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Structural formula
Structure of nifedipine
Non-proprietary name Nifedipine
other names
  • 3,5-dimethyl-1,4-dihydro-2,6-dimethyl-4- (2-nitrophenyl) pyridine-3,5-dicarboxylate
  • Dimethyl [2,6-dimethyl-4- (2-nitrophenyl) -1,4-dihydropyridine-3,5-dicarboxylate] ( Pharmacopoeia )
  • 4- (2-nitrophenyl) -2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylic acid dimethyl ester
  • Latin : Nifedipinum
Molecular formula C 17 H 18 N 2 O 6
Brief description

yellowish, crystalline powder

External identifiers / databases
CAS number 21829-25-4
EC number 244-598-3
ECHA InfoCard 100.040.529
PubChem 4485
DrugBank DB01115
Wikidata Q39111
Drug information
ATC code

C08 CA05

Drug class

Antihypertensive drugs

Mechanism of action

Calcium antagonist

Molar mass 346.33 g · mol -1
Melting point
  • 169-173 ° C ( polymorph I)
  • 161–163 ° C (Polymorph II)
  • 135 ° C (polymorph III)
  • very bad in water (56.3 mg l −1 at 25 ° C)
  • Easily soluble in acetone , little in ethanol
safety instructions
Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances
07 - Warning


H and P phrases H: 302
P: no P-phrases
Toxicological data
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Nifedipine is a drug from the group of calcium antagonists of the 1,4-dihydropyridine type, it lowers blood pressure by expanding the smooth muscles of the vessels . Therapeutically, nifedipine is mainly used to treat arterial hypertension, coronary heart disease and Raynaud's syndrome . The administration of nifedipine is contraindicated in unstable angina pectoris and acute myocardial infarction. Nifedipine is very sensitive to light.


Nifedipine ( Adalat ) was synthesized for the first time in the late 1960s by Friedrich Bossert (born 1920) and by Wulf Vater . In 1969 Albrecht Fleckenstein was commissioned by Bayer AG to investigate the drug's mechanism of action.

At the beginning of the 1970s, nifedipine was classified in the calcium antagonist category. Based on this, further 1,4-dihydropyridines were developed and brought onto the market, the so-called 2nd generation dihydropyridines.

Manufacture and extraction

Nifedipine is produced according to a Hantzsch dihydropyridine synthesis by reacting 2-nitrobenzaldehyde with methyl acetoacetate ( methyl acetoacetate) in the presence of ammonia :

Nifedipine synthesis 01.svg

Nifedipine is an intense yellow crystalline substance that decomposes rapidly when exposed to light

Mechanism of action

Nifedipine blocks the influx of calcium ions into the cells of the vascular smooth muscles, which has a vasodilating effect. At therapeutic doses, nifedipine, like the other calcium antagonists of the dihydropyridine type, has no relevant effect on the heart muscle cells.


Nifedipine is approved for the treatment of essential hypertension , hypertensive emergencies, Raynaud's syndrome and stable angina pectoris. In addition, it has proven effective in the treatment of premature labor (off label). To treat anal fissures , nifedipine can be used as a 0.2% cream.

Side effects and unwanted effects

The most important side effect of nifedipine is an (excessive) drop in blood pressure. Headaches can occur especially at the beginning of therapy. Another common side effect is a general feeling of weakness. Rare side effects include: dyspepsia (indigestion), abdominal pain, constipation, bloating, belching, vomiting, dry mouth, anorexia (loss of appetite), malaise, dyspnea (shortness of breath), nervousness, insomnia, somnolence, hypoesthesia , agitation, jaundice, sweating, arthralgia (joint pain ), Muscle cramps, fever, weak vision, increased urination and reflex tachycardia.

In 2007 there were indications that, contrary to the doctrinal opinion, nifedipine not only affects the blood vessels, but at least in animal experiments it also affects the hypertensive heart. In animal experiments, nifedipine changes the genetic information for the formation of transport proteins . A comparison of the patterns of these activated and deactivated genes with those found in diseased human hearts suggests that nifedipine can have an undesirable effect, at least on the diseased human heart.


The administration of nifedipine is contraindicated in the following diseases: cardiogenic shock, unstable angina pectoris , acute myocardial infarction (heart attack) (within the first 4 weeks), high-grade aortic valve stenosis, simultaneous administration of rifampicin .

Due to the risk of triggering constrictions of the coronary arteries, nifedipine is only used very cautiously in emergency medicine when coronary heart disease is suspected.

