nicardipine

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

{{Infobox drug

| Watchedfields = changed

| verifiedrevid = 462260009

| IUPAC_name = 2-[benzyl(methyl)amino]ethylmethyl-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate

| image = Nicardipine.svg

| caption = Above: molecular structure of nicardipine

Below: 3D representation of a nicardipine molecule

| image2 = Nicardipine 3D.png

| tradename = Cardene

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

| MedlinePlus = a695032

| pregnancy_category =

| legal_status = Rx-only

| routes_of_administration = Oral, intravenous

| bioavailability =

| protein_bound = >95%

| metabolism =

| elimination_half-life = 8.6 hours

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

| CAS_number = 55985-32-5

| ATC_prefix = C08

| ATC_suffix = CA04

| ATC_supplemental =

| PubChem = 4474

| IUPHAR_ligand = 2559

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| DrugBank = DB00622

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 4319

| ChEBI = 7550

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = CZ5312222S

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

| KEGG = D08270

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 1484

| C = 26

| H = 29

| N = 3

| O = 6

| smiles = O=C(OCCN(Cc1ccccc1)C)\C2=C(\N/C(=C(/C(=O)OC)C2c3cccc([N+]([O-])=O)c3)C)C

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C26H29N3O6/c1-17-22(25(30)34-4)24(20-11-8-12-21(15-20)29(32)33)23(18(2)27-17)26(31)35-14-13-28(3)16-19-9-6-5-7-10-19/h5-12,15,24,27H,13-14,16H2,1-4H3

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = ZBBHBTPTTSWHBA-UHFFFAOYSA-N

| melting_point = 136-138

}}

Nicardipine (Cardene) is a medication used to treat angina and hypertension, especially for hemorrhagic stroke patients.{{Cite book | vauthors = Hemphill JC, Smith WS, Gress DR |title=Harrison's Principles of Internal Medicine |date=2022 |publisher=McGraw Hill |isbn=978-1-264-26850-4 |edition=21st |location=New York |chapter=Chapter 429: Subarachnoid Hemorrhage}} It belongs to the dihydropyridine class of calcium channel blockers (CCBs). It is also used for Raynaud's phenomenon. It is available in by mouth and intravenous formulations. It has been used in percutaneous coronary intervention.{{cite journal | vauthors = Huang RI, Patel P, Walinsky P, Fischman DL, Ogilby JD, Awar M, Frankil C, Savage MP | title = Efficacy of intracoronary nicardipine in the treatment of no-reflow during percutaneous coronary intervention | journal = Catheterization and Cardiovascular Interventions | volume = 68 | issue = 5 | pages = 671–676 | date = November 2006 | pmid = 17034064 | doi = 10.1002/ccd.20885 | s2cid = 37071966 }}

Its mechanism of action and clinical effects closely resemble those of nifedipine and the other dihydropyridine calcium channel blockers (amlodipine, felodipine), except that nicardipine is more selective for cerebral and coronary blood vessels. It is primarily a peripheral arterial vasodilator, thus unlike the nitrovasodilators (nitroglycerin and nitroprusside), cardiac preload is minimally affected. It has the longest duration among parenteral CCBs.{{cite book | vauthors = Freeman BS | date = 2014 | chapter = Vasodilators | veditors = Freeman BS, Berger JS | title = Anesthesiology Core Review: Part One Basic Exam. | publisher = McGraw Hill | chapter-url = https://accessanesthesiology.mhmedical.com/content.aspx?bookid=974§ionid=61590560 | isbn = 978-0-07-182137-7 }}{{cite book | vauthors = Sutters M | date = 2022 | chapter = Hypertensive urgencies & emergencies. | veditors = Papadakis MA, McPhee SJ, Rabow MW, McQuaid KR | title = Current Medical Diagnosis & Treatment | publisher = McGraw Hill | chapter-url = https://accessmedicine.mhmedical.com/content.aspx?bookid=3081§ionid=258962164 | isbn = 978-1-2642-6938-9 }} As its use may lead to reflex tachycardia, it is advisable to use it in conjunction with a beta-blocker. In the setting of a ruptured brain aneurysm, nicardipine may be used (if nimodipine is unavailable) to reduce blood pressure and as prevention or treatment against cerebral vasospasm.

