Hydralazine

Identification

Summary

Hydralazine is an antihypertensive agent used for the management of essential hypertension or severe hypertension associated with conditions requiring immediate action, heart failure, and pre-eclampsia or eclampsia .

Brand Names

Apresoline, Bidil

Generic Name

Hydralazine

DrugBank Accession Number

DB01275

Background

Originally developed in the 1950s as a malaria treatment, hydralazine showed antihypertensive ability and was soon repurposed.¹⁵ Hydralazine is a hydrazine derivative vasodilator used alone or as adjunct therapy in the treatment of hypertension and only as adjunct therapy in the treatment of heart failure.^10,19,20 Hydralazine is no longer a first line therapy for these indications since the development of newer antihypertensive medications.¹⁷

Hydralazine hydrochloride was FDA approved on 15 January 1953.¹⁸

Type

Small Molecule

Groups

Approved

Structure

Similar Structures

Weight: Average: 160.1759
Monoisotopic: 160.074896276
Chemical Formula: C₈H₈N₄

Synonyms

(1Z)-1(2H)-Phthalazinone hydrazone
(2H)-Phthalazinone hydrazone
1-Hydrazinophthalazine
1-Phthalazinylhydrazine
6-Hydralazine
Hidralazina
Hydralazin
Hydralazine
Hydralazinum
Hydrallazine
Hydrazinophthalazine
Hydrazone 1(2H)-phthalazinone
Hypophthalin
Idralazina
Phthalazin-1-ylhydrazine

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Pharmacology

Indication

Hydralazine is indicated alone or adjunct to standard therapy to treat essential hypertension.¹⁹ A combination product with isosorbide dinitrate is indicated as an adjunct therapy in the treatment of heart failure.²⁰

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Associated Conditions

Indication Type	Indication	Combined Product Details	Approval Level	Dose Form
Management of	Essential hypertension		••••••••••••
Used in combination to treat	Heart failure	Combination Product in combination with: Isosorbide dinitrate (DB00883)	••••••••••••	••••••
Management of	Hypertensive crisis		••• •••••
Management of	Severe hypertension		••••••••••••	•••••••••• •••••••••• ••••••••

Contraindications & Blackbox Warnings

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Pharmacodynamics

Hydralazine interferes with calcium transport to relax arteriolar smooth muscle and lower blood pressure.¹⁹ Hydralazine has a short duration of action of 2-6h.¹⁰ This drug has a wide therapeutic window, as patients can tolerate doses of up to 300mg.¹⁹ Patients should be cautioned regarding the risk of developing systemic lupus erythematosus syndrome.¹⁹

Mechanism of action

Hydralazine may interfere with calcium transport in vascular smooth muscle by an unknown mechanism to relax arteriolar smooth muscle and lower blood pressure.^10,12 The interference with calcium transport may be by preventing influx of calcium into cells, preventing calcium release from intracellular compartments, directly acting on actin and myosin, or a combination of these actions.¹¹ This decrease in vascular resistance leads to increased heart rate, stroke volume, and cardiac output.¹⁹

Hydralazine also competes with protocollagen prolyl hydroxylase (CPH) for free iron.¹² This competition inhibits CPH mediated hydroxylation of HIF-1α, preventing the degradation of HIF-1α.¹² Induction of HIF-1α and VEGF promote proliferation of endothelial cells and angiogenesis.¹²

Target	Actions	Organism
AMembrane primary amine oxidase	inhibitor	Humans
UHypoxia-inducible factor 1-alpha	inducer	Humans
UProlyl 4-hydroxylase subunit alpha-1	inhibitor	Humans

Absorption

Taking oral hydralazine with food improves the bioavailability of the drug.¹³ An intravenous dose of 0.3mg/kg leads to an AUC of 17.5-29.4µM*min and a 1mg/kg oral dose leads to an AUC of 4.0-30.4µM*min.¹⁴ The C_max of oral hydralazine is 0.12-1.31µM depending on the acetylator status of patients.¹⁴

Volume of distribution

The volume of distribution is 1.34±0.79L/kg in congestive heart failure patients and 1.98±0.22L/kg in hypertensive patients.⁹

Protein binding

Hydralazine is 87% protein bound in serum¹⁹ likely to human serum albumin.²

Metabolism

Acetylation is a minor metabolic pathway for hydralazine; the major pathway is hydroxylation followed by glucuronidation.⁴ There are 5 identified metabolic pathways for hydralazine.^1,7,5,4,6,8

Hydralazine can be metabolized to phthalazine or α-ketoglutarate hydrazone.^1,4 These metabolites can be further converted to phthalazinone or hydralazine can be metabolized directly to phthalazinone.^1,4

Hydralazine can undergo a reversible converstion to the active hydralazine acetone hydrazone.^6,8

Hydralazine is spontaneously converted to the active pyruvic acid hydrazone or the pyruvic acid hydrazone tricyclic dehydration product, and these metabolites can convert back and forth between these 2 forms.^1,5

