Nisoldipine

Nisoldipine
Clinical data
Trade names	Sular, Baymycard, Syscor
AHFS/Drugs.com	Monograph
MedlinePlus	a696009
Routes of; administration	Oral
ATC code	C08CA07 (WHO) ;
Legal status
Legal status	US: ℞-only ;
Pharmacokinetic data
Bioavailability	4–8%
Protein binding	>99%
Metabolism	CYP3A4
Elimination half-life	7–12 hours
Excretion	70–80% via urine
Identifiers
	IUPAC name (RS)-Isobutyl methyl 2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate;
CAS Number	63675-72-9 ;
PubChem CID	4499;
IUPHAR/BPS	2524;
DrugBank	DB00401 ;
ChemSpider	4343 ;
UNII	4I8HAB65SZ;
KEGG	D00618 ;
ChEBI	CHEBI:7577 ;
ChEMBL	ChEMBL1726 ;
CompTox Dashboard (EPA)	DTXSID0023371 ;
ECHA InfoCard	100.058.534
Chemical and physical data
Formula	C20H24N2O6
Molar mass	388.414 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC1=C(C(C(=C(N1)C)C(=O)OCC(C)C)c2ccccc2[N+](=O)[O-])C(=O)OC;
	InChI InChI=1S/C20H24N2O6/c1-11(2)10-28-20(24)17-13(4)21-12(3)16(19(23)27-5)18(17)14-8-6-7-9-15(14)22(25)26/h6-9,11,18,21H,10H2,1-5H3; Key:VKQFCGNPDRICFG-UHFFFAOYSA-N;
	(verify)

Nisoldipine is a pharmaceutical drug used for the treatment of chronic angina pectoris and hypertension. It is a calcium channel blocker of the dihydropyridine class. It is sold in the United States under the proprietary name Sular. Nisoldipine has tropism for cardiac blood vessels.^[1]

It was patented in 1975 and approved for medical use in 1990.^[2]

Contraindications

Nisoldipine is contraindicated in people with cardiogenic shock, unstable angina, myocardial infarction, and during pregnancy and lactation.^[3]

Adverse effects

Common side effects are headache, confusion, fast heartbeat, and edema. Hypersensitivity reactions are rare and include angioedema.^[3]

Interactions

The substance is metabolized by the liver enzyme CYP3A4. Consequently, CYP3A4 inducers such as rifampicin or carbamazepine could reduce the effectiveness of nisoldipine, while CYP3A4 inhibitors such as ketoconazole increase the amount of nisoldipine in the body more than 20-fold. Grapefruit juice also increases nisoldipine concentrations by inhibiting CYP3A4.^[3]

Pharmacology

Mechanism of action

Nisoldipine is a calcium channel blocker that selectively inhibits L-type calcium channels.^[3]

References

^ Knorr, Andreas M. (1995). "Why is nisoldipine a specific agent in ischemic left ventricular dysfunction?". The American Journal of Cardiology. 75 (13): E36–E40. doi:10.1016/S0002-9149(99)80446-9. PMID 7726122.
^ Fischer, Jnos; Ganellin, C. Robin (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 464. ISBN 9783527607495.
^ ^a ^b ^c ^d Haberfeld, H, ed. (2019). Austria-Codex (in German). Vienna: Österreichischer Apothekerverlag. Syscor 5 mg-Filmtabletten.

External links

Diseases Database (DDB): 30009
Mielcarek J, Grobelny P, Szamburska O (2005). "The effect of beta-carotene on the photostability of nisoldipine". Methods Find Exp Clin Pharmacol. 27 (3): 167–71. doi:10.1358/mf.2005.27.3.890873. PMID 15834448.
Missan S, Zhabyeyev P, Dyachok O, Jones SE, McDonald TF (November 2003). "Block of cardiac delayed-rectifier and inward-rectifier K+ currents by nisoldipine". Br. J. Pharmacol. 140 (5): 863–70. doi:10.1038/sj.bjp.0705518. PMC 1574108. PMID 14530219.
Hamilton S, Houle L, Thadani U (1999). "Rapid-release and coat-core formulations of nisoldipine in treatment of hypertension, angina, and heart failure". Heart Dis. 1 (5): 279–88. PMID 11720635.

[1] Knorr, Andreas M. (1995). "Why is nisoldipine a specific agent in ischemic left ventricular dysfunction?". The American Journal of Cardiology. 75 (13): E36–E40. doi:10.1016/S0002-9149(99)80446-9. PMID 7726122.

[2] Fischer, Jnos; Ganellin, C. Robin (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 464. ISBN 9783527607495.

[AC-3] Haberfeld, H, ed. (2019). Austria-Codex (in German). Vienna: Österreichischer Apothekerverlag. Syscor 5 mg-Filmtabletten.

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