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Details

Stereochemistry ACHIRAL
Molecular Formula C8H8N4
Molecular Weight 160.1759
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of HYDRALAZINE

SMILES

NNC1=C2C=CC=CC2=CN=N1

InChI

InChIKey=RPTUSVTUFVMDQK-UHFFFAOYSA-N
InChI=1S/C8H8N4/c9-11-8-7-4-2-1-3-6(7)5-10-12-8/h1-5H,9H2,(H,11,12)

HIDE SMILES / InChI

Description

Hydralazine is a direct-acting vasodilator that is used as an antihypertensive agent. Hydralazine works by relaxing blood vessels (arterioles more than venules) and increasing the supply of blood and oxygen to the heart while reducing its workload. It also functions as an antioxidant. It inhibits membrane-bound enzymes that form reactive oxygen species, such as superoxides. Excessive superoxide counteracts NO-induced vasodilation. Hydralazine is used for the treatment of essential hypertension, alone or as an adjunct. Also for the management of severe hypertension when the drug cannot be given orally or when blood pressure must be lowered immediately, congestive heart failure (in combination with cardiac glycosides and diuretics and/or with isosorbide dinitrate), and hypertension secondary to pre-eclampsia/eclampsia.

CNS Activity

Approval Year

Targets

Targets

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Hydralazine Hydrochloride
PubMed

PubMed

TitleDatePubMed
Clinical consequences of polymorphic acetylation of basic drugs.
1977 Sep
Acute hemodynamic effects of pinacidil and hydralazine in essential hypertension.
1985 Mar
Therapeutic implications of hypertension-induced glomerular injury. Comparison of enalapril and a combination of hydralazine, reserpine, and hydrochlorothiazide in an experimental model.
1985 Sep 27
Comparative study of endralazine and hydralazine for the treatment of hypertension uncontrolled by a beta-blocker and diuretic.
1986
Therapeutic advantage of converting enzyme inhibitors in arresting progressive renal disease associated with systemic hypertension in the rat.
1986 Jun
Isolated minimal change nephropathy associated with diclofenac.
1987 Jul 18
Prevention of arterial disease in experimental renal hypertension.
1990 Apr
Features of the acute hypotensive action of carvedilol and its ameliorating effect on myocardial ischemia.
1991
Renal arteriolar diameters in spontaneously hypertensive rats. Vascular cast study.
1991 Jul
Effects of hydralazine and increased cardiac output on recombinant tissue plasminogen activator-induced thrombolysis in canine pulmonary embolism.
1991 Mar
Myocardial ischemia during vasodilator therapy in a canine model of pulmonary hypertension and coronary insufficiency.
1992 May
High-throughput measurement of the Tp53 response to anticancer drugs and random compounds using a stably integrated Tp53-responsive luciferase reporter.
2002 Jun
Olmesartan improves endothelin-induced hypertension and oxidative stress in rats.
2004 Jul
Contrasting effects of chronic ethanol feeding on centrally and peripherally evoked hypotension in telemetered female rats.
2004 Mar
Protein adduct-trapping by hydrazinophthalazine drugs: mechanisms of cytoprotection against acrolein-mediated toxicity.
2004 Mar
Reactivity of hydrazinophthalazine drugs with the lipid peroxidation products acrolein and crotonaldehyde.
2004 Sep 21
A phase I study of hydralazine to demethylate and reactivate the expression of tumor suppressor genes.
2005 Apr 29
Life-threatening milk-alkali syndrome resulting from antacid ingestion during pregnancy.
2005 Apr 4
Calcium channel blockades exhibit anti-inflammatory and antioxidative effects by augmentation of endothelial nitric oxide synthase and the inhibition of angiotensin converting enzyme in the N(G)-nitro-L-arginine methyl ester-induced hypertensive rat aorta: vasoprotective effects beyond the blood pressure-lowering effects of amlodipine and manidipine.
2005 Aug
Effect of AT1 receptor antagonism on vascular and circulating inflammatory mediators in SHR: role of NF-kappaB/IkappaB system.
2005 Jan
Up-regulation of HLA class-I antigen expression and antigen-specific CTL response in cervical cancer cells by the demethylating agent hydralazine and the histone deacetylase inhibitor valproic acid.
2006 Dec 27
Podocyte injury underlies the glomerulopathy of Dahl salt-hypertensive rats and is reversed by aldosterone blocker.
2006 Jun
Antihypertensive drugs clonidine, diazoxide, hydralazine and furosemide regulate the production of cytokines by placentas and peripheral blood mononuclear cells in normal pregnancy.
2006 May
Beneficial effects of the Rho kinase inhibitor Y27632 in murine puromycin aminonucleoside nephrosis.
2008
Pharmacologic profiling of human and rat cytochrome P450 1A1 and 1A2 induction and competition.
2008 Dec
Hypertension induces somatic cellular senescence in rats and humans by induction of cell cycle inhibitor p16INK4a.
2008 Jul
4-Hydrazino-2-(methyl-sulfan-yl)-pyrimidine.
2009 Jan 31
Resveratrol attenuates angiotensin II-induced interleukin-6 expression and perivascular fibrosis.
2009 Jun
D-penicillamine-induced autoimmunity: relationship to macrophage activation.
2009 Sep
Chitosan nanoparticle-based neuronal membrane sealing and neuroprotection following acrolein-induced cell injury.
2010 Jan 29
Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2.
2011 Jul 14
Early treatment with olmesartan prevents juxtamedullary glomerular podocyte injury and the onset of microalbuminuria in type 2 diabetic rats.
2012 May
Patents

