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Carfenazine

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Carfenazine
Carphenazine.svg
Clinical data
Other namesProketazine, Carphenazin
License data
Routes of
administration 		Oral
ATC code
  • none
Legal status
Legal status
  • Withdrawn
Identifiers
  • 1-(10-{3-[4-(2-Hydroxyethyl)piperazin-1-yl]propyl}-10H-phenothiazin-2-yl)propan-1-one
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.018.249 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C24H31N3O2S
Molar mass 425.59 g·mol−1
3D model (JSmol)
  • CCC(=O)c1ccc2Sc3ccccc3N(CCCN4CCN(CCO)CC4)c2c1
  • 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,2,5,10-17H2,1H3
  • Key:XZSMZRXAEFNJCU-UHFFFAOYSA-N

Carfenazine (INN; former development code WY-2445; BAN carphenazine; USAN carphenazine maleate; brand name Proketazine; former development code NSC-71755) is an antipsychotic and tranquilizer of the phenothiazine group that was withdrawn from the market. [1] [2] [3]

Contents

Synthesis

Thieme Synthesis: Patent: Carphenazine synthesis.svg
Thieme Synthesis: Patent:

The alkylation reaction between 2-propionyl phenothiazine (1) and 1-bromo-3-chloropropane (2) gives 1-[10-(3-chloropropyl)phenothiazin-2-yl]propan-1-one (3). A second alkylation step, this time with 2-(1-Piperazinyl)ethanol (4), completes the synthesis of carfenazine (5).

Although above procedure is proof-of-concept, bear in mind no protecting group.[ clarification needed ] Other patent uses ketalization technique.[ clarification needed ]

Analogs

References

  1. ↑ 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.
  2. ↑ William Andrew Publishing (22 October 2013). Pharmaceutical Manufacturing Encyclopedia, 3rd Edition. Elsevier. pp. 862–. ISBN   978-0-8155-1856-3.
  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–. ISBN   978-1-60831-708-0.
  4. ↑ Zhuraulev, S.V. et al, Zh. Obshch. Khim., 1962, 32, 2244
  5. ↑ M. H. Sherlock, N. Sperber, U.S. patent 2,985,654 (1961 to Schering)
  6. ↑ R. F. Tislow et al., U.S. patent 3,023,146 (1962 to American Home Products).


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