Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C20H25ClN2O5.C4H4O4 |
Molecular Weight | 524.9489 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 1 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CCOC(=O)C1=C(COCCN)NC(=C([C@]1([H])c2ccccc2Cl)C(=O)OC)C.C(\[H])(=C(\[H])/C(=O)O)/C(=O)O
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
Molecular Formula | C4H4O4 |
Molecular Weight | 116.0723 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 1 |
Optical Activity | NONE |
Molecular Formula | C20H25ClN2O5 |
Molecular Weight | 408.8766 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
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 |
---|---|---|---|
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: - |
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Jun 26 02:43:07 UTC 2021
by
admin
on
Sat Jun 26 02:43:07 UTC 2021
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Record UNII |
12WW9T2ITA
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Record Status |
Validated (UNII)
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Record Version |
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-
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135969-53-8
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SUB125921
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C175110
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2377031
Created by
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12WW9T2ITA
Created by
admin on Sat Jun 26 02:43:07 UTC 2021 , Edited by admin on Sat Jun 26 02:43:07 UTC 2021
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69165622
Created by
admin on Sat Jun 26 02:43:07 UTC 2021 , Edited by admin on Sat Jun 26 02:43:07 UTC 2021
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Related Record | Type | Details | ||
---|---|---|---|---|
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PARENT -> SALT/SOLVATE | |||
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PARENT -> SALT/SOLVATE | |||
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RACEMATE -> ENANTIOMER |
Related Record | Type | Details | ||
---|---|---|---|---|
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ACTIVE MOIETY |