Nifedipine

Numéro de catalogue: B3420541

Numéro CAS: 193689-82-6

Poids moléculaire: 346.3 g/mol

Clé InChI: HYIMSNHJOBLJNT-UHFFFAOYSA-N

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Vue d'ensemble

1. Description

6. Synthesis routes and methods III

2. Mécanisme d'action

7. Synthesis routes and methods IV

3. Propriétés

8. Synthesis routes and methods V

4. Synthesis routes and methods I

9. Retrosynthesis analysis

5. Synthesis routes and methods II

10. Avertissement

Description

Nifedipine appears as odorless yellow crystals or powder. Tasteless. (NTP, 1992)
This compound is a dihydropyridine, a methyl ester and a C-nitro compound. It has a role as a calcium channel blocker, a vasodilator agent, a tocolytic agent and a human metabolite.
This compound, or BAY a 1040, is a first generation dihydropyridine L-type calcium channel blocker, similar to [nicardipine]. This compound was developed by Bayer and first described in the literature, along with other dihydropyridines, in 1972. Since this compound's development, second and third generation dihydropyridines have been developed with slower onsets and longer durations of action. The most popular of the third generation dihydropyridines is [amlodipine]. this compound was granted FDA approval on 31 December 1981.
This compound is a Dihydropyridine Calcium Channel Blocker. The mechanism of action of this compound is as a Calcium Channel Antagonist.
This compound is a first generation calcium channel blocker used to treat hypertension and angina pectoris. This compound therapy is associated with a low rate of serum enzyme elevations and has been linked to several instances of clinically apparent acute liver injury.
This compound is a natural product found in Homo sapiens with data available.
This compound is a dihydropyridine calcium channel blocking agent. This compound inhibits the transmembrane influx of extracellular calcium ions into myocardial and vascular smooth muscle cells, causing dilatation of the main coronary and systemic arteries and decreasing myocardial contractility. This agent also inhibits the drug efflux pump P-glycoprotein which is overexpressed in some multi-drug resistant tumors and may improve the efficacy of some antineoplastic agents. (NCI04)
This compound can cause developmental toxicity, female reproductive toxicity and male reproductive toxicity according to state or federal government labeling requirements.
A potent vasodilator agent with calcium antagonistic action. It is a useful anti-anginal agent that also lowers blood pressure.

Mécanisme D'action

Nifedipine blocks voltage gated L-type calcium channels in vascular smooth muscle and myocardial cells. This blockage prevents the entry of calcium ions into cells during depolarization, reducing peripheral arterial vascular resistance and dilating coronary arteries. These actions reduce blood pressure and increase the supply of oxygen to the heart, alleviating angina.
The principal physiologic action of this compound is to inhibit the transmembrane influx of extracellular calcium ions across the membranes of myocardial cells and vascular smooth muscle cells, without changing serum calcium concentrations. Calcium plays important roles in the excitation-contraction coupling processes of the heart and vascular smooth muscle cells and in the electrical discharge of the specialized conduction cells of the heart. The membranes of these cells contain numerous channels that carry a slow inward current and that are selective for calcium. Activation of these slow calcium channels contributes to the plateau phase (phase 2) of the action potential of cardiac and vascular smooth muscle cells. The exact mechanism whereby this compound inhibits calcium ion influx across the slow calcium channels is not known, but the drug is thought to inhibit ion-control gating mechanisms of the channel, deform the slow channel, and/or interfere with release of calcium from the sarcoplasmic reticulum. By inhibiting calcium influx, this compound inhibits the contractile processes of cardiac and vascular smooth muscle, thereby dilating the main coronary and systemic arteries.
This compound is a peripheral arterial vasodilator which acts directly on vascular smooth muscle. The binding of this compound to voltage-dependent and possibly receptor-operated channels in vascular smooth muscle results in an inhibition of calcium influx through these channels. Stores of intracellular calcium in vascular smooth muscle are limited and thus dependent upon the influx of extracellular calcium for contraction to occur. The reduction in calcium influx by this compound causes arterial vasodilation and decreased peripheral vascular resistance which results in reduced arterial blood pressure.

