyntheticsMorphine Family

14-Hydroxymorphine · 14β-Hydroxymorphine · 14β-Hydroxymorphone · 2,4-Dinitrophenylmorphine · 6-Methyldihydromorphine · 6-Methylenedihydrodesoxymorphine · 6-Acetyldihydromorphine/6-Monoacetyldihydromorphine · Acetyldihydromorphine · Azidomorphine · Chlornaltrexamine · Chloromorphide · Dihydrodesoxymorphine (Desomorphine) · Dihydromorphine · Ethyldihydromorphine · Hydromorphinol · Methyldesorphine · N-Phenethylnormorphine · Pseudomorphine

3,6 Diesters of Morphine

Diacetyldihydromorphine (Dihydroheroin) · Dibenzoylmorphine · Dibutanoylmorphine · Dipropanoylmorphine · Disalicyloylmorphine · heroin (Diacetylmorphine) · Heroin-7,8-Oxide · Nicomorphine

Codeine-Dionine Family

14-Hydroxydihydrocodeine · Acetylcodeine · Benzylmorphine · codeine methylbromide · Desocodeine · methyldihydromorphine (Dihydroheterocodeine) · Ethylmorphine (Dionine) · Heterocodeine · Isocodeine · Morpholinylethylmorphine (Pholcodine) · Myrophine · Nalodeine · Transisocodeine

Morphinones

14-Ethoxymetopon · 14-Methoxymetopon · 14β-Hydroxymorphone · 14-O-Methyloxymorphone · 14-Phenylpropoxymetopon · 7-Spiroindanyloxymorphone · 8,14-Dihydroxydihydromorphinone · Acetylmorphone · Ethyldihydromorphinone · Hydromorphinone · Hydromorphone · Hydroxycodeine · Methyldihydromorphinone · Metopon · Morphinol · Morphinone · N-Phenethyl-14-ethoxymetopon · Oxymorphol · Oxymorphone · Pentamorphone · Semorphone

Codeinones

1-carboxy-14-hydroxydihydrocodeinone · 1-carbethoxy-14-hydroxydihydrocodeinone · thebacon (Acetyldihydrocodeinone / Dihydrocodeinone enol acetate) · Codeinone · Codorphone · Codoxime · Hydrocodone · Monodihydrocodeineone · Oxycodone

Dihydrocodeine Series

14-hydroxydihydrocodeine · Acetyldihydrocodeine · Dihydrocodeine · Dihydrodesoxycodeine/Desocodeine · Dihydroisocodeine · Nicocodeine · Nicodicodeine

Nitrogen morphine Derivatives

Codeine-N-Oxide · Heroin-N-Oxide · Hydromorphone-N-Oxide · Morphine-N-Oxide

Hydrazones

Hydromorphazone · Morphazone · Oxymorphazone 

Others

α-chlorocodide · Pholcodine

Active Opiate
Metabolites

Codeine-N-Oxide (Genocodeine) · Dihydromorphine-6-glucuronide · Hydromorphone-N-Oxide · Heroin-7,8-Oxide · Morphine-6-glucuronide · 6-Acetylmorphine · Morphine-N-Oxide (Genomorphine) · Naltrexol · Norcodeine · Normorphine

MorphinansMorphinan Series

4-chlorophenylpyridomorphinan · Cyclorphan · Dextro-3-hydroxy-N-allylmorphinan · Dimemorfan · Levargorphan · Levallorphan · Levorphanol · Levorphan · Levophenacylmorphan · Levomethorphan · Norlevorphanol · N-Methylmorphinan · Oxilorphan · Phenomorphan · methorphan / Racemethorphan · morphanol / Racemorphanol · Ro4-1539 · Stephodeline · Xorphanol

Others

1-Nitroaknadinine · 14-episinomenine · 5,6-Dihydronorsalutaridine · 6-Ketonalbuphine · Aknadinine · Butorphanol · Cephakicine · Cephasamine · Cyprodime · Drotebanol · Fenfangjine G · Nalbuphine · Sinococuline · Sinomenine (Cocculine) · Tannagine

Benzomorphans

5,9-DEHB · Alazocine · Anazocine · Bremazocine · Cogazocine · Cyclazocine · Dezocine · Eptazocine · Etazocine · Ethylketocyclazocine · Fluorophen · Ketazocine · Metazocine · Pentazocine · Phenazocine · Quadazocine · Thiazocine · Tonazocine · Volazocine · Zenazocine

4-PhenylpiperidinesPethidines
(Meperidines)

Allylnorpethidine · Anileridine · Benzethidine · Carperidine · Difenoxin · Diphenoxylate · Etoxeridine (Carbetidine) · Furethidine · Hydroxypethidine (Bemidone) · Hydroxymethoxypethidine · Morpheridine · Oxpheneridine (Carbamethidine) · Meperidine-N-Oxide · Pethidine (Meperidine) · pethidine Intermediate A · pethidine Intermediate B (Norpethidine) · pethidine Intermediate C (Pethidinic Acid) · Pheneridine · Phenoperidine · Piminodine · Properidine (Ipropethidine) · Sameridine

