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Hydralazine

Product Name
Hydralazine
CAS No.
86-54-4
Chemical Name
Hydralazine
Synonyms
c5968;ba5968;c-5068;apressin;ciba5968;apresolin;aprezolin;NSC 126699;apresoline;hidralazin
CBNumber
CB1855362
Molecular Formula
C8H8N4
Formula Weight
160.18
MOL File
86-54-4.mol
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Hydralazine Property

Melting point:
172°C
Boiling point:
276.07°C (rough estimate)
Density 
1.2583 (rough estimate)
refractive index 
1.5872 (estimate)
pka
pKa 6.820± 0.005(H2O,t = 25.0,Iundefined) (Uncertain)
Water Solubility 
4.8mg/L(22.5 ºC)
BCS Class
3
CAS DataBase Reference
86-54-4
IARC
3 (Vol. 24, Sup 7) 1987
NIST Chemistry Reference
1(2H)-phthalazinone, hydrazone(86-54-4)
EPA Substance Registry System
Hydralazine (86-54-4)
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Safety

Toxicity
LD50 in mice, rats (mg/kg): 122, 90 orally; 101, 40 i.p. (Dorigotti)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H301Toxic if swalloed

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P405Store locked up.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
PH016716
Product name
(1E)-1(2H)Phthalazinone hydrazone
Purity
AldrichCPR
Packaging
1G
Price
$134
Updated
2023/06/20
American Custom Chemicals Corporation
Product number
API0005868
Product name
HYDRALAZINE
Purity
95.00%
Packaging
0.5G
Price
$171
Updated
2021/12/16
American Custom Chemicals Corporation
Product number
API0005868
Product name
HYDRALAZINE
Purity
95.00%
Packaging
500MG
Price
$697.34
Updated
2021/12/16
American Custom Chemicals Corporation
Product number
API0005868
Product name
HYDRALAZINE
Purity
95.00%
Packaging
5G
Price
$2001.04
Updated
2021/12/16
Crysdot
Product number
CD11041318
Product name
1-Hydrazinylphthalazine
Purity
95+%
Packaging
10g
Price
$255
Updated
2021/12/16
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Hydralazine Chemical Properties,Usage,Production

Description

Cross-reactions between hydrazine derivatives occur. Hydralazine may sometimes cause flushing and reversible Lupus erythematosis

Chemical Properties

Yiellow Solid

Originator

Apresoline HCl,Ciba,US,1952

Uses

Hydralazine is widely used cardiovascular drug dilating arterioies by relaxation of artetiolar smooth muscles.

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 1-hydrazino derivative of phthalazine; 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

Biological Functions

The vasodilation produced by hydralazine (Apresoline) depends in part on the presence of an intact blood vessel endothelium. This implies that hydralazine causes the release of nitric oxide, which acts on the vascular smooth muscle to cause relaxation. In addition, hydralazine may produce vasodilation by activating K+ channels.

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.

Mechanism of action

Hydralazine exhibits an antihypertensive effect by directly relaxing smooth muscles of the vessels. It has an effect on arterial vessels while having a minimal effect on venous vessels. As a result, resistance of peripheral vessels decreases, and blood pressure is reduced (diastolic more than systolic).
It does not have a substantial effect on nonvascular smooth musculature or cardiac tissues. Homeostatic circulatory reflexes remain natural, and the resulting hypotension activates cardiovascular reflexes, which are expressed as an increase of heart work, power, and volume of cardiac output. Therefore, it is most effectively used in combination with β-blockers.

Pharmacology

Hydralazine produces widespread but apparently not uniform vasodilation; that is, vascular resistance is decreased more in cerebral, coronary, renal, and splanchnic beds than in skeletal muscle and skin. Renal blood flow and ultimately glomerular filtration rate may be slightly increased after acute treatment with hydralazine. However, after several days of therapy, the renal blood flow is usually no different from that before drug use.
In therapeutic doses, hydralazine produces little effect on nonvascular smooth muscle or on the heart. Its pharmacological actions are largely confined to vascular smooth muscle and occur predominantly on the arterial side of the circulation; venous capacitance is much less affected. Because cardiovascular reflexes and venous capacitance are not affected by hydralazine, postural hypotension is not a clinical concern. Hydralazine treatment does, however, result in an increase in cardiac output.This action is brought about by the combined effects of a reflex increase in sympathetic stimulation of the heart, an increase in plasma renin, and salt and water retention. These effects limit the hypotensive usefulness of hydralazine to such an extent that it is rarely used alone.

Clinical Use

Hydralazine is generally reserved for moderately hypertensive ambulatory patients whose blood pressure is not well controlled either by diuretics or by drugs that interfere with the sympathetic nervous system. It is almost always administered in combination with a diuretic (to prevent Na+ retention) and a β-blocker, such as propranolol (to attenuate the effects of reflex cardiac stimulation and hyperreninemia). The triple combination of a diuretic, β-blocker, and hydralazine constitutes a unique hemodynamic approach to the treatment of hypertension, since three of the chief determinants of blood pressure are affected: cardiac output (β-blocker),plasma volume (diuretic), and peripheral vascular resistance (hydralazine).
Although hydralazine is available for intravenous administration and has been used in the past for hypertensive emergencies, it is not generally employed for this purpose. The onset of action after intravenous injection is relatively slow, and its actions are somewhat unpredictable in comparison with those of several other vasodilators.

