Nifedipine

Base Information

• Chemical Name: Nifedipine
• CAS No.: 21829-25-4
• Deprecated CAS: 101539-70-2,101554-38-5,101554-38-5,11104-22-6
• Molecular Formula: C17H18N2O6
• Molecular Weight: 346.34
• Hs Code.: 29333990
• European Community (EC) Number: 244-598-3
• NSC Number: 757242
• UNII: I9ZF7L6G2L
• DSSTox Substance ID: DTXSID2025715
• Nikkaji Number: J3.467C
• Wikipedia: Nifedipine
• Wikidata: Q39111
• NCI Thesaurus Code: C29290
• RXCUI: 7417
• Pharos Ligand ID: QHYV239QLPDL
• Metabolomics Workbench ID: 43341
• ChEMBL ID: CHEMBL193
• Mol file: 21829-25-4.mol

Synonyms:Adalat;Bay 1040;BAY a 1040;Bay-1040;BAY-a-1040;Bay1040;BAYa1040;Cordipin;Cordipine;Corinfar;Fenigidin;Korinfar;Monohydrochloride, Nifedipine;Nifangin;Nifedipine;Nifedipine GTIS;Nifedipine Monohydrochloride;Nifedipine-GTIS;Procardia;Procardia XL;Vascard

Chemical Property of Nifedipine

Chemical Property:

• Appearance/Colour: yellow crystalline solid
• Vapor Pressure: 2.68E-08mmHg at 25°C
• Melting Point: 171-175 °C
• Refractive Index: 1.584
• Boiling Point: 475.3 °C at 760 mmHg
• PKA: pKa -0.9/>13(DMF,t undefined) (Uncertain)
• Flash Point: 241.2 °C
• PSA: 110.45000
• Density: 1.271 g/cm³
• LogP: 3.02760
• Storage Temp.: 2-8°C
• Solubility.: DMSO: soluble
• Water Solubility.: <0.1 g/100 mL at 19.5℃
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 5
• Exact Mass: 346.11648630
• Heavy Atom Count: 25
• Complexity: 608

Purity/Quality:

99%MIN ^*data from raw suppliers

Nifedipine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,Xi
• Hazard Codes: Xn,Xi
• Statements: 22-36/37/38
• Safety Statements: 26-36

MSDS Files:

Total 1 MSDS from other Authors

Useful:

• Drug Classes: Cardiovascular Agents
• Canonical SMILES: CC1=C(C(C(=C(N1)C)C(=O)OC)C2=CC=CC=C2[N+](=O)[O-])C(=O)OC
• Recent ClinicalTrials: Postpartum Hypertension Study
• Recent EU Clinical Trials: Pregnancy ANtihypertensive Drugs: which Agent is best?
• Recent NIPH Clinical Trials: ACRoss-AMI
• Uses: Long-term coronary vasodilators. This product can increase coronary blood flow, reducing myocardial oxygen consumption.it is used for acute and chronic coronary insufficiency,especially the angina and myocardial infarction. Used as an antihypertensive and antianginal. A dihydorpyridine calcium channel blocker Nifedipine is used for preventing and relieving angina pectoris attacks, for hypertension, and as an ingredient in combination therapy for chronic cardiac insufficiency. 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).
• Description: Nifedipine (21829-25-4) is a clinically useful L-type calcium blocker.
• Therapeutic Function: Coronary vasodilator
• Clinical Use: The prototype of this class, nifedipine, has potent peripheralvasodilatory properties. It inhibits the voltage-dependentcalcium channel in the vascular smooth muscle but has littleor no direct depressant effect on the SA or AV nodes, eventhough it inhibits calcium current in normal and isolated cardiactissues. Nifedipine is more effective in patients whoseanginal episodes are caused by coronary vasospasm and isused in the treatment of vasospastic angina as well as classicangina pectoris. Because of its strong vasodilatory properties,it is used in selected patients to treat hypertension.
• Drug interactions: Potentially hazardous interactions with other drugs Aminophylline: possibly increases aminophylline concentration. Anaesthetics: enhanced hypotensive effect. Anti-arrhythmics: concentration of dronedarone increased. Antibacterials: metabolism accelerated by rifampicin; metabolism possibly inhibited by clarithromycin, erythromycin and telithromycin. Antidepressants: metabolism possibly inhibited by fluoxetine; concentration reduced by St John’s wort; enhanced hypotensive effect with MAOIs. Antiepileptics: effect reduced by carbamazepine, barbiturates, phenytoin and primidone. Antifungals: metabolism possibly inhibited by itraconazole and ketoconazole; concentration increased by micafungin; negative inotropic effect possibly increased with itraconazole. Antihypertensives: enhanced hypotensive effect, increased risk of first dose hypotensive effect of post-synaptic alpha-blockers; occasionally severe hypotension and heart failure with beta-blockers. Antivirals: concentration possibly increased by ritonavir; use telaprevir with caution. Cardiac glycosides: digoxin concentration possibly increased. Ciclosporin: may increase ciclosporin level, but not a problem in practice; nifedipine concentration may be increased. Cytotoxics: metabolism of vincristine possibly reduced. Grapefruit juice: concentration increased - avoid. Magnesium salts: profound hypotension with IV magnesium. Tacrolimus: increased tacro

