Pharmacological effects Chemical properties Uses Production methods Category Toxicity grading Acute toxicity Flammability and hazard characteristics Storage Characteristics Extinguishing agent
ChemicalBook > CAS DataBase List > Nifedipine

Nifedipine

Pharmacological effects Chemical properties Uses Production methods Category Toxicity grading Acute toxicity Flammability and hazard characteristics Storage Characteristics Extinguishing agent
Product Name
Nifedipine
CAS No.
21829-25-4
Chemical Name
Nifedipine
Synonyms
Procardia;diMethyl 2,6-diMethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate;ADALAT;Orix;Anifed;Oxcord;ADALATE;CITILAT;NIFELAT;bay1040
CBNumber
CB6260129
Molecular Formula
C17H18N2O6
Formula Weight
346.33
MOL File
21829-25-4.mol
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Nifedipine Property

Melting point:
171-175 °C
Boiling point:
481.08°C (rough estimate)
Density 
1.2109 (rough estimate)
refractive index 
1.5486 (estimate)
storage temp. 
2-8°C
solubility 
DMSO: soluble
form 
powder
pka
pKa -0.9/>13(DMF,t undefined) (Uncertain)
color 
yellow
Water Solubility 
<0.1 g/100 mL at 19.5 ºC
Merck 
14,6528
BCS Class
2
Stability:
Stable for 1 year from date of purchase as supplied. Solutions are not stable and must be used within one working day.
InChIKey
CYCWGQFQPAYBHG-UHFFFAOYSA-N
CAS DataBase Reference
21829-25-4(CAS DataBase Reference)
NIST Chemistry Reference
Nifedipine(21829-25-4)
EPA Substance Registry System
Dimethyl 1,4-dihydro-2,6-dimethyl-4-(2-nitrophenyl)-3,5-pyridinedicarboxylate (21829-25-4)
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Safety

Hazard Codes 
Xn,Xi
Risk Statements 
22-36/37/38
Safety Statements 
26-36
WGK Germany 
1
RTECS 
US7975000
HazardClass 
IRRITANT
HS Code 
29333990
Hazardous Substances Data
21829-25-4(Hazardous Substances Data)
Toxicity
LD50 in mice, rats (mg/kg): 494, 1022 orally; 4.2, 15.5 i.v. (Vater)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
BP462
Product name
Nifedipine
Purity
British Pharmacopoeia (BP) Reference Standard
Packaging
100MG
Price
$211
Updated
2024/03/01
Sigma-Aldrich
Product number
481981
Product name
Nifedipine
Purity
Relatively selective blocker of L-type Ca
Packaging
250mg
Price
$82.8
Updated
2024/03/01
Sigma-Aldrich
Product number
1463508
Product name
Nifedipine
Purity
United States Pharmacopeia (USP) Reference Standard
Packaging
125mg
Price
$358
Updated
2024/03/01
TCI Chemical
Product number
N0528
Product name
Nifedipine
Purity
>98.0%(HPLC)(E)
Packaging
10g
Price
$71
Updated
2024/03/01
TCI Chemical
Product number
N0528
Product name
Nifedipine
Purity
>98.0%(HPLC)(E)
Packaging
25g
Price
$129
Updated
2024/03/01
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Nifedipine Chemical Properties,Usage,Production

Pharmacological effects

Nifedipine is a kind of dihydropyridine calcium antagonists, it can inhibit the Ca2 + uptake of cardiac and vascular smooth muscles, and it can expand the coronary artery , increase coronary blood flow,and improve myocardial ischemic tolerance, at the same time, it can expand peripheral arteries and reduce peripheral vascular resistance,and relieve coronary artery spasm, and increase coronary blood flow, improve myocardial ischemia,in order to decrease the blood pressure. Small doses do not affect blood pressure, when expanding coronary artery ,it is a better anti-angina drug .It is used for the prevention and treatment of angina pectoris,with no adverse effects on respiratory function, its efficacy is best particularly for angina pectoris coronary spasm and obstructive airway disease with angina , its efficacy is superior to β-blockers.It is also applied to all types of high blood pressure, including severe and resistant hypertension. Treatment of refractory congestive heart failure may be taking this long. It is also used for the treatment of primary pulmonary hypertension, diffuse esophageal spasm and bronchial asthma, duodenal ulcers, urinary tract obstruction, exercise-induced asthma, achalasia.
Nifedipine has a certain selectivity on vascular smooth muscles , the direct negative inotropic effect and denaturation effect on the heart are weak, systemic administration of it does not cause the heart rate slowing down ,on the contrary, the heart rate performances reflected increase.
The above information is edited by the chemicalbook of Tian Ye.