Prodines

Allylprodine · Isopromedol · meprodine (α-meprodine / β-meprodine) · MPPP (Desmethylprodine) · PEPAP · prodine (α-prodine / β-prodine) · Prosidol · Trimeperidine (Promedol)

Ketobemidones

Acetoxyketobemidone · Droxypropine · Ketobemidone · Methylketobemidone · Propylketobemidone

OthersAlvimopan · Loperamide · PicenadolOpen Chain
OpioidsAmidones

Dextromethadone · Dextroisomethadone · Dipipanone · Hexalgon (Norpipanone) · Isomethadone · Levoisomethadone · Levomethadone · Methadone · methadone intermediate · Normethadone · Norpipanone · phenadoxone (Heptazone) · Pipidone

Methadols

Dimepheptanol (Racemethadol) · Levacetylmethadol · Noracetylmethadol

Moramides

Dextromoramide · Levomoramide · Moramide intermediate · Racemoramide

Thiambutenes

Diethylthiambutene · Dimethylthiambutene · Ethylmethylthiambutene · Piperidylthiambutene · Pyrrolidinylthiambutene · Thiambutene · Tipepidine

Phenalkoxams

Dextropropoxyphene (Propoxyphene) · Dimenoxadol · Dioxaphetyl Butyrate · Levopropoxyphene · Norpropoxyphene

Ampromides

Diampromide · Phenampromide · Propiram

Others

IC-26 · Isoaminile · Lefetamine · R-4066

Anilidopiperidines

3-Allylfentanyl · 3-Methylfentanyl · 3-Methylthiofentanyl · Alfentanil · α-methylacetylfentanyl · α-methylfentanyl · α-methylthiofentanyl · Benzylfentanyl · β-hydroxyfentanyl · β-hydroxythiofentanyl · β-methylfentanyl · Brifentanil · Carfentanil · Fentanyl · Lofentanil · Mirfentanil · Ocfentanil · Ohmefentanyl · Parafluorofentanyl · Phenaridine · Remifentanil · Sufentanil · Thenylfentanyl · Thiofentanyl · Trefentanil

Oripavine
derivatives

6,14-Endoethenotetrahydrooripavine · 7-PET · Acetorphine · Alletorphine · BU-48 · Buprenorphine · Butorphine · Cyprenorphine · Dihydroetorphine · diprenorphine (M5050) · Etorphine · 18,19-Dehydrobuprenorphine (HS-599) · N-cyclopropylmethyl-noretorphine · Nepenthone · Norbuprenorphine · Thevinone · Thienorphine

Phenazepines

Ethoheptazine · Meptazinol · Metheptazine · Metethoheptazine · Proheptazine

Pirinitramides

Bezitramide · Piritramide

Benzimidazoles

Clonitazene · Etonitazene · Nitazene

Indoles

18-MC · 7-Acetoxymitragynine · 7-Hydroxymitragynine · Akuammidine · Akuammine · Eseroline · Hodgkinsine · Ibogaine · Mitragynine · Noribogaine · Pericine · ψ-Akuammigine

Diphenylmethylpiperazines

BW373U86 · DPI-221 · DPI-287 · DPI-3290 · SNC-80

Opioid peptides
see also: The Opioid Peptides

Casomorphin · DADLE · DALDA · DAMGO · Dermenkephalin · Dermorphin · Deltorphin · DPDPE · Dynorphin · Endomorphin · Endorphin · Enkephalin · Gliadorphin · Morphiceptin · Nociceptin · Octreotide · Opiorphin · Rubiscolin · TRIMU 5

Others

3-(3-Methoxyphenyl)-3-ethoxycarbonyltropane · Azaprocin · BDPC · Bisnortilidine · BRL-52537 · C-8813 · Ciramadol · Enadoline · Faxeladol · Herkinorin · J-113,397 · JTC-801 · Methopholine · NNC 63-0532 · Nortilidine · O-Desmethyltramadol · Phenadone · Prodilidine · Profadol · Ro64-6198 · Salvinorin A · SB-612,111 · SC-17599 · RWJ-394,674 · TAN-67 · Tapentadol · Tecodine · Tifluadom · Tilidine · Tramadol · Trimebutine · Viminol · W-18 ·

Opioid Antagonists
&
Inverse-Agonists

5'-Guanidinonaltrindole · β-Funaltrexamine · 6β-Naltrexol · Alvimopan · Amiphenazole · Binaltorphimine · Chlornaltrexamine · Clocinnamox · Cyclazocine · Cyprodime · diprenorphine (M5050) · Fedotozine · JDTic · Levallorphan · Methocinnamox · Methylnaltrexone · Nalfurafine · Nalmefene · Nalmexone · Naloxazone · Naloxonazine · Naloxone · naloxone benzoylhydrazone · Nalorphine · Naltrexone · Naltriben · Naltrindole · Norbinaltorphimine · Oxilorphan · S-allyl-3-hydroxy-17-thioniamorphinan (SAHTM)

This analgesic-related article is a stub. You can help Wikipedia by expanding it.v • d • eRetrieved from "http:en.boinc.org/boinc/Tilidine"Categories: Opioids | Analgesics | Acetates | Analgesic stubs

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Keywords related to tilidine

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