Nitrendipine

Structural formula
Simplified structural formula without specifying the stereochemistry - 1: 1 mixture ( racemate )
General
Non-proprietary name	Nitrendipine
other names	( RS ) -Ethyl-5- (methoxycarbonyl) -2,6-dimethyl-4- (3-nitrophenyl) -1,4-dihydropyridine-3-carboxylate ( IUPAC )
Molecular formula	C 18 H 20 N 2 O 6
External identifiers / databases
CAS number 39562-70-4 EC number 254-513-1 ECHA InfoCard 100.049.540 PubChem 4507 DrugBank DB01054 Wikidata Q416584
Drug information
ATC code	C08 CA08
Drug class	Antihypertensive drugs
Mechanism of action	Calcium antagonist
properties
Molar mass	360.36 g · mol -1
Physical state	firmly
Melting point	158-160 ° C
solubility	Water: 77.2 mg l −1 at 25 ° C
safety instructions
Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed GHS labeling of hazardous substances Caution H and P phrases H: 312-332 P: 280
Toxicological data	2540 mg kg −1 ( LD 50 ,  mouse ,  oral )
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Nitrendipine is a drug from the group of calcium antagonists of the 1,4-dihydropyridine type. It lowers blood pressure significantly by expanding the smooth muscles of the blood vessels . It is used therapeutically to treat arterial hypertension .

Mechanism of action

Nitrendipine blocks the influx of calcium into the heart muscle cells, the smooth muscles and the excitation and conduction system of the heart. In the heart, this leads to reduced contractility (negative inotropic ) and reduced O ₂ consumption. On the smooth muscles, it causes the small arteries ( arterioles ) to widen and thus reduce the afterload . Nitrendipine is a dihydropyridine. At therapeutic doses, the effect of nitrendipine and other dihydropyridine calcium antagonists is hardly on the heart, but almost exclusively on the blood vessels.

Indications

Nitrendipine is approved in Germany for the therapy of essential arterial hypertension and as Bayotensin ^® acute for the treatment of hypertensive emergencies .

Side effects

Often lower leg edema , headache and flushing occur , as well as occasionally dizziness , fatigue and hypoesthesia .

Rare side effects are tachycardia , palpitation , nausea, bloating, diarrhea, and increased urination.

Contraindications

In cardiogenic shock, unstable angina pectoris , myocardial infarction (within the first 4 weeks) and children (insufficient experience), the administration of nitrendipine is contraindicated .

Trade names

Monopreparations

Bayotensin (D), Baypress (A, CH), Jutapress (D), numerous generics (D)

Combination preparations

Baroprine (A), Cenipres (A), Eneas (D)

Stereochemistry

Nitrendipine contains a stereocenter and consists of two enantiomers, more precisely two atropisomers . This is a racemate , i.e. a 1: 1 mixture of ( R ) - and ( S ) -form:

Enantiomers of nitrendipine
CAS number: 80890-07-9	CAS number: 80873-62-7

Individual evidence

1. ↑ Entry on nitrendipine. In: Römpp Online . Georg Thieme Verlag, accessed on November 10, 2014.
2. ↑ ^{a b} Entry on nitrendipine in the ChemIDplus database of the United States National Library of Medicine (NLM) .
3. ↑ ^{a b} Data sheet Nitrendipine ~ 98% from Sigma-Aldrich , accessed on April 16, 2011 ( PDF ).
4. ↑ Rote Liste Service GmbH (Ed.): Rote Liste 2017 - drug directory for Germany (including EU approvals and certain medical devices) . Rote Liste Service GmbH, Frankfurt / Main, 2017, edition 57, ISBN 978-3-946057-10-9 , p. 204.

This article is about a health issue. It is not used for self-diagnosis and does not replace a diagnosis by a doctor. Please note the information on health issues !