Chemical properties

Yellow crystals. Melting point 172-174 ℃. Soluble in acetone, chloroform, ethyl acetate, dissolved in hot methanol, insoluble in water. It easily deteriorates in case of light.

Uses

Long-term coronary vasodilators. This product can increase coronary blood flow, reducing myocardial oxygen consumption.it is used for acute and chronic coronary insufficiency,especially the angina and myocardial infarction.

Production methods

O-nitrobenzaldehyde, methyl acetoacetate, methanol, ammonia are refluxed together , then froze , crystallize,after filtration, nifedipine crude is obtained . The crude product is recrystallized through methanol .then the product is derived , yield rate is 50%.

Category

Toxic substances

Toxicity grading

Highly toxic

Acute toxicity

Oral-rat LD50: 1022 mg/kg; Oral-Mouse LD50: 310 mg/kg.

Flammability and hazard characteristics

Combustion produces toxic fumes of nitrogen oxides; medicinal side effects: low blood pressure, cardiac disease, local blood flow disease, high blood sugar, psychosis.

Storage Characteristics

Ventilated , low-temperature, drying; and it is kept separately from food raw materials warehouse.

Extinguishing agent

Dry powder, foam, sand, carbon dioxide, water spray.

Description

Nifedipine (21829-25-4) is a clinically useful L-type calcium blocker.

Chemical Properties

Yellow Crystalline Solid

Originator

Adalat,Bayer,W. Germany,1975

Uses

Used as an antihypertensive and antianginal. A dihydorpyridine calcium channel blocker

Uses

Nifedipine is used for preventing and relieving angina pectoris attacks, for hypertension, and as an ingredient in combination therapy for chronic cardiac insufficiency.

Uses

For the management of vasospastic angina, chronic stable angina, hypertension, and Raynaud's phenomenon. May be used as a first line agent for left ventricular hypertrophy and isolated systolic hypertension (long-acting agents).

Definition

ChEBI: Nifedipine is a dihydropyridine, a methyl ester and a C-nitro compound. It has a role as a calcium channel blocker, a vasodilator agent, a tocolytic agent and a human metabolite.

Manufacturing Process

45 grams 2-nitrobenzaldehyde, 80 cc acetoacetic acid methyl ester, 75 cc methanol and 32 cc ammonia are heated under reflux for several hours, filtered off, cooled and, after suction-filtration, 75 grams of yellow crystals of MP 172° to 174°C are obtained, according to US Patent 3,485,847.

brand name

Adalat (Bayer); Afeditab (Watson);Procardia (Pfizer).

Therapeutic Function

Coronary vasodilator

World Health Organization (WHO)

Nifedipine is a dihydropyridine calcium channel blocker. It is listed in the WHO Model List of Essential Drugs. The 10mg tablet is retained on the list for short-term treatment of hypertension. Sustained-release preparations are advised for long-term treatment.

General Description

Nifedipine, 1,4-dihydro-2, 6-dimethyl-4-(2-nitrophenyl)-3,5-pyridinedicarboxylate dimethyl ester(Adalat, Procardia), is a dihydropyridine derivative thatbears no structural resemblance to the other calcium antagonists.It is not a nitrate, but its nitro group is essential for itsantianginal effect. As a class, the dihydropyridines possessa central pyridine ring that is partially saturated. To this, positions2 and 6 are substituted with an alkyl group that mayplay a role in the agent’s duration of action. In addition, positions3 and 5 are carboxylic groups that must be protectedwith an ester functional group. Depending on the type ofester used at these sites, the agent can be distributed to variousparts of the body. Finally, position 4 requires an aromaticsubstitution possessing an electron-withdrawinggroup (i.e., Cl or NO2) in the ortho and/or meta position.

General Description

Odorless yellow crystals or powder. Tasteless.

Air & Water Reactions

Aqueous solutions are very sensitive to light. . Insoluble in water.

Reactivity Profile

Nifedipine is sensitive to light.

Fire Hazard

Flash point data for Nifedipine are not available; however, Nifedipine is probably combustible.