Hydralazine can be converted to hydrazinophthalazinone, which is further converted to the active acetylhydrazinophthalazinone.^1,4

The final metabolic process hydralazine can undergo is the conversion to an unnamed hydralazine metabolite, which is further metabolized to 3-methyl-s-triazolophthalazine (MTP).¹ MTP can be metabolized to 9-hydroxy-methyltriazolophthalazine or 3-hydroxy-methyltriazolophthalazine; the latter is converted to triazolophthalazine.¹

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Hydralazine

Route of elimination

<10% of hydralazine is recovered in the feces; 65-90% is recovered in the urine.⁹

Half-life

Hydralazine has a half life of 2.2-7.8h in rapid acetylators and 2.0-5.8h in slow acetylators.^4,19 The half life in heart failure patients is 57-241 minutes with an average of 105 minutes and in hypertensive patients is 200 minutes for rapid acetylators and 297 minutes for slow acetylators.⁹

Hydralazine is subject to polymorphic acetylation;¹⁶ slow acetylators generally have higher plasma levels of hydralazine and require lower doses to maintain control of pressure. However, other factors, such as acetylation being a minor metabolic pathway for hydralazine, will contribute to differences in elimination rates.

Clearance

The majority of hydralazine clearance is extrahepatic- 55% for rapid acetylators and 70% for slow acetylators.⁹ The average clearance in congestive heart failure patients is 1.77±0.48L/kg/h,⁹ while hypertensive patients have an average clearance of 42.7±8.9mL/min/kg.¹⁴

Adverse Effects

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Toxicity

The oral LD₅₀ in rats is 173-187mg/kg and the highest known dose an adult human has survived is 10g orally.¹⁹

Patients experiencing an overdose may present with hypotension, tachycardia, headache, flushing, myocardial ischemia, myocardial infarction, cardiac arrhythmia, and shock.¹⁹ Overdose can be treated through emptying the gastric contents and administering activated charcoal, though these treatments may cause further arrhythmias and shock.¹⁹ Supportive and symptomatic treatment should be administered.¹⁹

