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CAS 103129-82-4

CAS 103129-82-4

Chemistry, 1 End Use API, 10 Related Intermediates

Manufacturers/Suppliers

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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.