Propriétés

IUPAC Name	dimethyl 2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate	Source
Source	PubChem
URL	https://pubchem.ncbi.nlm.nih.gov
Description	Data deposited in or computed by PubChem

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	Source
Source	PubChem
URL	https://pubchem.ncbi.nlm.nih.gov
Description	Data deposited in or computed by PubChem

InChI Key	HYIMSNHJOBLJNT-UHFFFAOYSA-N	Source
Source	PubChem
URL	https://pubchem.ncbi.nlm.nih.gov
Description	Data deposited in or computed by PubChem

Canonical SMILES	CC1=C(C(C(=C(N1)C)C(=O)OC)C2=CC=CC=C2[N+](=O)[O-])C(=O)OC	Source
Source	PubChem
URL	https://pubchem.ncbi.nlm.nih.gov
Description	Data deposited in or computed by PubChem

Molecular Formula	C17H18N2O6	Source
Record name	NIFEDIPINE
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Record name	nifedipine
Source	Wikipedia
URL	https://en.wikipedia.org/wiki/Nifedipine
Description	Chemical information link to Wikipedia.

Source	PubChem
URL	https://pubchem.ncbi.nlm.nih.gov
Description	Data deposited in or computed by PubChem

Related CAS	60299-11-8 (mono-hydrochloride)	Source
Record name	Nifedipine [USAN:USP:INN:BAN:JAN]
Source	ChemIDplus
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DSSTOX Substance ID	DTXSID2025715	Source
Record name	Nifedipine
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Molecular Weight	346.3 g/mol	Source
Source	PubChem
URL	https://pubchem.ncbi.nlm.nih.gov
Description	Data deposited in or computed by PubChem

Physical Description	Nifedipine appears as odorless yellow crystals or powder. Tasteless. (NTP, 1992), Solid	Source
Record name	NIFEDIPINE
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Record name	Nifedipine
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Solubility	less than 1 mg/mL at 67.1 °F (NTP, 1992), Insoluble, Solubility at 20 °C (g/L): acetone 250, methylene chloride 160, chloroform 140, ethyl acetate 50, methanol 26, ethanol 17, In water, 1.7X10-5 mol/L = 5.9 mg/L at 25 °C, 1.77e-02 g/L	Source
Record name	NIFEDIPINE
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Record name	Nifedipine
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Record name	Nifedipine
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Record name	Nifedipine
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Description	The Human Metabolome Database (HMDB) is a freely available electronic database containing detailed information about small molecule metabolites found in the human body.
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Vapor Pressure	2.6X10-8 mm Hg at 25 °C	Source
Record name	Nifedipine
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Mechanism of Action	Nifedipine blocks voltage gated L-type calcium channels in vascular smooth muscle and myocardial cells. This blockage prevents the entry of calcium ions into cells during depolarization, reducing peripheral arterial vascular resistance and dilating coronary arteries. These actions reduce blood pressure and increase the supply of oxygen to the heart, alleviating angina., The principal physiologic action of nifedipine is to inhibit the transmembrane influx of extracellular calcium ions across the membranes of myocardial cells and vascular smooth muscle cells, without changing serum calcium concentrations. Calcium plays important roles in the excitation-contraction coupling processes of the heart and vascular smooth muscle cells and in the electrical discharge of the specialized conduction cells of the heart. The membranes of these cells contain numerous channels that carry a slow inward current and that are selective for calcium. Activation of these slow calcium channels contributes to the plateau phase (phase 2) of the action potential of cardiac and vascular smooth muscle cells. The exact mechanism whereby nifedipine inhibits calcium ion influx across the slow calcium channels is not known, but the drug is thought to inhibit ion-control gating mechanisms of the channel, deform the slow channel, and/or interfere with release of calcium from the sarcoplasmic reticulum. By inhibiting calcium influx, nifedipine inhibits the contractile processes of cardiac and vascular smooth muscle, thereby dilating the main coronary and systemic arteries., Nifedipine is a peripheral arterial vasodilator which acts directly on vascular smooth muscle. The binding of nifedipine to voltage-dependent and possibly receptor-operated channels in vascular smooth muscle results in an inhibition of calcium influx through these channels. Stores of intracellular calcium in vascular smooth muscle are limited and thus dependent upon the influx of extracellular calcium for contraction to occur. The reduction in calcium influx by nifedipine causes arterial vasodilation and decreased peripheral vascular resistance which results in reduced arterial blood pressure.	Source
Record name	Nifedipine
Source	DrugBank
URL	https://www.drugbank.ca/drugs/DB01115
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Record name	Nifedipine
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Impurities	Dimethyl 2,6-dimethyl-4-(2-nitrophenyl)pyridine-3,5-dicarboxylate, Dimethyl 2,6-dimethyl-4-(2_nitrosophenyl)pyridine-3,5-dicarboxylate, Methyl 2-(2-nitrobenzylidene)-3-oxobutanoate, Methyl 3-aminobut-2-enoate	Source
Record name	Nifedipine
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Color/Form	Yellow crystals
CAS No.	21829-25-4, 193689-82-6, 915092-63-6	Source
Record name	NIFEDIPINE
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Record name	3,5-Pyridinedicarboxylic acid, 1,4-dihydro-2,6-dimethyl-4-(2-nitrophenyl)-, dimethyl ester, radical ion(1-)
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Record name	Nifedipine
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Record name	3,5-Pyridinedicarboxylic acid, 1,4-dihydro-2,6-dimethyl-4-(2-nitrophenyl)-, 3,5-dimethyl ester, radical ion(1+)
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Record name	Nifedipine [USAN:USP:INN:BAN:JAN]
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Record name	nifedipine
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Record name	NIFEDIPINE
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Record name	Nifedipine
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Melting Point	342 to 345 °F (NTP, 1992), 172-174 °C, 172 - 174 °C	Source
Record name	NIFEDIPINE
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Record name	Nifedipine
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Synthesis routes and methods I