Pathways

Not Available

Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">

Interacting Gene/Enzyme	Allele name	Genotype(s)	Defining Change(s)	Type(s)	Description	Details
Arylamine N-acetyltransferase 1	NAT1*14A	Not Available	G > A \| T > A \| C > A	ADR Inferred	Associated with systemic lupus erythematosus.	Details
Arylamine N-acetyltransferase 1	NAT1*14B	Not Available	G > A	ADR Inferred	Associated with systemic lupus erythematosus.	Details
Arylamine N-acetyltransferase 1	NAT1*15	Not Available	C > T	ADR Inferred	Associated with systemic lupus erythematosus.	Details
Arylamine N-acetyltransferase 1	NAT1*17	Not Available	C > T	ADR Inferred	Associated with systemic lupus erythematosus.	Details
Arylamine N-acetyltransferase 1	NAT1*19A	Not Available	C > T	ADR Inferred	Associated with systemic lupus erythematosus.	Details
Arylamine N-acetyltransferase 1	NAT1*19B	Not Available	C > T \| C > T	ADR Inferred	Associated with systemic lupus erythematosus.	Details
Arylamine N-acetyltransferase 1	NAT1*22	Not Available	A > T	ADR Inferred	Associated with systemic lupus erythematosus.	Details
Arylamine N-acetyltransferase 2	NAT2*5A	Not Available	T > C \| C > T	ADR Inferred	Associated with systemic lupus erythematosus.	Details
Arylamine N-acetyltransferase 2	NAT2*5B	Not Available	T > C \| C > T \| A > G	ADR Inferred	Associated with systemic lupus erythematosus.	Details
Arylamine N-acetyltransferase 2	NAT2*5C	Not Available	T > C \| A > G	ADR Inferred	Associated with systemic lupus erythematosus.	Details
Arylamine N-acetyltransferase 2	NAT2*5D	Not Available	T > C	ADR Inferred	Associated with systemic lupus erythematosus.	Details
Arylamine N-acetyltransferase 2	NAT2*5E	Not Available	T > C \| G > A	ADR Inferred	Associated with systemic lupus erythematosus.	Details
Arylamine N-acetyltransferase 2	NAT2*5F	Not Available	T > C \| C > T \| C > T \| A > G	ADR Inferred	Associated with systemic lupus erythematosus.	Details
Arylamine N-acetyltransferase 2	NAT2*5G	Not Available	T > C \| C > T \| C > T \| A > G	ADR Inferred	Associated with systemic lupus erythematosus.	Details
Arylamine N-acetyltransferase 2	NAT2*5H	Not Available	T > C \| C > T \| A > G \| S287 Frameshift	ADR Inferred	Associated with systemic lupus erythematosus.	Details
Arylamine N-acetyltransferase 2	NAT2*5I	Not Available	T > C \| C > T \| A > T \| A > G	ADR Inferred	Associated with systemic lupus erythematosus.	Details
Arylamine N-acetyltransferase 2	NAT2*5J	Not Available	T > C \| C > T \| G > A	ADR Inferred	Associated with systemic lupus erythematosus.	Details
Arylamine N-acetyltransferase 2	NAT2*6A	Not Available	G > A \| C > T	ADR Inferred	Associated with systemic lupus erythematosus.	Details
Arylamine N-acetyltransferase 2	NAT2*6B	Not Available	G > A	ADR Inferred	Associated with systemic lupus erythematosus.	Details
Arylamine N-acetyltransferase 2	NAT2*6C	Not Available	G > A \| C > T \| A > G	ADR Inferred	Associated with systemic lupus erythematosus.	Details
Arylamine N-acetyltransferase 2	NAT2*6D	Not Available	G > A \| C > T \| T > C	ADR Inferred	Associated with systemic lupus erythematosus.	Details
Arylamine N-acetyltransferase 2	NAT2*6E	Not Available	G > A \| C > T	ADR Inferred	Associated with systemic lupus erythematosus.	Details
Arylamine N-acetyltransferase 2	NAT2*7A	Not Available	G > A	ADR Inferred	Associated with systemic lupus erythematosus.	Details
Arylamine N-acetyltransferase 2	NAT2*7B	Not Available	G > A \| C > T	ADR Inferred	Associated with systemic lupus erythematosus.	Details
Arylamine N-acetyltransferase 2	NAT2*10	Not Available	G > A	ADR Inferred	Associated with systemic lupus erythematosus.	Details
Arylamine N-acetyltransferase 2	NAT2*12D	Not Available	G > A \| A > G	ADR Inferred	Associated with systemic lupus erythematosus.	Details
Arylamine N-acetyltransferase 2	NAT2*14A	Not Available	G > A	ADR Inferred	Associated with systemic lupus erythematosus.	Details
Arylamine N-acetyltransferase 2	NAT2*14B	Not Available	G > A \| C > T	ADR Inferred	Associated with systemic lupus erythematosus.	Details
Arylamine N-acetyltransferase 2	NAT2*14C	Not Available	G > A \| T > C \| C > T \| A > G	ADR Inferred	Associated with systemic lupus erythematosus.	Details
Arylamine N-acetyltransferase 2	NAT2*14D	Not Available	G > A \| C > T \| G > A	ADR Inferred	Associated with systemic lupus erythematosus.	Details
Arylamine N-acetyltransferase 2	NAT2*14E	Not Available	G > A \| A > G	ADR Inferred	Associated with systemic lupus erythematosus.	Details
Arylamine N-acetyltransferase 2	NAT2*14F	Not Available	G > A \| T > C \| A > G	ADR Inferred	Associated with systemic lupus erythematosus.	Details
Arylamine N-acetyltransferase 2	NAT2*14G	Not Available	G > A \| C > T \| A > G	ADR Inferred	Associated with systemic lupus erythematosus.	Details
Arylamine N-acetyltransferase 2	NAT2*17	Not Available	A > C	ADR Inferred	Associated with systemic lupus erythematosus.	Details
Arylamine N-acetyltransferase 2	NAT2*19	Not Available	C > T	ADR Inferred	Associated with systemic lupus erythematosus.	Details

Interactions

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This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.

Drug	Interaction
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Abacavir	Abacavir may decrease the excretion rate of Hydralazine which could result in a higher serum level.
Abaloparatide	The risk or severity of adverse effects can be increased when Hydralazine is combined with Abaloparatide.
Abemaciclib	The serum concentration of Abemaciclib can be increased when it is combined with Hydralazine.
Acalabrutinib	The serum concentration of Acalabrutinib can be increased when it is combined with Hydralazine.
Acebutolol	Acebutolol may increase the hypotensive activities of Hydralazine.

Food Interactions

Take with or without food. Food increases exposure to hydralazine, though this may not be clinically significant.

Products

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Product Ingredients

Ingredient	UNII	CAS	InChI Key
Hydralazine hydrochloride	FD171B778Y	304-20-1	ZUXNZUWOTSUBMN-UHFFFAOYSA-N

Product Images

International/Other Brands

Alphapress (Alphapharm) / Aprezin (Johnson) / Cesoline W (Pharmasant) / Cesoline Y (Pharmasant) / Diazide (The Central) / Hidral (Biocontrol) / Pressfall (Nisshin Seiyaku) / Serpathiazide (Washington)

Brand Name Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Apresoline	Solution	20 mg / mL	Intravenous	Sterimax Inc	1992-12-31	Not applicable
Apresoline hydrochloride	Tablet, coated	50 mg/1	Oral	Novartis Pharmaceuticals Corporation	1953-01-15	2010-10-07
Apresoline hydrochloride	Tablet, coated	25 mg/1	Oral	Novartis Pharmaceuticals Corporation	1953-01-15	2010-10-07
Apresoline hydrochloride	Tablet, coated	50 mg/1	Oral	Physicians Total Care, Inc.	1995-02-17	2010-10-07
Apresoline hydrochloride	Tablet, coated	100 mg/1	Oral	Novartis Pharmaceuticals Corporation	1953-01-15	2010-10-07

Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Apo-hydralazine	Tablet	50 mg	Oral	Apotex Corporation	1991-12-31	Not applicable
Apo-hydralazine	Tablet	25 mg	Oral	Apotex Corporation	1991-12-31	Not applicable
Apo-hydralazine	Tablet	10 mg	Oral	Apotex Corporation	1990-12-31	Not applicable
Hydralazine	Tablet	25 mg/1	Oral	Cardinal Health	2009-09-14	2020-11-30
Hydralazine	Tablet	25 mg/1	Oral	Nivagen Pharmaceuticals, Inc.	2017-02-15	Not applicable

Over the Counter Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End	Region	Image
ไดลาซิน 25	Tablet, coated	25 mg	Oral	บริษัท พอนด์ เคมีคอล จำกัด	2017-10-21	Not applicable

Mixture Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End
BiDil	Hydralazine hydrochloride (37.5 mg/1) + Isosorbide dinitrate (20 mg/1)	Tablet, film coated	Oral	Arbor Pharmaceuticals	2005-06-23	2015-12-31
BiDil	Hydralazine hydrochloride (37.5 mg/1) + Isosorbide dinitrate (20 mg/1)	Tablet, film coated	Oral	Remedy Repack	2013-10-08	2013-10-09
BiDil	Hydralazine hydrochloride (37.5 mg/1) + Isosorbide dinitrate (20 mg/1)	Tablet, film coated	Oral	Azurity	2012-12-05	Not applicable
Hydralazine HCl and Hydrochlorothiazide	Hydralazine hydrochloride (50 mg/1) + Hydrochlorothiazide (50 mg/1)	Capsule	Oral	Par Pharmaceutical	1985-10-21	2009-10-29
Hydralazine HCl and Hydrochlorothiazide	Hydralazine hydrochloride (25 mg/1) + Hydrochlorothiazide (25 mg/1)	Capsule	Oral	Par Pharmaceutical	1985-10-21	2009-10-29

Chemical Identifiers

UNII: 26NAK24LS8
CAS number: 86-54-4
InChI Key: RPTUSVTUFVMDQK-UHFFFAOYSA-N
InChI: InChI=1S/C8H8N4/c9-11-8-7-4-2-1-3-6(7)5-10-12-8/h1-5H,9H2,(H,11,12)
IUPAC Name: 1-hydrazinylphthalazine
SMILES: NNC1=NN=CC2=CC=CC=C12

References

Synthesis Reference

U.S. Patent 2,484,029.

