Details
Stereochemistry | ACHIRAL |
Molecular Formula | C17H18N2O6 |
Molecular Weight | 346.3346 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
COC(=O)C1=C(C)NC(C)=C(C1C2=C(C=CC=C2)[N+]([O-])=O)C(=O)OC
InChI
InChIKey=HYIMSNHJOBLJNT-UHFFFAOYSA-N
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
Molecular Formula | C17H18N2O6 |
Molecular Weight | 346.3346 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
DescriptionSources: http://www.drugbank.ca/drugs/DB01115Curator's Comment: Description was created based on several sources, including
http://www.accessdata.fda.gov/drugsatfda_docs/label/2011/020198s023lbl.pdf
Sources: http://www.drugbank.ca/drugs/DB01115
Curator's Comment: Description was created based on several sources, including
http://www.accessdata.fda.gov/drugsatfda_docs/label/2011/020198s023lbl.pdf
Nifedipine has been formulated as both a long- and short-acting 1,4-dihydropyridine calcium channel blocker. Nifedipine is sold under the brand names Adalat and Procardia among others. 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. Nifedipine is used 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).
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/3368504
Curator's Comment: nifedipine can easily cross the blood-brain barrier in the rat
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2095229 Sources: http://www.genome.jp/dbget-bin/www_bget?D00437 |
2.0 µM [IC50] | ||
Target ID: CHEMBL1940 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2435904 |
1.0 nM [Ki] | ||
Target ID: CHEMBL1075226 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25893973 |
37.5 µM [IC50] | ||
Target ID: CHEMBL340 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24399740 |
7.8 µM [IC50] | ||
Target ID: Cholangiocarcinoma, Mz-ChA-1, human Sources: https://www.ncbi.nlm.nih.gov/pubmed/21179572 |
15.0 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | PROCARDIA Approved UseI. Vasospastic Angina
PROCARDIA (nifedipine) is indicated for the management of vasospastic angina confirmed by
any of the following criteria: 1) classical pattern of angina at rest accompanied by ST segment
elevation, 2) angina or coronary artery spasm provoked by ergonovine, or 3) angiographically
demonstrated coronary artery spasm. In those patients who have had angiography, the presence of
significant fixed obstructive disease is not incompatible with the diagnosis of vasospastic angina,
provided that the above criteria are satisfied. PROCARDIA may also be used where the clinical
presentation suggests a possible vasospastic component but where vasospasm has not been
confirmed, e.g., where pain has a variable threshold on exertion or when angina is refractory to
nitrates and/or adequate doses of beta blockers.
II. Chronic Stable Angina
(Classical Effort-Associated Angina)
PROCARDIA is indicated for the management of chronic stable angina (effort-associated
angina) without evidence of vasospasm in patients who remain symptomatic despite adequate
doses of beta blockers and/or organic nitrates or who cannot tolerate those agents. Launch Date1981 |
|||
Primary | PROCARDIA Approved UseI. Vasospastic Angina
PROCARDIA (nifedipine) is indicated for the management of vasospastic angina confirmed by
any of the following criteria: 1) classical pattern of angina at rest accompanied by ST segment
elevation, 2) angina or coronary artery spasm provoked by ergonovine, or 3) angiographically
demonstrated coronary artery spasm. In those patients who have had angiography, the presence of
significant fixed obstructive disease is not incompatible with the diagnosis of vasospastic angina,
provided that the above criteria are satisfied. PROCARDIA may also be used where the clinical
presentation suggests a possible vasospastic component but where vasospasm has not been
confirmed, e.g., where pain has a variable threshold on exertion or when angina is refractory to
nitrates and/or adequate doses of beta blockers.
