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Hydralazine hydrochloride

Product Name
Hydralazine hydrochloride
CAS No.
304-20-1
Chemical Name
Hydralazine hydrochloride
Synonyms
Apulon;Lopres;Asozart;Hyperex;Lopress;apresine;Dralzine;HSDB 434;Rolazine;Hyperazin
CBNumber
CB5113442
Molecular Formula
C8H9ClN4
Formula Weight
196.64
MOL File
304-20-1.mol
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Hydralazine hydrochloride Property

Melting point:
273°C
Boiling point:
322.13°C (rough estimate)
Density 
1.2961 (rough estimate)
refractive index 
1.6110 (estimate)
storage temp. 
2-8°C
solubility 
Soluble in water, slightly soluble in ethanol (96 per cent), very slightly soluble in methylene chloride
color 
White to Almost white
PH
pH (20g/l, 25℃) : 3.5~4.5
Water Solubility 
Soluble in water. Slightly soluble in diethyl ether and alcohol.
Merck 
14,4763
BRN 
3568329
BCS Class
3
Stability:
Stable. Incompatible with strong oxidizing agents.
InChIKey
ZUXNZUWOTSUBMN-UHFFFAOYSA-N
CAS DataBase Reference
304-20-1(CAS DataBase Reference)
EPA Substance Registry System
1(2H)-Phthalazinone, hydrazone, monohydrochloride (304-20-1)
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Safety

Hazard Codes 
Xn
Risk Statements 
22-36/37/38
Safety Statements 
26-36/37/39-45
RIDADR 
UN 2811 6.1/PG 3
WGK Germany 
3
RTECS 
TH9000000
TSCA 
Yes
HazardClass 
6.1
PackingGroup 
III
HS Code 
29339900
Hazardous Substances Data
304-20-1(Hazardous Substances Data)
Toxicity
LD50 oral in rat: 280mg/kg
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H301Toxic if swalloed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
H1753
Product name
Hydralazine hydrochloride
Packaging
5g
Price
$72.3
Updated
2024/03/01
Sigma-Aldrich
Product number
PHR3184
Product name
Hydralazine Hydrochloride
Purity
pharmaceutical secondary standard, certified reference material
Packaging
500MG
Price
$200
Updated
2024/03/01
Sigma-Aldrich
Product number
1313006
Product name
Hydralazine hydrochloride
Purity
United States Pharmacopeia (USP) Reference Standard
Packaging
200mg
Price
$436
Updated
2024/03/01
TCI Chemical
Product number
H0409
Product name
1-Hydrazinophthalazine Hydrochloride
Purity
>99.0%(HPLC)(T)
Packaging
5g
Price
$40
Updated
2024/03/01
TCI Chemical
Product number
H0409
Product name
1-Hydrazinophthalazine Hydrochloride
Purity
>99.0%(HPLC)(T)
Packaging
25g
Price
$158
Updated
2024/03/01
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Hydralazine hydrochloride Chemical Properties,Usage,Production

Description

Hydralazine is an orally bioavailable vasodilator and antihypertensive agent. It decreases DNA methylation in Jurkat cells at a concentration of 10 μM and inhibits extracellular and intracellular production of reactive oxygen species (ROS) in rat macrophages activated by phorbol 12-myristate 13-acetate (PMA; ) at a concentration of 100 μM. Hydralazine (100 μM) also decreases nitric oxide production and mRNA expression of inducible nitric oxide synthase (iNOS) in rat macrophages activated by LPS (Item Nos. 19660| 19661| 19662) and interferon-γ (IFN-γ). It reduces contraction of rat aortic arterial strips induced by potassium and norepinephrine (; IC50s = 2.2 and 3.06 mM, respectively). Hydralazine (2.6 mg/kg) lowers mean arterial blood pressure (MAP) by 41.76% in conscious rats. Formulations containing hydralazine have been used in the treatment of high blood pressure and heart failure.

Chemical Properties

White Crystalline Solid

Originator

Apresoline HCl,Ciba,US,1952

Uses

Hydralazine hydrochloride has been used:

  • as a vasodilator to study its effects on hypertension in T-cell frequencies in juvenile rats
  • as a semicarbazide-sensitive amine oxidase (SSAO) inhibitor to study its effects on myocardial ischemia-reperfusion (I/R) injury
  • as a vasodilator to study its effects on insulin secretion and glucose tolerance

Uses

Inhibits DNA methyltransferase and modulates epigenetic regulation of gene expression. Non-selective MAO-A/B inhibitor; semicarbazide sensitive amine oxidase inhibitor. Antihypertensive

Uses

Hydralazine is a non-nucleoside analog that inhibits DNA methylation and reactivates the expression of tumor suppressor genes. Non-selective MAO-A/B inhibitor; semicarbazide-sensitive amine oxidase inhibitor. Antihypertensive.

