Nifedipine

Nifedipine Basic information
Pharmacological effects Chemical properties Uses Production methods Category Toxicity grading Acute toxicity Flammability and hazard characteristics Storage Characteristics Extinguishing agent
Product Name:Nifedipine
Synonyms: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
CAS:21829-25-4
MF:C17H18N2O6
MW:346.33
EINECS:244-598-3
Product Categories:Dihydropyridine Class Chemicals;Functional Materials;Photopolymerization Initiators;Pharmaceutical;Active Pharmaceutical Ingredients;Cardiovascular APIs;Cardiovascular Drugs;Ion Channels;Isotopically Labeled Pharmaceutical Reference Standard;CAPOTEN;Dihydropyridine;Pharmaceutical intermediate;Calcium channel;Intermediates & Fine Chemicals;Pharmaceuticals;21829-25-4
Mol File:21829-25-4.mol
Nifedipine Structure
Nifedipine Chemical 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
pkapKa -0.9/>13(DMF,t undefined) (Uncertain)
color yellow
Water Solubility <0.1 g/100 mL at 19.5 ºC
Merck 14,6528
BCS Class2
Stability:Stable for 1 year from date of purchase as supplied. Solutions are not stable and must be used within one working day.
InChIKeyCYCWGQFQPAYBHG-UHFFFAOYSA-N
CAS DataBase Reference21829-25-4(CAS DataBase Reference)
NIST Chemistry ReferenceNifedipine(21829-25-4)
EPA Substance Registry SystemDimethyl 1,4-dihydro-2,6-dimethyl-4-(2-nitrophenyl)-3,5-pyridinedicarboxylate (21829-25-4)
Safety Information
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 Data21829-25-4(Hazardous Substances Data)
ToxicityLD50 in mice, rats (mg/kg): 494, 1022 orally; 4.2, 15.5 i.v. (Vater)
MSDS Information
ProviderLanguage
Nifedipine English
SigmaAldrich English
ACROS English
Nifedipine Usage And Synthesis
Pharmacological effectsNifedipine 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 propertiesYellow 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.
UsesLong-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 methodsO-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%.
CategoryToxic substances
Toxicity gradingHighly toxic
Acute toxicityOral-rat LD50: 1022 mg/kg; Oral-Mouse LD50: 310 mg/kg.
Flammability and hazard characteristicsCombustion produces toxic fumes of nitrogen oxides; medicinal side effects: low blood pressure, cardiac disease, local blood flow disease, high blood sugar, psychosis.
Storage CharacteristicsVentilated , low-temperature, drying; and it is kept separately from food raw materials warehouse.
Extinguishing agentDry powder, foam, sand, carbon dioxide, water spray.
DescriptionNifedipine (21829-25-4) is a clinically useful L-type calcium blocker.
Chemical PropertiesYellow Crystalline Solid
OriginatorAdalat,Bayer,W. Germany,1975
UsesFor 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).
UsesNifedipine is used for preventing and relieving angina pectoris attacks, for hypertension, and as an ingredient in combination therapy for chronic cardiac insufficiency.
UsesUsed as an antihypertensive and antianginal. A dihydorpyridine calcium channel blocker
DefinitionChEBI: 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 Process45 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 nameAdalat (Bayer); Afeditab (Watson);Procardia (Pfizer).
Therapeutic FunctionCoronary 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 DescriptionNifedipine, 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 DescriptionOdorless yellow crystals or powder. Tasteless.
Air & Water ReactionsAqueous solutions are very sensitive to light. . Insoluble in water.
Reactivity ProfileNifedipine is sensitive to light.
Fire HazardFlash point data for Nifedipine are not available; however, Nifedipine is probably combustible.
Biological ActivityL-type calcium channel blocker.
Biochem/physiol ActionsNifedipine 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 actionNifedipin 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 UseThe 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.
SynthesisNifedipine, 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.

Synthesis_21829-25-4

Drug interactionsPotentially 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







MetabolismNifedipine 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)
References1) 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 materialsEthyl cyanoacetate-->Diethyl oxalate-->Benzaldehyde-->2-Nitrotoluene-->Methyl acetoacetate-->2-Nitrobenzaldehyde-->4-Aminobenzaldehyde-->Ammonia
Preparation ProductsNisoldipine
NIFEDIPINE IMP. C (EP) AS E/Z-MIXTURE: METHYL (E/Z)-2-(2-NITROBENZYLIDENE)-3-OXOBUTANOATE Dacthal NISOLDIPINE-D4 (2-NITROPHENYL-D4) NIFEDIPINE NITROSOPHENYLPYRIDINE ANALOG USP(CRM STANDARD) NIFEDIPINE IMP. B (EP): DIMETHYL 2,6-DIMETHYL-4-(2-NITROSOPHENYLPYRIDINE3,5-DICARBOXYLATE] MM(CRM STANDARD) R-Lercanidipine NIFEDIPINE, (1,4-DIHYDRO-2,6-DIMETHYL-4-(2-NITRO- NISOLDIPINE-D7 NIFEDIPINE - REFERENCE SPECTRUM 4-HYDROXYNISOLDIPINE 4-Acetoxynisoldipine OXIDIZED NIFEDIPINE Chromium picolinate NIFEDIPINE IMPURITY B R-Lercanidipine-d3 NIFEDIPINE NITROPHENYLPYRIDINE ANALOG (25 MG) 4-HYDROXYNISOLDIPINE-D6 S-Lercanidipine

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