Procedure details

2-Nitrobenzaldehyde-diacetate (0.1 mole, 25.4 g), methyl acetoacetate (0.2 mole, 23.2 g) and NH4OH (12 ml) were heated in methanol (20 ml) in the presence of pyridine for several (7) hours. After cooling to 15° C. the precipitated product was filtered off. The crude product was crystallized from acetic acid to yield 4-(2'-nitrophenyl)-2,6-dimethyl-3,5-dicarbmethoxy-1,4-dihydropyridine (21.7 g, 62% of the theory), m.p. 172°-174° C.

Name

2-Nitrobenzaldehyde diacetate

Quantity

25.4 g

Type

reactant

Reaction Step One

Name

methyl acetoacetate

Quantity

23.2 g

Type

reactant

Reaction Step One

Name

NH4OH

Quantity

12 mL

Type

reactant

Reaction Step One

Name

pyridine

Quantity

0 (± 1) mol

Type

reactant

Reaction Step One

[Compound]

Name

( 7 )

Quantity

0 (± 1) mol

Type

reactant

Reaction Step One

Name

methanol

Quantity

20 mL

Type

reactant

Reaction Step One

Name

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

Details

Synthesis routes and methods II

Procedure details

2-Nitrobenzaldehyde-diacetate (0.1 mole, 25.4 g), methyl acetoacetate (0.21 mole, 26 g), NH4OH (12 ml) and methanol (45 ml) were heated under reflux for 5 hours. After cooling to 15° C. the precipitated product was filtered off. The crystallization of the crude product from acetic acid yielded 4-(2'-nitrophenyl)-2,6 dimethyl-3,5-dicarbmethoxy-1,4-dihydropyridine (19.0 g, 55% of the theory), m.p. 173°-174° C.