Definition

ChEBI: The hydrochloride salt of hydralazine; a direct-acting vasodilator that is used as an antihypertensive agent.

Manufacturing Process

30 parts by weight of phthalazone are converted to 1-chlorophthalazine by the method described in Ber. d. deutsch. chem. Ges., vol 26, page 521 (1893). The freshly obtained yet moist chloro compound is heated on the water bath for two hours in a mixture of 100 parts by volume of ethyl alcohol and 90 parts by volume of hydrazine hydrate. Preferably after filtering, 1-hydrazinephthalazine crystallizes out in yellow needles on cooling.
It is filtered with suction and washed with cold ethyl alcohol. The compound is crystallized from methyl alcohol, and melts, when rapidly heated, at 172° to 173°C. On warming in alcoholic or aqueous hydrochloric acid, the hydrochloride of MP 273°C (with decomposition) is obtained.

brand name

Apresoline (Novartis); Dralzine (Teva).

Therapeutic Function

Antihypertensive

General Description

Hydralazine hydrochloride,1-hydrazinophthalazine monohydrochloride(Apresoline hydrochloride), originated from the work of achemist attempting to produce some unusual chemicalcompounds and from the observation that this compoundhad antihypertensive properties. It occurs as yellow crystalsand is soluble in water to the extent of about 3%. A 2%aqueous solution has a pH of 3.5 to 4.5.

Contact allergens

Hydralazine is a hydrazine derivative used as a antihypertensive drug. Skin rashes have been described during treatment. Exposure occurs mainly in the pharmaceutical industry. Cross-sensitivity is frequent with hydrazine, which is considered to be a potent sensitizer.

Biochem/physiol Actions

Hydralazine hydrochloride has therapeutic effects against heart failure and high blood pressure.

Mechanism of action

The only drug in this group, hydralazine, does not fit neatly into the other mechanistic classes, in part because its mechanism of action is not entirely clear. It appears to have multiple, direct effects on the VSM. Hydralazine, a phthalazine-substituted hydrazine antihypertensive drug with a pKa of 7.3, is highly specific for arterial vessels, producing its vasodilation by a couple of different mechanisms. First, it causes smooth muscle hyperpolarization, quite likely through the opening of K+ channels. Activation therefore increases the efflux of potassium ions from the cells, causing hyperpolarization of VSM cells and, thus, prolonging the opening of the potassium channel and sustaining a greater vasodilation on arterioles than on veins. It also may inhibit the second messenger, IP3-induced release of calcium from the smooth muscle sarcoplasmic reticulum (the PIP2 signal transduction pathway). Finally, hydralazine stimulates the formation of NO by the vascular endothelium, leading to cGMP-mediated vasodilation. The arterial vasodilator action of hydralazine reduces systemic vascular resistance and arterial pressure. Diastolic blood pressure usually is decreased more than systolic pressure is. The hydralazine-induced decrease in blood pressure and peripheral resistance causes a reflex response, which is accompanied by increased heart rate, cardiac output, stroke volume, and an increase in plasma renin activity. It has no direct effect on the heart. This reflex response could offset the hypotensive effect of arteriolar dilation, limiting its antihypertensive effectiveness. Hydralazine also causes sodium and water retention and expansion of plasma volume, which could develop tolerance to its antihypertensive effect during prolonged therapy. Thus, coadministration of a diuretic improves the therapeutic outcome.

Pharmacokinetics

Hydralazine is well absorbed from the GI tract and is metabolized in the GI mucosa (prehepatic systemic metabolism) and in the liver by acetylation, hydroxylation, and conjugation with glucuronic acid. Little of the hydralazine dose is excreted unchanged in urine but mainly as metabolites, which are without significant therapeutic activity. A small amount of hydralazine is reportedly converted to a hydrazone, most likely with vitamin B6 (pyridoxine), which may be responsible for some its neurotoxic effects. Following the oral administration of hydralazine, its antihypertensive effect begins in 20 to 30 minutes and lasts 2 to 4 hours. The plasma half-life of hydralazine generally is 2 to 4 hours but, in some patients, may be up to 8 hours (i.e., slow acetylators). In slow acetylator patients or those with impaired renal function, the plasma concentrations for hydralazine are increased and, possibly, prolonged. Approximately 85% of hydralazine in the blood is bound to plasma proteins following administration of usual doses.
First-pass acetylation in the GI mucosa and liver is related to genetic acetylator phenotype. Acetylation phenotype is an important determinant of the plasma concentrations of hydralazine when the same dose of hydralazine is administered orally. Slow acetylators have an autosomal recessive trait that results in a relative deficiency of the hepatic enzyme N-acetyl transferase, thus prolonging the elimination half-life of hydralazine. This population of hypertensive patients will require an adjustment in dose to reduce the increased overactive response. Approximately 50% of African Americans and Caucasians, and the majority of American Indians, Eskimos, and Orientals are rapid acetylators of hydralazine. This population of patients will have subtherapeutic plasma concentrations of hydralazine because of its rapid metabolism to inactive metabolites and shorter elimination times. Patients with hydralazine-induced systemic lupus erythematosus frequently are slow acetylators.

