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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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S M Delaney et al.
The Journal of pharmacology and experimental therapeutics, 285(2), 568-572 (1998-05-15)
Selective inhibitors of adenosine production, degradation and transport were used to potentiate in vivo levels of adenosine and to determine the source of both basal and N-methyl-D-aspartate (NMDA)-induced increases in levels of endogenous adenosine in vivo. Male Sprague-Dawley rats receiving
H Deguchi et al.
Blood, 90(6), 2345-2356 (1997-10-06)
Dilazep, an antiplatelet agent, is generally used as an antithrombotic drug in clinical practice. Dilazep is also known to exert cytoprotective and antioxidant effects on endothelial cells. However, its effect on the endothelial or monocyte procoagulant activity is unknown. In
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)
M Griffiths et al.
The Biochemical journal, 328 ( Pt 3), 739-743 (1998-02-07)
Mammalian equilibrative nucleoside transporters are typically divided into two classes, es and ei, based on their sensitivity or resistance respectively to inhibition by nitrobenzylthioinosine (NBMPR). Previously, we have reported the isolation of a cDNA clone encoding a prototypic es-type transporter
Yukihiko Kawasaki et al.
Pediatrics international : official journal of the Japan Pediatric Society, 57(4), 650-655 (2015-01-24)
We examined the epidemiology, clinical manifestations, and prognosis of pediatric systemic lupus erythematosus (SLE) in Fukushima Prefecture, Japan over a 35 year period. We collected the medical records of 37 patients diagnosed with SLE between 1977 and 2013. These children
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