DILAZEP DIHYDROCHLORIDE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C31H44N2O10.2ClH
Molecular Weight	677.61
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

Cl.Cl.COC1=CC(=CC(OC)=C1OC)C(=O)OCCCN2CCCN(CCCOC(=O)C3=CC(OC)=C(OC)C(OC)=C3)CC2

InChI

InChIKey=VILIWRRWAWKXRW-UHFFFAOYSA-N

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

HIDE SMILES / InChI

Molecular Formula	C31H44N2O10
Molecular Weight	604.6885
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/7016654 | https://www.ncbi.nlm.nih.gov/pubmed/8858972

Dilazep is a coronary and cerebral vasodilator as an adenosine reuptake inhibitor. Dilazep is an inhibitor of platelet aggregation and of membrane transport of nucleosides. Dilazep is also known to have a vasodilating effect on renal vessels and is often used in patients with ischaemic heart disease, cerebral ischemia or renal dysfunction to improve tissue circulation.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Equilibrative nucleoside transporter 1 7 Target ID: CHEMBL1997 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25454272	Inhibitor 8297		17.5 nM [IC50]
Equilibrative nucleoside transporter 2 4 Target ID: CHEMBL3509606 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25454272	Inhibitor 8297		8800.0 nM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Cerebral infarction 14 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15386824	Preventing	Not Provided 504	Unknown Approved Use Unknown
Beta-thalassemia 7 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10774700	Primary	Phase II 1132	Unknown Approved Use Unknown
Diabetic nephropathy 35 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10937516	Primary	Not Provided 504	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Molecular cloning and characterization of a nitrobenzylthioinosine-insensitive (ei) equilibrative nucleoside transporter from human placenta.	1997 Dec 15	9396714
Molecular cloning and functional characterization of nitrobenzylthioinosine (NBMPR)-sensitive (es) and NBMPR-insensitive (ei) equilibrative nucleoside transporter proteins (rENT1 and rENT2) from rat tissues.	1997 Nov 7	9353301
Chimeric constructs between human and rat equilibrative nucleoside transporters (hENT1 and rENT1) reveal hENT1 structural domains interacting with coronary vasoactive drugs.	1998 Aug 21	9705281
Dipyridamole and dilazep suppress oxygen radicals in puromycin aminonucleoside nephrosis rats.	1998 Nov	9824428
Molecular cloning and functional characterization of inhibitor-sensitive (mENT1) and inhibitor-resistant (mENT2) equilibrative nucleoside transporters from mouse brain.	2000 Dec 1	11085929
Endothelin-1 gene expression in endothelial cells is potently inhibited by a vasodilator, dilazep.	2004 Jun	15253106
Interaction of the novel adenosine uptake inhibitor 3-[1-(6,7-diethoxy-2-morpholinoquinazolin-4-yl)piperidin-4-yl]-1,6-dimethyl-2,4(1H,3H)-quinazolinedione hydrochloride (KF24345) with the es and ei subtypes of equilibrative nucleoside transporters.	2004 Mar	14634039
Nucleobase transport by human equilibrative nucleoside transporter 1 (hENT1).	2011 Sep 16	21795683
Loss of equilibrative nucleoside transporter 1 in mice leads to progressive ectopic mineralization of spinal tissues resembling diffuse idiopathic skeletal hyperostosis in humans.	2013 May	23184610
Screening of a chemical library reveals novel PXR-activating pharmacologic compounds.	2015 Jan 5	25455453
Lack of the nucleoside transporter ENT1 results in the Augustine-null blood type and ectopic mineralization.	2015 Jun 4	25896650

Patents

Sample Use Guides

In Vivo Use Guide

Dilazep dihydrochloride was administered orally at 300 mg/day for 24 months in 15 of these patients

Route of Administration: Oral

In Vitro Use Guide

The effect of dilazep or adenosine on the mechanical function was examined in both palmitoyl-L-camitine (PALCAR) treated heart (PALCAR-treated heart experiments) and normal (PALCAR-untreated) heart (normal heart experiments). Dilazep, adenosine or vehicle was infused into the aortic cannula for 45 mm at a constant flow rate of 0.1 ml/min. In the PALCAR-treated heart experiments, PALCAR was infused into the aortic cannula at the constant flow rate of 0.1 ml /min for 10 min from 10 min after the start of infusion of dilazep, adenosine or vehicle. The experimental condition and protocol of the normal heart experiments were essentially the same as in the PALCAR-treated heart experiments, except for an infusion of KHB buffer instead of PALCAR solution. In each group, LVSP, LVEDP and LVDP were recorded continuously before and during the infusion of dilazep, adenosine or vehicle.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:23:21 GMT 2023` Edited by `admin` on `Fri Dec 15 15:23:21 GMT 2023`
Record UNII	LV48LW10EO
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

DILAZEP DIHYDROCHLORIDE

Common Name

English

NSC-760096

Code

English

1,4-BIS(3-(3,4,5-TRIMETHOXYBENZOYLOXY)PROPYL)HOMOPIPERAZINE DIHYDROCHLORIDE

Systematic Name

English

Dilazep dihydrochloride [WHO-DD]

Common Name

English

DILAZEP DIHYDROCHLORIDE [MI]

Common Name

English

Code System Code Type Description

PUBCHEM

29976