Nisoldipine

{{Short description|Antihypertensive drug of the calcium channel blocker class}}

{{Drugbox

| Verifiedfields = changed

| verifiedrevid = 408341052

| IUPAC_name = (RS)-Isobutyl methyl 2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate

| image = Nisoldipine structure.svg

| image_class = skin-invert-image

| width = 240

| alt = Skeletal formula of nisoldipine

| image2 = Nisoldipine-3D-balls.png

| alt2 = Ball-and-stick model of the nisoldipine molecule

| tradename = Sular, Baymycard, Syscor

| Drugs.com = {{drugs.com|monograph|nisoldipine}}

| MedlinePlus = a696009

| pregnancy_AU =

| pregnancy_US = C

| pregnancy_category =

| legal_AU =

| legal_UK =

| legal_US = Rx-only

| legal_status =

| routes_of_administration = Oral

| bioavailability = 4–8%

| protein_bound = >99%

| metabolism = CYP3A4

| elimination_half-life = 7–12 hours

| excretion = 70–80% via urine

| CAS_number_Ref = {{cascite|correct|??}}

| CAS_number = 63675-72-9

| ATC_prefix = C08

| ATC_suffix = CA07

| ATC_supplemental =

| PubChem = 4499

| IUPHAR_ligand = 2524

| DrugBank_Ref = {{drugbankcite|changed|drugbank}}

| DrugBank = DB00401

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 4343

| UNII_Ref = {{fdacite|changed|FDA}}

| UNII = 4I8HAB65SZ

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = D00618

| ChEBI_Ref = {{ebicite|changed|EBI}}

| ChEBI = 7577

| ChEMBL_Ref = {{ebicite|changed|EBI}}

| ChEMBL = 1726

| C=20 | H=24 | N=2 | O=6

| smiles=CC1=C(C(C(=C(N1)C)C(=O)OCC(C)C)c2ccccc2[N+](=O)[O-])C(=O)OC

| StdInChI=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

| StdInChIKey=VKQFCGNPDRICFG-UHFFFAOYSA-N

}}

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.{{cite journal | vauthors = Knorr AM | title = Why is nisoldipine a specific agent in ischemic left ventricular dysfunction? | journal = The American Journal of Cardiology | volume = 75 | issue = 13 | pages = 36E–40E | date = April 1995 | pmid = 7726122 | doi = 10.1016/S0002-9149(99)80446-9 }}

It was patented in 1975 and approved for medical use in 1990.{{cite book | vauthors = Fischer J, Ganellin CR |title=Analogue-based Drug Discovery |date=2006 |publisher=John Wiley & Sons |isbn=9783527607495 |page=464 |url=https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA464 |language=en}}

Contraindications

Nisoldipine is contraindicated in people with cardiogenic shock, unstable angina, myocardial infarction, and during pregnancy and lactation.{{cite book|title=Austria-Codex|at=Syscor 5 mg-Filmtabletten| veditors = Haberfeld H |publisher=Österreichischer Apothekerverlag |location=Vienna |year=2019 |language=de}}

Adverse effects

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

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.