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Also known as: 105979-17-7, Benidipene, Benidipine [inn], 119065-60-0, 5-o-[(3r)-1-benzylpiperidin-3-yl] 3-o-methyl (4r)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate, 4g9t91js7e
Molecular Formula
C28H31N3O6
Molecular Weight
505.6  g/mol
InChI Key
QZVNQOLPLYWLHQ-ZEQKJWHPSA-N
FDA UNII
4G9T91JS7E

Benidipine
Benidipine has the formula 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridine-dicarboxylic acid methyl 1-(phenylmethyl)-3-piperidinyl ester hydrochloride. It is a synthetic dihydropyridine derivative that has anti-hypertensive and anti-anginal actions. It was originated in Japan by Kyowa Hakko, it is submitted for FDA approval and it is currently available in some Asian countries like India and Japan.
1 2D Structure

Benidipine

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
5-O-[(3R)-1-benzylpiperidin-3-yl] 3-O-methyl (4R)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
2.1.2 InChI
InChI=1S/C28H31N3O6/c1-18-24(27(32)36-3)26(21-11-7-12-22(15-21)31(34)35)25(19(2)29-18)28(33)37-23-13-8-14-30(17-23)16-20-9-5-4-6-10-20/h4-7,9-12,15,23,26,29H,8,13-14,16-17H2,1-3H3/t23-,26-/m1/s1
2.1.3 InChI Key
QZVNQOLPLYWLHQ-ZEQKJWHPSA-N
2.1.4 Canonical SMILES
CC1=C(C(C(=C(N1)C)C(=O)OC2CCCN(C2)CC3=CC=CC=C3)C4=CC(=CC=C4)[N+](=O)[O-])C(=O)OC
2.1.5 Isomeric SMILES
CC1=C([C@H](C(=C(N1)C)C(=O)O[C@@H]2CCCN(C2)CC3=CC=CC=C3)C4=CC(=CC=C4)[N+](=O)[O-])C(=O)OC
2.2 Other Identifiers
2.2.1 UNII
4G9T91JS7E
2.3 Synonyms
2.3.1 Depositor-Supplied Synonyms

1. 105979-17-7

2. Benidipene

3. Benidipine [inn]

4. 119065-60-0

5. 5-o-[(3r)-1-benzylpiperidin-3-yl] 3-o-methyl (4r)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate

6. 4g9t91js7e

7. Benidipine (inn)

8. Benidipino

9. Benidipinum

10. Benidipinum [latin]

11. Benidipino [spanish]

12. Ncgc00185768-01

13. Unii-4g9t91js7e

14. Benidipine [mi]

15. Benidipine [who-dd]

16. Schembl24516

17. Chembl2105555

18. Chembl3303980

19. Dtxsid0022648

20. Hy-b1448a

21. Zinc21992076

22. Akos015895389

23. Zinc100014880

24. Db09231

25. Mrf-0000234

26. Ncgc00185768-03

27. Cs-0111103

28. 79b177

29. D07509

30. Ab01209735-01

31. Ab01566847_01

32. A801348

33. Q11336997

34. (+-)-(r*)-3-((r*)-1-benzyl-3-piperidyl) Methyl 1,4-dihydro-2,6-dimethyl-4-(m-nitrophenyl)-3,5-pyridinedicarboxylate

35. (+/-)-(r*)-3-((r*)-1-benzyl-3-piperidyl) Methyl 1,4-dihydro-2,6-dimethyl-4-(m-nitrophenyl)-3,5-pyridinedicarboxylate

36. (+/-)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic Acid-3-(1-benzyl-3-piperidyl) Ester-5-methyl Ester

37. (4r)-rel-1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic Acid Methyl (3r)-1-(phenylmethyl)-3-piperidinyl Ester

38. Methyl (3r)-1-(phenylmethyl)piperidin-3-yl (4r)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate

39. O5-[(3r)-1-benzyl-3-piperidyl] O3-methyl (4r)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate

2.4 Create Date
2005-06-24
3 Chemical and Physical Properties
Molecular Weight 505.6 g/mol
Molecular Formula C28H31N3O6
XLogP34.6
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count8
Rotatable Bond Count8
Exact Mass505.22128572 g/mol
Monoisotopic Mass505.22128572 g/mol
Topological Polar Surface Area114 Ų
Heavy Atom Count37
Formal Charge0
Complexity933
Isotope Atom Count0
Defined Atom Stereocenter Count2
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Indication

Benidipine is a potent and long-lasting drug indicated for the treatment of cardiovascular diseases such as hypertension, renoparenchymal hypertension and angina pectoris.


5 Pharmacology and Biochemistry
5.1 Pharmacology

Benidipine reduces systolic and diastolic blood pressure as well as to present decreases in heart rate pulse after treatment. It is reported also a decrease urinary protein excretion and serum triglycerides. Different studies have shown benidipine anti-oxidative activity, stimulation of NO production, suppression of adhesion molecules expression, stimulation of osteoblast differentiation, suppression of the proliferation of vascular smooth muscle cells and mesangial cells, as well as myocardial protection. The enhancement of NO production is associated with the cardioprotective and antiartheriosclerotic effects of benidipine.


