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Legal status	Withdrawn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former development code NSC-71755) is an antipsychotic and tranquilizer of the phenothiazine group that was withdrawn from the market.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

Synthesis

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

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

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).