Fanetizole

Fanetizole

Clinical data
Other names	CP-48,810
Pharmacokinetic data
Protein binding	%
Identifiers
IUPAC name 4-Phenyl-N-(2-phenylethyl)-1,3-thiazol-2-amine
CAS Number	79069-94-6
PubChem CID	54339
ChemSpider	49083
UNII	BH48F620JA
CompTox Dashboard (EPA)	DTXSID9048695
Chemical and physical data
Formula	C17H16N2S
Molar mass	280.39 g·mol−1
3D model (JSmol)	Interactive image
SMILES n1c(csc1NCCc2ccccc2)c3ccccc3
InChI InChI=1S/C17H16N2S/c1-3-7-14(8-4-1)11-12-18-17-19-16(13-20-17)15-9-5-2-6-10-15/h1-10,13H,11-12H2,(H,18,19) Key:WEEYMMXMBFJUAI-UHFFFAOYSA-N
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Fanetizole is a drug that has immunoregulating activity. ^[1]

Synthesis

Reaction of β-phenethylamine (1) with ammonium thiocyanate (2) gives the thiourea (3). Treatment of that product with phenacyl bromide (4) produces fanetizole (5). ^[2]

Other syntheses: ^{[3] [4]}

References

1. Rocklin RE, Hemady Z, Matloff S, Kiselis I, Lima M. Correction of an in vitro immunoregulatory defect in atopic subjects by the immunostimulating drug fanetizole mesylate (CP-48,810). Int J Immunopharmacol. 1984;6(1):1-8. doi: 10.1016/0192-0561(84)90028-6. PMID: 6233230.
2. Joseph G. Lombardino, U.S. patent 4,307,106 (1981 to Pfizer Corp SRL).
3. Pastre, Julio C.; Browne, Duncan L.; O’Brien, Matthew; Ley, Steven V. (2013). "Scaling Up of Continuous Flow Processes with Gases Using a Tube-in-Tube Reactor: Inline Titrations and Fanetizole Synthesis with Ammonia". Organic Process Research & Development. 17 (9): 1183–1191. doi:10.1021/op400152r.
4. Lin, Pei-Ying; Hou, Rei-Sheu; Wang, Huey-Min; Kang, Iou-Jiun; Chen, Ling-Ching (2009). "Efficient Synthesis of 2-Aminothiazoles and Fanetizole in Liquid PEG-400 at Ambient Conditions". Journal of the Chinese Chemical Society. 56 (3): 455–458. doi:10.1002/jccs.200900068.