ニフェジピン
カタログ番号:
B1678770
CAS番号:
21829-25-4
分子量:
346.3 g/mol
InChIキー:
HYIMSNHJOBLJNT-UHFFFAOYSA-N
注意:
研究専用です。人間または獣医用ではありません。
概要
説明
ニフェジピンは、ジヒドロピリジン系カルシウム拮抗薬であり、主に狭心症、高血圧、レイノー現象、早産などの治療に使用されます . ニフェジピンは、バイエル社によって開発され、1972年に文献に記載されました . ニフェジピンは、心臓筋および平滑筋細胞へのカルシウムイオンの流入を阻害することで作用し、血管拡張と血圧低下をもたらします .
2. 製法
合成経路および反応条件: ニフェジピンは、アルデヒド、β-ケトエステル、アンモニアを縮合させるHantzsch反応により合成できます . たとえば、メチルアセト酢酸とオルトニトロベンズアルデヒドをアンモニアの存在下で反応させると、ニフェジピンが生成されます .
工業生産方法: 工業的には、ニフェジピンは、ポリビニルピロリドンなどの水溶性ポリマーを使用して固体分散体として調製され、バイオアベイラビリティが向上しています . 別の方法では、ナノ沈殿法や乳化溶媒蒸発法などの技術を使用して、ニフェジピンを負荷したポリマーナノ粒子を調製します .
3. 化学反応解析
反応の種類: ニフェジピンは、還元、酸化、置換など、さまざまな化学反応を起こします。 たとえば、亜鉛と塩酸の系を使用して還元できます .
一般的な試薬と条件：
主要な生成物：
4. 科学研究への応用
ニフェジピンは、幅広い科学研究への応用があります：
作用機序
科学的研究の応用
Nifedipine has a wide range of scientific research applications:
生化学分析
Biochemical Properties
Nifedipine’s primary role in biochemical reactions is as an inhibitor of L-type calcium channels . By blocking these channels, Nifedipine prevents the influx of calcium ions into cells, which is a crucial step in muscle contraction and neurotransmitter release .
Cellular Effects
Nifedipine has a profound effect on various types of cells, particularly those in the heart and blood vessels . By inhibiting calcium influx, Nifedipine reduces the contractility of cardiac and smooth muscle cells, leading to a decrease in blood pressure . It also influences cell signaling pathways related to calcium homeostasis and can affect gene expression related to these pathways .
Molecular Mechanism
Nifedipine exerts its effects at the molecular level primarily through its interaction with L-type calcium channels . It binds to the alpha-1 subunit of these channels, causing a conformational change that prevents the passage of calcium ions . This inhibition can lead to downstream effects on gene expression and cellular metabolism .
Temporal Effects in Laboratory Settings
In laboratory settings, the effects of Nifedipine can be observed to change over time. It is almost completely absorbed in the gastrointestinal tract but has a bioavailability of 45-68%, partly due to first-pass metabolism . Over time, the drug is metabolized and excreted, and its effects diminish .
Dosage Effects in Animal Models
The effects of Nifedipine in animal models have been shown to vary with dosage . At lower doses, Nifedipine effectively reduces blood pressure without significant adverse effects. At higher doses, it can cause hypotension and reflex tachycardia .
Metabolic Pathways
Nifedipine is metabolized primarily in the liver by the cytochrome P450 system . It undergoes extensive first-pass metabolism, leading to the formation of several metabolites .
Transport and Distribution
After absorption, Nifedipine is distributed throughout the body. It is highly lipophilic, allowing it to cross cell membranes easily . It is also highly protein-bound in plasma, which can affect its distribution .
Subcellular Localization
As a lipophilic compound, Nifedipine can diffuse across cell membranes and reach various subcellular compartments . Its primary site of action, the L-type calcium channels, are located in the cell membrane . It can also affect intracellular calcium stores and other subcellular structures .
準備方法
Synthetic Routes and Reaction Conditions: Nifedipine can be synthesized through the Hantzsch reaction, which involves the condensation of an aldehyde, a β-keto ester, and ammonia . For example, methyl acetoacetate and ortho-nitrobenzaldehyde are reacted in the presence of ammonia to form nifedipine .
