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Details

Stereochemistry RACEMIC
Molecular Formula C35H38N4O6
Molecular Weight 610.7007
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MANIDIPINE

SMILES

CC1=C(C(c2cccc(c2)N(=O)=O)C(=C(C)N1)C(=O)OCCN3CCN(CC3)C(c4ccccc4)c5ccccc5)C(=O)OC

InChI

InChIKey=ANEBWFXPVPTEET-UHFFFAOYSA-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

HIDE SMILES / InChI

Molecular Formula C35H38N4O6
Molecular Weight 610.7007
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description
Curator's Comment:: description was created based on several sources, including

Manidipine is 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. In addition, manidipine does not significantly affect norepinephrine levels, suggesting a lack of sympathetic activation. It has a gradual onset of action and a long duration of action enabling once daily administration. Furthermore, manidipine dilates both the efferent and the afferent renal arterioles and appears to have beneficial renal effects unrelated to its antihypertensive effect. Once-daily oral manidipine is an effective and generally well tolerated antihypertensive agent for younger and elderly adult patients with mild-to-moderate hypertension. In particular, in a large double-blind trial, the incidence of ankle oedema was significantly lower in manidipine than in amlodipine recipients. Manidipine is also effective in hypertensive patients with comorbidities, such as type 2 diabetes mellitus and/or renal impairment, and appears to improve insulin sensitivity without affecting metabolic function. Thus, manidipinerepresents a first-line treatment option for patients with essential mild-to-moderate hypertension.

CNS Activity

Curator's Comment:: antihypertensive drug with blocking action on renal nerve activity is capable of maintaining renal blood flow and that those associated with reflex-induced enhancement of nerve activity exert deteriorating effects on renal blood flow.

Originator

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
400.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Catalepsy induced by manidipine, a calcium channel blocker, in mice.
1996 Apr
Role of angiotensin II in reflex tachycardia during hypotension caused by a calcium channel blocker.
1996 Jul
Regional vascular effects of MPC-1304, a novel dihydropyridine derivative, in conscious normotensive and spontaneously hypertensive rats.
1996 Jun
Effect of manidipine hydrochloride, a calcium antagonist, on isoproterenol-induced left ventricular hypertrophy.
1998 Jan
Catalepsy induced by calcium channel blockers in mice.
1998 Mar
Inhibition of human cytochrome P450 enzymes by 1,4-dihydropyridine calcium antagonists: prediction of in vivo drug-drug interactions.
2000 Feb-Mar
Antihypertensive efficacy of manidipine and enalapril in hypertensive diabetic patients.
2000 Jun
Interaction of digoxin with antihypertensive drugs via MDR1.
2002 Feb 15
Effect of manidipine on gene expression and protein level of oxidative stress-related proteins: p22phox and HO-1: relevance for antihypertensive and anti-remodeling effects.
2004 Apr
Calcium channel blockades exhibit anti-inflammatory and antioxidative effects by augmentation of endothelial nitric oxide synthase and the inhibition of angiotensin converting enzyme in the N(G)-nitro-L-arginine methyl ester-induced hypertensive rat aorta: vasoprotective effects beyond the blood pressure-lowering effects of amlodipine and manidipine.
2005 Aug
Effect of successful hypertension control by manidipine or lisinopril on albuminuria and left ventricular mass in diabetic hypertensive patients with microalbuminuria.
2005 Aug
Manidipine versus enalapril monotherapy in patients with hypertension and type 2 diabetes mellitus: a multicenter, randomized, double-blind, 24-week study.
2005 Feb
Patents