Name

2-Nitrobenzaldehyde diacetate

Quantity

25.4 g

Type

reactant

Reaction Step One

Name

methyl acetoacetate

Quantity

26 g

Type

reactant

Reaction Step One

Name

NH4OH

Quantity

12 mL

Type

reactant

Reaction Step One

Name

methanol

Quantity

45 mL

Type

reactant

Reaction Step One

Name

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

Details

Synthesis routes and methods III

Procedure details

One proceeds as described in Example 7 except that 0.4 mole of 2-nitro-benzaldehyde, 0.415 mole of a 25% aqueous ammonium hydroxide solution and 1.40 moles of methyl acetoacetate are used. Thus 112.1 g of nifedipine are obtained, yield 81%, m.p.: 172°-175° C. The product complies with the requirements of USP XXI without further purification.

Name

2-nitro-benzaldehyde

Quantity

0.4 mol

Type

reactant

Reaction Step One

Name

ammonium hydroxide

Quantity

0 (± 1) mol

Type

reactant

Reaction Step Two

Name

methyl acetoacetate

Quantity

1.4 mol

Type

reactant

Reaction Step Three

Name

nifedipine

Yield

81%

Details

Synthesis routes and methods IV

Procedure details

Into a 1-liter glass reactor 60.4 g (0.4 mole) of 2-nitro-benzaldehyde, 102.1 g (0.88 mole) of methyl acetoacetate, 28.25 g (0.415 mole) of a 25% aqueous ammonium hydroxide solution and 150 ml of methanol are weighed in. The reactor is closed, whereupon the reaction mixture is heated to boiling at a temperature of 101°-103° C. and a pressure of 2.0-2.2 bar for 5 hours. The reaction mixture is cooled to 0°-5° C., the precipitated product is filtered and washed with methanol. Thus 110.5 g of nifedipine are obtained, yield 79.8%, m.p.: 171.5°-175° C.

Name

2-nitro-benzaldehyde

Quantity

60.4 g

Type

reactant

Reaction Step One

Name

methyl acetoacetate

Quantity

102.1 g

Type

reactant

Reaction Step One

Name

ammonium hydroxide

Quantity

0 (± 1) mol

Type

reactant

Reaction Step One

Name

methanol

Quantity

150 mL

Type

solvent

Reaction Step One

Name

nifedipine

Yield

79.8%

Details

Synthesis routes and methods V

Procedure details

Nifedipine-isothiocyanate was also coupled to casein, ovalbumin and keyhole limpet hemocyanin using the procedures described above. An alternate procedure for the coupling of nifedipine-isothiocyanate to various proteins (i.e., bovine serum albumin, ovalbumin, casein and keyhole limpet hemocyanin) was to dissolve the protein (20 mg) in 2 ml of 100 mM sodium bicarbonate (pH 9.0) and then incubate with 0.8 mg of nifedipine-isothiocyanate (dissolved in ethanol to make the final concentration of ethanol in the incubation medium 38 percent) for 24 hours at 37° C. with shaking in the dark. This alternate procedure is useful for producing nifedipine conjugates at high protein concentrations.

Name

Nifedipine isothiocyanate

Quantity

0 (± 1) mol

Type

reactant

Reaction Step One

Name

nifedipine isothiocyanate

Quantity

0 (± 1) mol

Type

reactant

Reaction Step Two

Name

nifedipine isothiocyanate

Quantity

0.8 mg

Type

reactant

Reaction Step Three

Name

sodium bicarbonate

Quantity

2 mL

Type

solvent

Reaction Step Four

Name

ethanol

Quantity

0 (± 1) mol

Type

solvent

Reaction Step Five

Name

ethanol

Quantity

0 (± 1) mol

Type

solvent

Reaction Step Six

Name

nifedipine

Details

Retrosynthesis Analysis

AI-Powered Synthesis Planning: Our tool employs the Template_relevance Pistachio, Template_relevance Bkms_metabolic, Template_relevance Pistachio_ringbreaker, Template_relevance Reaxys, Template_relevance Reaxys_biocatalysis model, leveraging a vast database of chemical reactions to predict feasible synthetic routes.

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Top-N result to add to graph	6

Feasible Synthetic Routes

Reactant of Route 1

Nifedipine

Reactant of Route 2

Nifedipine

Reactant of Route 3

Nifedipine

Reactant of Route 4

Nifedipine

Reactant of Route 5

Nifedipine

Reactant of Route 6

Nifedipine

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