Side effects

Most side effects associated with hydralazine administration are due to vasodilation and the reflex hemodynamic changes that occur in response to vasodilation. These side effects include headache, flushing, nasal congestion, tachycardia, and palpitations. More serious manifestations include myocardial ischemia and heart failure. These untoward effects of hydralazine are greatly attenuated when the drug is administered in conjunction with a β-blocker.
When administered chronically in high doses, hydralazine may produce a rheumatoidlike state that when fully developed, resembles disseminated lupus erythematosus.

Synthesis

Hydralazine, 1-hydrazinonaphthalazine (22.6.4), is synthesized by the oxidative chlorination of phthalide with simultaneous hydrolysis of product, which results in hydroxyphthalide (22.6.1), which upon reaction with hydrazine changes to phthalazone (22.6.2). This undergoes a reaction with phosphorous oxychloride, forming 1-chlorophthalazine (22.6.3), in which substitution of the chlorine atom with hydrazine gives the desired hydralazine (22.6.4).

Metabolism

Hydralazine is well absorbed (65–90%) after oral administration. Its peak antihypertensive effect occurs in about 1 hour, and its duration of action is about 6 hours.
The major pathways for its metabolism include ring hydroxylation, with subsequent glucuronide conjugation and N-acetylation. Hydralazine exhibits a first-pass effect in that a large part of an orally administered dose is metabolized before the drug reaches the systemic circulation. The first-pass metabolism occurs in the intestinal mucosa (mostly N-acetylation) and the liver. The primary excretory route is through renal elimination, and about 80% of an oral dose appears in the urine within 48 hours. About 10% is excreted unchanged in the feces.
Approximately 85% of the hydralazine in plasma is bound to plasma proteins. Although this does not appear to be a major therapeutic concern, the potential for interactions with other drugs that also bind to plasma proteins does exist. The plasma half-life of hydralazine in patients with normal renal function is 1.5 to 3 hours.
Interestingly, the half-life of the antihypertensive effect is somewhat longer than the plasma half-life. This may occur because hydralazine is specifically accumulated in artery walls, where it may continue to exert a vasodilator action even though plasma concentrations are low.
The plasma half-life of hydralazine may be increased fourfold or fivefold in patients with renal failure. If renal failure is present, therefore, both the antihypertensive and toxic effects of hydralazine may be enhanced. Since N-acetylation of hydralazine is an important metabolic pathway and depends on the activity of the enzyme N-acetyltransferase, genetically determined differences in the activity of this enzyme in certain individuals (known as slow acetylators) will result in higher plasma levels of hydralazine; therefore, the drug’s therapeutic or toxic effects may be increased.

Purification Methods

It crystallises from MeOH. UV: max 656nm at pH ~11. It complexes with Bi3+ , Zn2+ , Fe2+ and Co2+ .

Hydralazine Preparation Products And Raw materials

Raw materials

Preparation Products

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Hydralazine Suppliers

J & K SCIENTIFIC LTD.
Tel
010-82848833 400-666-7788
Fax
86-10-82849933
Email
jkinfo@jkchemical.com
Country
China
ProdList
94657
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76
Hangzhou Yuhao Chemical Technology Co., Ltd
Tel
0571-82693216
Fax
+86-571-82880190
Email
info@yuhaochemical.com
Country
China
ProdList
9387
Advantage
52
BOC Sciences
Tel
1-631-485-4226; 16314854226
Email
info@bocsci.com
Country
United States
ProdList
14055
Advantage
65
ChemStrong Scientific Co.,Ltd
Tel
0755-0755-66853366 13670046396
Fax
0755-28363542
Email
sales@chem-strong.com
Country
China
ProdList
18043
Advantage
56
Chizhou Kailong Import and Export Trade Co., Ltd.
Tel
Fax
-
Email
xg01_gj@163.com
Country
China
ProdList
9484
Advantage
50
Amadis Chemical Company Limited
Tel
571-89925085
Fax
0086-571-89925065
Email
sales@amadischem.com
Country
China
ProdList
131957
Advantage
58
Aikon International Limited
Tel
025-66113011 13155353615
Fax
(7)02557626880
Email
qzhang@aikonchem.com
Country
China
ProdList
15394
Advantage
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Chengdu Saint - Kay Biotechnology Co., Ltd.
Tel
028-85157043 15882256948
Email
676046971@qq.com
Country
China
ProdList
4390
Advantage
58
Shaanxi Jiandu Pharmaceutical Chemical Co. Ltd.
Tel
029-88380327 17691182729
Fax
029-88380327
Email
1018@dideu.com
Country
China
ProdList
1993
Advantage
58
Shenzhen Polymeri Biochemical Technology Co., Ltd.
Tel
+86-400-002-6226 +86-13028896684;
Email
sales@rrkchem.com
Country
China
ProdList
56902
Advantage
58
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View Lastest Price from Hydralazine manufacturers

WUHAN FORTUNA CHEMICAL CO., LTD
Product
Hydralazine 86-54-4
Price
US $10.00/g
Min. Order
1g
Purity
98.0%
Supply Ability
1kg/month
Release date
2021-11-08
Shaanxi Dideu Medichem Co. Ltd
Product
Hydralazine 86-54-4
Price
US $0.00-0.00/Kg
Min. Order
1KG
Purity
99.0%
Supply Ability
500 MT
Release date
2020-05-09

86-54-4, HydralazineRelated Search:


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