Industrial Production Methods: In industrial settings, nifedipine is often prepared as a solid dispersion using water-soluble polymers like polyvinylpyrrolidone to enhance its bioavailability . Another method involves the preparation of nifedipine-loaded polymeric nanoparticles using techniques like nanoprecipitation and emulsion-solvent evaporation .
化学反応の分析
Types of Reactions: Nifedipine undergoes various chemical reactions, including reduction, oxidation, and substitution. For instance, it can be reduced using a zinc and hydrochloric acid system .
Common Reagents and Conditions:
Reduction: Zinc and hydrochloric acid are commonly used for the reduction of nifedipine.
Oxidation: Nifedipine can be oxidized to form nitrosophenylpyridine derivatives when exposed to ultraviolet light.
Major Products:
類似化合物との比較
ニフェジピンは、アムロジピン、ニカルジピン、フェロジピンなどの他のカルシウム拮抗薬と比較されることがよくあります . これらの化合物はいずれも作用機序が似ていますが、ニフェジピンは、作用発現が速く、半減期が短い点が特徴です . これは、急性高血圧性緊急時の管理に特に役立ちます .
類似化合物：
- アムロジピン
- ニカルジピン
- フェロジピン
- イスラジピン
- ニモジピン
- ニトレンジピン
- ラシジピン
ニフェジピンの独自の薬物動態プロファイルとそのさまざまな心血管疾患の治療における有効性は、医学療法におけるその重要性を強調しています。
特性
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 | |
| Source | CAMEO Chemicals | |
| URL | https://cameochemicals.noaa.gov/chemical/20738 | |
| Description | CAMEO Chemicals is a chemical database designed for people who are involved in hazardous material incident response and planning. CAMEO Chemicals contains a library with thousands of datasheets containing response-related information and recommendations for hazardous materials that are commonly transported, used, or stored in the United States. CAMEO Chemicals was developed by the National Oceanic and Atmospheric Administration's Office of Response and Restoration in partnership with the Environmental Protection Agency's Office of Emergency Management. | |
| Explanation | CAMEO Chemicals and all other CAMEO products are available at no charge to those organizations and individuals (recipients) responsible for the safe handling of chemicals. However, some of the chemical data itself is subject to the copyright restrictions of the companies or organizations that provided the data. | |
| 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 | |
| URL | https://pubchem.ncbi.nlm.nih.gov/substance/?source=chemidplus&sourceid=0021829254 | |
| Description | ChemIDplus is a free, web search system that provides access to the structure and nomenclature authority files used for the identification of chemical substances cited in National Library of Medicine (NLM) databases, including the TOXNET system. | |
DSSTOX Substance ID |
DTXSID2025715 |
Source
|
| Record name | Nifedipine | |
| Source | EPA DSSTox | |
| URL | https://comptox.epa.gov/dashboard/DTXSID2025715 | |
| Description | DSSTox provides a high quality public chemistry resource for supporting improved predictive toxicology. | |
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 | |
| Source | CAMEO Chemicals | |
| URL | https://cameochemicals.noaa.gov/chemical/20738 | |
| Description | CAMEO Chemicals is a chemical database designed for people who are involved in hazardous material incident response and planning. CAMEO Chemicals contains a library with thousands of datasheets containing response-related information and recommendations for hazardous materials that are commonly transported, used, or stored in the United States. CAMEO Chemicals was developed by the National Oceanic and Atmospheric Administration's Office of Response and Restoration in partnership with the Environmental Protection Agency's Office of Emergency Management. | |
| Explanation | CAMEO Chemicals and all other CAMEO products are available at no charge to those organizations and individuals (recipients) responsible for the safe handling of chemicals. However, some of the chemical data itself is subject to the copyright restrictions of the companies or organizations that provided the data. | |
| Record name | Nifedipine | |
| Source | Human Metabolome Database (HMDB) | |
| URL | http://www.hmdb.ca/metabolites/HMDB0015247 | |
| Description | The Human Metabolome Database (HMDB) is a freely available electronic database containing detailed information about small molecule metabolites found in the human body. | |
| Explanation | HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications. | |
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 | |
| Source | CAMEO Chemicals | |
| URL | https://cameochemicals.noaa.gov/chemical/20738 | |
| Description | CAMEO Chemicals is a chemical database designed for people who are involved in hazardous material incident response and planning. CAMEO Chemicals contains a library with thousands of datasheets containing response-related information and recommendations for hazardous materials that are commonly transported, used, or stored in the United States. CAMEO Chemicals was developed by the National Oceanic and Atmospheric Administration's Office of Response and Restoration in partnership with the Environmental Protection Agency's Office of Emergency Management. | |
