DILAZEP DIHYDROCHLORIDE MONOHYDRATE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C31H44N2O10.2ClH.H2O
Molecular Weight	695.626
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of DILAZEP DIHYDROCHLORIDE MONOHYDRATE

Structure Search

SMILES

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

InChI

InChIKey=KJDHWPSHIIFNAK-UHFFFAOYSA-N

InChI=1S/C31H44N2O10.2ClH.H2O/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;1H2

HIDE SMILES / InChI

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

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	H2O
Molecular Weight	18.0153
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 8 Target ID: CHEMBL1997 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25454272	Inhibitor 8504		17.5 nM [IC50]
Equilibrative nucleoside transporter 2 4 Target ID: CHEMBL3509606 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25454272	Inhibitor 8504		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 511	Unknown Approved Use Unknown
Beta-thalassemia 7 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10774700	Primary	Phase II 1147	Unknown Approved Use Unknown
Diabetic nephropathy 37 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10937516	Primary	Not Provided 511	Unknown Approved Use Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
173 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2724090/	600 mg single, oral dose: 600 mg route of administration: Oral experiment type: SINGLE co-administered:		DILAZEP DIHYDROCHLORIDE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
3 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2724090/	600 mg single, oral dose: 600 mg route of administration: Oral experiment type: SINGLE co-administered:		DILAZEP DIHYDROCHLORIDE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN

Doses

Dose	Population	Adverse events
300 mg/day 1 times / day steady, oral Studied dose Dose: 300 mg/day, 1 times / day Route: oral Route: steady Dose: 300 mg/day, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/11340355/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/11340355/	Sources: https://pubmed.ncbi.nlm.nih.gov/11340355/
300 mg/day 1 times / day steady, oral Studied dose Dose: 300 mg/day, 1 times / day Route: oral Route: steady Dose: 300 mg/day, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/11834877/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/11834877/	Sources: https://pubmed.ncbi.nlm.nih.gov/11834877/
0.2 mg/kg single, intravenous Studied dose Dose: 0.2 mg/kg Route: intravenous Route: single Dose: 0.2 mg/kg Sources: https://pubmed.ncbi.nlm.nih.gov/3280614/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/3280614/	Other AEs: headache... Other AEs: headache (2 pts severe; 5 pts moderate, 7 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/3280614/

AEs

AE	Significance	Dose	Population
headache	2 pts severe; 5 pts moderate, 7 patients	0.2 mg/kg single, intravenous Studied dose Dose: 0.2 mg/kg Route: intravenous Route: single Dose: 0.2 mg/kg Sources: https://pubmed.ncbi.nlm.nih.gov/3280614/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/3280614/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2252	inhibitor 2438	inhibitor 2507	inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
MRP5 31 CYP1A2 2153 CYP2C19 2057 MRP4 290 CYP19A1 429	P-gp 2052

Drug as perpetrator

Target	Modality	Activity
CYP2C9 2497	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzMzk3IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDEyNjA3NSJ9fQ==	inconclusive [IC50 12.5893 uM]
CYP2C19 2141	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzNjIyIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDEyNjA3NSJ9fQ==	inconclusive [IC50 7.9433 uM]
CYP1A2 2333	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzMzU2IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDEyNjA3NSJ9fQ==	no [IC50 >10 uM]
CYP2D6 2546	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwyODkiLCJ1c2VfY3VzdG9tX3F1ZXJ5Ijp0cnVlLCJzZWFyY2hfdGVybSI6IiIsInRleHRfZmlsdGVyIjoiQ0hFTUJMMTI2MDc1In19	no [IC50 >10 uM]
MRP5 80	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwyMDQ2MjU4IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDEyNjA3NSJ9fQ==	no [IC50 >50 uM]
CYP19A1 430	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/3074#section=BioAssay-Results Page: 14.0	no
MRP4 345	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwxNzQzMTI4IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDEyNjA3NSJ9fQ==	yes [IC50 20 uM]
CYP3A4 2633	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzNDAiLCJ1c2VfY3VzdG9tX3F1ZXJ5Ijp0cnVlLCJzZWFyY2hfdGVybSI6IiIsInRleHRfZmlsdGVyIjoiQ0hFTUJMMTI2MDc1In19	yes [IC50 7.9433 uM]

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
P-gp 2052	substrate 4014 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/3074#section=BioAssay-Results Page: 3 \| 156	no

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/3074#section=BioAssay-Results Page: 6.0

PubMed

Title	Date	PubMed
Lack of the nucleoside transporter ENT1 results in the Augustine-null blood type and ectopic mineralization.	2015-06-04	25896650
Screening of a chemical library reveals novel PXR-activating pharmacologic compounds.	2015-01-05	25455453
Loss of equilibrative nucleoside transporter 1 in mice leads to progressive ectopic mineralization of spinal tissues resembling diffuse idiopathic skeletal hyperostosis in humans.	2013-05	23184610
Nucleobase transport by human equilibrative nucleoside transporter 1 (hENT1).	2011-09-16	21795683
Endothelin-1 gene expression in endothelial cells is potently inhibited by a vasodilator, dilazep.	2004-06	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.	2004-03	14634039
Molecular cloning and functional characterization of inhibitor-sensitive (mENT1) and inhibitor-resistant (mENT2) equilibrative nucleoside transporters from mouse brain.	2000-12-01	11085929
Dipyridamole and dilazep suppress oxygen radicals in puromycin aminonucleoside nephrosis rats.	1998-11	9824428
Chimeric constructs between human and rat equilibrative nucleoside transporters (hENT1 and rENT1) reveal hENT1 structural domains interacting with coronary vasoactive drugs.	1998-08-21	9705281
Molecular cloning and characterization of a nitrobenzylthioinosine-insensitive (ei) equilibrative nucleoside transporter from human placenta.	1997-12-15	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.	1997-11-07	9353301

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 `Mon Mar 31 21:40:38 GMT 2025` Edited by `admin` on `Mon Mar 31 21:40:38 GMT 2025`
Record UNII	6435U1X26I
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

DILAZEP HYDROCHLORIDE HYDRATE

Preferred Name

English

DILAZEP DIHYDROCHLORIDE MONOHYDRATE

Common Name

English

DILAZEP HYDROCHLORIDE HYDRATE [JAN]

Common Name

English

Code System Code Type Description

FDA UNII

6435U1X26I

Created by admin on Mon Mar 31 21:40:38 GMT 2025 , Edited by admin on Mon Mar 31 21:40:38 GMT 2025

PRIMARY

PUBCHEM

11954260

Created by admin on Mon Mar 31 21:40:38 GMT 2025 , Edited by admin on Mon Mar 31 21:40:38 GMT 2025

PRIMARY

EVMPD

SUB123160

Created by admin on Mon Mar 31 21:40:38 GMT 2025 , Edited by admin on Mon Mar 31 21:40:38 GMT 2025

PRIMARY

SMS_ID

100000145201

Created by admin on Mon Mar 31 21:40:38 GMT 2025 , Edited by admin on Mon Mar 31 21:40:38 GMT 2025

PRIMARY

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Related Record Type Details


					F8KLC2BD5Z

DILAZEP

ACTIVE MOIETY

Details

SMILES

InChI

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

Originator

Approval Year

Targets

Conditions

Approved Use

Approved Use

Approved Use

Cmax

T1/2

Doses

AEs

Overview

OverviewOther

Drug as perpetrator​

Drug as victim

Tox targets

PubMed

Patents

Sample Use Guides

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

C_max

T_1/2

Drug as perpetrator