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Details

Stereochemistry ABSOLUTE
Molecular Formula C35H38N4O6
Molecular Weight 610.7007
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MANIDIPINE, (S)-

SMILES

CC1=C([C@]([H])(c2cccc(c2)N(=O)=O)C(=C(C)N1)C(=O)OCCN3CCN(CC3)C(c4ccccc4)c5ccccc5)C(=O)OC

InChI

InChIKey=ANEBWFXPVPTEET-YTTGMZPUSA-N
InChI=1S/C35H38N4O6/c1-24-30(34(40)44-3)32(28-15-10-16-29(23-28)39(42)43)31(25(2)36-24)35(41)45-22-21-37-17-19-38(20-18-37)33(26-11-6-4-7-12-26)27-13-8-5-9-14-27/h4-16,23,32-33,36H,17-22H2,1-3H3/t32-/m0/s1

HIDE SMILES / InChI

Molecular Formula C35H38N4O6
Molecular Weight 610.7007
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment:: The description was created based on several sources, including https://clinicaltrials.gov/ct2/show/NCT03106597 | https://www.ncbi.nlm.nih.gov/pubmed/10440102

Manidipine, (S)- is enantiomer of Manidipine a lipophilic, third-generation dihydropyridine calcium channel antagonist with a high degree of selectivity for the vasculature, thereby inducing marked peripheral vasodilation with negligible cardiodepression. Manidipine has different pharmacological effects and (S)-manidipine is shown to be about 30–80 times more potent than (R)-manidipine in its antihypertensive action and in the radioligand binding assay. Patch-clamp experiments revealed that the S-enantiomers of manidipine displayed a faster onset of action and produced a greater blockade than the R-enantiomer. Also, manidipine enantiomers have markedly different pharmacokinetics and the S/R ratio for (S)- and (R)-enantiomer concentrations is 2.0

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions
PubMed

PubMed

TitleDatePubMed
Enantioselective determination of R-(-)-manidipine and S-(+)-manidipine in human plasma by a sensitive and selective chiral LC-MS/MS assay.
2017 Dec
Patents

Patents

Sample Use Guides

Manidipine 10 to 40 mg once daily for 4 weeks
Route of Administration: Oral
GH3 cells were used for activity evaluation. the cells grown on glass coverslips were loaded with 5 mM 1-[2-(5-carboxyoxazol-2-yl)- 6-aminobenzofuran- 5-oxyx-2(-21-amino-51-methylphenoxy)-ethane-N,N,N1,N1-tetraace-tic acid pentaacetoxymethyl ester (fura-2AM) in Krebs–Ringer saline solution (5.5 mM KCl, 160 mM NaCl, 1.2 mM MgCl , 1.5 mM CaCl , 10 mM glucose, and 10 mM Hepes-NaOH, pH 7.4) for 1 h at room temperature. At the end of fura-2AM loading, the coverslip was introduced into a microscope chamber (Medical System, Greenvale, NY) on an inverted Nikon Diaphot fluorescence microscope. The cells were kept in Krebs–Ringer saline solution throughout the experiment. All the drugs tested were introduced into the microscope chamber by fast injection. When the depolarizing extracellular Kq solution (55 mM) was used, the osmolarity of the solution was kept constant by accordingly reducing the extracellular Naq concentration. A 100-W Xenon Lamp (Osram, Germany) with a computer-operated filter wheel bearing two different interference filters (340 and 380 nm) illuminated the microscopic field with UV light, alternating the wavelength at an interval of 500 ms. The interval between each pair of illuminations was 2 s, and the interval between filter movements was 1 s. Consequently, [Ca2++] was measured every 3 s. Emitted light was passed through a 400-nm dichroic mirror, filtered at 510 nm, and collected by a CCD camera connected to a light amplifier. Images were digitized and analyzed with a Magiscan image processor. Using a calibration curve, the Tardis software calculated the [Ca2++] corresponding to each pair of images from the ratio between the intensity of the light emitted when the cells were illuminated at both 340 and 380 nm.
Substance Class Chemical
Created
by admin
on Sat Jun 26 16:19:35 UTC 2021
Edited
by admin
on Sat Jun 26 16:19:35 UTC 2021
Record UNII
M40WCZ5X76
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
MANIDIPINE, (S)-
Common Name English
3,5-PYRIDINEDICARBOXYLIC ACID, 1,4-DIHYDRO-2,6-DIMETHYL-4-(3-NITROPHENYL)-, 2-(4-(DIPHENYLMETHYL)-1-PIPERAZINYL)ETHYL METHYL ESTER, (4S)-
Systematic Name English
(S)-(+)-MANIDIPINE
Common Name English
(+)-MANIDIPINE
Common Name English
3,5-PYRIDINEDICARBOXYLIC ACID, 1,4-DIHYDRO-2,6-DIMETHYL-4-(3-NITROPHENYL)-, 2-(4-(DIPHENYLMETHYL)-1-PIPERAZINYL)ETHYL METHYL ESTER, (S)-
Systematic Name English
Code System Code Type Description
EPA CompTox
126451-47-6
Created by admin on Sat Jun 26 16:19:36 UTC 2021 , Edited by admin on Sat Jun 26 16:19:36 UTC 2021
PRIMARY
FDA UNII
M40WCZ5X76
Created by admin on Sat Jun 26 16:19:36 UTC 2021 , Edited by admin on Sat Jun 26 16:19:36 UTC 2021
PRIMARY
CAS
126451-47-6
Created by admin on Sat Jun 26 16:19:36 UTC 2021 , Edited by admin on Sat Jun 26 16:19:36 UTC 2021
PRIMARY
PUBCHEM
13632718
Created by admin on Sat Jun 26 16:19:36 UTC 2021 , Edited by admin on Sat Jun 26 16:19:36 UTC 2021
PRIMARY
Related Record Type Details
RACEMATE -> ENANTIOMER