Based on the available clinical studies, it is not yet possible to conclusively assess the risk of nifedipine use during pregnancy . This is especially true for the period before the 20th week of pregnancy. Since nifedipine has been shown to be embryotoxic / foetotoxic in animal experiments , therapy with nifedipine remains contraindicated before the end of the 20th week of pregnancy.

Use of nifedipine as a labor suppressant

Nifedipine can also be used as a labor suppressant ( off-label use ). Several studies have confirmed the tolerability and effectiveness of these agents in comparison with other labor inhibitors , such as β 2 -sympathomimetics and prostaglandin antagonists. In the presence of hypertension or diabetes mellitus, the calcium antagonists have advantages over the β 2 sympathomimetics. They have less common and less severe side effects than this.

Use of nifedipine in glaucoma

Nifedipine has led to a significant reduction in central retinal venous pressure in patients with open-angle glaucoma (an increase in pressure in the central retinal vein is considered to be a risk factor for glaucoma , similar to high intraocular pressure ). The effect was particularly pronounced in glaucoma patients with Flammer's syndrome : after three weeks of low-dose nifedipine therapy, central retinal venous pressure fell by an average of 16.07 mm Hg, and in glaucoma patients without Flammer's syndrome by 7.28 mm Hg .

Trade names


Adalat (D, A, CH), Aprical (D), Buconif (A), Cardipin (CH), Cisday (D), Corinfar (D), Corotrend (CH), Ecodipin (CH), Fedip (A), Jutadilat (D), Nifeclair (D), Nifedicor (CH), Nifecor (D), Nifelat (D), Nifical (D), Ospocard (A), numerous generics (D, A, CH)

Combination preparations

AteNif (D), Belnif (D), Beta-Adalat (A, CH), Bresben (D), Nifetanol (D), Nif-Ten (D, A, CH), Sali-Adalat (D), Tredalat (D )

Individual evidence

  1. a b European Pharmacopoeia Commission (ed.): EUROPEAN PHARMACOPOE 5TH EDITION . tape 5.0-5.8 , 2006.
  2. a b c A. Burger, KT Koller: Polymorphism and Pseudopolymorphism on Nifedipine. In: Sci. Pharm. 64, 1996, pp. 293-301.
  3. a b c Entry on nifedipine in the ChemIDplus database of the United States National Library of Medicine (NLM) .
  4. a b Data sheet Nifedipine ≥98% (TLC), powder from Sigma-Aldrich , accessed on April 16, 2011 ( PDF ).
  5. Entry on nifedipine in Pharmawiki , accessed on January 28, 2017.
  6. ^ Wolf-Dieter Müller-Jahncke , Christoph Friedrich , Ulrich Meyer: Medicinal history . 2., revised. and exp. Edition. Knowledge Verlags-Gesellschaft, Stuttgart 2005, ISBN 3-8047-2113-3 , p. 173 f .
  7. U.S. Patent 3,485,847 (Bayer, December 31, 1969).
  8. ^ A. Kleemann , J. Engel, B. Kutscher, D. Reichert: Pharmaceutical Substances - Synthesis, Patents, Applications. 4th edition. Thieme-Verlag, Stuttgart 2001, ISBN 1-58890-031-2 .
  9. K. Aktories, U. Förstermann, F. Hofmann, K. Starke: General and special pharmacology and toxicology. 9th edition. Urban & Fischer Verlag / Elsevier, Munich / Jena 2006, ISBN 3-437-44490-5 , pp. 626–629.
  10. Entry on nifedipine cream in Pharmawiki , accessed on January 28, 2017.
  11. Reinhard Larsen: Anesthesia and intensive medicine in cardiac, thoracic and vascular surgery. 5th edition. Springer, Berlin / Heidelberg / New York et al. 1999, ISBN 3-540-65024-5 , p. 63 f.
  12. Janine Drexler: More safety for hypertensive patients. Fraunhofer-Gesellschaft, press release from October 11, 2007 at the Informationsdienst Wissenschaft (, accessed on August 24, 2015.
  13. M. Smollich: Nifedipine in hypertension during pregnancy - indication and prenatal toxicological safety. GRIN, 2009, ISBN 978-3-640-24380-8 .
  14. L. Fang, S. Turtschi, M. Mozaffarieh: The effect of nifedipine on retinal venous pressure of glaucoma patients with the Flammer syndrome. In: Graefes Arch Clin Exp Ophthalmol. 253 (6), Jun 2015, pp. 935-939. doi: 10.1007 / s00417-015-3001-7 .
  15. Red List online, as of October 2009.
  16. AM comp. d. Switzerland, as of October 2009.
  17. AGES-PharmMed, as of October 2009.