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Chemical compound
Talipexole
Trade names Domin Other names Alefexole
AHFS /
Drugs.com
International Drug Names
Routes of administration Oral
ATC code
Legal status
In general: ℞ (Prescription only)
6-allyl-5,6,7,8-tetrahydro-4H -[1,3]thiazolo[4,5-d ]azepin-2-amine
CAS Number
PubChem
CID
IUPHAR/BPS
ChemSpider
UNII
ChEMBL
CompTox Dashboard (
EPA )
Formula C 10 H 15 N 3 S
Molar mass 209.31 g·mol−1 3D model (
JSmol )
n1c2c(sc1N)CCN(CC2)C\C=C
DIHYDROCHLORIDE: C=CCN1CCC2=C(CC1)SC(=N2)N
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)
N Key:DHSSDEDRBUKTQY-UHFFFAOYSA-N
N
N Y
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(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
Synthesis:
[5] Patents:
[6]
[7] Sino:
[8]
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
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.).
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