Tìm theo
Nifedipine
Các tên gọi khác (11 ) :
  • 4-(2'-Nitrophenyl)-2,6-dimethyl-1,4-dihydropyridin-3,5-dicarbonsaeuredimethylester
  • Adalat
  • Adapine
  • Coracten
  • Nifecard
  • Nifecor
  • Nifedipine
  • Nifedipino
  • Nifedipinum
  • Nifedipres
  • Procardia
Thuốc tim mạch
Thuốc Gốc
Small Molecule
CAS: 21829-25-4
ATC: C08CA05
ĐG : Actavis Group , http://www.actavis.com
CTHH: C17H18N2O6
PTK: 346.3346
Nifedipine has been formulated as both a long- and short-acting 1,4-dihydropyridine calcium channel blocker. It acts primarily on vascular smooth muscle cells by stabilizing voltage-gated L-type calcium channels in their inactive conformation. By inhibiting the influx of calcium in smooth muscle cells, nifedipine prevents calcium-dependent myocyte contraction and vasoconstriction. A second proposed mechanism for the drug’s vasodilatory effects involves pH-dependent inhibition of calcium influx via inhibition of smooth muscle carbonic anhydrase. Nifedipine is used to treat hypertension and chronic stable angina.
Nhận Dạng Quốc Tế & Đặc Tính Hóa Học
Công thức hóa học
C17H18N2O6
Phân tử khối
346.3346
Monoisotopic mass
346.116486318
InChI
InChI=1S/C17H18N2O6/c1-9-13(16(20)24-3)15(14(10(2)18-9)17(21)25-4)11-7-5-6-8-12(11)19(22)23/h5-8,15,18H,1-4H3
InChI Key
InChIKey=HYIMSNHJOBLJNT-UHFFFAOYSA-N
IUPAC Name
3,5-dimethyl 2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
Traditional IUPAC Name
nifedipine
SMILES
COC(=O)C1=C(C)NC(C)=C(C1C1=CC=CC=C1[N+]([O-])=O)C(=O)OC
Độ tan chảy
172-174 °C
Độ hòa tan
Insoluble
logP
2.20
logS
-4.3
pKa (Strongest Basic)
5.33
PSA
110.45 Å2
Refractivity
92.16 m3·mol-1
Polarizability
33.85 Å3
Rotatable Bond Count
6
H Bond Acceptor Count
5
H Bond Donor Count
1
Physiological Charge
0
Number of Rings
2
Bioavailability
1
Rule of Five
true
Ghose Filter
true
Dược Lực Học : 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.
Cơ Chế Tác Dụng : Nifedipine has been formulated as both a long- and short-acting 1,4-dihydropyridine calcium channel blocker. It acts primarily on vascular smooth muscle cells by stabilizing voltage-gated L-type calcium channels in their inactive conformation. By inhibiting the influx of calcium in smooth muscle cells, nifedipine prevents calcium-dependent myocyte contraction and vasoconstriction. A second proposed mechanism for the drug’s vasodilatory effects involves pH-dependent inhibition of calcium influx via inhibition of smooth muscle carbonic anhydrase. Nifedipine is used to treat hypertension and chronic stable angina. 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.
Dược Động Học :
▧ Absorption :
Rapidly and fully absorbed following oral administration.
▧ Protein binding :
92-98%
▧ Metabolism :
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
Độc Tính : 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)
Chỉ Định : 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).
Tương Tác Thuốc :
  • Amobarbital The barbiturate, amobarbital, decreases the effect of the calcium channel blocker, nifedipine.
  • Aprobarbital The barbiturate, aprobarbital, decreases the effect of the calcium channel blocker, nifedipine.
  • Butabarbital The barbiturate, butabarbital, decreases the effect of the calcium channel blocker, nifedipine.
  • Butalbital The barbiturate, butalbital, decreases the effect of the calcium channel blocker, nifedipine.
  • Butethal The barbiturate, butethal, decreases the effect of the calcium channel blocker, nifedipine.
  • Cimetidine Cimetidine may increase the effect of the calcium channel blocker, nifedipine.
  • Cisapride Cisapride may increase the effect and toxicity of nifedipine.
  • Cyclosporine Increased risk of gingivitis
  • Dihydroquinidine barbiturate Decreased quinidine effect, increased nifedipine effect
  • Etravirine Nifedipine, when used concomitantly with etravirine (a strong CYP3A4 inducer), may experience a decrease in serum concentration. It is recommended to monitor nifedipine therapy for reduced effectiveness.
