Dilazep

Dilazep
Clinical data
Trade names	Comelian Kowa
AHFS/Drugs.com	International Drug Names
ATC code	C01DX10 (WHO) ;
Identifiers
	IUPAC name 3-(4-{3-[(3,4,5-Trimethoxyphenyl)carbonyloxy]propyl}-1,4-diazepan-1-yl)propyl 3,4,5-trimethoxybenzoate;
CAS Number	35898-87-4 ;
PubChem CID	3074;
IUPHAR/BPS	4717;
ChemSpider	2965 ;
UNII	F8KLC2BD5Z;
KEGG	D07843 ;
ChEBI	CHEBI:92842;
ChEMBL	ChEMBL126075 ;
CompTox Dashboard (EPA)	DTXSID9045425 ;
Chemical and physical data
Formula	C31H44N2O10
Molar mass	604.697 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C(OCCCN2CCCN(CCCOC(=O)c1cc(OC)c(OC)c(OC)c1)CC2)c3cc(OC)c(OC)c(OC)c3;
	InChI InChI=1S/C31H44N2O10/c1-36-24-18-22(19-25(37-2)28(24)40-5)30(34)42-16-8-12-32-10-7-11-33(15-14-32)13-9-17-43-31(35)23-20-26(38-3)29(41-6)27(21-23)39-4/h18-21H,7-17H2,1-6H3 ; Key:QVZCXCJXTMIDME-UHFFFAOYSA-N ;
	(verify)

Dilazep is a vasodilator that acts as an adenosine reuptake inhibitor.^[1]^[2]

It is used for the treatment of cardiopathy and renal disorders.^[3]

Synthesis

The reaction of bis-(3-hydroxypropyl)-ethylene diamine (1) with 1-Bromo-3-chloropropane (2) gives homopiperazine [19970-80-0] (3). Esterification by reaction with 3,4,5-Trimethoxybenzoyl Chloride [4521-61-3] (4) completed the synthesis of Dilazep (5).

References

^ Deguchi H, Takeya H, Wada H, Gabazza EC, Hayashi N, Urano H, Suzuki K (September 1997). "Dilazep, an antiplatelet agent, inhibits tissue factor expression in endothelial cells and monocytes". Blood. 90 (6): 2345–56. doi:10.1182/blood.V90.6.2345. PMID 9310485.
^ PubChem. "Dilazep". pubchem.ncbi.nlm.nih.gov. Retrieved 2021-08-18.
^ "Pharmaceuticals". Kowa Company Ltd.
^ GB1107470 idem Herbert Arnold, Kurt Pahls, Rolf Rebling,Norbert Brock, Hans-Dieter Lenke, U.S. patent 3,532,685 (1970 to Asta Werke Ag Chem Fab).
^ Schlögl, K., Schlögl, R. (1964). "Über pharmakodynamisch wirksame 3,4,5-Trimethoxybenzoate und verwandte Ester von symmetrischen Bis-hydroxyalkylpiperazinen und-dialkylpolymethylendiaminen". Monatshefte für Chemie. 95 (3): 922–941. doi:10.1007/BF00908805.

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[1] Deguchi H, Takeya H, Wada H, Gabazza EC, Hayashi N, Urano H, Suzuki K (September 1997). "Dilazep, an antiplatelet agent, inhibits tissue factor expression in endothelial cells and monocytes". Blood. 90 (6): 2345–56. doi:10.1182/blood.V90.6.2345. PMID 9310485.

[2] PubChem. "Dilazep". pubchem.ncbi.nlm.nih.gov. Retrieved 2021-08-18.

[3] "Pharmaceuticals". Kowa Company Ltd.

[4] GB1107470 idem Herbert Arnold, Kurt Pahls, Rolf Rebling,Norbert Brock, Hans-Dieter Lenke, U.S. patent 3,532,685 (1970 to Asta Werke Ag Chem Fab).

[5] Schlögl, K., Schlögl, R. (1964). "Über pharmakodynamisch wirksame 3,4,5-Trimethoxybenzoate und verwandte Ester von symmetrischen Bis-hydroxyalkylpiperazinen und-dialkylpolymethylendiaminen". Monatshefte für Chemie. 95 (3): 922–941. doi:10.1007/BF00908805.

[1]

v t e Vasodilators used in cardiac diseases (C01D)
Nitrovasodilators	Nitroglycerin # Isosorbide dinitrate # Isosorbide mononitrate Itramin tosilate Linsidomine Molsidomine Nicorandil Pentaerythritol tetranitrate Propatylnitrate Tenitramine Trolnitrate
Quinolone vasodilators	Flosequinan^‡
Others	Benziodarone Carbocromen Cinepazet Cloridarol Dilazep Efloxate Etafenone Gapicomine Heptaminol Hexobendine Imolamine Levosimendan Nesiritide Nicorandil Oxyfedrine Pimobendan Prenylamine Serelaxin Trapidil Vericiguat
^#WHO-EM ^‡Withdrawn from market Clinical trials: ^†Phase III ^§Never to phase III

Synthesis

See also

References