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Talipexole

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
Clinical data
Trade namesDomin
Other namesAlefexole
AHFS/Drugs.comInternational Drug Names
Routes of
administration
Oral
ATC code
  • none
Legal status
Legal status
  • In general: ℞ (Prescription only)
Identifiers
  • 6-allyl-5,6,7,8-tetrahydro-4H-[1,3]thiazolo[4,5-d]azepin-2-amine
CAS Number
  • 101626-70-4 N
  • DIHYDROCHLORIDE: 36085-73-1  36085-73-1 Y
PubChem CID
  • 5374
IUPHAR/BPS
  • 5442
ChemSpider
  • 5181 N
UNII
  • 7AM2J46Z1Y
  • DIHYDROCHLORIDE: 9R6E1D8H1O Y
ChEMBL
  • ChEMBL1289023 N
CompTox Dashboard (EPA)
  • DTXSID8046321
Chemical and physical data
FormulaC10H15N3S
Molar mass209.31 g·mol−1
3D model (JSmol)
  • Interactive image
  • DIHYDROCHLORIDE: Interactive image
  • 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
 NY (what is this?)  (verify)

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 edit

 
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 edit

  • B-HT-958 [83718-64-3]
  • Azepexole [36067-73-9]
  • Pramipexole

References edit

  1. ^ PharmaLetter 22 July 1996 First Launch In Japan For Talipexole
  2. ^ EvaluatePharma Database. Page accessed 9 December 2014
  3. ^ 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.
  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.).

talipexole, ht920, domnin, dopamine, agonist, that, marketed, treatment, parkinson, disease, japan, boehringer, ingelheim, introduced, 1996, december, 2014, approved, marketing, europe, clinical, datatrade, namesdominother, namesalefexoleahfs, drugs, comintern. 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 TalipexoleClinical dataTrade namesDominOther namesAlefexoleAHFS Drugs comInternational Drug NamesRoutes ofadministrationOralATC codenoneLegal statusLegal statusIn general Prescription only IdentifiersIUPAC name 6 allyl 5 6 7 8 tetrahydro 4H 1 3 thiazolo 4 5 d azepin 2 amineCAS Number101626 70 4 NDIHYDROCHLORIDE 36085 73 1 36085 73 1 YPubChem CID5374IUPHAR BPS5442ChemSpider5181 NUNII7AM2J46Z1YDIHYDROCHLORIDE 9R6E1D8H1O YChEMBLChEMBL1289023 NCompTox Dashboard EPA DTXSID8046321Chemical and physical dataFormulaC 10H 15N 3SMolar mass209 31 g mol 13D model JSmol Interactive imageDIHYDROCHLORIDE Interactive imageSMILES n1c2c sc1N CCN CC2 C C CDIHYDROCHLORIDE C CCN1CCC2 C CC1 SC N2 NInChI 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 NKey DHSSDEDRBUKTQY UHFFFAOYSA N N N Y what is this verify Talipexole is a D2 dopamine receptor agonist and interacts with both pre and post synaptic receptors It also is an a2 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 edit nbsp 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 editB HT 958 83718 64 3 Azepexole 36067 73 9 PramipexoleReferences edit PharmaLetter 22 July 1996 First Launch In Japan For Talipexole EvaluatePharma Database Page accessed 9 December 2014 a b Benkert O Muller 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 nbsp This drug article relating to the nervous system is a stub You can help Wikipedia by expanding it vte Retrieved from https en wikipedia org w index php title Talipexole amp oldid 1188418022, wikipedia, wiki, book, books, library,

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