Biological Activity

L-type calcium channel blocker.

Biochem/physiol Actions

Nifedipine is a L-type Ca2+ channel blocker; and induces apoptosis in human glioblastoma cells. Nifedipine has neuroprotection activity and protects substantia nigra. Nifedipine has antioxidant potential. Nifedipine downregulates inflammatory cytokines like macrophage inflammatory protein-2 (MIP-2), tumor necrosis factor-α (TNF-α). Nifedipine has antihypertensive properties. Nifedipine inhibits extracellular region of adenosine A2a receptor (ADORA2A) gene.

Mechanism of action

Nifedipin causes relaxation of smooth musculature, dilation of coronary and peripheral arteries, and reduction of peripheral resistance and arterial blood pressure, and enhances oxygen supply to the heart.

Clinical Use

The prototype of this class, nifedipine, has potent peripheralvasodilatory properties. It inhibits the voltage-dependentcalcium channel in the vascular smooth muscle but has littleor no direct depressant effect on the SA or AV nodes, eventhough it inhibits calcium current in normal and isolated cardiactissues. Nifedipine is more effective in patients whoseanginal episodes are caused by coronary vasospasm and isused in the treatment of vasospastic angina as well as classicangina pectoris. Because of its strong vasodilatory properties,it is used in selected patients to treat hypertension.

Synthesis

Nifedipine, dimethyl ether 1,4-dihydro-2,6-dimethyl-4-(2??-nitrophenyl)-3,5- piridindicarboxylic acid (19.3.16), is synthesized by a Hantsch synthesis from two molecules of a |?-dicarbonyl compound?amethyl acetoacetate, using as the aldehyde component?a 2-nitrobenzaldehyde and ammonia. The sequence of the intermediate stages of synthesis has not been completely established.

Drug interactions

Potentially hazardous interactions with other drugs
Aminophylline: possibly increases aminophylline concentration.
Anaesthetics: enhanced hypotensive effect.
Anti-arrhythmics: concentration of dronedarone increased.
Antibacterials: metabolism accelerated by rifampicin; metabolism possibly inhibited by clarithromycin, erythromycin and telithromycin.
Antidepressants: metabolism possibly inhibited by fluoxetine; concentration reduced by St John’s wort; enhanced hypotensive effect with MAOIs.
Antiepileptics: effect reduced by carbamazepine, barbiturates, phenytoin and primidone.
Antifungals: metabolism possibly inhibited by itraconazole and ketoconazole; concentration increased by micafungin; negative inotropic effect possibly increased with itraconazole.
Antihypertensives: enhanced hypotensive effect, increased risk of first dose hypotensive effect of post-synaptic alpha-blockers; occasionally severe hypotension and heart failure with beta-blockers.
Antivirals: concentration possibly increased by ritonavir; use telaprevir with caution.
Cardiac glycosides: digoxin concentration possibly increased.
Ciclosporin: may increase ciclosporin level, but not a problem in practice; nifedipine concentration may be increased.
Cytotoxics: metabolism of vincristine possibly reduced.
Grapefruit juice: concentration increased - avoid.
Magnesium salts: profound hypotension with IV magnesium.
Tacrolimus: increased tacro

Metabolism

Nifedipine is metabolised in the gut wall and oxidised in the liver via the cytochrome P450 isoenzyme CYP3A4, to inactive metabolites. Excreted mainly as metabolites via the kidney

storage

+4°C (desiccate)

References

1) Vater et al., (1972), (Pharmacology of 4-(2′-nitrophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylic acid dimethyl ester (Nifedipine, BAY a 1040); Arzneimittelforschung, 22 1

Nifedipine Preparation Products And Raw materials

Raw materials

2-Nitrotoluene 4-Aminobenzaldehyde Diethyl oxalate Methyl acetoacetate Benzaldehyde 2-Nitrobenzaldehyde Ethyl cyanoacetate

Preparation Products

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Nifedipine Suppliers

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View Lastest Price from Nifedipine manufacturers

Sinoway Industrial co., ltd.
Product
Nifedipine 21829-25-4
Price
US $0.00-0.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
20tons
Release date
2024-05-15
WUHAN FORTUNA CHEMICAL CO., LTD
Product
Nifedipine 21829-25-4
Price
US $0.00-0.00/Kg/Drum
Min. Order
1KG
Purity
98.0%-102.0%
Supply Ability
1000kg
Release date
2021-06-02
Hebei Weibang Biotechnology Co., Ltd
Product
Nifedipine 21829-25-4
Price
US $1.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
10 mt
Release date
2024-11-14