Sample Use Guides

In Vivo Use Guide
Initial dose: 10 mg orally 4 times a day for the first 2 to 4 days. Increase to 25 mg orally 4 times a day for the balance of the first week. For the second and subsequent weeks, increase dosage to 50 mg orally 4 times a day.
Route of Administration: Oral
In Vitro Use Guide
Hydralazine (0.03-10 mmol.L(-1)) inhibited the activities of both PKA and PKG with IC50 of 1.2 and 2.5 mmol.L(-1), respectively
Name Type Language
HYDRALAZINE
INN   MI   VANDF   WHO-DD  
INN  
Official Name English
1-HYDRAZINOPHTHALAZINE
Systematic Name English
HYDRALAZINE [WHO-DD]
Common Name English
HYDRALAZINE [MI]
Common Name English
HYDRALAZINE [INN]
Common Name English
NSC-126699
Code English
HYDRALAZINE [IARC]
Common Name English
HYDRALAZINE [VANDF]
Common Name English
PHTHALAZINE, 1-HYDRAZINO-
Systematic Name English
HIDRAL
Brand Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 334611
Created by admin on Tue Oct 22 00:48:54 UTC 2019 , Edited by admin on Tue Oct 22 00:48:54 UTC 2019
WHO-ATC C02DB02
Created by admin on Tue Oct 22 00:48:54 UTC 2019 , Edited by admin on Tue Oct 22 00:48:54 UTC 2019
WHO-ESSENTIAL MEDICINES LIST 12.3
Created by admin on Tue Oct 22 00:48:54 UTC 2019 , Edited by admin on Tue Oct 22 00:48:54 UTC 2019
FDA ORPHAN DRUG 166703
Created by admin on Tue Oct 22 00:48:54 UTC 2019 , Edited by admin on Tue Oct 22 00:48:54 UTC 2019
NDF-RT N0000175379
Created by admin on Tue Oct 22 00:48:54 UTC 2019 , Edited by admin on Tue Oct 22 00:48:54 UTC 2019
WHO-VATC QC02LG02
Created by admin on Tue Oct 22 00:48:54 UTC 2019 , Edited by admin on Tue Oct 22 00:48:54 UTC 2019
WHO-VATC QC02DB02
Created by admin on Tue Oct 22 00:48:54 UTC 2019 , Edited by admin on Tue Oct 22 00:48:54 UTC 2019
LIVERTOX 482
Created by admin on Tue Oct 22 00:48:54 UTC 2019 , Edited by admin on Tue Oct 22 00:48:54 UTC 2019
NCI_THESAURUS C270
Created by admin on Tue Oct 22 00:48:54 UTC 2019 , Edited by admin on Tue Oct 22 00:48:54 UTC 2019
NDF-RT N0000175564
Created by admin on Tue Oct 22 00:48:54 UTC 2019 , Edited by admin on Tue Oct 22 00:48:54 UTC 2019
