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Nicardipine

Antihypertensive drug of the calcium channel blocker class

Field	Value
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
image_class	skin-invert-image
<!--Clinical data-->	caption	Above: molecular structure of nicardipine
image2	Nicardipine 3D.png
image_class2	bg-transparent
tradename	Cardene
Drugs.com
MedlinePlus	a695032
legal_status	Rx-only
routes_of_administration	Oral, intravenous
protein_bound	95%
elimination_half-life	8.6 hours
<!--Identifiers-->	CAS_number_Ref
CAS_number	55985-32-5
ATC_prefix	C08
ATC_suffix	CA04
PubChem	4474
IUPHAR_ligand	2559
DrugBank_Ref
DrugBank	DB00622
ChemSpiderID_Ref
ChemSpiderID	4319
ChEBI	7550
UNII_Ref
UNII	CZ5312222S
KEGG_Ref
KEGG	D08270
ChEMBL_Ref
ChEMBL	1484
<!--Chemical data-->	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
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
StdInChIKey	ZBBHBTPTTSWHBA-UHFFFAOYSA-N
melting_point	136-138

Below: 3D representation of a nicardipine molecule | Drugs.com = | elimination_half-life = 8.6 hours Nicardipine (Cardene) is a medication used to treat angina and hypertension, especially for hemorrhagic stroke patients. 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.

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. 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. Nicardipine was approved by the FDA in December 1988. The patent for both Cardene and Cardene SR expired in October 1995.

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. 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. Other scenarios for usage of Nicardipine include subarachnoid hemorrhage and hypertensive crisis of pregnancy.

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. 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. Reflex tachycardia is a common compensatory response to vasodilation. These side effects are usually mild and resolve following adjustment in dosage of the medication or discontinuation.

References

(2022). "Harrison's Principles of Internal Medicine". McGraw Hill.
(November 2006). "Efficacy of intracoronary nicardipine in the treatment of no-reflow during percutaneous coronary intervention". Catheterization and Cardiovascular Interventions.
(2014). "Anesthesiology Core Review: Part One Basic Exam.". McGraw Hill.
(2022). "Current Medical Diagnosis & Treatment". McGraw Hill.
(2006). "Analogue-based Drug Discovery". John Wiley & Sons.
"Nicardipine". U.S. National Library of Medicine.
(2011-06-27). "CLUE: a randomized comparative effectiveness trial of IV nicardipine versus labetalol use in the emergency department". Critical Care.
(February 2007). "Comparison of nicardipine versus esmolol in attenuating the hemodynamic responses to anesthesia emergence and extubation". Journal of Cardiothoracic and Vascular Anesthesia.
(February 2022). "Antihypertensive Medications for Severe Hypertension in Pregnancy: A Systematic Review and Meta-Analysis". Healthcare.
(February 1990). "Intravenous nicardipine hydrochloride: treatment of patients with severe hypertension". American Heart Journal.
(January 2016). "Hemodynamic effects of intravenous nicardipine in severely pre-eclamptic women with a hypertensive crisis". Ultrasound in Obstetrics & Gynecology.
(2018-01-22). "Abstract WP328: Suppression of Tachycardia and Cost Effectiveness of Bisoprolol Transdermal Patch Addition to Intravenous Nicardipine in Antihypertensive Treatment for Acute Intracerebral Hemorrhage". Stroke.

Info: Wikipedia Source

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calcium-channel-blockers cyp2d6-inhibitors dihydropyridines 3-nitrophenyl-compounds drugs-developed-by-hoffmann-la-roche carboxylate-esters amines glycine-receptor-agonists glycine-receptor-antagonists gabaa-receptor-negative-allosteric-modulators methyl-esters benzyl-compounds

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