U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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 of DILAZEP DIHYDROCHLORIDE

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

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

Targets

Primary TargetPharmacologyConditionPotency
17.5 nM [IC50]
8800.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Molecular cloning and characterization of a nitrobenzylthioinosine-insensitive (ei) equilibrative nucleoside transporter from human placenta.
1997 Dec 15
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
Chimeric constructs between human and rat equilibrative nucleoside transporters (hENT1 and rENT1) reveal hENT1 structural domains interacting with coronary vasoactive drugs.
1998 Aug 21
Dipyridamole and dilazep suppress oxygen radicals in puromycin aminonucleoside nephrosis rats.
1998 Nov
Molecular cloning and functional characterization of inhibitor-sensitive (mENT1) and inhibitor-resistant (mENT2) equilibrative nucleoside transporters from mouse brain.
2000 Dec 1
Endothelin-1 gene expression in endothelial cells is potently inhibited by a vasodilator, dilazep.
2004 Jun
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
Nucleobase transport by human equilibrative nucleoside transporter 1 (hENT1).
2011 Sep 16
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
Screening of a chemical library reveals novel PXR-activating pharmacologic compounds.
2015 Jan 5
Lack of the nucleoside transporter ENT1 results in the Augustine-null blood type and ectopic mineralization.
2015 Jun 4
Patents

Sample Use Guides

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
  • Download
Name Type Language
DILAZEP DIHYDROCHLORIDE
JAN   MI   WHO-DD  
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
Created by admin on Fri Dec 15 15:23:21 GMT 2023 , Edited by admin on Fri Dec 15 15:23:21 GMT 2023
PRIMARY
EPA CompTox
DTXSID201017379
Created by admin on Fri Dec 15 15:23:21 GMT 2023 , Edited by admin on Fri Dec 15 15:23:21 GMT 2023
PRIMARY
FDA UNII
LV48LW10EO
Created by admin on Fri Dec 15 15:23:21 GMT 2023 , Edited by admin on Fri Dec 15 15:23:21 GMT 2023
PRIMARY
CAS
20153-98-4
Created by admin on Fri Dec 15 15:23:21 GMT 2023 , Edited by admin on Fri Dec 15 15:23:21 GMT 2023
PRIMARY
ChEMBL
CHEMBL126075
Created by admin on Fri Dec 15 15:23:21 GMT 2023 , Edited by admin on Fri Dec 15 15:23:21 GMT 2023
PRIMARY
SMS_ID
100000087509
Created by admin on Fri Dec 15 15:23:21 GMT 2023 , Edited by admin on Fri Dec 15 15:23:21 GMT 2023
PRIMARY
MERCK INDEX
m4492
Created by admin on Fri Dec 15 15:23:21 GMT 2023 , Edited by admin on Fri Dec 15 15:23:21 GMT 2023
PRIMARY Merck Index
EVMPD
SUB01733MIG
Created by admin on Fri Dec 15 15:23:21 GMT 2023 , Edited by admin on Fri Dec 15 15:23:21 GMT 2023
PRIMARY
NSC
760096
Created by admin on Fri Dec 15 15:23:21 GMT 2023 , Edited by admin on Fri Dec 15 15:23:21 GMT 2023
PRIMARY
ECHA (EC/EINECS)
243-548-8
Created by admin on Fri Dec 15 15:23:21 GMT 2023 , Edited by admin on Fri Dec 15 15:23:21 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
SOLVATE->ANHYDROUS
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY