CAS 103129-82-4 manufacturers and suppliers on PharmaCompass

CAS 103129-82-4

Granules India Limited has high volume world-class facilities for APIs, PFIs, & FDFs, serving customers in over 80 countries.

Virtual Booth

Contact Supplier

Jai Radhe Sales is your partner for all your sourcing needs.

CHEMISTRY

Discover Molecule Insights

Chemistry

Click the arrow to open the dropdown

Click the button for full data set

Also known as: (s)-amlodipine, 103129-82-4, S-amlodipine, Levoamlodipine, Levamlodipine [inn], L-amlodipine

Molecular Formula

C₂₀H₂₅ClN₂O₅

Molecular Weight

408.9 g/mol

InChI Key

HTIQEAQVCYTUBX-KRWDZBQOSA-N

FDA UNII

0P6NLP6806

Levamlodipine, also known as S-amlodipine, is a pharmacologically active enantiomer of [amlodipine], an antihypertensive medication. Levamlodipine belongs to the dihydropyridine group of calcium channel blockers. This medication was first marketed in Russia and India before being granted FDA approval. The names S-amlodipine and levamlodipine may be used interchangeably as both substances are the same, however. As a racemic mixture, amlodipine contains (R) and (S)-amlodipine isomers, but only (S)-amlodipine as the active moiety possesses therapeutic activity. Levamlodipine was granted FDA approval on 19 December 2019.

1 2D Structure

CAS 103129-82-4

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

3-O-ethyl 5-O-methyl (4S)-2-(2-aminoethoxymethyl)-4-(2-chlorophenyl)-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate

2.1.2 InChI

InChI=1S/C20H25ClN2O5/c1-4-28-20(25)18-15(11-27-10-9-22)23-12(2)16(19(24)26-3)17(18)13-7-5-6-8-14(13)21/h5-8,17,23H,4,9-11,22H2,1-3H3/t17-/m0/s1

2.1.3 InChI Key

HTIQEAQVCYTUBX-KRWDZBQOSA-N

2.1.4 Canonical SMILES

CCOC(=O)C1=C(NC(=C(C1C2=CC=CC=C2Cl)C(=O)OC)C)COCCN

2.1.5 Isomeric SMILES

CCOC(=O)C1=C(NC(=C([C@@H]1C2=CC=CC=C2Cl)C(=O)OC)C)COCCN

2.2 Other Identifiers

2.2.1 UNII

0P6NLP6806

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 2-((2-aminoethoxy)methyl)-4-(2-chlorophenyl)-3-ethoxy-carbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyridine

2.3.2 Depositor-Supplied Synonyms

1. (s)-amlodipine

2. 103129-82-4

3. S-amlodipine

4. Levoamlodipine

5. Levamlodipine [inn]

6. L-amlodipine

7. Amlodipine, (s)-

8. Unii-0p6nlp6806

9. Chebi:53796

10. 0p6nlp6806

11. (4s)-2-[(2-aminoethoxy)methyl]-4-(2-chlorophenyl)-1,4-dihydro-6-methyl-3,5-pyridinedicarboxylic Acid 3-ethyl 5-methyl Ester

12. 3-ethyl 5-methyl (s)-2-((2-aminoethoxy)methyl)-4-(2-chlorophenyl)-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate

13. Levoamlodipine Besylate

14. 3,5-pyridinedicarboxylic Acid, 2-((2-aminoethoxy)methyl)-4-(2-chlorophenyl)-1,4-dihydro-6-methyl-, 3-ethyl 5-methyl Ester, (4s)-

15. 3-ethyl 5-methyl (4s)-2-((2-aminoethoxy)methyl)-4-(2-chlorophenyl)-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate

16. 3-ethyl 5-methyl (4s)-2-[(2-aminoethoxy)methyl]-4-(2-chlorophenyl)-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate

17. (-)-amlodipine

18. 3,5-pyridinedicarboxylic Acid, 2-[(2-aminoethoxy)methyl]-4-(2-chlorophenyl)-1,4-dihydro-6-methyl-, 3-ethyl 5-methyl Ester, (4s)-