WHO-ATC C02LG02
Created by admin on Tue Oct 22 00:48:54 UTC 2019 , Edited by admin on Tue Oct 22 00:48:54 UTC 2019
Code System Code Type Description
CAS
86-54-4
Created by admin on Tue Oct 22 00:48:54 UTC 2019 , Edited by admin on Tue Oct 22 00:48:54 UTC 2019
PRIMARY
LactMed
86-54-4
Created by admin on Tue Oct 22 00:48:54 UTC 2019 , Edited by admin on Tue Oct 22 00:48:54 UTC 2019
PRIMARY
RXCUI
5470
Created by admin on Tue Oct 22 00:48:54 UTC 2019 , Edited by admin on Tue Oct 22 00:48:54 UTC 2019
PRIMARY RxNorm
IUPHAR
7326
Created by admin on Tue Oct 22 00:48:54 UTC 2019 , Edited by admin on Tue Oct 22 00:48:54 UTC 2019
PRIMARY
PUBCHEM
3637
Created by admin on Tue Oct 22 00:48:54 UTC 2019 , Edited by admin on Tue Oct 22 00:48:54 UTC 2019
PRIMARY
DRUG BANK
DB01275
Created by admin on Tue Oct 22 00:48:54 UTC 2019 , Edited by admin on Tue Oct 22 00:48:54 UTC 2019
PRIMARY
EVMPD
SUB08059MIG
Created by admin on Tue Oct 22 00:48:54 UTC 2019 , Edited by admin on Tue Oct 22 00:48:54 UTC 2019
PRIMARY
EPA CompTox
86-54-4
Created by admin on Tue Oct 22 00:48:54 UTC 2019 , Edited by admin on Tue Oct 22 00:48:54 UTC 2019
PRIMARY
ChEMBL
CHEMBL276832
Created by admin on Tue Oct 22 00:48:54 UTC 2019 , Edited by admin on Tue Oct 22 00:48:54 UTC 2019
PRIMARY
WIKIPEDIA
HYDRALAZINE
Created by admin on Tue Oct 22 00:48:54 UTC 2019 , Edited by admin on Tue Oct 22 00:48:54 UTC 2019
PRIMARY
INN
1
Created by admin on Tue Oct 22 00:48:54 UTC 2019 , Edited by admin on Tue Oct 22 00:48:54 UTC 2019
PRIMARY
ECHA (EC/EINECS)
201-680-3
Created by admin on Tue Oct 22 00:48:54 UTC 2019 , Edited by admin on Tue Oct 22 00:48:54 UTC 2019
PRIMARY
MERCK INDEX
M6072
Created by admin on Tue Oct 22 00:48:54 UTC 2019 , Edited by admin on Tue Oct 22 00:48:54 UTC 2019
PRIMARY Merck Index
NCI_THESAURUS
C62032
Created by admin on Tue Oct 22 00:48:54 UTC 2019 , Edited by admin on Tue Oct 22 00:48:54 UTC 2019
PRIMARY
MESH
D006830
Created by admin on Tue Oct 22 00:48:54 UTC 2019 , Edited by admin on Tue Oct 22 00:48:54 UTC 2019
PRIMARY