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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;CITILAT;ADALATE;NIFELAT;bay1040
CBNumber:
CB6260129
Molecular Formula:
C17H18N2O6
Molecular Weight:
346.33
MDL Number:
MFCD00057326
MOL File:
21829-25-4.mol
MSDS File:
SDS
Last updated:2026-03-06 11:42:52
Product description Number Pack Size Price
Nifedipine European Pharmacopoeia (EP) Reference Standard N0750000 50 mg $153
Nifedipine British Pharmacopoeia (BP) Reference Standard BP462 100MG $197
Nifedipine Relatively selective blocker of L-type Ca 481981 250mg $85.1
Nifedipine United States Pharmacopeia (USP) Reference Standard 1463508 125mg $352
Nifedipine >98.0%(HPLC)(E) N0528 10g $71
More product size

Nifedipine Properties

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.
Cosmetics Ingredients Functions ANTIOXIDANT
InChI 1S/C17H18N2O6/c1-9-13(16(20)24-3)15(14(10(2)18-9)17(21)25-4)11-7-5-6-8-12(11)19(22)23/h5-8,15,18H,1-4H3
InChIKey CYCWGQFQPAYBHG-UHFFFAOYSA-N
SMILES COC(=O)C1=C(C)NC(C)=C(C1c2ccccc2[N+]([O-])=O)C(=O)OC
CAS DataBase Reference 21829-25-4(CAS DataBase Reference)
EWG's Food Scores 1
FDA UNII I9ZF7L6G2L
Proposition 65 List Nifedipine
ATC code C08CA05,C08CA55
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)
UNSPSC Code 41116107
NACRES NA.77

Pharmacokinetic data

Protein binding 92-98%
Excreted unchanged in urine <1%
Volume of distribution 1.4(L/kg)
Biological half-life 1.4-11 (depends on preparation) / Unchanged

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS07
Signal word  Warning
Hazard statements  H302
Precautionary statements  P301+P312+P330
PPE dust mask type N95 (US), Eyeshields, Gloves
Hazard Codes  Xn,Xi
Risk Statements  22-36/37/38
Safety Statements  26-36
WGK Germany  1
RTECS  US7975000
HazardClass  IRRITANT
HS Code  29333990
Storage Class 11 - Combustible Solids
Hazard Classifications Acute Tox. 4 Oral
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)
NFPA 704
0
2 0

Nifedipine price More Price(59)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich N0750000 Nifedipine European Pharmacopoeia (EP) Reference Standard 21829-25-4 50 mg $153 2025-07-31 Buy
Sigma-Aldrich BP462 Nifedipine British Pharmacopoeia (BP) Reference Standard 21829-25-4 100MG $197 2025-07-31 Buy
Sigma-Aldrich 481981 Nifedipine Relatively selective blocker of L-type Ca 21829-25-4 250mg $85.1 2025-07-31 Buy
Sigma-Aldrich 1463508 Nifedipine United States Pharmacopeia (USP) Reference Standard 21829-25-4 125mg $352 2025-07-31 Buy
TCI Chemical N0528 Nifedipine >98.0%(HPLC)(E) 21829-25-4 10g $71 2025-07-31 Buy
Product number Packaging Price Buy
N0750000 50 mg $153 Buy
BP462 100MG $197 Buy
481981 250mg $85.1 Buy
1463508 125mg $352 Buy
N0528 10g $71 Buy

Nifedipine Chemical Properties,Uses,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

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).

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

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

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 compoundamethyl acetoacetate, using as the aldehyde componenta 2-nitrobenzaldehyde and ammonia. The sequence of the intermediate stages of synthesis has not been completely established.

Synthesis_21829-25-4

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] W VATER. [Pharmacology of 4-(2’-nitrophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylic acid dimethyl ester (Nifedipine, BAY a 1040)].[J]. Arzneimittel-Forschung-Drug Research, 1972, 22 1: 1-14.

105-45-3
552-89-6
21829-25-4
Synthesis of Nifedipine from Methyl acetoacetate and 2-Nitrobenzaldehyde
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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 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 NifedipineNIFEDIPINE
CAS:21829-25-4
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 XL Sepamit Tibricol