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Carfenazine

Chemical compound

Carfenazine
Summary

Chemical compound

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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former development code NSC-71755) is an antipsychotic and tranquilizer of the phenothiazine group that was withdrawn from the market.

Synthesis

3023146}} (1962 to [[American Home Products]]).</ref>

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. Other patent uses ketalization technique.

Analogs

  • Butaperazine, uses butanoyl and not propanoyl group
  • Fluphenazine, analog with trifluoromethyl on position 2 of the phenothiazine ring.

References

References

  1. (14 November 2014). "The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies". Springer.
  2. William Andrew Publishing. (22 October 2013). "Pharmaceutical Manufacturing Encyclopedia, 3rd Edition". Elsevier.
  3. (2011). "Drugs in Pregnancy and Lactation: A Reference Guide to Fetal and Neonatal Risk". Lippincott Williams & Wilkins.
  4. Zhuraulev, S.V. et al, Zh. Obshch. Khim., 1962, 32, 2244
  5. M. H. Sherlock, N. Sperber, {{US patent. 2985654 (1961 to [[Schering-Plough. Schering]])
  6. R. F. Tislow et al., {{US patent. 3023146 (1962 to [[American Home Products]]).
Wikipedia Source

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phenothiazines typical-antipsychotics withdrawn-drugs hydroxyethyl-compounds
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