Carfenazine (INN) (former developmental code name WY-2445), or carphenazine (BAN), also known as carphenazine maleate (USAN) (brand name Proketazine; former developmental code name NSC-71755), is an antipsychotic and tranquilizer of the phenothiazine group that was withdrawn from the market.[1][2][3]
The alkylation reaction between 2-Propionyl Phenothiazine [92-33-1] (1) and 1-Bromo-3-chloropropane (2) gives 1-[10-(3-chloropropyl)phenothiazin-2-yl]propan-1-one [95157-45-2] (3). A second alkylation step, this time with 2-(1-Piperazinyl)ethanol [103-76-4] (4) completes the synthesis of Carfenazine (5).
NB: Although above procedure is proof-of-concept, bear in mind no protecting group {Other patent uses ketalization technique}
^Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 224–. ISBN978-1-4757-2085-3.
^William Andrew Publishing (22 October 2013). Pharmaceutical Manufacturing Encyclopedia, 3rd Edition. Elsevier. pp. 862–. ISBN978-0-8155-1856-3.
^Briggs GG, Freeman RK, Yaffe SJ (2011). Drugs in Pregnancy and Lactation: A Reference Guide to Fetal and Neonatal Risk. Lippincott Williams & Wilkins. pp. 213–. ISBN978-1-60831-708-0.
^Zhuraulev, S.V. et al, Zh. Obshch. Khim., 1962, 32, 2244
^M. H. Sherlock, N. Sperber, U.S. patent 2,985,654 (1961 to Schering)
carfenazine, former, developmental, code, name, 2445, carphenazine, also, known, carphenazine, maleate, usan, brand, name, proketazine, former, developmental, code, name, 71755, antipsychotic, tranquilizer, phenothiazine, group, that, withdrawn, from, market, . Carfenazine INN former developmental code name WY 2445 or carphenazine BAN also known as carphenazine maleate USAN brand name Proketazine former developmental code name NSC 71755 is an antipsychotic and tranquilizer of the phenothiazine group that was withdrawn from the market 1 2 3 CarfenazineClinical dataOther namesProketazine CarphenazinLicense dataUS FDA ProketazineRoutes ofadministrationOralATC codenoneLegal statusLegal statusWithdrawnIdentifiersIUPAC name 1 10 3 4 2 Hydroxyethyl piperazin 1 yl propyl 10H phenothiazin 2 yl propan 1 oneCAS Number2622 30 2PubChem CID18104IUPHAR BPS7140DrugBankDB01038ChemSpider17100UNIICLY16Y8Z7EChEBICHEBI 51235ChEMBLChEMBL1201328CompTox Dashboard EPA DTXSID8022745ECHA InfoCard100 018 249Chemical and physical dataFormulaC 24H 31N 3O 2SMolar mass425 59 g mol 13D model JSmol Interactive imageSMILES CCC O c1ccc2Sc3ccccc3N CCCN4CCN CCO CC4 c2c1InChI InChI 1S C24H31N3O2S c1 2 22 29 19 8 9 24 21 18 19 27 20 6 3 4 7 23 20 30 24 11 5 10 25 12 14 26 15 13 25 16 17 28 h3 4 6 9 18 28H 2 5 10 17H2 1H3Key XZSMZRXAEFNJCU UHFFFAOYSA NSynthesis edit nbsp Thieme Synthesis 4 Patent 5 6 The alkylation reaction between 2 Propionyl Phenothiazine 92 33 1 1 and 1 Bromo 3 chloropropane 2 gives 1 10 3 chloropropyl phenothiazin 2 yl propan 1 one 95157 45 2 3 A second alkylation step this time with 2 1 Piperazinyl ethanol 103 76 4 4 completes the synthesis of Carfenazine 5 NB Although above procedure is proof of concept bear in mind no protecting group Other patent uses ketalization technique Analogues edit Butaperazine uses butanoyl Butyryl and not propanoyl group Fluphenazine selfsame but trifluoromethyl on position 2 of the phenothiazine ring References edit Elks J 14 November 2014 The Dictionary of Drugs Chemical Data Chemical Data Structures and Bibliographies Springer pp 224 ISBN 978 1 4757 2085 3 William Andrew Publishing 22 October 2013 Pharmaceutical Manufacturing Encyclopedia 3rd Edition Elsevier pp 862 ISBN 978 0 8155 1856 3 Briggs GG Freeman RK Yaffe SJ 2011 Drugs in Pregnancy and Lactation A Reference Guide to Fetal and Neonatal Risk Lippincott Williams amp Wilkins pp 213 ISBN 978 1 60831 708 0 Zhuraulev S V et al Zh Obshch Khim 1962 32 2244 M H Sherlock N Sperber U S patent 2 985 654 1961 to Schering R F Tislow et al U S patent 3 023 146 1962 to American Home Products 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 Carfenazine amp oldid 1155210968, wikipedia, wiki, book, books, library,
