U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry RACEMIC
Molecular Formula C28H30FN3OS.C4H4O4
Molecular Weight 591.693
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of MONATEPIL MALEATE

SMILES

OC(=O)\C=C/C(O)=O.FC1=CC=C(C=C1)N2CCN(CCCC(=O)NC3C4=C(CSC5=C3C=CC=C5)C=CC=C4)CC2

InChI

InChIKey=ZDZXCYHMVFLGMT-BTJKTKAUSA-N
InChI=1S/C28H30FN3OS.C4H4O4/c29-22-11-13-23(14-12-22)32-18-16-31(17-19-32)15-5-10-27(33)30-28-24-7-2-1-6-21(24)20-34-26-9-4-3-8-25(26)28;5-3(6)1-2-4(7)8/h1-4,6-9,11-14,28H,5,10,15-20H2,(H,30,33);1-2H,(H,5,6)(H,7,8)/b;2-1-

HIDE SMILES / InChI

Molecular Formula C4H4O4
Molecular Weight 116.0722
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Molecular Formula C28H30FN3OS
Molecular Weight 475.621
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description

Monatepil is a calcium antagonist that, as do existing calcium antagonists, inhibits the influx of extracellular Ca 2 + through voltage-dependent Ca 2 + channels. It is a new type of antihypertensive agent. Its unique chemical structure was specially designed with intrinsic calcium antagonist and a1 -adrenoceptor-blocking moieties, creating a dual mechanism of action. Positive effects on plasma lipid metabolism are derived from the a1 -adrenoceptor-blocking activity and the antiatherosclerotic effect derives from the calcium antagonist properties. The novel structure of monatepil produces a slow onset of action and a long-lasting antihypertensive effect in experimental animals.

Approval Year

PubMed

PubMed

TitleDatePubMed
Inhibition of vasoconstriction by AJ-2615, a novel calcium antagonist with alpha(1)-adrenergic receptor blocking activity in human conduit arteries used as bypass grafts.
2001 Sep
Patents

Sample Use Guides

In Vivo Use Guide
Treatment of essential hypertension: The initial dose of monatepil was 30 mg/day in monotherapy and 15 mg/day in combination therapy; the daily dose was titrated to 60 mg/day according to the antihypertensive response.
Route of Administration: Oral
In Vitro Use Guide
Treatment of human skin fibroblasts with 2 x 10(-5) M of monatepil for 6 hours resulted in an increase in LDL receptor mRNA to 163% of the control level
Substance Class Chemical
Created
by admin
on Tue Oct 22 06:17:52 UTC 2019
Edited
by admin
on Tue Oct 22 06:17:52 UTC 2019
Record UNII
W456I35SKD
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
MONATEPIL MALEATE
JAN   USAN  
USAN  
Official Name English
MONATEPIL MALEATE[MI]
Common Name English
MONATEPIL MALEATE [USAN]
Common Name English
(+/-)-N-(6,11-DIHYDRODIBENZO(B,E)THIEPIN-11-YL)-4-(P-FLUOROPHENYL)-1-PIPERAZINEBUTYRAMIDE MALEATE (1:1)
Common Name English
1-PIPERAZINEBUTANAMIDE, N-(6,11-DIHYDRODIBENZO(B,E)THIEPIN-11-YL)-4-(4-FLUOROPHENYL)-, (+/-)-, (Z)-2-BUTENEDIOATE (1:1)
Systematic Name English
AJ-2615
Code English
MONATEPIL MALEATE [JAN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C333
Created by admin on Tue Oct 22 06:17:53 UTC 2019 , Edited by admin on Tue Oct 22 06:17:53 UTC 2019
Code System Code Type Description
CAS
132046-06-1
Created by admin on Tue Oct 22 06:17:53 UTC 2019 , Edited by admin on Tue Oct 22 06:17:53 UTC 2019
SUPERCEDED
NCI_THESAURUS
C81688
Created by admin on Tue Oct 22 06:17:53 UTC 2019 , Edited by admin on Tue Oct 22 06:17:53 UTC 2019
PRIMARY
CAS
103379-03-9
Created by admin on Tue Oct 22 06:17:53 UTC 2019 , Edited by admin on Tue Oct 22 06:17:53 UTC 2019
PRIMARY
CAS
185537-12-6
Created by admin on Tue Oct 22 06:17:53 UTC 2019 , Edited by admin on Tue Oct 22 06:17:53 UTC 2019
SUPERCEDED
MERCK INDEX
M832
Created by admin on Tue Oct 22 06:17:53 UTC 2019 , Edited by admin on Tue Oct 22 06:17:53 UTC 2019
PRIMARY
ChEMBL
CHEMBL172853
Created by admin on Tue Oct 22 06:17:53 UTC 2019 , Edited by admin on Tue Oct 22 06:17:53 UTC 2019
PRIMARY
PUBCHEM
5282401
Created by admin on Tue Oct 22 06:17:53 UTC 2019 , Edited by admin on Tue Oct 22 06:17:53 UTC 2019
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY