21829-25-4 Category:
  • #LGM Pharma is a Nifedipine CAS# 21829-25-4 API supplier distributor based in the USA. Inquire about DMF, cGMP, price, availability, delivery, purity, and more.
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  • #LGM Pharma offers this active ingredient but not the finished dosage forms.

Product Details:

  • CAS No: 21829-25-4
  • AHFC code: 24:28.1
  • Synonyms:
  • ATC Code: C08CA05
  • Chemical Formula: C21H26N2O7
  • Molecular Weight: 346.3346
  • Assay/Purity: Typically NLT 98%
  • DrugBank: DB01115 (APRD00590)
  • SMILES: COC(=O)C1=C(C)NC(C)=C(C1C1=CC=CC=C1[N+]([O-])=O)C(=O)OC
  • PubChem: 4485
  • IUPAC: 3,5-dimethyl 2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate

Additional Details

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).
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.
Mode 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 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.
Hepatic metabolism via cytochrome P450 system. Predominantly metabolized by CYP3A4, but also by CYP1A2 and CYP2A6 isozymes.
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)
General Reference:
Brown MJ, Palmer CR, Castaigne A, de Leeuw PW, Mancia G, Rosenthal T, Ruilope LM: Morbidity and mortality in patients randomised to double-blind treatment with a long-acting calcium-channel blocker or diuretic in the International Nifedipine GITS study: Intervention as a Goal in Hypertension Treatment (INSIGHT). Lancet. 2000 Jul 29;356(9227):366-72. Pubmed Poole-Wilson PA, Kirwan BA, Voko Z, de Brouwer S, van Dalen FJ, Lubsen J: Safety of nifedipine GITS in stable angina: the ACTION trial. Cardiovasc Drugs Ther. 2006 Feb;20(1):45-54. Pubmed Odou P, Ferrari N, Barthelemy C, Brique S, Lhermitte M, Vincent A, Libersa C, Robert H: Grapefruit juice-nifedipine interaction: possible involvement of several mechanisms. J Clin Pharm Ther. 2005 Apr;30(2):153-8. Pubmed Grossman E, Messerli FH, Grodzicki T, Kowey P: Should a moratorium be placed on sublingual nifedipine capsules given for hypertensive emergencies and pseudoemergencies? JAMA. 1996 Oct 23-30;276(16):1328-31. Pubmed Takahashi D, Oyunzul L, Onoue S, Ito Y, Uchida S, Simsek R, Gunduz MG, Safak C, Yamada S: Structure-activity relationships of receptor binding of 1,4-dihydropyridine derivatives. Biol Pharm Bull. 2008 Mar;31(3):473-9. Pubmed Varon J, Marik PE: Clinical review: the management of hypertensive crises. Crit Care. 2003 Oct;7(5):374-84. Epub 2003 Jul 16. Pubmed
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