Technology Process of Nifedipine

There total 26 articles about Nifedipine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

acetoacetic acid methyl ester (105-45-3) + 2-nitro-benzaldehyde (552-89-6) → nifedipine (21829-25-4)

Guidance literature:

With C₂₃H₃BF₁₆N₂O; ammonium acetate; In toluene; at 100 ℃; for 10h;

Reference yield: 82.6%

1-methoxy-1-(2'-nitrophenyl)-N-(2'-nitrophenyl)methylenemethaneamine (126192-87-8) + methyl 3-aminocrotonate (14205-39-1) → nifedipine (21829-25-4)

Guidance literature:

In methanol; acetic acid;

Reference yield: 82.6%

1-methoxy-1-(2'-nitrophenyl)-N-(2'-nitrophenyl)methylenemethaneamine (126192-87-8) + acetoacetic acid methyl ester (105-45-3) + methyl 3-aminocrotonate (14205-39-1) → nifedipine (21829-25-4)

Guidance literature:

In methanol; for 36h; Heating;

DOI:10.1080/00397919208021077

upstream raw materials:

methyl 3-aminocrotonate

2-(o-nitro)phenyl-4,4-dimethyloxazolidine

2-(o-nitro)phenyl-tetrahydro-(2H)-1,3-oxazine

2-nitro-benzaldehyde

Downstream raw materials:

2-(2-Dimethylamino-ethyl)-6-methyl-4-(2-nitro-phenyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid dimethyl ester

2,6-Bis-(2-dimethylamino-ethyl)-4-(2-nitro-phenyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid dimethyl ester

2-Methyl-6-(2-morpholin-4-yl-ethyl)-4-(2-nitro-phenyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid dimethyl ester

2,6-Bis-(2-morpholin-4-yl-ethyl)-4-(2-nitro-phenyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid dimethyl ester

Refernces

• 1、 Fedorova,Koryakova,Valova,Ovchinnikova,Titova,Rusinov,Charushin. "Catalytic effect of nanosized metal oxides on the Hantzsch reaction". . p. 566 - 572. Retrieved 2010.
• 2、 Palmer, Robert B.,Andro, Tina M.,Natale, Nicholas R.,Andersen, Niels H.. "Conformational preferences and dynamics of 4-isoxazolyl-1,4-dihydropyridine calcium channel antagonists as determined by variable-temperature NMR and NOE experiments". . p. 495 - 504. Retrieved 1996.
• 3、 Wu, Cunluo,Bian, Qilong,Ding, Tao,Tang, Mingming,Zhang, Wenkai,Xu, Yuanqing,Liu, Baoying,Xu, Hao,Li, Hai-Bei,Fu, Hua. "Photoinduced Iron-Catalyzed ipso-Nitration of Aryl Halides via Single-Electron Transfer". . p. 9561 - 9568. Retrieved 2021/08/06.
• 4、 -. "Preparation method of nifedipine". Paragraph 0051-0061. . Retrieved 2020/07/02.