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^Y
PubChemCID	3074
IUPHAR/BPS	4717
ChemSpider	2965^Y
UNII	F8KLC2BD5Z
KEGG	D07843^Y
ChEBI	CHEBI:92842
ChEMBL	ChEMBL126075^Y
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^Y Key:QVZCXCJXTMIDME-UHFFFAOYSA-N^Y
(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 the homopiperazine derivative 3. Esterification by reaction with 3,4,5-trimethoxybenzoyl chloride (4) completes the synthesis of dilazep (5).^[4][5][6]

Synthesis of dilazep

See also

• Hexobendine, a drug with similar chemical structure

References

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. Thieme
5. 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)
6. 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.