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| Record name | Nifedipine | |
| Source | DrugBank | |
| URL | https://www.drugbank.ca/drugs/DB01115 | |
| Description | The DrugBank database is a unique bioinformatics and cheminformatics resource that combines detailed drug (i.e. chemical, pharmacological and pharmaceutical) data with comprehensive drug target (i.e. sequence, structure, and pathway) information. | |
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| Record name | Nifedipine | |
| Source | Hazardous Substances Data Bank (HSDB) | |
| URL | https://pubchem.ncbi.nlm.nih.gov/source/hsdb/7775 | |
| Description | The Hazardous Substances Data Bank (HSDB) is a toxicology database that focuses on the toxicology of potentially hazardous chemicals. It provides information on human exposure, industrial hygiene, emergency handling procedures, environmental fate, regulatory requirements, nanomaterials, and related areas. The information in HSDB has been assessed by a Scientific Review Panel. | |
| Record name | Nifedipine | |
| Source | Human Metabolome Database (HMDB) | |
| URL | http://www.hmdb.ca/metabolites/HMDB0015247 | |
| Description | The Human Metabolome Database (HMDB) is a freely available electronic database containing detailed information about small molecule metabolites found in the human body. | |
| Explanation | HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications. | |
Vapor Pressure |
2.6X10-8 mm Hg at 25 °C |
Source
|
| Record name | Nifedipine | |
| Source | Hazardous Substances Data Bank (HSDB) | |
| URL | https://pubchem.ncbi.nlm.nih.gov/source/hsdb/7775 | |
| Description | The Hazardous Substances Data Bank (HSDB) is a toxicology database that focuses on the toxicology of potentially hazardous chemicals. It provides information on human exposure, industrial hygiene, emergency handling procedures, environmental fate, regulatory requirements, nanomaterials, and related areas. The information in HSDB has been assessed by a Scientific Review Panel. | |
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 | |
| Description | The DrugBank database is a unique bioinformatics and cheminformatics resource that combines detailed drug (i.e. chemical, pharmacological and pharmaceutical) data with comprehensive drug target (i.e. sequence, structure, and pathway) information. | |
| Explanation | Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode) | |
| Record name | Nifedipine | |
| Source | Hazardous Substances Data Bank (HSDB) | |
| URL | https://pubchem.ncbi.nlm.nih.gov/source/hsdb/7775 | |
| Description | The Hazardous Substances Data Bank (HSDB) is a toxicology database that focuses on the toxicology of potentially hazardous chemicals. It provides information on human exposure, industrial hygiene, emergency handling procedures, environmental fate, regulatory requirements, nanomaterials, and related areas. The information in HSDB has been assessed by a Scientific Review Panel. | |
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 | |
| Source | Hazardous Substances Data Bank (HSDB) | |
| URL | https://pubchem.ncbi.nlm.nih.gov/source/hsdb/7775 | |
| Description | The Hazardous Substances Data Bank (HSDB) is a toxicology database that focuses on the toxicology of potentially hazardous chemicals. It provides information on human exposure, industrial hygiene, emergency handling procedures, environmental fate, regulatory requirements, nanomaterials, and related areas. The information in HSDB has been assessed by a Scientific Review Panel. | |
Color/Form |
Yellow crystals | |
CAS No. |
21829-25-4, 193689-82-6, 915092-63-6 |
Source
|
| Record name | NIFEDIPINE | |
| Source | CAMEO Chemicals | |
| URL | https://cameochemicals.noaa.gov/chemical/20738 | |
| Description | CAMEO Chemicals is a chemical database designed for people who are involved in hazardous material incident response and planning. CAMEO Chemicals contains a library with thousands of datasheets containing response-related information and recommendations for hazardous materials that are commonly transported, used, or stored in the United States. CAMEO Chemicals was developed by the National Oceanic and Atmospheric Administration's Office of Response and Restoration in partnership with the Environmental Protection Agency's Office of Emergency Management. | |
| Explanation | CAMEO Chemicals and all other CAMEO products are available at no charge to those organizations and individuals (recipients) responsible for the safe handling of chemicals. However, some of the chemical data itself is subject to the copyright restrictions of the companies or organizations that provided the data. | |
| Record name | 3,5-Pyridinedicarboxylic acid, 1,4-dihydro-2,6-dimethyl-4-(2-nitrophenyl)-, dimethyl ester, radical ion(1-) | |
| Source | CAS Common Chemistry | |
| URL | https://commonchemistry.cas.org/detail?cas_rn=193689-82-6 | |