It was patented in 1973 and approved for medical use in 1981.{{cite book | vauthors = Fischer J, Ganellin CR |title=Analogue-based Drug Discovery |date=2006 |publisher=John Wiley & Sons |isbn=978-3-527-60749-5 |page=464 |url=https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA464 |language=en}} Nicardipine was approved by the FDA in December 1988. The patent for both Cardene and Cardene SR expired in October 1995.{{cite web | url = https://www.nlm.nih.gov/medlineplus/druginfo/meds/a695032.html | title = Nicardipine | work = Medline Plus | publisher = U.S. National Library of Medicine }}

Medical uses

= Hypertensive emergency =

Nicardipine is a calcium channel blocker used primarily for the management of hypertension and angina. It is particularly effective in the treatment of acute and severe hypertension, including hypertensive emergency.{{cite journal | vauthors = Peacock WF, Varon J, Baumann BM, Borczuk P, Cannon CM, Chandra A, Cline DM, Diercks D, Hiestand B, Hsu A, Jois-Bilowich P, Kaminski B, Levy P, Nowak RM, Schrock JW | title = CLUE: a randomized comparative effectiveness trial of IV nicardipine versus labetalol use in the emergency department | journal = Critical Care | volume = 15 | issue = 3 | pages = R157 | date = 2011-06-27 | pmid = 21707983 | pmc = 3219031 | doi = 10.1186/cc10289 | doi-access = free }} This is due to the rapid onset and short half-life of this drug, which allows for precision in the control of blood pressure.

= Other =

Nicardipine is also used commonly in the perioperative setting for blood pressure fluctuations during surgery.{{cite journal | vauthors = Kovac AL, Masiongale A | title = Comparison of nicardipine versus esmolol in attenuating the hemodynamic responses to anesthesia emergence and extubation | language = English | journal = Journal of Cardiothoracic and Vascular Anesthesia | volume = 21 | issue = 1 | pages = 45–50 | date = February 2007 | pmid = 17289479 | doi = 10.1053/j.jvca.2006.08.005 }} Other scenarios for usage of Nicardipine include subarachnoid hemorrhage and hypertensive crisis of pregnancy.{{cite journal | vauthors = Awaludin A, Rahayu C, Daud NA, Zakiyah N | title = Antihypertensive Medications for Severe Hypertension in Pregnancy: A Systematic Review and Meta-Analysis | journal = Healthcare | volume = 10 | issue = 2 | pages = 325 | date = February 2022 | pmid = 35206939 | pmc = 8872490 | doi = 10.3390/healthcare10020325 | doi-access = free }}

Side effects

Nicardipine is associated to a wide range of side effects, due mainly to its vasodilatory effects. Common adverse effects include dizziness, fainting, flushing and peripheral edema.{{cite journal | vauthors = Wallin JD | title = Intravenous nicardipine hydrochloride: treatment of patients with severe hypertension | journal = American Heart Journal | volume = 119 | issue = 2 Pt 2 | pages = 434–437 | date = February 1990 | pmid = 2405613 | doi = 10.1016/S0002-8703(05)80064-X }} This is a direct result to the relaxation of blood vessels and lower systemic vascular resistance.

Hypotension is another frequently observed side effect, particularly seen in scenarios when this medication is used intravenously for hypertensive emergencies.{{cite journal | vauthors = Cornette J, Buijs EA, Duvekot JJ, Herzog E, Roos-Hesselink JW, Rizopoulos D, Meima M, Steegers EA | title = Hemodynamic effects of intravenous nicardipine in severely pre-eclamptic women with a hypertensive crisis | journal = Ultrasound in Obstetrics & Gynecology | volume = 47 | issue = 1 | pages = 89–95 | date = January 2016 | pmid = 25721057 | doi = 10.1002/uog.14836 }} Reflex tachycardia is a common compensatory response to vasodilation.{{Cite journal | vauthors = Yamamoto R, Suzuki S, Sugawara R, isito J, Koizumi H, Momoo T, Tanaka F |date=2018-01-22 |title=Abstract WP328: Suppression of Tachycardia and Cost Effectiveness of Bisoprolol Transdermal Patch Addition to Intravenous Nicardipine in Antihypertensive Treatment for Acute Intracerebral Hemorrhage |url=https://www.ahajournals.org/doi/10.1161/str.49.suppl_1.WP328 |journal=Stroke |volume=49 |issue=Suppl_1 |pages=AWP328 |doi=10.1161/str.49.suppl_1.WP328|url-access=subscription }} These side effects are usually mild and resolve following adjustment in dosage of the medication or discontinuation.