en Talipexole

Talipexole
Clinical data
Trade names	Domin
Other names	Alefexole
AHFS/Drugs.com	International Drug Names
Routes of; administration	Oral
ATC code	none;
Legal status
Legal status	In general: ℞ (Prescription only);
Identifiers
	IUPAC name 6-allyl-5,6,7,8-tetrahydro-4H-[1,3]thiazolo[4,5-d]azepin-2-amine;
CAS Number	101626-70-4 ; DIHYDROCHLORIDE: 36085-73-1 36085-73-1 ;
PubChem CID	5374;
IUPHAR/BPS	5442;
ChemSpider	5181 ;
UNII	7AM2J46Z1Y; DIHYDROCHLORIDE: 9R6E1D8H1O ;
ChEMBL	ChEMBL1289023 ;
CompTox Dashboard (EPA)	DTXSID8046321 ;
Chemical and physical data
Formula	C10H15N3S
Molar mass	209.31 g·mol−1
3D model (JSmol)	Interactive image; DIHYDROCHLORIDE: Interactive image;
	SMILES n1c2c(sc1N)CCN(CC2)C\C=C; ; DIHYDROCHLORIDE: C=CCN1CCC2=C(CC1)SC(=N2)N;
	InChI InChI=1S/C10H15N3S/c1-2-5-13-6-3-8-9(4-7-13)14-10(11)12-8/h2H,1,3-7H2,(H2,11,12) ; Key:DHSSDEDRBUKTQY-UHFFFAOYSA-N ;
	(what is this?) (verify)

Talipexole (B-HT920, Domnin) is a dopamine agonist that is marketed as a treatment for Parkinson's Disease in Japan by Boehringer Ingelheim; it was introduced in 1996.^[1] As of December 2014 it was not approved for marketing in the US nor in Europe.^[2]

Talipexole is a D₂ dopamine receptor agonist and interacts with both pre- and post-synaptic receptors. It also is an α2-adrenergic agonist.^[3]

The main side effects are drowsiness, dizziness, hallucinations and minor gastrointestinal complaints.^[3] In Japan, Ministry of Health, Labour and Welfare mandated in 2008 that Boehringer add a warning to the label concerning the risk of sudden onset of sleep.^[4]^: 15

Synthesis

The N-alkylation of azepan-4-one [105416-56-6] (1) with allyl bromide in the presence of potassium carbonate gives 1-allyl-azepan-4-one (2). This is halogenated with molecular bromine in acetic acid to give 1-allyl-5-bromohexahydro-4-azepinone (3). The last step involves cyclization with thiourea (4) in refluxing ethanol, completing the synthesis of talipexole (5).

References

^ PharmaLetter 22 July 1996 First Launch In Japan For Talipexole
^ EvaluatePharma Database. Page accessed 9 December 2014
^ ^a ^b Benkert O, Müller-Siecheneder F, Wetzel H (1995). "Dopamine agonists in schizophrenia: a review". European Neuropsychopharmacology. 5 Suppl: 43–53. doi:10.1016/0924-977x(95)00022-h. PMID 8775758. S2CID 1600286.
^ Japanese Ministry of Health, Labour and Welfare March 2008 Pharmaceuticals and Medical Devices Safety Information No. 245
^ Serradell, M.N.; Blancafort, P.; Castaner, J.; Thorpe, P.J. Drugs Fut 1980,5(10),481.
^ Gerhart Dipl-Chem Dr Griss, 3 More » idem, DE 2040510 (1972 to Thomae Gmbh Dr K).
^ G Griss, M Kleemann, W Grell, H Ballhause, U.S. patent 3,804,849 (1974 to Boehringer Sohn Ingelheim
^ Deng Xianglin, et al. CN 104031072 (2014 to Chongqing Zen Pharmaceutical Co Ltd.).

This drug article relating to the nervous system is a stub. You can help Wikipedia by expanding it.

[1] PharmaLetter 22 July 1996 First Launch In Japan For Talipexole

[2] EvaluatePharma Database. Page accessed 9 December 2014

[Talipexole-3] Benkert O, Müller-Siecheneder F, Wetzel H (1995). "Dopamine agonists in schizophrenia: a review". European Neuropsychopharmacology. 5 Suppl: 43–53. doi:10.1016/0924-977x(95)00022-h. PMID 8775758. S2CID 1600286.

[4] Japanese Ministry of Health, Labour and Welfare March 2008 Pharmaceuticals and Medical Devices Safety Information No. 245

[5] Serradell, M.N.; Blancafort, P.; Castaner, J.; Thorpe, P.J. Drugs Fut 1980,5(10),481.

[6] Gerhart Dipl-Chem Dr Griss, 3 More » idem, DE 2040510 (1972 to Thomae Gmbh Dr K).

[7] G Griss, M Kleemann, W Grell, H Ballhause, U.S. patent 3,804,849 (1974 to Boehringer Sohn Ingelheim

[8] Deng Xianglin, et al. CN 104031072 (2014 to Chongqing Zen Pharmaceutical Co Ltd.).

[1]

[2]

[3]

[4]

[5]

[6]

[7]

[8]

Agama	Bahasa	Biografi	Budaya	Ekonomi	Elektronika
Film	Filsafat	Geografi	Indonesia	Ilmu	Lingkungan
Masyarakat	Matematika	Militer	Mitologi	Musik	Olahraga
Pendidikan	Politik	Sastra	Sejarah	Seni	Teknologi

Talipexole

Synthesis

See also

References

Portal di Ensiklopedia Dunia