Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C20H25ClN2O5.C4H4O4 |
Molecular Weight | 524.948 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 1 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
OC(=O)\C=C/C(O)=O.CCOC(=O)C1=C(COCCN)NC(C)=C([C@@H]1C2=C(Cl)C=CC=C2)C(=O)OC
InChI
InChIKey=TZNOWAJJWCGILX-HNUXRKMMSA-N
InChI=1S/C20H25ClN2O5.C4H4O4/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;5-3(6)1-2-4(7)8/h5-8,17,23H,4,9-11,22H2,1-3H3;1-2H,(H,5,6)(H,7,8)/b;2-1-/t17-;/m0./s1
Levalmodipine (S-amlodipine) is an active enantiomer of amlodipine, a calcium antagonist that inhibits the transmembrane influx of calcium ions into vascular smooth muscle and cardiac muscle. Experimental data suggest that S-amlodipine binds to both dihydropyridine and nondihydropyridine binding sites. The contractile processes of cardiac muscle and vascular smooth muscle are dependent upon the movement of extracellular calcium ions into these cells through specific ion channels. S-Amlodipine inhibits calcium ion influx across cell membranes selectively, with a greater effect on vascular smooth muscle cells than on cardiac muscle cells. Enantiomerically pure S-amlodipine is marketed in some countries worldwide, while racemate, containing active S-enantiomer an inactive R-enantiomer is marketed in the USA and indicated for the treatment of hypertension and coronary artery disease.
Approval Year
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
2.71 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29559771/ |
5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered: TELMISARTAN |
LEVAMLODIPINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
3.1 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17213004/ |
5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered: |
LEVAMLODIPINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
147.43 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29559771/ |
5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered: TELMISARTAN |
LEVAMLODIPINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
161.7 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17213004/ |
5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered: |
LEVAMLODIPINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
45.1 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29559771/ |
5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered: TELMISARTAN |
LEVAMLODIPINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
55 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17213004/ |
5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered: |
LEVAMLODIPINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://www.mdpi.com/1420-3049/22/11/1879 Page: - |
no [IC50 >50 uM] | |||
Sources: https://www.mdpi.com/1420-3049/22/11/1879 Page: - |
no [IC50 >50 uM] | |||
Sources: https://www.mdpi.com/1420-3049/22/11/1879 Page: - |
no [IC50 >50 uM] | |||
Sources: https://www.mdpi.com/1420-3049/22/11/1879 Page: - |
no [IC50 >50 uM] | |||
Sources: https://www.mdpi.com/1420-3049/22/11/1879 Page: - |
yes [IC50 40.12 uM] | |||
Sources: https://www.mdpi.com/1420-3049/22/11/1879 Page: - |
yes [IC50 9.55 uM] | |||
Sources: https://www.mdpi.com/1420-3049/22/11/1879 Page: - |
yes [Ki 21.45 uM] | |||
Sources: https://www.mdpi.com/1420-3049/22/11/1879 Page: - |
yes [Ki 7.22 uM] | |||
Sources: https://www.mdpi.com/1420-3049/22/11/1879 Page: - |
yes [Ki 8.95 uM] |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://dmd.aspetjournals.org/content/42/2/245 Page: - |
unlikely | |||
Sources: https://dmd.aspetjournals.org/content/42/2/245 Page: - |
unlikely | |||
Sources: https://dmd.aspetjournals.org/content/42/2/245 Page: - |
unlikely | |||
Sources: https://dmd.aspetjournals.org/content/42/2/245 Page: - |
unlikely | |||
yes | ||||
Sources: https://dmd.aspetjournals.org/content/42/2/245 Page: - |
yes | |||
Sources: https://dmd.aspetjournals.org/content/42/2/245 Page: - |
yes | |||
Page: - |
yes | yes (pharmacogenomic study) Comment: Amlodipine pharmacokinetics was affected by the genetic polymorphisms of the ABCB1 gene in humans. Page: - |
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Code System | Code | Type | Description | ||
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135969-53-8
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DTXSID801027742
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SUB125921
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C175110
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2377031
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HI-46
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12WW9T2ITA
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100000151631
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69165622
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12WW9T2ITA
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ACTIVE MOIETY
PARENT (SALT/SOLVATE)
SUBSTANCE RECORD