II. Chronic Stable Angina
(Classical Effort-Associated Angina)
PROCARDIA is indicated for the management of chronic stable angina (effort-associated
angina) without evidence of vasospasm in patients who remain symptomatic despite adequate
doses of beta blockers and/or organic nitrates or who cannot tolerate those agents. Launch Date1981 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
78.5 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3609112/ |
10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered: |
NIFEDIPINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
148 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3609112/ |
10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered: |
NIFEDIPINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
2.2 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3609112/ |
10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered: |
NIFEDIPINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
8% |
unknown |
NIFEDIPINE plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
90 mg single, oral Overdose |
healthy, 2 years |
Disc. AE: Tachycardia, Hyperglycemia... AEs leading to discontinuation/dose reduction: Tachycardia (grade 5, 1 patient) Sources: Hyperglycemia (grade 5, 1 patient) |
200 mg single, oral Overdose |
healthy, 34 years |
Disc. AE: Hypotension, Acidosis... AEs leading to discontinuation/dose reduction: Hypotension (1 patient) Sources: Acidosis (1 patient) Hyperglycemia (1 patient) |
2400 mg single, oral Overdose |
unknown, 37 years |
Disc. AE: Intestinal infarction... AEs leading to discontinuation/dose reduction: Intestinal infarction (1 patient) Sources: |
300 mg single, oral Overdose |
unknown, 54 years |
Disc. AE: Reflex tachycardia... AEs leading to discontinuation/dose reduction: Reflex tachycardia (1 patient) Sources: |
600 mg single, oral Overdose |
unknown, 57 years |
Disc. AE: Hypotension, Tachycardia... AEs leading to discontinuation/dose reduction: Hypotension (1 patient) Sources: Tachycardia (1 patient) Flushing (1 patient) |
900 mg single, oral Overdose |
unhealthy, 59 years |
Disc. AE: Hypotension, Hyperglycemia... AEs leading to discontinuation/dose reduction: Hypotension (grade 4, 1 patient) Sources: Hyperglycemia (1 patient) |
180 mg 1 times / day steady, oral Highest studied dose Dose: 180 mg, 1 times / day Route: oral Route: steady Dose: 180 mg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: |
DLT: Edema... Dose limiting toxicities: Edema (30%) Sources: |
30 mg 1 times / day steady, oral Recommended Dose: 30 mg, 1 times / day Route: oral Route: steady Dose: 30 mg, 1 times / day Sources: |
unhealthy, mean 33.3 years Health Status: unhealthy Age Group: mean 33.3 years Sex: F Sources: |
Disc. AE: Nausea, Vomiting... AEs leading to discontinuation/dose reduction: Nausea (1 patient) Sources: Vomiting (1 patient) Headache (1 patient) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Hyperglycemia | grade 5, 1 patient Disc. AE |
90 mg single, oral Overdose |
healthy, 2 years |
Tachycardia | grade 5, 1 patient Disc. AE |
90 mg single, oral Overdose |
healthy, 2 years |
Acidosis | 1 patient Disc. AE |
200 mg single, oral Overdose |
healthy, 34 years |
Hyperglycemia | 1 patient Disc. AE |
200 mg single, oral Overdose |
healthy, 34 years |
Hypotension | 1 patient Disc. AE |
200 mg single, oral Overdose |
healthy, 34 years |
Intestinal infarction | 1 patient Disc. AE |
2400 mg single, oral Overdose |
unknown, 37 years |
Reflex tachycardia | 1 patient Disc. AE |
300 mg single, oral Overdose |
unknown, 54 years |
Flushing | 1 patient Disc. AE |
600 mg single, oral Overdose |
unknown, 57 years |
Hypotension | 1 patient Disc. AE |
600 mg single, oral Overdose |
unknown, 57 years |
Tachycardia | 1 patient Disc. AE |
600 mg single, oral Overdose |
unknown, 57 years |
Hyperglycemia | 1 patient Disc. AE |
900 mg single, oral Overdose |
unhealthy, 59 years |
Hypotension | grade 4, 1 patient Disc. AE |
900 mg single, oral Overdose |
unhealthy, 59 years |
Edema | 30% DLT |
180 mg 1 times / day steady, oral Highest studied dose Dose: 180 mg, 1 times / day Route: oral Route: steady Dose: 180 mg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: |