General References

Hofstra AH: Metabolism of hydralazine: relevance to drug-induced lupus. Drug Metab Rev. 1994;26(3):485-505. doi: 10.3109/03602539408998315. [Article]
Bolattin M, Nandibewoor S, Joshi S, Dixit S, Chimatadar S: Interaction of Hydralazine with Human Serum Albumin and Effect of β-Cyclodextrin on Binding: Insights from Spectroscopic and Molecular Docking Techniques Industrial & Engineering Chemistry Research. 2016 Apr 24;55(19):5454-5464. [Article]
Machado JD, Gomez JF, Betancor G, Camacho M, Brioso MA, Borges R: Hydralazine reduces the quantal size of secretory events by displacement of catecholamines from adrenomedullary chromaffin secretory vesicles. Circ Res. 2002 Nov 1;91(9):830-6. doi: 10.1161/01.res.0000039530.30495.6f. [Article]
Reidenberg MM, Drayer D, DeMarco AL, Bello CT: Hydralazine elimination in man. Clin Pharmacol Ther. 1973 Nov-Dec;14(6):970-7. doi: 10.1002/cpt1973146970. [Article]
Haegele KD, Skrdlant HB, Talseth T, McNay JL, Shepherd AM, Clementi WA: Quantitative analysis of hydralazine pyruvic acid hydrazone, the major plasma metabolite of hydralazine. J Chromatogr. 1980 Jan 4;187(1):171-9. doi: 10.1016/s0021-9673(00)87883-8. [Article]
Talseth T, McNay JL, Haegele KD: Hypotensive effect of the hydralazine--acetone hydrazone in conscious rabbits: evidence for its back-conversion to hydralazine in vivo. J Cardiovasc Pharmacol. 1982 May-Jun;4(3):370-4. doi: 10.1097/00005344-198205000-00005. [Article]
Reece PA: Hydralazine and related compounds: chemistry, metabolism, and mode of action. Med Res Rev. 1981 Spring;1(1):73-96. [Article]
Iwaki M, Ogiso T, Ito Y: Pharmacokinetics and biotransformation of hydralazine acetone hydrazone, a metabolite of hydralazine, in the rat. J Pharm Sci. 1989 Oct;78(10):867-73. doi: 10.1002/jps.2600781018. [Article]
Mulrow JP, Crawford MH: Clinical pharmacokinetics and therapeutic use of hydralazine in congestive heart failure. Clin Pharmacokinet. 1989 Feb;16(2):86-9. doi: 10.2165/00003088-198916020-00003. [Article]
Herman LL, Tivakaran VS: Hydralazine . [Article]
Jacobs M: Mechanism of action of hydralazine on vascular smooth muscle. Biochem Pharmacol. 1984 Sep 15;33(18):2915-9. doi: 10.1016/0006-2952(84)90216-8. [Article]
Knowles HJ, Tian YM, Mole DR, Harris AL: Novel mechanism of action for hydralazine: induction of hypoxia-inducible factor-1alpha, vascular endothelial growth factor, and angiogenesis by inhibition of prolyl hydroxylases. Circ Res. 2004 Jul 23;95(2):162-9. Epub 2004 Jun 10. [Article]
Walden RJ, Hernandez R, Witts D, Graham BR, Prichard BN: Effect of food on the absorption of hydralazine in man. Eur J Clin Pharmacol. 1981;20(1):53-8. doi: 10.1007/bf00554667. [Article]
Ludden TM, McNay JL Jr, Shepherd AM, Lin MS: Variability of plasma hydralazine concentrations in male hypertensive patients. Arthritis Rheum. 1981 Aug;24(8):987-93. doi: 10.1002/art.1780240802. [Article]
Aeddula NR, Pathireddy S, Ansari A, Juran PJ: Hydralazine-associated antineutrophil cytoplasmic antibody vasculitis with pulmonary-renal syndrome. BMJ Case Rep. 2018 Nov 8;2018. pii: bcr-2018-227161. doi: 10.1136/bcr-2018-227161. [Article]
Timbrell JA, Harland SJ, Facchini V: Polymorphic acetylation of hydralazine. Clin Pharmacol Ther. 1980 Sep;28(3):350-5. doi: 10.1038/clpt.1980.173. [Article]
McInnes G (2007). 84. In Comprehensive Hypertension (pp. 1037-1048). Elsevier. [ISBN:978-0-323-03961-1]
FDA Approved Drug Products: Apresoline Hydralazine Hydrochloride Tablets and Injections (Discontinued) [Link]
FDA Approved Drug Products: Hydralazine Hydrochloride Oral Tablets [Link]
FDA Approved Drug Products: Hydralazine and Isosorbide Dinitrate Oral Tablets [Link]

External Links

Human Metabolome Database: HMDB0015400
KEGG Drug: D08044
KEGG Compound: C07040
PubChem Compound: 3637
PubChem Substance: 46507533
ChemSpider: 3511
BindingDB: 81461
RxNav: 5470
ChEBI: 5775
ChEMBL: CHEMBL276832
ZINC: ZINC000012360535
Therapeutic Targets Database: DAP000728
PharmGKB: PA449894
PDBe Ligand: HLZ
RxList: RxList Drug Page
Drugs.com: Drugs.com Drug Page
Wikipedia: Hydralazine

PDB Entries

3ltw

MSDS

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Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">

Phase	Status	Purpose	Conditions	Count
4	Completed	Diagnostic	Hypertension / Type 2 Diabetes Mellitus	1
4	Completed	Prevention	Chronic Hemodialysis (ESRD)	1
4	Completed	Treatment	Congestive Heart Failure (CHF)	1
4	Completed	Treatment	Hypertension	2
4	Completed	Treatment	Stage II Hypertension	1

Pharmacoeconomics

Manufacturers

Not Available

Packagers

Advanced Pharmaceutical Services Inc.
American Regent
Amerisource Health Services Corp.
APP Pharmaceuticals
A-S Medication Solutions LLC
Camber Pharmaceuticals Inc.
Cardinal Health
Caremark LLC
Direct Dispensing Inc.
DispenseXpress Inc.
Dispensing Solutions
Diversified Healthcare Services Inc.
General Injectables and Vaccines Inc.
Glenmark Generics Ltd.
Goldline Laboratories Inc.
Heartland Repack Services LLC
Heritage Pharmaceuticals
Hetero Drugs Ltd.
Ivax Pharmaceuticals
Kaiser Foundation Hospital
Lake Erie Medical and Surgical Supply
Luitpold Pharmaceuticals Inc.
Major Pharmaceuticals
Mckesson Corp.
Murfreesboro Pharmaceutical Nursing Supply
Mutual Pharmaceutical Co.
Nucare Pharmaceuticals Inc.
Palmetto Pharmaceuticals Inc.
Par Pharmaceuticals
PCA LLC
PD-Rx Pharmaceuticals Inc.
Pharmedix
Physicians Total Care Inc.
Pliva Inc.
Prepackage Specialists
Prepak Systems Inc.
Qualitest
Remedy Repack
Sandhills Packaging Inc.
Southwood Pharmaceuticals
Teva Pharmaceutical Industries Ltd.
UDL Laboratories
United Research Laboratories Inc.
Vangard Labs Inc.

Dosage Forms

Form	Route	Strength
Solution	Parenteral	20 mg
Solution	Intravenous	20 mg
Tablet, film coated	Oral	25 mg
Tablet, film coated	Oral	50 mg
Solution	Intravenous	20 mg / mL
Powder		20 mg/1ampoule
Injection, powder, for solution	Intravenous	20 mg/ampoule
Tablet, coated	Oral	10 mg/1
Tablet, coated	Oral	100 mg/1
Tablet, coated	Oral	25 mg/1
Tablet, coated	Oral	50 mg/1
Tablet, film coated	Oral
Solution	Parenteral	20.00 mg
Solution	Intravenous	20.000 mg
Capsule	Oral
Injection	Intramuscular; Intravascular	20 mg/1mL
Injection	Intramuscular; Intravenous	20 mg/1mL
Injection, solution	Intramuscular; Intravenous	20 mg/1mL
Tablet	Oral	10 mg/1
Tablet	Oral	100 mg/1
Tablet	Oral	25 mg/1
Tablet	Oral	50 mg/1
Tablet, film coated	Oral	10 mg/1
Tablet, film coated	Oral	100 mg/1
Tablet, film coated	Oral	25 mg/1
Tablet, film coated	Oral	50 mg/1
Injection	Intramuscular; Intravenous
Tablet	Oral	10 mg
Tablet, film coated	Oral	10 mg
Solution	Parenteral	20.000 mg
Tablet	Oral	25 mg
Tablet	Oral	50 mg
Solution	Intramuscular	20.000 mg
Tablet, coated	Oral
Tablet	Oral	83.000 mg
Tablet, coated	Oral	50 mg
Tablet	Oral
Tablet, coated	Oral	10 mg
Tablet, coated	Oral	25 mg
Tablet, sugar coated	Oral	25 mg

Prices

Unit description	Cost	Unit
Hydralazine 20 mg/ml vial	18.0USD	ml
Hydralazine 100 mg tablet	1.65USD	tablet
Hydralazine-HCTZ 50-50 mg capsule	1.2USD	capsule
HydrALAZINE HCl 100 mg tablet	1.05USD	tablet
Hydralazine-HCTZ 25-25 mg capsule	0.81USD	capsule
Hydralazine-HCTZ 100-50 mg capsule	0.75USD	capsule
HydrALAZINE HCl 50 mg tablet	0.67USD	tablet
Apresoline 50 mg tablet	0.65USD	tablet
HydrALAZINE HCl 25 mg tablet	0.53USD	tablet
HydrALAZINE HCl 10 mg tablet	0.47USD	tablet
Hydralazine 50 mg tablet	0.44USD	tablet
Hydralazine 25 mg tablet	0.35USD	tablet
Apo-Hydralazine 50 mg Tablet	0.29USD	tablet
Novo-Hylazin 50 mg Tablet	0.29USD	tablet
Apo-Hydralazine 25 mg Tablet	0.24USD	tablet
Hydralazine 10 mg tablet	0.22USD	tablet
Apo-Hydralazine 10 mg Tablet	0.11USD	tablet
Novo-Hylazin 10 mg Tablet	0.11USD	tablet

DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.

Patents

Patent Number	Pediatric Extension	Approved	Expires (estimated)	Region
US6465463	No	2002-10-15	2020-09-08
US6784177	No	2004-08-31	2020-09-08

Properties

State

Solid

Experimental Properties

Property	Value	Source
melting point (°C)	172-173 °C	U.S. Patent 2,484,029.
boiling point (°C)	251.3	ChemSpider
water solubility	<1mg/mL	ChemSpider
logP	1.00	SANGSTER (1993)
pKa	7.3	Machado (2002)

Predicted Properties

Property	Value	Source
Water Solubility	2.64 mg/mL	ALOGPS
logP	0.66	ALOGPS
logP	0.75	Chemaxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	17.69	Chemaxon
pKa (Strongest Basic)	8.88	Chemaxon
Physiological Charge	1	Chemaxon
Hydrogen Acceptor Count	4	Chemaxon
Hydrogen Donor Count	2	Chemaxon
Polar Surface Area	63.83 Å²	Chemaxon
Rotatable Bond Count	1	Chemaxon
Refractivity	50.23 m³·mol^-1	Chemaxon
Polarizability	16.06 Å³	Chemaxon
Number of Rings	2	Chemaxon
Bioavailability	1	Chemaxon
Rule of Five	Yes	Chemaxon
Ghose Filter	Yes	Chemaxon
Veber's Rule	No	Chemaxon
MDDR-like Rule	No	Chemaxon