Clinical Use

Hydralazine hydrochloride is useful in the treatment ofmoderate-to-severe hypertension. It is often used in conjunctionwith less potent antihypertensive agents, becauseside effects occur frequently when it is used alone in adequatedoses. In combinations, it can be used in lower andsafer doses. Its action appears to be centered on the smoothmuscle of the vascular walls, with a decrease in peripheralresistance to blood flow. This results in increased bloodflow through the peripheral blood vessels. It also has theunique property of increasing renal blood flow, an importantconsideration in patients with renal insufficiency.Hydralazine hydrochloride acts on vascular smooth muscleto cause relaxation. Its mechanism of action is unclear. Itinterferes with Ca2+ entry andCa2+release from intracellularstores and reportedly causes activation of guanylate cyclase,resulting in increased levels of cGMP. All of thesebiochemical events can cause vasodilation.

Drug interactions

The coadministration of diuretics and other hypotensive drugs may have a synergistic effect, resulting in a marked decrease in blood pressure.

Metabolism

Hydralazine undergoes considerable first-pass metabolism by acetylation in the gastrointestinal mucosa and liver. The rate of metabolism is genetically determined and depends upon the acetylator status of the individual. Systemic metabolism in the liver is by hydroxylation of the ring system and conjugation with glucuronic acid; most sources suggest that N-acetylation is not of major importance in systemic clearance and that therefore acetylator status does not affect elimination. Hydralazine is excreted mainly in urine as metabolites.

Purification Methods

It crystallises from MeOH and has m 172-173o(dec). [Druey et al. Helv Chim Acta 34 195 1951, Beilstein 25 III/IV 4552.] It is an antihypertensive.

Hydralazine hydrochloride Preparation Products And Raw materials

Raw materials

Preparation Products

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Hydralazine hydrochloride Suppliers

J & K SCIENTIFIC LTD.
Tel
010-82848833 400-666-7788
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86-10-82849933
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jkinfo@jkchemical.com
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China
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96815
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Meryer (Shanghai) Chemical Technology Co., Ltd.
Tel
4006608290; 18621169109
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86-21-61259102
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market03@meryer.com
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China
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Alfa Aesar
Tel
400-6106006
Fax
021-67582001/03/05
Email
saleschina@alfa-asia.com
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China
ProdList
30132
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TCI (Shanghai) Development Co., Ltd.
Tel
021-67121386
Fax
021-67121385
Email
Sales-CN@TCIchemicals.com
Country
China
ProdList
24539
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Ark Pharm, Inc.
Tel
847-367-3680
Fax
847-367-3681
Email
sales@arkpharminc.com
Country
United States
ProdList
1670
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Energy Chemical
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021-021-58432009 400-005-6266
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021-58436166
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sales8178@energy-chemical.com
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China
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Beijing Ouhe Technology Co., Ltd
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010-82967028 13552068683
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+86-10-82967029
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2355560935@qq.com
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China
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12426
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Adamas Reagent, Ltd.
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400-6009262 16621234537
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021-64823266
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zhangsn@titansci.com
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China
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14113
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Shanghai Hanhong Scientific Co.,Ltd.
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021-54306202 13764082696;
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info@hanhongsci.com
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China
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42982
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Chemsky(shanghai)International Co.,Ltd.
Tel
021-50135380
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shchemsky@sina.com
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China
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32344
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View Lastest Price from Hydralazine hydrochloride manufacturers

WUHAN FORTUNA CHEMICAL CO., LTD
Product
Hydralazine hydrochloride 304-20-1
Price
US $0.00-0.00/Kg/Drum
Min. Order
1KG
Purity
98%min HPLC
Supply Ability
500KGS
Release date
2021-07-14
Anhui Ruihan Technology Co., Ltd
Product
Hydralazine hydrochloride 304-20-1
Price
US $30.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
1000t/year
Release date
2023-09-07
Hebei Mojin Biotechnology Co., Ltd
Product
Hydralazine hydrochloride 304-20-1
Price
US $0.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
50000KG/month
Release date
2023-09-05

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