Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C19H20N2O7 |
| Molecular Weight | 388.3713 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
COC(=O)C1=C(C)NC(C)=C([C@H]1C2=C(C=CC=C2)[N+]([O-])=O)C(=O)OCC(C)=O
InChI
InChIKey=NCUCGYYHUFIYNU-KRWDZBQOSA-N
InChI=1S/C19H20N2O7/c1-10(22)9-28-19(24)16-12(3)20-11(2)15(18(23)27-4)17(16)13-7-5-6-8-14(13)21(25)26/h5-8,17,20H,9H2,1-4H3/t17-/m0/s1
| Molecular Formula | C19H20N2O7 |
| Molecular Weight | 388.3713 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
S-aranidipine or (S)-MPC-1304 is an enantiomer of MPC-1304 (methyl 2-oxopropyl 1,4-dihydro-2,6-di-methyl-4-(2-nitrophenyl)-3,5-pyridinedicarboxylate), a calcium entry blocker. The Ca2+ entry blocking activity of the (S) enantiomer of MPC-1304 was approximately 150 times greater than that of its (R) enantiomer. Likewise, the antihypertensive effect of the (S) enantiomer was twice as great as that of MPC-1304 (racemate) in conscious spontaneously hypertensive rats, while the (R) enantiomer was ineffective. Thus, most of the pharmacological activity of MPC-1304 resides in its (S) configuration.
Originator
Sources: Ohno, S., O. Komatsu, K. Mizukoshi, N. Akimatsu and N. Oda, 1991, Synthesis of metabolites of MPC-1304, a new calcium antagonist, and related compounds and optical resolution of MPC-1304 and related compounds, J. Pharmacobio-Dyn. 14, s-108
Curator's Comment: reference retrieved from https://www.ncbi.nlm.nih.gov/pubmed/8519282
Approval Year
Sample Use Guides
0.1, 0.3 and 1 mg/kg p.o. (S)-MPC-1304 (S-aranidipine) showed marked hypotensive effects in conscious spontaneously hypertensive rats
Route of Administration:
Oral
| Substance Class |
Chemical
Created
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admin
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Edited
Mon Mar 31 23:03:36 GMT 2025
by
admin
on
Mon Mar 31 23:03:36 GMT 2025
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| Record UNII |
D594X9Z4OS
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| Record Status |
Validated (UNII)
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148372-44-5
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RACEMATE -> ENANTIOMER |