  • Ginseng Ginseng increases the effect and toxicity of nifedipine
  • Heptabarbital The barbiturate, heptabarbital, decreases the effect of the calcium channel blocker, nifedipine.
  • Hexobarbital The barbiturate, hexobarbital, decreases the effect of the calcium channel blocker, nifedipine.
  • Imatinib Imatinib increases the effect and toxicity of nifedipine
  • Melatonin Melatonin can possibly decrease the effect of nifedipine
  • Methohexital The barbiturate, methohexital, decreases the effect of the calcium channel blocker, nifedipine.
  • Methylphenobarbital The barbiturate, methylphenobarbital, decreases the effect of the calcium channel blocker, nifedipine.
  • 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.
  • Primidone The barbiturate, primidone, decreases the effect of the calcium channel blocker, nifedipine.
  • Quinidine Decreased quinidine effect, increased nifedipine effect
  • Quinidine barbiturate Decreased quinidine effect, increased nifedipine effect
  • Quinupristin Synercid increases the effect of ziprasidone
  • Rifampicin Rifampin decreases the effect of the calcium channel blocker, nifedipine.
  • Secobarbital The barbiturate, secobarbital, decreases the effect of the calcium channel blocker, nifedipine.
  • St. John's Wort St. John's Wort decreases the effect of nifedipine
  • 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.
  • 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.
  • Talbutal The barbiturate, talbutal, decreases the effect of the calcium channel blocker, nifedipine.
  • 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.
  • 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.
  • 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.
  • Tizanidine Nifedipine may decrease the metabolism and clearance of Tizanidine. Consider alternate therapy or use caution during co-administration.
  • Treprostinil Additive hypotensive effect. Monitor antihypertensive therapy during concomitant use.
  • 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.
Liều Lượng & Cách Dùng : Capsule - Oral - 10 mg
Capsule - Oral - 20 mg
Tablet, extended release - Oral - 20 mg
Tablet, extended release - Oral - 30 mg
Tablet, extended release - Oral - 60 mg
Tablet, film coated, extended release - Oral - 30 mg
Tablet, film coated, extended release - Oral - 60 mg
Tablet, film coated, extended release - Oral - 90 mg
Dữ Kiện Thương Mại
Giá thị trường
Nhà Sản Xuất
  • Công ty : Bayer
    Sản phẩm biệt dược : Adalat
  • Công ty :
    Sản phẩm biệt dược : Adapine
  • Công ty :
    Sản phẩm biệt dược : Afeditab
  • Công ty :
    Sản phẩm biệt dược : Afeditab CR
  • Công ty :
    Sản phẩm biệt dược : Coracten
  • Công ty :
    Sản phẩm biệt dược : Nifecard
  • Công ty :
    Sản phẩm biệt dược : Nifecor
  • Công ty :
    Sản phẩm biệt dược : Nifedical
  • Công ty :
    Sản phẩm biệt dược : NifedicalXL
  • Công ty :
    Sản phẩm biệt dược : Nifedipres
  • Công ty : Pfizer
    Sản phẩm biệt dược : Procardia
  • Công ty : Pfizer
    Sản phẩm biệt dược : Procardia XL
Đóng gói
Tài Liệu Tham Khảo Thêm
drugbank
http://www.drugbank.ca/drugs/DB01115
PubChem Compound
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=4485
PubChem Substance
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=46505103
KEGG Compound
http://www.genome.jp/dbget-bin/www_bget?cpd:C07266
KEGG Drug
http://www.genome.jp/dbget-bin/www_bget?drug:D00437
ChemSpider
http://www.chemspider.com/Chemical-Structure.4330.html
BindingDB
http://www.bindingdb.org/bind/chemsearch/marvin/MolStructure.jsp?monomerid=50000778
National Drug Code Directory
http://www.hipaaspace.com/Medical_Billing/Coding/National.Drug.Codes/PDF/0378-3475-01
PharmGKB
http://www.pharmgkb.org/drug/PA450631
Wikipedia
http://en.wikipedia.org/wiki/Nifedipine
RxList
http://www.rxlist.com/cgi/generic2/nifedip.htm
Drugs.com
http://www.drugs.com/nifedipine.html
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