19. S-amlodipine Besylate

20. S-amlodipine Gentisate

21. D0i2wv

22. Levamlodipine (hypertension)

23. Schembl41283

24. Levamlodipine [who-dd]

25. Chembl2111097

26. Dtxsid50904504

27. Htiqeaqvcytubx-krwdzbqosa-n

28. Hms3885m19

29. Bcp22052

30. Mfcd09832686

31. S3674

32. Akos015896087

33. Am90308

34. Bcp9000849

35. Ccg-268748

36. Db09237

37. Agsav301 Component Levamlodipine

38. Bs-42190

39. Hy-14744

40. Levamlodipine (hypertension), Sk Chemicals

41. S-amlodipine (hypertension), Sk Chemicals

42. Ls-194044

43. Cs-0003533

44. A14935

45. D97381

46. A800681

47. En300-19633977

48. Q-101935

49. Q6534831

50. 2-((2-aminoethoxy)methyl)-4-(2-chlorophenyl)-3-ethoxy-carbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyridine

51. 3-o-ethyl 5-o-methyl (4s)-2-(2-aminoethoxymethyl)-4-(2-chlorophenyl)-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate

2.4 Create Date

2006-10-25

3 Chemical and Physical Properties

Molecular Formula	C₂₀H₂₅ClN₂O₅
Molecular Weight	408.9 g/mol
XLogP3	3
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	7
Rotatable Bond Count	10
Exact Mass	g/mol
Monoisotopic Mass	g/mol
Topological Polar Surface Area	99.9
Heavy Atom Count	28
Formal Charge	0
Complexity	647
Isotope Atom Count	0
Defined Atom Stereocenter Count	1
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

Levamlodipine is indicated alone or in combination to treat hypertension in adults and children.

FDA Label

5 Pharmacology and Biochemistry

5.1 ATC Code

C - Cardiovascular system

C08 - Calcium channel blockers

C08C - Selective calcium channel blockers with mainly vascular effects

C08CA - Dihydropyridine derivatives

C08CA17 - Levamlodipine

5.2 Absorption, Distribution and Excretion

Absorption

Oral levamlodipine has a Tmax of 6-12h and a bioavailability of 64-90%. Absorption of levamlodipine is not significantly affected by food. 20mg or oral s-amlodipine besylate reaches a Cmax of 6.131.29ng/mL with a Tmax of 8.43.6h and an AUC of 35172h\*ng/mL. 20mg or oral s-amlodipine maleate reaches a Cmax of 5.071.09ng/mL with a Tmax of 10.73.4h and an AUC of 33088h\*ng/mL.

Route of Elimination

Levamlodipine is 60% eliminated in urine with 10% eliminated as the unmetabolized drug.

Volume of Distribution

The volume of distribution of levamlodipine is similar to amlodipine. The volume of distribution of amlodipine is 21L/kg.

Clearance

The oral clearance of S-amlodipine besylate is 6.91.6mL/min/kg and the oral clearance of S-amlodipine maleate is 7.32.1mL/min/kg.

5.3 Metabolism/Metabolites

Levamlodipine is 90% metabolized to inactive metabolites. Incubation with liver microsomes has shown that this metabolism is primarily mediated by CYP3A4. Levamlodipine's dehydrogenation to a pyridine metabolite (M9) is the most important metabolic pathway in human liver microsomes. This derivative can be further oxidatively deaminated or O-dealkylated, but does not appear to undergo O-demethylation like racemic amlodipine.

5.4 Biological Half-Life

Levamlodipine has a half life of 30-50h.

5.5 Mechanism of Action

Levamlodipine blocks the transmembrane influx of calcium through L-type calcium channels into the vascular and cardiac smooth muscles resulting in vasodilation and a subsequent decrease in blood pressure. Levamlodipine inhibits calcium influx in vascular smooth muscle to a greater degree than in cardiac muscle, leading to decreased peripheral vascular resistance and lowered blood pressure. In vitro studies have shown a negative inotropic effect but this is unlikely to be clinically relevant.

Market Place

Home

Post Enquiry

Market Place

CAS 103129-82-4 manufacturers and suppliers on PharmaCompass

CAS 103129-82-4

CHEMISTRY

Discover Molecule Insights

What are you looking for?