Details of the Drug

General Information of Drug (ID: DMA12HL)

Drug Name
Azelnidipine
Synonyms
Azelnidipine; Azelnidipine [INN]; Calblock; RS-9054; 123524-52-7; 3,5-PYRIDINEDICARBOXYLIC ACID, 2-AMINO-1,4-DIHYDRO-6-METHYL-4-(3-NITROPHENYL)-, 3-[1-(DIPHENYLMETHYL)-3-AZETIDINYL] 5-(1-METHYLETHYL) ESTER; 3-(1-Benzhydrylazetidin-3-yl) 5-isopropyl 2-amino-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate; C33H34N4O6; CS 905; CS-905; DSSTox_CID_120; DSSTox_GSID_20120; DSSTox_RID_75382; MFCD00865803; NCGC00167436-01; NCGC00167436-02
Indication
Disease Entry ICD 11 Status REF
Hypertension BA00-BA04 Approved [1]
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 2 Molecular Weight (mw) 582.6
Logarithm of the Partition Coefficient (xlogp) 6
Rotatable Bond Count (rotbonds) 10
Hydrogen Bond Donor Count (hbonddonor) 2
Hydrogen Bond Acceptor Count (hbondacc) 9
ADMET Property
Elimination
In one study, following a single 4mg oral dose of 14C-labeled azelnidipine in humans, about 26% of the drug was thought to br excreted in the urine and 63% in the feces during the 1 week period post administration [2]
Half-life
The concentration or amount of drug in body reduced by one-half in 16 C 28 hours [3]
Metabolism
The drug is metabolized via the hepatic [4]
Vd
The volume of distribution (Vd) of drug is 1749 L [3]
Chemical Identifiers
Formula
C33H34N4O6
IUPAC Name
3-O-(1-benzhydrylazetidin-3-yl) 5-O-propan-2-yl 2-amino-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
Canonical SMILES
CC1=C(C(C(=C(N1)N)C(=O)OC2CN(C2)C(C3=CC=CC=C3)C4=CC=CC=C4)C5=CC(=CC=C5)[N+](=O)[O-])C(=O)OC(C)C
InChI
ZKFQEACEUNWPMT-UHFFFAOYSA-N
InChIKey
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
Cross-matching ID
PubChem CID
65948
ChEBI ID
CHEBI:31247
CAS Number
123524-52-7
DrugBank ID
DB09230
INTEDE ID
DR0166
Combinatorial Drugs (CBD) Click to Jump to the Detailed CBD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 3A4 (CYP3A4)
Main DME 		DE4LYSA CP3A4_HUMAN Substrate [5]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Androgen receptor (AR) OTUBKAZZ ANDR_HUMAN Gene/Protein Processing [6]
Cytochrome P450 2J2 (CYP2J2) OTJBTEH8 CP2J2_HUMAN Gene/Protein Processing [7]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
2 Nada T, Nomura M, Koshiba K, Kawano T, Mikawa J, Ito S: Clinical study with azelnidipine in patients with essential hypertension. Antiarteriosclerotic and cardiac hypertrophy-inhibitory effects and influence on autonomic nervous activity. Arzneimittelforschung. 2007;57(11):698-704. doi: 10.1055/s-0031-1296670.
3 Determination of azelnidipine by LCCESI-MS and its application to a pharmacokinetic study in healthy Chinese volunteers
4 Clinical use of azelnidipine in the treatment of hypertension in Chinese patients
5 KEGG: new perspectives on genomes, pathways, diseases and drugs. Nucleic Acids Res. 2017 Jan 4;45(D1):D353-D361. (DRUG:D01145)
6 Quantitative high-throughput profiling of environmental chemicals and drugs that modulate farnesoid X receptor. Sci Rep. 2014 Sep 26;4:6437. doi: 10.1038/srep06437.
7 Inhibitory effects of antihypertensive drugs on human cytochrome P450 2J2 activity: Potent inhibition by azelnidipine and manidipine. Chem Biol Interact. 2019 Jun 1;306:1-9.