Predicted ADMET Features

Property	Value	Probability
Human Intestinal Absorption	+	0.9854
Blood Brain Barrier	+	0.9487
Caco-2 permeable	+	0.8867
P-glycoprotein substrate	Non-substrate	0.686
P-glycoprotein inhibitor I	Non-inhibitor	0.9478
P-glycoprotein inhibitor II	Non-inhibitor	0.9826
Renal organic cation transporter	Non-inhibitor	0.8279
CYP450 2C9 substrate	Non-substrate	0.8971
CYP450 2D6 substrate	Non-substrate	0.9116
CYP450 3A4 substrate	Non-substrate	0.7467
CYP450 1A2 substrate	Inhibitor	0.9106
CYP450 2C9 inhibitor	Non-inhibitor	0.9071
CYP450 2D6 inhibitor	Non-inhibitor	0.9231
CYP450 2C19 inhibitor	Non-inhibitor	0.9025
CYP450 3A4 inhibitor	Inhibitor	0.526
CYP450 inhibitory promiscuity	Low CYP Inhibitory Promiscuity	0.5294
Ames test	AMES toxic	0.9107
Carcinogenicity	Non-carcinogens	0.7719
Biodegradation	Not ready biodegradable	1.0
Rat acute toxicity	3.2187 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.9253
hERG inhibition (predictor II)	Non-inhibitor	0.8589

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	splash10-01q9-1900000000-f91e3313037f100cda4a
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	splash10-03di-0900000000-d31fd54f379f4812178d
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0a4i-1900000000-9335ad3a2c549922182e
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	splash10-01ox-6900000000-f987386056bc83a6f9f4
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	splash10-056r-0900000000-e4b73bef19648942bf09
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	splash10-004i-0900000000-75ae1b387070d2671ab4
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0udl-9500000000-1e012c2a16b637d3cd06
Predicted 1H NMR Spectrum	1D NMR	Not Applicable
Predicted 13C NMR Spectrum	1D NMR	Not Applicable

Chromatographic Properties

Collision Cross Sections (CCS)

Adduct	CCS Value (Å²)	Source type	Source
[M-H]-	134.4621392	predicted	DarkChem Lite v0.1.0
[M-H]-	134.3885392	predicted	DarkChem Lite v0.1.0
[M-H]-	128.11522	predicted	DeepCCS 1.0 (2019)
[M+H]+	135.0616392	predicted	DarkChem Lite v0.1.0
[M+H]+	134.9165392	predicted	DarkChem Lite v0.1.0
[M+H]+	131.94301	predicted	DeepCCS 1.0 (2019)
[M+Na]+	134.9794392	predicted	DarkChem Lite v0.1.0
[M+Na]+	134.6814392	predicted	DarkChem Lite v0.1.0
[M+Na]+	140.85289	predicted	DeepCCS 1.0 (2019)

Targets

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Details1. Membrane primary amine oxidase

Kind: Protein
Organism: Humans
Pharmacological action: Yes
Actions: Inhibitor

General Function: Tryptamine:oxygen oxidoreductase (deaminating) activity
Specific Function: Cell adhesion protein that participates in lymphocyte extravasation and recirculation by mediating the binding of lymphocytes to peripheral lymph node vascular endothelial cells in an L-selectin-in...
Gene Name: AOC3
Uniprot ID: Q16853
Uniprot Name: Membrane primary amine oxidase
Molecular Weight: 84621.27 Da

References

Claud P, Padovani P, Guichard JP, Artur Y, Laine R: Involvement of semicarbazide-sensitive amine oxidase in tresperimus metabolism in human and in rat. Drug Metab Dispos. 2001 May;29(5):735-41. [Article]
Vidrio H, Medina M, Gonzalez-Romo P, Lorenzana-Jimenez M, Diaz-Arista P, Baeza A: Semicarbazide-sensitive amine oxidase substrates potentiate hydralazine hypotension: possible role of hydrogen peroxide. J Pharmacol Exp Ther. 2003 Nov;307(2):497-504. Epub 2003 Sep 11. [Article]
Vidrio H: Semicarbazide-sensitive amine oxidase: role in the vasculature and vasodilation after in situ inhibition. Auton Autacoid Pharmacol. 2003 Oct-Dec;23(5-6):275-83. [Article]
Vidrio H, Medina M: 2-bromoethylamine, a suicide inhibitor of semicarbazide-sensitive amine oxidase, increases hydralazine hypotension in rats. J Cardiovasc Pharmacol. 2005 Sep;46(3):316-24. [Article]
Vidrio H, Medina M: Hypotensive effect of hydroxylamine, an endogenous nitric oxide donor and SSAO inhibitor. J Neural Transm (Vienna). 2007;114(6):863-5. Epub 2007 Mar 26. [Article]
Gronvall JL, Garpenstrand H, Oreland L, Ekblom J: An autoradiographic method of visualising semicarbazide-sensitive amine oxidase activity in mouse tissue sections. Neurobiology (Bp). 2000;8(2):167-77. [Article]
Gronvall JL, Garpenstrand H, Oreland L, Ekblom J: Autoradiographic imaging of formaldehyde adducts in mice: possible relevance for vascular damage in diabetes. Life Sci. 1998;63(9):759-68. [Article]
Lizcano JM, Fernandez de Arriba A, Tipton KF, Unzeta M: Inhibition of bovine lung semicarbazide-sensitive amine oxidase (SSAO) by some hydrazine derivatives. Biochem Pharmacol. 1996 Jul 26;52(2):187-95. [Article]
Lyles GA, McDougall SA: The enhanced daily excretion of urinary methylamine in rats treated with semicarbazide or hydralazine may be related to the inhibition of semicarbazide-sensitive amine oxidase activities. J Pharm Pharmacol. 1989 Feb;41(2):97-100. [Article]
Barrand MA, Callingham BA: The interaction of hydralazine with a semicarbazide-sensitive amine oxidase in brown adipose tissue of the rat. Its use as a radioactive ligand for the enzyme. Biochem J. 1985 Dec 1;232(2):415-23. [Article]
Barrand MA, Fox SA: Amine oxidase activities in brown adipose tissue of the rat: identification of semicarbazide-sensitive (clorgyline-resistant) activity at the fat cell membrane. J Pharm Pharmacol. 1984 Oct;36(10):652-8. [Article]