5.2 MeSH Pharmacological Classification

Calcium Channel Blockers

A class of drugs that act by selective inhibition of calcium influx through cellular membranes. (See all compounds classified as Calcium Channel Blockers.)


Vasodilator Agents

Drugs used to cause dilation of the blood vessels. (See all compounds classified as Vasodilator Agents.)


5.3 ATC Code

C - Cardiovascular system

C08 - Calcium channel blockers

C08C - Selective calcium channel blockers with mainly vascular effects

C08CA - Dihydropyridine derivatives

C08CA15 - Benidipine


5.4 Absorption, Distribution and Excretion

Absorption

Benidipine is rapidly absorbed after oral administration reaching a maximum concentration within 2 hours. The short period of time needed for maximum concentration to get reached is a particular characteristic of benidipine when compared with other calcium channel blockers. The registered maximum concentration and AUC are dose-dependent and it can go from 0.55-3.89 ng/ml and 1.04-6.7 ng.h/ml respectively when administered in a dose of 2-8 mg.


Route of Elimination

The percentage of urinary excretion after oral administration is of approximate 36% of the administered dose. Most of the remaining dose is excreted in feces, making bile excretion the major elimination pathway of benidipine. From the eliminated drug, none of it is expressed in the form of the unchanged drug.


Volume of Distribution

Benidipine is highly distributed to the tissues mainly in the liver and kidneys and plasma. It does not present a high accumulation following repeated oral administrations.


5.5 Metabolism/Metabolites

Benidipine is almost completely metabolized in the liver. From different reports, it is thought that benidipine is mainly metabolized by CYP3A. Some of the formed metabolites are N-desbenzylbenidipine and dehydrobenidipine. Analysis on the formation of metabolites has indicated that the metabolism is mainly performed by CYP3A4 and CYP3A5.


5.6 Biological Half-Life

The elimination half-life of benidipine is registered to be of approximate 1 hour.


5.7 Mechanism of Action

Benidipine is a tripe calcium channel inhibitor by inhibiting L, N and T type calcium channel. It presents a very long-lasting activity that can be explained by its high affinity for cell membranes from the DHP binding site; this characteristic indicated a long-lasting pharmacological activity of benidipine. The additional property of benidipine is the vascular selectivity towards peripheral blood vessels.


API Reference Price

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07-Aug-2024
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ABOUT THIS PAGE

Benidipine Manufacturers

A Benidipine manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of Benidipine, including repackagers and relabelers. The FDA regulates Benidipine manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. Benidipine API Manufacturers are required to adhere to Good Manufacturing Practices (GMP) to ensure that their products are consistently manufactured to meet established quality criteria.

click here to find a list of Benidipine manufacturers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PhamaCompass.

Benidipine Suppliers

A Benidipine supplier is an individual or a company that provides Benidipine active pharmaceutical ingredient (API) or Benidipine finished formulations upon request. The Benidipine suppliers may include Benidipine API manufacturers, exporters, distributors and traders.

click here to find a list of Benidipine suppliers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PharmaCompass.

Benidipine GMP

Benidipine Active pharmaceutical ingredient (API) is produced in GMP-certified manufacturing facility.

GMP stands for Good Manufacturing Practices, which is a system used in the pharmaceutical industry to make sure that goods are regularly produced and monitored in accordance with quality standards. The FDA’s current Good Manufacturing Practices requirements are referred to as cGMP or current GMP which indicates that the company follows the most recent GMP specifications. The World Health Organization (WHO) has its own set of GMP guidelines, called the WHO GMP. Different countries can also set their own guidelines for GMP like China (Chinese GMP) or the EU (EU GMP).

PharmaCompass offers a list of Benidipine GMP manufacturers, exporters & distributors, which can be sorted by USDMF, JDMF, KDMF, CEP (COS), WC, API price, and more, enabling you to easily find the right Benidipine GMP manufacturer or Benidipine GMP API supplier for your needs.

Benidipine CoA

A Benidipine CoA (Certificate of Analysis) is a formal document that attests to Benidipine's compliance with Benidipine specifications and serves as a tool for batch-level quality control.

Benidipine CoA mostly includes findings from lab analyses of a specific batch. For each Benidipine CoA document that a company creates, the USFDA specifies specific requirements, such as supplier information, material identification, transportation data, evidence of conformity and signature data.

Benidipine may be tested according to a variety of international standards, such as European Pharmacopoeia (Benidipine EP), Benidipine JP (Japanese Pharmacopeia) and the US Pharmacopoeia (Benidipine USP).

Inform the supplier about your product requirements, specifying if you need a product with particular monograph like EP (Ph. Eur.), USP, JP, BP, or any other quality. In addition, clarify whether you need hydrochloride (HCl), anhydricum, base, micronisatum or a specific level of purity. To find reputable suppliers, utilize the filters and select those certified by GMP, FDA, or any other certification as per your requirement.
For your convenience, we have listed synonyms and CAS numbers to help you find the best supplier. The use of synonyms and CAS numbers can be helpful in identifying potential suppliers, but it is crucial to note that they might not always indicate the exact same product. It is important to confirm the product details with the supplier before making a purchase to ensure that it meets your requirements.
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