Home > Compound List > Compound details
21829-25-4 molecular structure
click picture or here to close

3,5-dimethyl 2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate

ChemBase ID: 986
Molecular Formular: C17H18N2O6
Molecular Mass: 346.33462
Monoisotopic Mass: 346.11648631
SMILES and InChIs

SMILES:
O(C(=O)C1=C(NC(=C(C1c1c([N+](=O)[O-])cccc1)C(=O)OC)C)C)C
Canonical SMILES:
COC(=O)C1=C(C)NC(=C(C1c1ccccc1[N+](=O)[O-])C(=O)OC)C
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
InChIKey:
HYIMSNHJOBLJNT-UHFFFAOYSA-N

Cite this record

CBID:986 http://www.chembase.cn/molecule-986.html

Collapse All Expand All

NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
3,5-dimethyl 2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
IUPAC Traditional name
procardia xl
3,5-dimethyl 2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
Brand Name
Adalat
Adalat 10
Adalat 20
Adalat 5
Adalat CC
Adalat CR
Adalat Crono
Adalat Ft
Adalat Gits
Adalat Gits 30
Adalat LA
Adalat LP
Adalat Oros
Adalat PA
Adalat Retard
Adalate
Adapine
Adapress
Alat
Aldipin
Alfadal
Alonix
Alonix S
Alpha-Nifedipine Retard
Angipec
Anifed
Anpine
Apo-Nifed
Aprical
Bonacid
Calcibloc
Calcigard
Calcilat
Camont
Cardifen
Cardilat
Cardionorm
Chronadalate
Chronadalate Lp
Citilat
Coracten
Coral
Cordafen
Cordaflex
Cordalat
Cordicant
Cordilan
Cordipin
Corinfar
Corotrend
Corynphar
Depin
Dignokonstant
Dilafed
Dilcor
Dipinkor
Duranifin
Ecodipi
Ecodipin
Ecodipin E
Fedcor
Fedcor Retard
Fenamon
Fenamon Sr
Fenihidin
Fenihidine
Glopir
Hadipin
Hexadilat
Introcar
Kordafen
Macorel
Megalat
Myogard
N1fedilat
Nedipin
Nicardia
Nifangin
Nifar
Nifdemin
Nifebene
Nifecard
Nifecor
Nifedepat
Nifedicor
Nifedin
Nifedine
Nifedipine Retard
Nifedipres
Nifedirex LP
Nifelan
Nifelat
Nifelat Q
Nifelate
Nifensar XL
Nificard
Nifidine
Nifipen
Niphedipine
Orix
Oxcord
Pidilat
Procardia
Procardia XL
Sepamit
Tibricol
Zenusin
Adalat, Procardia
Synonyms
Nifedipine
Dimethyl 2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydro-3,5-pyridinedicarboxylate
Anifed
Afeditab CR
Nifediac
Nifedical
3,5-dimethyl 2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
Adalate
Aldipine
Cardiate
1,4-Dihydro-2,6-dimethyl-4-(2-nitrophenyl)-3,5-pyridine-dicarboxylic acid dimethyl ester
1,4-Dihydro-2,6-dimethyl-4-(2-nitrophenyl)-3,5-pyridinedicarboxylic acid dimethyl ester
Nifedipine
Adalat
Adipine
Angiopine
Calanif
Calcilat
Cardilate
Coracten
Coroday
Fenihidine
Fortipine
Glopir
Hypolar Retard
Nifecor
Nifedicor
Nifedipress
Nifelat
Nifedotard
Nifensar XL
Nimodrel
Nivaten
Procardia
Slofedipine
Tensipine
CAS Number
21829-25-4
EC Number
244-598-3
MDL Number
MFCD00057326
PubChem SID
24277855
160964449
46505103
PubChem CID
4485
CHEBI ID
7565
ATC CODE
C08CA05
CHEMBL
193
Chemspider ID
4330
DrugBank ID
DB01115
IUPHAR ligand ID
2514
KEGG ID
D00437
Unique Ingredient Identifier
I9ZF7L6G2L
Wikipedia Title
Nifedipine
Medline Plus
a684028

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
H Acceptors H Donor
LogD (pH = 5.5) 1.5918752  LogD (pH = 7.4) 1.8118262 
Log P 1.8154943  Molar Refractivity 92.1647 cm3
Polarizability 33.98248 Å3 Polar Surface Area 110.45 Å2
Rotatable Bonds Lipinski's Rule of Five true 
Log P 2.49  LOG S -4.29 
Solubility (Water) 1.77e-02 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
Chloroform expand Show data source
DMSO: soluble expand Show data source
ethanol: soluble expand Show data source
Insoluble expand Show data source
Methanol expand Show data source
Apperance
yellow powder expand Show data source
Yellow Solid expand Show data source
Melting Point
171 - 175°C expand Show data source
172-174°C expand Show data source
172-174°C expand Show data source
173°C (343.4°F) expand Show data source
Hydrophobicity(logP)
2 expand Show data source
3.406 expand Show data source
Storage Condition
-20°C expand Show data source
-20°C Freezer expand Show data source
Room Temperature (15-30°C) expand Show data source
Storage Warning
IRRITANT expand Show data source
RTECS
US7975000 expand Show data source
European Hazard Symbols
Harmful Harmful (Xn) expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
1 expand Show data source
Risk Statements
22 expand Show data source
R:22 expand Show data source
Safety Statements
26-36 expand Show data source
S:36/37/39 expand Show data source
TSCA Listed
false expand Show data source
GHS Pictograms
GHS07 expand Show data source
GHS Signal Word
Warning expand Show data source
GHS Hazard statements
H302 expand Show data source
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves expand Show data source
Storage Temperature
2-8°C expand Show data source
Admin Routes
Oral expand Show data source
Bioavailability
45-56% expand Show data source
Excretion
Renal: >50%, Biliary: 5-15% expand Show data source
Half Life
2 hours expand Show data source
Metabolism
Gastrointestinal, Hepatic expand Show data source
Protein Bound
92-98% expand Show data source
Pregnancy Category
C: (USA) expand Show data source
Gene Information
human ... ADORA2A(135), ADORA3(140), CACNA2D1(781), CYP1A2(1544), KCNH1(3756), TTR(7276)mouse ... Cacna1c(12288)rat ... Adora1(29290), Adora2a(25369), Cacna1c(24239), Cacna1d(29716), Kcnj1(24521), Kcnn4(65206), Tbxas1(24886) expand Show data source
Mechanism of Action
Calcium channel blocker expand Show data source
causing dilation of the coronary and systemic arteries, expand Show data source
increased oxygen delivery to the myocardial tissue, decreased total peripheral resistance, decreased systemic blood pressure, and decreased afterload. expand Show data source
Inhibits the influx of extracellular calcium through myocardial and vascular membrane pores by physically plugging the channel expand Show data source
The decrease in intracellular calcium inhibits the contractile processes of smooth muscle cells, expand Show data source
Purity
≥98% (HPLC) expand Show data source
95% expand Show data source
Salt Data
Free Base expand Show data source
Certificate of Analysis
Download expand Show data source
Download expand Show data source
Application(s)
Antihypertensive agent expand Show data source
Coronary vasodilator expand Show data source
Used to treat Prinzmetal's angina, hypertension, and other vascular disorders such as Raynaud's phenomenon expand Show data source

