Chemistry:Talipexole
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| Trade names | Domin |
| Other names | Alefexole |
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| Routes of administration | Oral |
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| Formula | C10H15N3S |
| Molar mass | 209.31 g·mol−1 |
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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).
See also
- B-HT-958 [83718-64-3]
- Azepexole [36067-73-9]
- Pramipexole
References
- ↑ PharmaLetter 22 July 1996 First Launch In Japan For Talipexole
- ↑ EvaluatePharma Database. Page accessed 9 December 2014
- ↑ 3.0 3.1 "Dopamine agonists in schizophrenia: a review". European Neuropsychopharmacology 5 Suppl: 43–53. 1995. doi:10.1016/0924-977x(95)00022-h. PMID 8775758.
- ↑ 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 patent 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 patent 104031072 (2014 to Chongqing Zen Pharmaceutical Co Ltd.).
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