QuickView for nifedipine (compound)

Summary
General Info

PubChem

PubChem Compound 10383105

Name:	Nifedipine
PubChem Compound ID:	10383105
Description:	A potent vasodilator agent with calcium antagonistic action. It is a useful anti-anginal agent that also lowers blood pressure.
Molecular formula:	C₁₇H₁₈N₂O₆
Molecular weight:	348.327 g/mol

DrugBank

Identification

Name:	Nifedipine
Name (isomeric):	DB01115
Drug Type:	small molecule
Description:	A potent vasodilator agent with calcium antagonistic action. It is a useful anti-anginal agent that also lowers blood pressure.
Brand:	Ecodipi, Zenusin, Nifar, Cordipin, Adalat Retard, Depin, Cardifen, Oxcord, Kordafen, Adalat Gits 30, Coral, Adalat 10, Corynphar, Dilafed, Alonix, Fenihidin, Alonix S, Cordicant, Calcigard, Nifidine, Aldipin, Introcar, Apo-Nifed, Adapine, Nifedipres, Corotrend, Nifedepat, Aprical, Cordalat, Nifedipine Retard, Corinfar, Nifangin, Adapress, Adalat LP, Camont, Fenamon, Pidilat, Tibricol, Fedcor, Hexadilat, Megalat, Nifdemin, Coracten, Nifelat, Nifelat Q, Hadipin, Orix, Chronadalate, Macorel, Nedipin, Alfadal, Adalat LA, Adalat CR, Nifipen, Adalat 20, Nifecor, Adalat CC, Calcibloc, Fenihidine, Sepamit, Nifecard, Anifed, Adalat, Glopir, Procardia XL, Procardia, Adalat 5, Nifedicor, Nifedin, Fenamon Sr, Adalate, Myogard, Cordafen, Ecodipin, Adalat Oros, Chronadalate Lp, Nifelan, Nicardia, Fedcor Retard, Cardionorm, Nifedine, Bonacid, Alpha-Nifedipine Retard, Anpine, Cardilat, Adalat Gits, Nifebene, Nificard, Nifedirex LP, Cordaflex, Adalat PA, Alat, Duranifin, Nifensar XL, Citilat, Dipinkor, Niphedipine, Dilcor, Adalat Ft, N1fedilat, Cordilan, Adalat Crono, Calcilat, Angipec, Nifelate, Ecodipin E, Dignokonstant
Category:	Vasodilator Agents, Tocolytic Agents, Calcium Channel Blockers, Dihydropyridines
CAS number:	21829-25-4

Pharmacology

Indication:	For the management of vasospastic angina, chronic stable angina, hypertension, and Raynaud's phenomenon. May be used as a first line agent for left ventricular hypertrophy and isolated systolic hypertension (long-acting agents).
Pharmacology:	Nifedipine, the prototype of the dihydropyridine class of calcium channel blockers (CCBs), is similar to other dihydropyridines including amlodipine, felodipine, isradipine, and nicardipine. There are at least five different types of calcium channels in Homo sapiens: L-, N-, P/Q-, R- and T-type. CCBs target L-type calcium channels, the major channe... show more » Nifedipine, the prototype of the dihydropyridine class of calcium channel blockers (CCBs), is similar to other dihydropyridines including amlodipine, felodipine, isradipine, and nicardipine. There are at least five different types of calcium channels in Homo sapiens: L-, N-, P/Q-, R- and T-type. CCBs target L-type calcium channels, the major channel in muscle cells that mediates contraction. Similar to other DHP CCBs, nifedipine binds directly to inactive calcium channels stabilizing their inactive conformation. Since arterial smooth muscle depolarizations are longer in duration than cardiac muscle depolarizations, inactive channels are more prevalent in smooth muscle cells. Alternative splicing of the alpha-1 subunit of the channel gives nifedipine additional arterial selectivity. At therapeutic sub-toxic concentrations, nifedipine has little effect on cardiac myocytes and conduction cells. By blocking the calcium channels, Nifedipine inhibits the spasm of the coronary artery and dilates the systemic arteries, results in a increase of myocardial oxygen supply and a decrease in systemic blood pressure. show less «
Mechanism of Action:	Nifedipine decreases arterial smooth muscle contractility and subsequent vasoconstriction by inhibiting the influx of calcium ions through L-type calcium channels. Calcium ions entering the cell through these channels bind to calmodulin. Calcium-bound calmodulin then binds to and activates myosin light chain kinase (MLCK). Activated MLCK catalyzes ... show more » Nifedipine decreases arterial smooth muscle contractility and subsequent vasoconstriction by inhibiting the influx of calcium ions through L-type calcium channels. Calcium ions entering the cell through these channels bind to calmodulin. Calcium-bound calmodulin then binds to and activates myosin light chain kinase (MLCK). Activated MLCK catalyzes the phosphorylation of the regulatory light chain subunit of myosin, a key step in muscle contraction. Signal amplification is achieved by calcium-induced calcium release from the sarcoplasmic reticulum through ryanodine receptors. Inhibition of the initial influx of calcium inhibits the contractile processes of smooth muscle cells, causing dilation of the coronary and systemic arteries, increased oxygen delivery to the myocardial tissue, decreased total peripheral resistance, decreased systemic blood pressure, and decreased afterload. The vasodilatory effects of nifedipine result in an overall decrease in blood pressure. show less «
Absorption:	Rapidly and fully absorbed following oral administration.
Protein binding:	92-98%
Biotransformation:	Hepatic metabolism via cytochrome P450 system. Predominantly metabolized by CYP3A4, but also by CYP1A2 and CYP2A6 isozymes.
Route of elimination:	Nifedipine is extensively metabolized to highly water-soluble, inactive metabolites accounting for 60 to 80% of the dose excreted in the urine. The remainder is excreted in the feces in metabolized form, most likely as a result of biliary excretion.
Half Life:	2 hours
Toxicity:	Symptoms of overdose include dizziness, drowsiness, nausea, severe drop in blood pressure, slurred speech, and weakness. LD₅₀=494 mg/kg (orally in mice); LD₅₀=1022 mg/kg (orally in rats)
Affected organisms:	Humans and other mammals

