Nisoldipine

Structural formula
Structural formula without stereochemistry
General
Surname	Nisoldipine
other names	( RS ) -Isobutyl-1,4-dihydro-5-methoxylcarbonyl-2,6-dimethyl-4- (2-nitrophenyl) -3-pyridinecarboxylate (±) -Isobutyl-1,4-dihydro-5-methoxylcarbonyl-2,6-dimethyl-4- (2-nitrophenyl) -3-pyridinecarboxylate
Molecular formula	C 20 H 24 N 2 O 6
External identifiers / databases
CAS number 63675-72-9 (racemate) 103573-36-0 ( R ) -nisoldipine 103573-38-2 ( S ) -nisoldipine EC number 264-407-7 ECHA InfoCard 100.058.534 PubChem 4499 DrugBank DB00401 Wikidata Q3342150
Drug information
ATC code	C08 CA07
Drug class	Calcium antagonist
properties
Molar mass	388.42 g · mol -1
Physical state	firmly
Melting point	151-152 ° 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: 302-312-361-332-411 P: ?
Toxicological data	292 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 .

Nisoldipine ( INN ) is a dihydropyridine derivative . It is used in medicine as an antihypertensive agent and for the therapy of coronary heart disease .

Type and duration of the effect

Nisoldipine is used to treat essential hypertension and angina pectoris . In angina pectoris, it reduces the number of attacks by 67%. It is a calcium channel blocker of the dihydropyridine type. The effect is weaker compared to nifedipine.

The half-life in the body is between 10 and 15 hours. After intravenous administration, the elimination half-life is four hours. The elimination time is significantly increased by liver cirrhosis.

Distribution in the body

It is taken orally or intravenously. The nisoldipine is then almost completely converted and 90% of the metabolites formed are disposed of in the urine. Residues of approx. 0.1% of the original substance can be found in the urine.

Interactions

Grapefruit juice and cimetidine inhibit the metabolism of nisoldipine. In addition, fatty food leads to an increase in the maximum concentration in plasma, which can be avoided by taking the drug half an hour before eating.

Stereochemistry

Nisoldipine contains a stereocenter and consists of two enantiomers . This is a racemate , i.e. a 1: 1 mixture of ( R ) and ( S ) form:

Enantiomers of nisoldipine
( R ) -nisoldipine	( S ) -nisoldipine

Individual evidence

1. ↑ KA Chu, SH Yalkowsky (Ed.): An interesting relationship between drug absorption and melting point . In: International Journal of Pharmaceutics, Volume 373, No. 1-2, pp. 24-40, 2009.
2. ↑ Patent ES2055655 : Process for preparation of 3-isobutyl 5-methyl 2,6-dimethyl-4- (2-nitrophenyl) -1,4-dihydropyridine-3,5-dicarboxylate [nisoldipine]. Published on August 16, 1994 , inventor: C. Burgos Garcia, ML Izquierdo Ceinos & Co ..
3. ↑ There is not yet a harmonized classification for this substance . A labeling of nisoldipine in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on December 6, 2017, is reproduced from a self-classification by the distributor .
4. ↑ S. Wang, G. Yang, Z. Li, H. Liu & Co. (Eds.): Micellar liquid chromatography study of quantitative retention-activity relationships for antihypertensive drugs . In: Chromatographia , Vol. 64, No. 1-2, 2006, pp. 23-29.
5. ↑ ^{a b} D. D. Cella (Ed.): 2017 Nurse's Drug Handbook . 16th edition. Jones & Bartlett Learning, Burlington, 2017, ISBN 978-1-284-09933-1 , p. 795.
6. ↑ G. Bönner, E. Fritschka (Ed.): Calcium antagonists in clinic and practice . Springer-Verlag, Berlin 1991, ISBN 978-3-642-75411-1 , p. 42 (e-book).
7. ↑ ^{a b} Th. V. Armin, A. Maseri (Ed.): Predisposing Conditions for Acute Ischemia Syndromes . Springer-Verlag, Berlin 1989, ISBN 978-3-7985-0819-4 , p. 191.
8. ↑ l. H. Opie (Ed.): Clinical Use of Calcium Channel Antagonist Drugs . Kluwer Academic Publishers, Boston 1989, ISBN 978-1-4612-8208-2 , p. 16.
9. ↑ ^{a b} Rote Liste Service GmbH (Ed.): Rote Liste 2017 - drug directory for Germany (including EU approvals and certain medical devices) . Edition 57. Rote Liste Service GmbH, Frankfurt / Main, 2017, ISBN 978-3-946057-10-9 , p. 204.
10. ↑ ^{a b c} G. Bönner, E. Fritschka (Ed.): Calcium antagonists in clinic and practice , Springer-Verlag, Berlin, 1991, p. 41, ISBN 978-3-642-75411-1 , (e-book) .
11. ↑ JK Aronson (Ed.): Meyler's Side Effects of Cardiovascular Drugs . Elsevier, Berlin 2009, ISBN 978-0-444-53268-8 , p. 156.

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 !