Headache | 1 patient Disc. AE |
30 mg 1 times / day steady, oral Recommended Dose: 30 mg, 1 times / day Route: oral Route: steady Dose: 30 mg, 1 times / day Sources: |
unhealthy, mean 33.3 years Health Status: unhealthy Age Group: mean 33.3 years Sex: F Sources: |
Nausea | 1 patient Disc. AE |
30 mg 1 times / day steady, oral Recommended Dose: 30 mg, 1 times / day Route: oral Route: steady Dose: 30 mg, 1 times / day Sources: |
unhealthy, mean 33.3 years Health Status: unhealthy Age Group: mean 33.3 years Sex: F Sources: |
Vomiting | 1 patient Disc. AE |
30 mg 1 times / day steady, oral Recommended Dose: 30 mg, 1 times / day Route: oral Route: steady Dose: 30 mg, 1 times / day Sources: |
unhealthy, mean 33.3 years Health Status: unhealthy Age Group: mean 33.3 years Sex: F Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
moderate | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
weak [IC50 186 uM] | ||||
weak [IC50 472 uM] | ||||
weak | ||||
weak | ||||
yes | ||||
yes | ||||
Sources: https://pubmed.ncbi.nlm.nih.gov/11560876/ |
yes | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/11560876/ |
yes | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/11560876/ |
yes | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/14570758/ |
yes | |||
yes |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
major | yes (co-administration study) Comment: [ADALAT® XL®PRODUCT MONOGRAPH]: Use of ADALAT XL with drugs that result in strong inhibition of CYP 3A4, such as ketoconazole, clarithromycin, ritonavir, may lead to increased plasma levels of nifedipine and associated serious adverse events. Such concomitant use should be avoided. |
|||
minor | ||||
no |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
PubMed
Title | Date | PubMed |
---|---|---|
[Nifedipine prolongs a neuromuscular blockade caused by atracurium]. | 1992 |
|
Nerve growth factor-stimulated calcium uptake into PC12 cells: uniqueness of the channel and evidence for phosphorylation. | 1992 Apr |
|
Effect of different convulsants on calmodulin levels and proto-oncogene c-fos expression in the central nervous system. | 1992 Aug |
|
[The effect of hypotensive nifedipine therapy on renal secretory function in hypertensive patients in the course of both compensated and non-compensated chronic renal failure]. | 1992 Dec 7-14 |
|
[Sexual impotence caused by nifedipine]. | 1992 Jan 18 |
|
A randomized prospective comparison of nifedipine and bed rest versus bed rest alone in the management of preeclampsia remote from term. | 1992 Oct |
|
Lindane-induced convulsions in NMRI and OF1 mice: antagonism with (+)MK-801 and voltage-dependent calcium channel blockers. | 1992 Oct 16 |
|
Cortical blindness after nifedipine treatment. | 1992 Sep 19 |
|
Adverse neurologic events associated with rebound hypertension after using short-acting nifedipine in childhood hypertension. | 2001 Dec |
|
Effect of acute blood pressure reduction on endothelial function in the brachial artery of patients with essential hypertension. | 2001 Mar |
|
Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients. | 2001 Nov |
|
Influence of an abrupt increase in blood pressure on the blood-brain barrier permeability during acute hypertension and epileptic seizures. | 2001 Sep |
|
Calcineurin-GATA4 pathway is involved in beta-adrenergic agonist-responsive endothelin-1 transcription in cardiac myocytes. | 2001 Sep 14 |
|
The drug efflux pump MRP2: regulation of expression in physiopathological situations and by endogenous and exogenous compounds. | 2002 |
|
Oxidative stress and TGFbeta in kidney-transplanted patients with cyclosporin-induced hypertension. Effect of carvedilol and nifedipine. | 2002 Aug |
|
Effect of an orally active Na+/H+ exchange inhibitor, SMP-300, on experimental angina and myocardial infarction models in rats. | 2002 Feb |
|
Nifedipine or hydralazine as a first-line agent to control hypertension in severe preeclampsia. | 2002 Jan |
|
Evaluation of the safety of short-acting nifedipine in children with hypertension. | 2002 Jan |
|
Nifedipine prevents apoptosis of endothelial cells induced by oxidized low-density lipoproteins. | 2002 Jul |
|
