Monatepil

Monatepil
Names
	Preferred IUPAC name N-(6,11-Dihydrodibenzo[b,e]thiepin-11-yl)-4-[4-(4-fluorophenyl)piperazin-1-yl]butanamide
Identifiers
CAS Number	103377-41-9 ;
3D model (JSmol)	Interactive image;
ChemSpider	54798 ;
KEGG	D01171 ;
PubChem CID	60810;
UNII	N4MMI0J7PW ;
CompTox Dashboard (EPA)	DTXSID3048811 ;
	InChI InChI=1S/C28H30FN3OS/c29-22-11-13-23(14-12-22)32-18-16-31(17-19-32)15-5-10-27(33)30-28-24-7-2-1-6-21(24)20-34-26-9-4-3-8-25(26)28/h1-4,6-9,11-14,28H,5,10,15-20H2,(H,30,33) Key: WFNRNNUZFPVBSM-UHFFFAOYSA-N ;
	SMILES C1CN(CCN1CCCC(=O)NC2C3=CC=CC=C3CSC4=CC=CC=C24)C5=CC=C(C=C5)F;
Properties
Chemical formula	C28H30FN3OS
Molar mass	475.63 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Monatepil is a calcium channel blocker and α₁-adrenergic receptor antagonist used as an antihypertensive.^[1]

Synthesis

The synthesis of monatepil was first disclosed in patents filed by Dainippon Pharmaceutical.^[2]

The amino group of the dihydrodibenzothiepin (1) is first reacted with the acid chloride of 4-chlorobutyric acid, to give the amide (3). This is then used to alkylate para-fluorophenylpiperazine (4) to yield monatepil.^[2]^[3]

^ Sugimoto T, Hosoki K, Karasawa T (July 1995). "Relative contribution of alpha 1-adrenoceptor blocking activity to the hypotensive effect of the novel calcium antagonist monatepil". Journal of Cardiovascular Pharmacology. 26 (1): 55–60. doi:10.1097/00005344-199507000-00009. PMID 7564365. S2CID 1548014.
^ ^a ^b US patent 4749703, Hitoshi Uno, et al., "Calcium antagonist piperazine derivatives, and compositions therefor", issued 1988-06-07, assigned to Dainippon Pharmaceutical Co Ltd
^ Kurokawa, Mikio; Sato, Fuminori; Fujiwara, Iwao; et al. (1991). "A new class of calcium antagonists. 2. Synthesis and biological activity of 11-[4-[4-(4-fluorophenyl)-1-piperazinyl]butyryl]amino]-6,11-dihydrodibenzo[b,e]thiepin maleate and related compounds". Journal of Medicinal Chemistry. 34 (3): 927–934. doi:10.1021/jm00107a009. PMID 2002473.