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D5294

Sigma-Aldrich

Dilazep dihydrochloride

powder

Synonym(s):

ASTA C 4898, Cormelian, N,N′-bis(3-[3,4,5-Trimethoxybenzoyloxy]propyl)homopiperazine dihydrochloride

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About This Item

Empirical Formula (Hill Notation):
C31H44N2O10 · 2HCl
CAS Number:
20153-98-4
Molecular Weight:
677.61
EC Number:
243-548-8
MDL number:
MFCD00133267
UNSPSC Code:
12352200
PubChem Substance ID:
24278372
NACRES:
NA.77

form

powder

Quality Level

200

color

white

solubility

H2O: 10 mg/mL

storage temp.

2-8°C

SMILES string

Cl[H].Cl[H].COc1cc(cc(OC)c1OC)C(=O)OCCCN2CCCN(CCCOC(=O)c3cc(OC)c(OC)c(OC)c3)CC2

InChI

1S/C31H44N2O10.2ClH/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;2*1H

InChI key

VILIWRRWAWKXRW-UHFFFAOYSA-N

Gene Information

human ... ADORA1(134) , ADORA2A(135) , ADORA2B(136) , ADORA3(140)

General description

Dilazep comprises central cyclic diamine and phenyl rings connected via alkyl linkers.

Application

Dilazep dihydrochloride has been used in estrogen receptor (ERα) antagonistic assay. It has also been used as an equilibrative nucleoside transporter inhibitor (ENT 1 and 2) in cancer cell lines.

Biochem/physiol Actions

Dilazep is a equilibrative nucleoside transporter 1 (ENTs) inhibitor. It is an antianginal drug and an effective coronary vasodilator. Dilazep elicits anti-albuminuric effects and is an anti-platelet agent. It is a potent adenosine uptake inhibitor and suppresses effects of ischemia.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Effects of dilazep on coronary and systemic hemodynamics in humans
Marzilli M, et al.
American Heart Journal, 108(2), 276-285 (1984)
Daniel Krys et al.
FASEB journal : official publication of the Federation of American Societies for Experimental Biology, 33(12), 13837-13851 (2019-10-12)
Elevated proliferation rates in cancer can be visualized with positron emission tomography (PET) using 3'-deoxy-3'-l-[18F]fluorothymidine ([18F]FLT). This study investigates whether [18F]FLT transport proteins are regulated through hypoxia. Expression and function of human equilibrative nucleoside transporter (hENT)-1, hENT2, and thymidine kinase
Characterization of drug-induced transcriptional modules: towards drug repositioning and functional understanding
Iskar M, et al.
Molecular Systems Biology, 9(1), 662-662 (2013)
A study on dilazep: I. Mechanism of anti-ischemic action of dilazep is not coronary vasodilation but decreased cardiac mechanical function in the isolated, working rat heart
Ehsanul Hoque AN, et al.
Japanese Journal of Pharmacology, 67(3), 225-232 (1995)
Dilazep analogues for the study of equilibrative nucleoside transporters 1 and 2 (ENT1 and ENT2)
Playa H, et al.
Bioorganic & medicinal chemistry letters, 24(24), 5801-5804 (2014)
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