High-throughput measurement of the Tp53 response to anticancer drugs and random compounds using a stably integrated Tp53-responsive luciferase reporter. | 2002 Jun |
|
Delirium caused by donepezil: a case study. | 2002 Mar |
|
Short- and long-term influences of heavy metals on anionic drug efflux from renal proximal tubule. | 2002 May |
|
Depression--an adverse event with nifedipine. | 2002 Nov |
|
Symptomatic orthostasis with extended-release nifedipine and protease inhibitors. | 2002 Oct |
|
The nuclear pregnane X receptor: a key regulator of xenobiotic metabolism. | 2002 Oct |
|
[Pathogenetic basis of the application of calcium antagonists in the treatment of recurrent peptic ulcer]. | 2003 |
|
[Drug induced anosmia with nifedipine]. | 2003 Aug 23 |
|
Requirement of calcium and phosphate ions in expression of sodium-dependent vitamin C transporter 2 and osteopontin in MC3T3-E1 osteoblastic cells. | 2003 Jun 17 |
|
ETA receptor-mediated Ca2+ mobilisation in H9c2 cardiac cells. | 2003 Mar 1 |
|
An in vitro bioassay for xenobiotics using the SXR-driven human CYP3A4/lacZ reporter gene. | 2003 May-Jun |
|
Inhibitory effects of carvedilol on calcium channels in vascular smooth muscle cells. | 2003 Nov |
|
Induction of ABCC3 (MRP3) by pregnane X receptor activators. | 2003 Nov |
|
Fatality from administration of labetalol and crushed extended-release nifedipine. | 2003 Oct |
|
Clinical review: the management of hypertensive crises. | 2003 Oct |
|
Sertoli cell modulates MAA-induced apoptosis of germ cells throughout voltage-operated calcium channels. | 2004 Feb |
|
Comparison of the effects of a 7-day period of non-compliance on blood pressure control using three different antihypertensive agents. | 2004 Jul |
|
Proliferation of cultured human gingival fibroblasts caused by isradipine, a dihydropyridine-derivative calcium antagonist. | 2004 Jun 30 |
|
The effect of basic fibroblast growth factor on cell cycle in human gingival fibroblasts from nifedipine responder and non-responder. | 2004 Mar |
|
Adverse events associated with aggressive treatment of increased blood pressure. | 2004 May |
|
The solubilization of the poorly water soluble drug nifedipine by water soluble 4-sulphonic calix[n]arenes. | 2004 Nov |
|
Effect of nifedipine on endothelial function in normotensive smokers: potential contribution of increase in circulating hepatocyte growth factor. | 2004 Oct |
|
The effect of PAMAM dendrimer generation size and surface functional group on the aqueous solubility of nifedipine. | 2004 Oct 13 |
|
Recombinant CYP3A4*17 is defective in metabolizing the hypertensive drug nifedipine, and the CYP3A4*17 allele may occur on the same chromosome as CYP3A5*3, representing a new putative defective CYP3A haplotype. | 2005 Apr |
|
Examination of 209 drugs for inhibition of cytochrome P450 2C8. | 2005 Jan |
|
Ventricular arrhythmia following short-acting nifedipine administration. | 2005 Jul |
|
The effect of IL-1alpha and nifedipine on cell proliferation and DNA synthesis in cultured human gingival fibroblasts. | 2005 Jun |
|
Prediction of genotoxicity of chemical compounds by statistical learning methods. | 2005 Jun |
|
Isolation of CYP3A4 Inhibitors from the Black Cohosh (Cimicifuga racemosa). | 2005 Jun |
|
Nifedipine gastrointestinal therapeutic system--hypertension management to improve cardiovascular outcomes. | 2005 Sep |
|
Quantitative PCR assay for cytochromes P450 2B and 3A induction in rat precision-cut liver slices: correlation study with induction in vivo. | 2005 Sep-Oct |
Sample Use Guides
Therapy should be initiated with the 10 mg capsule. The starting dose is one 10 mg capsule, swallowed whole, 3 times/day. The usual effective dose range is 10–20 mg three times daily. Some patients, especially those with evidence of coronary artery spasm, respond only to higher doses, more frequent administration, or both. In such patients, doses of 20–30 mg three or four
times daily may be effective. Doses above 120 mg daily are rarely necessary. More than 180 mg per day is not recommended.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22923790
About 50% of the Ca(v) current was blocked by 10 uM of the L-type channel blocker nifedipine in human induced pluripotent stem cell-derived neurons.
