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

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
Immunological side-effects of antihypertensive drugs.
1979
Effects of chronic treatment with captopril (SQ 14,225), an orally active inhibitor of angiotensin I-converting enzyme, in spontaneously hypertensive rats.
1979 Apr
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
Suppression of ventricular arrhythmias after coronary artery ligation by pinacidil, a vasodilator drug.
1985 Sep-Oct
Drug-associated glomerulopathies.
1986
Comparative study of endralazine and hydralazine for the treatment of hypertension uncontrolled by a beta-blocker and diuretic.
1986
Clinical pharmacology and therapeutic role of prazosin and related alpha-adrenoceptor antagonists.
1986
Therapeutic advantage of converting enzyme inhibitors in arresting progressive renal disease associated with systemic hypertension in the rat.
1986 Jun
Inhibition of sympathoadrenal activity by atrial natriuretic factor in dogs.
1987 Apr
Isolated minimal change nephropathy associated with diclofenac.
1987 Jul 18
Vasodilators and regression of left ventricular hypertrophy. Hydralazine versus prazosin in hypertensive humans.
1987 May
Hydralazine-induced cholestatic jaundice following liver transplantation.
1989 Jan
Myocardial ischemia during isoflurane anesthesia: the effect of substituting halothane.
1989 Jun
Prevention of arterial disease in experimental renal hypertension.
1990 Apr
Changes of atrial natriuretic peptide and its messenger RNA with development and regression of cardiac hypertrophy in renovascular hypertensive rats.
1990 Jan
Acute cocaine toxicity: antagonism by agents interacting with adrenoceptors.
1990 Jun
Hemodynamic effects of adenosine agonists in the conscious spontaneously hypertensive rat.
1990 Sep
A comparison of enalapril with hydralazine-isosorbide dinitrate in the treatment of chronic congestive heart failure.
1991 Aug 1
Cardiotoxicity of hydralazine and minoxidil in the rat. Influence of age.
1991 Feb
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
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
Epigenetics of cervical cancer. An overview and therapeutic perspectives.
2005 Oct 25
2-bromoethylamine, a suicide inhibitor of semicarbazide-sensitive amine oxidase, increases hydralazine hypotension in rats.
2005 Sep
Role of connective tissue growth factor in vascular and renal damage associated with hypertension in rats. Interactions with angiotensin II.
2006 Dec
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
Antineoplastic effects of the DNA methylation inhibitor hydralazine and the histone deacetylase inhibitor valproic acid in cancer cell lines.
2006 Jan 31
Differential expression of components of the cardiomyocyte adrenomedullin/intermedin receptor system following blood pressure reduction in nitric oxide-deficient hypertension.
2006 Mar
Desensitization of platelet-derived growth factor receptor-beta by oxidized lipids in vascular cells and atherosclerotic lesions: prevention by aldehyde scavengers.
2006 Mar 31
Antihypertensive drugs clonidine, diazoxide, hydralazine and furosemide regulate the production of cytokines by placentas and peripheral blood mononuclear cells in normal pregnancy.
2006 May
Early and sustained benefit on event-free survival and heart failure hospitalization from fixed-dose combination of isosorbide dinitrate/hydralazine: consistency across subgroups in the African-American Heart Failure Trial.
2007 Apr 3
A randomised comparison of hydralazine and mini-bolus diazoxide for hypertensive emergencies in pregnancy: the PIVOT trial.
2007 Aug
The effects of DNA methylation and histone deacetylase inhibitors on human papillomavirus early gene expression in cervical cancer, an in vitro and clinical study.
2007 Feb 26
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
Simultaneous posterior ischemic optic neuropathy, cerebral border zone infarction, and spinal cord infarction after correction of malignant hypertension.
2008 Sep
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
Hydralazine for essential hypertension.
2010 Aug 4
Chitosan nanoparticle-based neuronal membrane sealing and neuroprotection following acrolein-induced cell injury.
2010 Jan 29
HDAC inhibition attenuates inflammatory, hypertrophic, and hypertensive responses in spontaneously hypertensive rats.
2010 Sep
Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2.
2011 Jul 14
Antiatherogenic effect of bisvanillyl-hydralazone, a new hydralazine derivative with antioxidant, carbonyl scavenger, and antiapoptotic properties.
2011 Jun
Angiotensin II-induced vascular endothelial dysfunction through RhoA/Rho kinase/p38 mitogen-activated protein kinase/arginase pathway.
2011 May
Early treatment with olmesartan prevents juxtamedullary glomerular podocyte injury and the onset of microalbuminuria in type 2 diabetic rats.
2012 May
Diesel exhaust induced pulmonary and cardiovascular impairment: the role of hypertension intervention.
2013 Apr 15
Acrolein and chloroacetaldehyde: an examination of the cell and cell-free biomarkers of toxicity.
2013 Feb 25
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