DETAILS

DETAILS

MP Biomedicals MP Biomedicals DrugBank DrugBank Selleck Chemicals Selleck Chemicals Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich TRC TRC
MP Biomedicals - 02151743 external link
Purity: 95%
Yellow crystalline powder
A calcium-channel blocker.
DrugBank - DB01115 external link
Item Information
Drug Groups approved
Description 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.
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 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.
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
Biotransformation Hepatic metabolism via cytochrome P450 system. Predominantly metabolized by CYP3A4, but also by CYP1A2 and CYP2A6 isozymes.
Absorption Rapidly and fully absorbed following oral administration.
Half Life 2 hours
Protein Binding 92-98%
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.
References
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]
External Links
Wikipedia
RxList
Drugs.com
Selleck Chemicals - S1808 external link
Research Area: Cardiovascular Disease
Biological Activity:
Nifedipine(Adalat), a potent vasodilator agent with calcium antagonistic action. It is a useful anti-anginal agent that also lowers blood pressure. Nifedipine(Adalat) is a dihydropyridine calcium channel blocker. Its main uses are as an antianginal (especially in Prinzmetal’s angina) and antihypertensive, although a large number of other uses have recently been found for this agent, such as Raynaud’s phenomenon, premature labor, and painful spasms of the esophagus in cancer and tetanus patients. It is also commonly used for the small subset of pulmonary hypertension patients whose symptoms respond to calcium channel blockers. [1]
Sigma Aldrich - N7634 external link
Frequently Asked Questions
Live Chat and Frequently Asked Questions are available for this Product.
Biochem/physiol Actions
L-type Ca2+ channel blocker; induces apoptosis in human glioblastoma cells.
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. N7634.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.
Toronto Research Chemicals - N457000 external link
Used as an antihypertensive and antianginal. A dihydorpyridine calcium channel blocker.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • 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
  • • http://en.wikipedia.org/wiki/Nifedipine
  • • Ali, S.L., et al.: Anal. Profiles Drug Subs., 18, 221 (1989)
  • • Soons, P.A., et al.: J. Pharm. Biomed. Anal., 9, 475 (1989)
  • • Brown, M.J., et al.: Lancet, 356, 366 (1989)
  • • Vater, W. et al., Arzneim.-Forsch., 1972, 22, 1; 15; 330, (pharmacol)
  • • Loev, B. et al., J. Med. Chem., 1974, 17, 956, (synth)
  • • Bossert, F. et al., Angew. Chem., Int. Ed., 1981, 20, 762, (rev)
  • • Pine, R.M. et al., Clin. Ther., 1984, 6, 245, (rev)
  • • Kurfurst, A. et al., Coll. Czech. Chem. Comm., 1984, 49, 2393, (pmr, cmr)
  • • Hugenholz, P.G., Handb. Exp. Pharmacol., 1985, 76, 459, (rev)
  • • Swanson, T.H. et al., Gen. Pharmacol., 1986, 17, 255, (rev)
  • • Krebs, R., Treat. Cardiovasc. Dis. Adalat, (Nifedipine), (Ed.), Schatteur, Stuttgart, 1986, (book)
  • • Ali, S.K., Anal. Profiles Drug Subst., 1989, 18, 221, (rev)
  • • Singh, H. et al., Tetrahedron, 1989, 45, 3967, (synth)
  • • Soons, P.A. et al., J. Pharm. Biomed. Anal., 1991, 9, 475, (hplc, rev)
  • • Lvai, L. et al., Synth. Commun., 1992, 22, 47, (synth)
  • • Otero, M.L. et al., Drugs, Suppl. 1, 1994, 48, (pharmacol, rev)
  • • Negwer, M., Organic-Chemical Drugs and their Synonyms, 7th edn., Akademie-Verlag, 1994, 5767, (synonyms)
  • • Martindale, The Extra Pharmacopoeia, 32nd edn., Pharmaceutical Press, 1999, 916
  • • Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, AEC750
  • Searching...Please wait...

PATENTS

PATENTS

PubChem iconPubChem Patent Google Patent Search IconGoogle Patent

INTERNET

INTERNET

Baidu iconBaidu google iconGoogle