Substance Class |
Chemical
Created
by
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on
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Record UNII |
I9ZF7L6G2L
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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WHO-VATC |
QC08GA01
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FDA ORPHAN DRUG |
57991
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NDF-RT |
N0000000069
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WHO-ATC |
C08GA01
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QC08CA55
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LIVERTOX |
NBK548324
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NCI_THESAURUS |
C333
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NDF-RT |
N0000007556
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C08CA55
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C08CA05
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QC08CA05
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WHO-ESSENTIAL MEDICINES LIST |
22.2
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NDF-RT |
N0000175421
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Code System | Code | Type | Description | ||
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NIFEDIPINE
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PRIMARY | Description. A yellow, crystalline powder.Solubility. Nifedipine is practically insoluble in water; freely soluble in acetone R; sparingly soluble in dehydrated ethanol R.Category. Cardiovascular drug; calcium-channel blocking agent.Storage. Nifedipine should be kept in a tightly closed container, protected from light.Additional information. CAUTION: Nifedipine decomposes on exposure to daylight, artificial light of certain wavelengths, andultraviolet light.Requirements: Nifedipine contains not less than 98.0% and not more than 102.0% of C17H18N2O6, calculated with reference to the driedsubstance.Note: Throughout the monograph perform the tests and the assay in the dark or under a suitable fluorescent light, using lowactinicglassware. | ||
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DB01115
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244-598-3
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3222
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DTXSID2025715
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D009543
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C29290
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I9ZF7L6G2L
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7565
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m7883
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2514
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NIFEDIPINE
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CHEMBL193
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757242
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Nifedipine
Created by
admin on Wed Apr 02 09:53:19 GMT 2025 , Edited by admin on Wed Apr 02 09:53:19 GMT 2025
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100000090371
Created by
admin on Wed Apr 02 09:53:19 GMT 2025 , Edited by admin on Wed Apr 02 09:53:19 GMT 2025
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1463508
Created by
admin on Wed Apr 02 09:53:19 GMT 2025 , Edited by admin on Wed Apr 02 09:53:19 GMT 2025
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Related Record | Type | Details | ||
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TARGET -> INHIBITOR |
BINDING
IC50
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TARGET -> INHIBITOR |
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TARGET -> INHIBITOR |
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DEGRADENT -> PARENT |
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METABOLIC ENZYME -> SUBSTRATE | |||
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SALT/SOLVATE -> PARENT |
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METABOLIC ENZYME -> SUBSTRATE | |||
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DEGRADENT -> PARENT |
LIGHT INDUCED DEGRADENT
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Related Record | Type | Details | ||
---|---|---|---|---|
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METABOLITE -> PARENT |
PLASMA
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METABOLITE -> PARENT |
MAJOR
URINE
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METABOLITE -> PARENT |
MINOR
URINE
|
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METABOLITE -> PARENT |
PLASMA; URINE
|
Related Record | Type | Details | ||
---|---|---|---|---|
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
IMPURITY -> PARENT |
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
Related Record | Type | Details | ||
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ACTIVE MOIETY |
Blocks L-type calcium channels
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