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Dilazep

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Chemical compound Pharmaceutical compound
Dilazep
Clinical data
Trade namesComelian Kowa
AHFS/Drugs.comInternational Drug Names
ATC code
Identifiers
IUPAC name
  • 3-(4-{3-propyl}-1,4-diazepan-1-yl)propyl 3,4,5-trimethoxybenzoate
CAS Number
PubChem CID
IUPHAR/BPS
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC31H44N2O10
Molar mass604.697 g·mol
3D model (JSmol)
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.

It is used for the treatment of cardiopathy and renal disorders.

Synthesis

Thieme Patent: Prec (page 935):

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

See also

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. 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.
Vasodilators used in cardiac diseases (C01D)
Nitrovasodilators
Quinolone vasodilators
Others
Purine receptor modulators
Receptor
(ligands)
P0 (adenine)
P1
(adenosine)
P2
(nucleotide)
P2X
(ATPTooltip Adenosine triphosphate)
P2Y
Transporter
(blockers)
CNTsTooltip Concentrative nucleoside transporters
ENTsTooltip Equilibrative nucleoside transporters
PMATTooltip Plasma membrane monoamine transporter
Enzyme
(inhibitors)
XOTooltip Xanthine oxidase
Others
Others
See also: Receptor/signaling modulators


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