21829-25-4, NifedipineRelated Search:

Dimethyl fumarate Dimethyl phthalate Dacthal Xylene Chromium picolinate Dimethyl sulfoxide Quinolinic acid Dimethyl phosphite ETHANE Dimethyl sulfate Chlorodimethylphenylsilane 2,5-PYRIDINEDICARBOXYLIC ACID 2,6-Lutidine Dimethyl ether N,N-Dimethylformamide Dimethyl carbonate Ceric ammonium nitrate Methyl 3-aminocrotonate

  • 1,4-Dihydro-2,6-dimethyl-4-(o-nitrophenyl)-3,5-pyridinedicarboxylic acid dimethyl
  • Nifedipine,1,4-Dihydro-2,6-dimethyl-4-(2-nitrophenyl)-3,5-pyridinedicarboxylic acid dimethyl ester
  • Nifedipine (125 mg)
  • Niter benzene horizontal
  • 1,4-dihydro-2,6-diMethyl-4-(2-nitrophenyl)pyridine-3,5-dicarboxylate
  • ALDIPIN ANIFED
  • ADALAT
  • ADALATE
  • 4-(2'-NITROPHENYL)-2,6-DIMETHYL-3,5-DICARBOMETHOXY-1,4-DIHYDROPYRIDINE
  • BAY A 1040
  • dimethyl 1,4-dihydro-2,6-dimethyl-4-(2'-nitrophenyl)-3,5-pyridinedicarboxylate
  • CITILAT
  • NIFELAT
  • NIFEDIPINE
  • NIFEDIPINE DDP
  • NIFEDIPINE ASSAY STANDARD BP(CRM STANDARD)
  • NIFEDIPINE BP STANDARD(CRM STANDARD)
  • NIFEDIPINE EPN(CRM STANDARD)
  • NIFEDIPINE MM(CRM STANDARD)
  • NIFEDIPINE REFERENCE SPECTRUM EPY(CRM STANDARD)
  • NIFEDIPINE USP(CRM STANDARD)
  • 1,4-DIHYDRO-2,6-DIMETHYL-4-(2-NITROPHENYL)-3,5-PYRIDINEDICARBOXYLIC ACID DIMETHYL ESTER
  • Anifed
  • Nifidepine
  • Nifedipine, Micronized, USP
  • 3,5-diMethyl 2,6-diMethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
  • Nifedipine, Adalat, Nifediac, Cordipin, Nifedical, Procardia
  • Nifedipine 5GR
  • NitedipineAdalat
  • Nifedipine-d4
  • diMethyl 2,6-diMethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
  • NifedipineNIFEDIPINE</NOBR><br>CAS:21829-25-4<BR>PHARMA-0503
  • 1,4-dihydro-2,6-dimethyl-4-(2-nitrophenyl)-3,5-pyridinedicarboxylicaciddime
  • 3,5-Pyridinedicarboxylic acid, 1,4-dihydro-2,6-dimethyl-4-(2-nitrophenyl)-, dimethyl ester
  • 4-(2’-nitrophenyl)-2,6-dimethyl-1,4-dihydropyridin-3,5-dicarbonsaeuredimethy
  • 5-pyridinedicarboxylicacid,1,4-dihydro-2,6-dimethyl-4-(2-nitrophenyl)-dim
  • Adalat CC
  • bay1040
  • corinfar
  • Dimethyl 1,4-dihydro-2,6-dimethyl-4-(o-nitrophenyl)-3,5-pyridinedicarboxylate
  • Dimethyl 2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydro-3,5-pyridinedicarboxylate
  • Dimethyl 4-(2-nitrophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate
  • dimethyl1,4-dihydro-2,6-dimethyl-4-(2’-nitrophenyl)-3,5-pyridinedicarboxylat
  • fenihidin
  • fenihidine
  • Hexadilat
  • Introcar
  • Kordafen
  • Methyl (4-(2-nitrophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate)
  • Nifedicor
  • Nifedin
  • nifedipine(uspgrade)
  • Nifelan
  • Nifensar XL
  • Orix
  • Oxcord
  • Pidilat
  • Procardia