Details2. Hypoxia-inducible factor 1-alpha

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Inducer

General Function: Ubiquitin protein ligase binding
Specific Function: Functions as a master transcriptional regulator of the adaptive response to hypoxia. Under hypoxic conditions, activates the transcription of over 40 genes, including erythropoietin, glucose transp...
Gene Name: HIF1A
Uniprot ID: Q16665
Uniprot Name: Hypoxia-inducible factor 1-alpha
Molecular Weight: 92669.595 Da

References

Knowles HJ, Tian YM, Mole DR, Harris AL: Novel mechanism of action for hydralazine: induction of hypoxia-inducible factor-1alpha, vascular endothelial growth factor, and angiogenesis by inhibition of prolyl hydroxylases. Circ Res. 2004 Jul 23;95(2):162-9. Epub 2004 Jun 10. [Article]

Details3. Prolyl 4-hydroxylase subunit alpha-1

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Inhibitor

General Function: Procollagen-proline 4-dioxygenase activity
Specific Function: Catalyzes the post-translational formation of 4-hydroxyproline in -Xaa-Pro-Gly- sequences in collagens and other proteins.
Gene Name: P4HA1
Uniprot ID: P13674
Uniprot Name: Prolyl 4-hydroxylase subunit alpha-1
Molecular Weight: 61048.775 Da

References

Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
Knowles HJ, Tian YM, Mole DR, Harris AL: Novel mechanism of action for hydralazine: induction of hypoxia-inducible factor-1alpha, vascular endothelial growth factor, and angiogenesis by inhibition of prolyl hydroxylases. Circ Res. 2004 Jul 23;95(2):162-9. Epub 2004 Jun 10. [Article]
Murad S, Tajima S, Pinnell SR: A paradoxical effect of hydralazine on prolyl and lysyl hydroxylase activities in cultured human skin fibroblasts. Arch Biochem Biophys. 1985 Sep;241(2):356-63. [Article]
Chen KH, Paz MA, Gallop PM: Collagen prolyl hydroxylation in WI-38 fibroblast cultures: action of hydralazine. In Vitro. 1977 Jan;13(1):49-54. [Article]

Enzymes

Details1. Cytochrome P450 3A4

Kind: Protein
Organism: Humans
Pharmacological action: No
Actions: Inhibitor

General Function: Vitamin d3 25-hydroxylase activity
Specific Function: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name: CYP3A4
Uniprot ID: P08684
Uniprot Name: Cytochrome P450 3A4
Molecular Weight: 57342.67 Da

References

Zhao XJ, Ishizaki T: Metabolic interactions of selected antimalarial and non-antimalarial drugs with the major pathway (3-hydroxylation) of quinine in human liver microsomes. Br J Clin Pharmacol. 1997 Nov;44(5):505-11. [Article]

Carriers

Details1. Serum albumin

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Binder

General Function: Toxic substance binding
Specific Function: Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name: ALB
Uniprot ID: P02768
Uniprot Name: Serum albumin
Molecular Weight: 69365.94 Da

References

Bolattin M, Nandibewoor S, Joshi S, Dixit S, Chimatadar S: Interaction of Hydralazine with Human Serum Albumin and Effect of β-Cyclodextrin on Binding: Insights from Spectroscopic and Molecular Docking Techniques Industrial & Engineering Chemistry Research. 2016 Apr 24;55(19):5454-5464. [Article]

Drug created at May 16, 2007 20:38 / Updated at February 20, 2024 23:55

Hydralazine

Identification

Structure for Hydralazine (DB01275)

Pharmacology

Interactions

Products

Categories

Chemical Identifiers

References

Clinical Trials

Pharmacoeconomics

Properties

Spectra

Collision Cross Sections (CCS)

Targets

References

References

References

Enzymes

References

Carriers

References