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

Details

Stereochemistry ABSOLUTE
Molecular Formula C33H34N4O6
Molecular Weight 582.6475
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

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

SMILES

CC(C)OC(=O)C1=C(C)NC(=C([C@@]1([H])c2cccc(c2)N(=O)=O)C(=O)OC3CN(C3)C(c4ccccc4)c5ccccc5)N

InChI

InChIKey=ZKFQEACEUNWPMT-NDEPHWFRSA-N
InChI=1S/C33H34N4O6/c1-20(2)42-32(38)27-21(3)35-31(34)29(28(27)24-15-10-16-25(17-24)37(40)41)33(39)43-26-18-36(19-26)30(22-11-6-4-7-12-22)23-13-8-5-9-14-23/h4-17,20,26,28,30,35H,18-19,34H2,1-3H3/t28-/m0/s1

HIDE SMILES / InChI

Molecular Formula C33H34N4O6
Molecular Weight 582.6475
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Azelnidipine is a dihydropyridine calcium channel antagonist being jointly developed by Daiichi Sankyo Inc (formerly Sankyo) and Ube Industries. Azelnidipine is a L-type calcium channel antagonist. Azelnidipine was approved by Pharmaceuticals and Medicals Devices Agency of Japan (PMDA) on Jan 31, 2003. Azelnidipine is indicated for the treatment of hypertension. Its trend name is Calblock. Azelnidipine has two enantiomers (R-(−)- and S-(+)-enantiomers) due to an asymmetric carbon at the 4-position, and the (R)-(−) enantiomer of dihydropyridine calcium antagonists is considered to possess intrinsic pharmacological activity. The pharmacological action of azelnidipine resides in the (R)-enantiomer. This is in marked contrast to other calcium channel blocker (CCB) in which the (S)-enantiomer is responsible for the biological activity. There were no significant differences in the inhibitory effects on TGF-b1-induced expression of COL1A1 mRNA among vitamin E - pretreated LX-2 cells treated with azelnidipine (racemate), (R)-(-)-azelnidipine or (S)-(+)-azelnidipine, although the L-type voltage-operated calcium channel blocking activity of (R)-(-)- enantiomer was more potent than that of the (S)-(+)- enantiomer.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Calblock

Approved Use

As a calcium channel antagonist, this medicine relaxes blood vessels in order to lower blood pressure. It is usually used to treat hypertension.

Launch Date

1.04397118E12
PubMed

PubMed

TitleDatePubMed
Azelnidipine is a calcium blocker that attenuates liver fibrosis and may increase antioxidant defence.
2012 Feb
Patents

Patents

Sample Use Guides

The normal dose for an adult is 8-16 mg of azelnidipine once daily, taken orally after breakfast. The maximum dosage is 16 mg/day. The initial dosage is to be 8 mg/day or less, to be adjusted as symptoms are monitored, up to 16 mg daily.
Route of Administration: Oral
Treatment with 10 ng·mL-1 TGF-b1 or 50 uM Ang II increased [Ca]i, and all calcium blockers at 100 nM, with the exception of (S)-(+)-azelnidipine, significantly reduced the TGF-b1- induced increase in [Ca]i.
Substance Class Chemical
Created
by admin
on Fri Jun 25 22:46:47 UTC 2021
Edited
by admin
on Fri Jun 25 22:46:47 UTC 2021
Record UNII
368RN01P1M
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
AZELNIDIPINE, (S)-
Common Name English
(S)-(+)-AZELNIDIPINE
Common Name English
(S)-AZELNIDIPINE
Common Name English
3,5-PYRIDINEDICARBOXYLIC ACID, 2-AMINO-1,4-DIHYDRO-6-METHYL-4-(3-NITROPHENYL)-, 3-(1-(DIPHENYLMETHYL)-3-AZETIDINYL) 5-(1-METHYLETHYL) ESTER, (4S)-
Systematic Name English
Code System Code Type Description
CAS
722455-09-6
Created by admin on Fri Jun 25 22:46:47 UTC 2021 , Edited by admin on Fri Jun 25 22:46:47 UTC 2021
PRIMARY
PUBCHEM
45107611
Created by admin on Fri Jun 25 22:46:47 UTC 2021 , Edited by admin on Fri Jun 25 22:46:47 UTC 2021
PRIMARY
FDA UNII
368RN01P1M
Created by admin on Fri Jun 25 22:46:47 UTC 2021 , Edited by admin on Fri Jun 25 22:46:47 UTC 2021
PRIMARY
Related Record Type Details
RACEMATE -> ENANTIOMER