Interactions

Food interaction:

Grapefruit down-regulates post-translational expression of CYP3A4, the major metabolizing enzyme of nifedipine. Grapefruit, in all forms (e.g. whole fruit, juice and rind), can significantly increase serum levels of nifedipine and may cause toxicity. Avoid grapefruit products while on this medication.

Avoid alcohol.

Take with low fat meal.

Avoid natural licorice.

Drug interaction:

Melatonin	Melatonin can possibly decrease the effect of nifedipine
Talbutal	The barbiturate, talbutal, decreases the effect of the calcium channel blocker, nifedipine.
Quinupristin	Synercid increases the effect of ziprasidone
Methohexital	The barbiturate, methohexital, decreases the effect of the calcium channel blocker, nifedipine.
Quinidine	Decreased quinidine effect, increased nifedipine effect

Melatonin	Melatonin can possibly decrease the effect of nifedipine
Talbutal	The barbiturate, talbutal, decreases the effect of the calcium channel blocker, nifedipine.
Quinupristin	Synercid increases the effect of ziprasidone
Methohexital	The barbiturate, methohexital, decreases the effect of the calcium channel blocker, nifedipine.
Quinidine	Decreased quinidine effect, increased nifedipine effect
Tacrolimus	The calcium channel blocker, Nifedipine, may increase the blood concentration of Tacrolimus. Monitor for changes in the therapeutic/toxic effects of Tacrolimus if Nifedipine therapy is initiated, discontinued or altered.
Cimetidine	Cimetidine may increase the effect of the calcium channel blocker, nifedipine.
Quinidine barbiturate	Decreased quinidine effect, increased nifedipine effect
Tipranavir	Tipranavir may decrease the metabolism and clearance of the calcium channel blocker, Nifedipine. Monitor for changes in Nifedipine therapeutic and adverse effects if Tipranavir is initiated, discontinued or dose changed.
Pentobarbital	The barbiturate, pentobarbital, decreases the effect of the calcium channel blocker, nifedipine.
Phenobarbital	The barbiturate, phenobarbital, may decrease the effect of the calcium channel blocker, nifedipine.
Imatinib	Imatinib increases the effect and toxicity of nifedipine
Cisapride	Cisapride may increase the effect and toxicity of nifedipine.
Aprobarbital	The barbiturate, aprobarbital, decreases the effect of the calcium channel blocker, nifedipine.
Treprostinil	Additive hypotensive effect. Monitor antihypertensive therapy during concomitant use.
Tizanidine	Nifedipine may decrease the metabolism and clearance of Tizanidine. Consider alternate therapy or use caution during co-administration.
Butabarbital	The barbiturate, butabarbital, decreases the effect of the calcium channel blocker, nifedipine.
Voriconazole	Voriconazole, a strong CYP3A4 inhibitor, may increase the serum concentration of nifedipine by decreasing its metabolism. Monitor for changes in the therapeutic and adverse effects of nifedipine if voriconazole is initiated, discontinued or dose changed.
Butethal	The barbiturate, butethal, decreases the effect of the calcium channel blocker, nifedipine.
Thiopental	The CYP3A4 inducer, Thiopental, may increase the metabolism and clearance of Nifedipine, a CYP3A4 substrate. Monitor for changes in the therapeutic/adverse effects of Nifedipine if Thiopental is initiated, discontinued or dose changed.
Ginseng	Ginseng increases the effect and toxicity of nifedipine
Methylphenobarbital	The barbiturate, methylphenobarbital, decreases the effect of the calcium channel blocker, nifedipine.
St. John's Wort	St. John's Wort decreases the effect of nifedipine
Secobarbital	The barbiturate, secobarbital, decreases the effect of the calcium channel blocker, nifedipine.
Hexobarbital	The barbiturate, hexobarbital, decreases the effect of the calcium channel blocker, nifedipine.
Rifampin	Rifampin decreases the effect of the calcium channel blocker, nifedipine.
Primidone	The barbiturate, primidone, decreases the effect of the calcium channel blocker, nifedipine.
Cyclosporine	Increased risk of gingivitis
Telithromycin	Telithromycin may reduce clearance of Nifedipine. Consider alternate therapy or monitor for changes in the therapeutic/adverse effects of Nifedipine if Telithromycin is initiated, discontinued or dose changed.
Tacrine	The metabolism of Tacrine, a CYP1A2 substrate, may be reduced by Nifedipine, a CYP1A2 inhibitors. Monitor the efficacy and toxicity of Tacrine if Nifedipine is initiated, discontinued or if the dose is changed.
Heptabarbital	The barbiturate, heptabarbital, decreases the effect of the calcium channel blocker, nifedipine.
Dihydroquinidine barbiturate	Decreased quinidine effect, increased nifedipine effect
Butalbital	The barbiturate, butalbital, decreases the effect of the calcium channel blocker, nifedipine.
Amobarbital	The barbiturate, amobarbital, decreases the effect of the calcium channel blocker, nifedipine.