| Description | CAS Common Chemistry is an open community resource for accessing chemical information. Nearly 500,000 chemical substances from CAS REGISTRY cover areas of community interest, including common and frequently regulated chemicals, and those relevant to high school and undergraduate chemistry classes. This chemical information, curated by our expert scientists, is provided in alignment with our mission as a division of the American Chemical Society. | |
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| Record name | Nifedipine | |
| Source | CAS Common Chemistry | |
| URL | https://commonchemistry.cas.org/detail?cas_rn=21829-25-4 | |
| Description | CAS Common Chemistry is an open community resource for accessing chemical information. Nearly 500,000 chemical substances from CAS REGISTRY cover areas of community interest, including common and frequently regulated chemicals, and those relevant to high school and undergraduate chemistry classes. This chemical information, curated by our expert scientists, is provided in alignment with our mission as a division of the American Chemical Society. | |
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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+) | |
| Source | CAS Common Chemistry | |
| URL | https://commonchemistry.cas.org/detail?cas_rn=915092-63-6 | |
| Description | CAS Common Chemistry is an open community resource for accessing chemical information. Nearly 500,000 chemical substances from CAS REGISTRY cover areas of community interest, including common and frequently regulated chemicals, and those relevant to high school and undergraduate chemistry classes. This chemical information, curated by our expert scientists, is provided in alignment with our mission as a division of the American Chemical Society. | |
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| Record name | Nifedipine [USAN:USP:INN:BAN:JAN] | |
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| Record name | Nifedipine | |
| Source | DrugBank | |
| URL | https://www.drugbank.ca/drugs/DB01115 | |
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| Record name | NIFEDIPINE | |
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| Record name | Nifedipine | |
| Source | Hazardous Substances Data Bank (HSDB) | |
| URL | https://pubchem.ncbi.nlm.nih.gov/source/hsdb/7775 | |
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| Record name | Nifedipine | |
| Source | Human Metabolome Database (HMDB) | |
| URL | http://www.hmdb.ca/metabolites/HMDB0015247 | |
| Description | The Human Metabolome Database (HMDB) is a freely available electronic database containing detailed information about small molecule metabolites found in the human body. | |
| Explanation | HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications. | |
Melting Point |
342 to 345 °F (NTP, 1992), 172-174 °C, 172 - 174 °C |
Source
|
| Record name | NIFEDIPINE | |
| Source | CAMEO Chemicals | |
| URL | https://cameochemicals.noaa.gov/chemical/20738 | |
| Description | CAMEO Chemicals is a chemical database designed for people who are involved in hazardous material incident response and planning. CAMEO Chemicals contains a library with thousands of datasheets containing response-related information and recommendations for hazardous materials that are commonly transported, used, or stored in the United States. CAMEO Chemicals was developed by the National Oceanic and Atmospheric Administration's Office of Response and Restoration in partnership with the Environmental Protection Agency's Office of Emergency Management. | |
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| Record name | Nifedipine | |
| Source | DrugBank | |
| URL | https://www.drugbank.ca/drugs/DB01115 | |
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| Record name | Nifedipine | |
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| URL | https://pubchem.ncbi.nlm.nih.gov/source/hsdb/7775 | |
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| Record name | Nifedipine | |
| Source | Human Metabolome Database (HMDB) | |
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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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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
[Compound]
Name
( 7 )
Quantity
0 (± 1) mol
Type
reactant
Reaction Step One
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
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
Yield
81%
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.
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
Retrosynthesis Analysis
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Strategy Settings
| Precursor scoring | Relevance Heuristic |
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| Min. plausibility | 0.01 |
| Model | Template_relevance |
| Template Set | Pistachio/Bkms_metabolic/Pistachio_ringbreaker/Reaxys/Reaxys_biocatalysis |
| Top-N result to add to graph | 6 |
Feasible Synthetic Routes
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