Carfenazine

Carfenazine
Clinical data
Other names	Proketazine, Carphenazin
License data	US FDA: Proketazine;
Routes of; administration	Oral
ATC code	none;
Legal status
Legal status	Withdrawn;
Identifiers
	IUPAC name 1-(10-{3-[4-(2-Hydroxyethyl)piperazin-1-yl]propyl}-10H-phenothiazin-2-yl)propan-1-one;
CAS Number	2622-30-2;
PubChem CID	18104;
IUPHAR/BPS	7140;
DrugBank	DB01038;
ChemSpider	17100;
UNII	CLY16Y8Z7E;
ChEBI	CHEBI:51235;
ChEMBL	ChEMBL1201328;
CompTox Dashboard (EPA)	DTXSID8022745 ;
ECHA InfoCard	100.018.249
Chemical and physical data
Formula	C24H31N3O2S
Molar mass	425.59 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCC(=O)c1ccc2Sc3ccccc3N(CCCN4CCN(CCO)CC4)c2c1;
	InChI 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 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former developmental code name NSC-71755), is an antipsychotic and tranquilizer of the phenothiazine group that was withdrawn from the market.^[1]^[2]^[3]

Synthesis

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

Butaperazine uses butanoyl (Butyryl) and not propanoyl group.
Fluphenazine selfsame but trifluoromethyl on position 2 of the phenothiazine ring.

References

^ 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 & 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).

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[Elks2014-1] 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.

[Publishing2013-2] William Andrew Publishing (22 October 2013). Pharmaceutical Manufacturing Encyclopedia, 3rd Edition. Elsevier. pp. 862–. ISBN 978-0-8155-1856-3.

[BriggsFreeman2011-3] 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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