Patents

Sample Use Guides

Manidipine 10 to 40 mg once daily for 4 weeks
Route of Administration: Oral
In Vitro Use Guide
Manidipine, at nanomolar concentrations, is efficacious in modulating gene transcriptions that are involved in proinflammatory changes of mesangial cells. Thus, manidipine, at pharmacological concentrations that are one to two orders of magnitude lower than those required for inhibition of agonist- or depolarization (K+)-induced vasoconstriction, causes changes in the activity of the genes that code for inflammatory mediators.
Substance Class Chemical
Created
by admin
on Sat Jun 26 16:19:33 UTC 2021
Edited
by admin
on Sat Jun 26 16:19:33 UTC 2021
Record UNII
6O4754US88
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
MANIDIPINE
INN   MI   WHO-DD  
INN  
Official Name English
FRANIDIPINE
Common Name English
(+/-)-MANIDIPINE
Common Name English
MANIDIPINE [MI]
Common Name English
MANIDIPINE [WHO-DD]
Common Name English
2-(4-(DIPHENYLMETHYL)-1-PIPERAZINYL)ETHYL METHYL (+/-)-1,4-DIHYDRO-2,6-DIMETHYL-4-(M-NITROPHENYL)-3,5-PYRIDINECARBOXYLATE
Common Name English
3,5-PYRIDINEDICARBOXYLIC ACID, 1,4-DIHYDRO-2,6-DIMETHYL-4-(3-NITROPHENYL)-, 3-(2-(4-(DIPHENYLMETHYL)-1-PIPERAZINYL)ETHYL) 5-METHYL ESTER
Common Name English
MANIDIPINE 6300
Common Name English
ARTEDIL
Brand Name English
MANIDIPINE [INN]
Common Name English
Classification Tree Code System Code
WHO-VATC QC08CA11
Created by admin on Sat Jun 26 16:19:33 UTC 2021 , Edited by admin on Sat Jun 26 16:19:33 UTC 2021
WHO-ATC C09BB12
Created by admin on Sat Jun 26 16:19:33 UTC 2021 , Edited by admin on Sat Jun 26 16:19:33 UTC 2021
WHO-VATC QC09BB12
Created by admin on Sat Jun 26 16:19:33 UTC 2021 , Edited by admin on Sat Jun 26 16:19:33 UTC 2021
NCI_THESAURUS C333
Created by admin on Sat Jun 26 16:19:33 UTC 2021 , Edited by admin on Sat Jun 26 16:19:33 UTC 2021
WHO-ATC C08CA11
Created by admin on Sat Jun 26 16:19:33 UTC 2021 , Edited by admin on Sat Jun 26 16:19:33 UTC 2021
Code System Code Type Description
FDA UNII
6O4754US88
Created by admin on Sat Jun 26 16:19:33 UTC 2021 , Edited by admin on Sat Jun 26 16:19:33 UTC 2021
PRIMARY
INN
6300
Created by admin on Sat Jun 26 16:19:33 UTC 2021 , Edited by admin on Sat Jun 26 16:19:33 UTC 2021
PRIMARY
MESH
C054218
Created by admin on Sat Jun 26 16:19:33 UTC 2021 , Edited by admin on Sat Jun 26 16:19:33 UTC 2021
PRIMARY
RXCUI
29275
Created by admin on Sat Jun 26 16:19:33 UTC 2021 , Edited by admin on Sat Jun 26 16:19:33 UTC 2021
PRIMARY RxNorm
DRUG CENTRAL
1631
Created by admin on Sat Jun 26 16:19:33 UTC 2021 , Edited by admin on Sat Jun 26 16:19:33 UTC 2021
PRIMARY
MERCK INDEX
M7078
Created by admin on Sat Jun 26 16:19:33 UTC 2021 , Edited by admin on Sat Jun 26 16:19:33 UTC 2021
PRIMARY Merck Index
NCI_THESAURUS
C81682
Created by admin on Sat Jun 26 16:19:33 UTC 2021 , Edited by admin on Sat Jun 26 16:19:33 UTC 2021
PRIMARY
CAS
89226-50-6
Created by admin on Sat Jun 26 16:19:33 UTC 2021 , Edited by admin on Sat Jun 26 16:19:33 UTC 2021
PRIMARY
WIKIPEDIA
Manidipine
Created by admin on Sat Jun 26 16:19:33 UTC 2021 , Edited by admin on Sat Jun 26 16:19:33 UTC 2021
PRIMARY
EVMPD
SUB08641MIG
Created by admin on Sat Jun 26 16:19:33 UTC 2021 , Edited by admin on Sat Jun 26 16:19:33 UTC 2021
PRIMARY
EPA CompTox
89226-50-6
Created by admin on Sat Jun 26 16:19:33 UTC 2021 , Edited by admin on Sat Jun 26 16:19:33 UTC 2021
PRIMARY
PUBCHEM
4008
Created by admin on Sat Jun 26 16:19:33 UTC 2021 , Edited by admin on Sat Jun 26 16:19:33 UTC 2021
PRIMARY
ChEMBL
CHEMBL1085699
Created by admin on Sat Jun 26 16:19:33 UTC 2021 , Edited by admin on Sat Jun 26 16:19:33 UTC 2021
PRIMARY
DRUG BANK
DB09238
Created by admin on Sat Jun 26 16:19:33 UTC 2021 , Edited by admin on Sat Jun 26 16:19:33 UTC 2021
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR
ENANTIOMER -> RACEMATE
ENANTIOMER -> RACEMATE
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY