Details of the Drug

General Information of Drug (ID: DMJSDBE)

Drug Name
Barnidipine
Synonyms
Barnidipine [INN]; Barnidipine HCl; Barnidipino; Barnidipino [INN-Spanish]; Barnidipinum; Barnidipinum [INN-Latin]; Libradin; Mepirodipine; VXMOONUMYLCFJD-DHLKQENFSA-N; Vasexten (TN); YM 09730; barnidipine; (S)-3-((S)-1-Benzylpyrrolidin-3-yl) 5-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate; 104713-75-9; 2VBY96ASWJ; AC1L9FD3; BCP07244; C27H29N3O6; CHEBI:135793; CHEMBL2103761; CHEMBL2110040; CTK8B6661; SCHEMBL49302; UNII-2VBY96ASWJ
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 491.5
Logarithm of the Partition Coefficient (xlogp) 4.2
Rotatable Bond Count (rotbonds) 8
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 8
ADMET Property
Absorption AUC
The area under the plot of plasma concentration (AUC) of drug is 2.85 mgh/L [1]
Absorption Cmax
The maximum plasma concentration (Cmax) of drug is 0.48 mcg/L [1]
Elimination
Barnidipine and its metabolites are metabolized into feces (60%), urine (40%) and breath (1%) [2]
Half-life
The concentration or amount of drug in body reduced by one-half in 20 hours [2]
Metabolism
The drug is metabolized via the hepatic [3]
Chemical Identifiers
Formula
C27H29N3O6
IUPAC Name
5-O-[(3S)-1-benzylpyrrolidin-3-yl] 3-O-methyl (4S)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
Canonical SMILES
CC1=C(C(C(=C(N1)C)C(=O)OC2CCN(C2)CC3=CC=CC=C3)C4=CC(=CC=C4)[N+](=O)[O-])C(=O)OC
InChI
VXMOONUMYLCFJD-DHLKQENFSA-N
InChIKey
1S/C27H29N3O6/c1-17-23(26(31)35-3)25(20-10-7-11-21(14-20)30(33)34)24(18(2)28-17)27(32)36-22-12-13-29(16-22)15-19-8-5-4-6-9-19/h4-11,14,22,25,28H,12-13,15-16H2,1-3H3/t22-,25-/m0/s1
Cross-matching ID
PubChem CID
443869
ChEBI ID
CHEBI:135793
CAS Number
104713-75-9
DrugBank ID
DB09227
INTEDE ID
DR0175

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 [4]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Cytochrome P450 2B6 (CYP2B6) OTOYO4S7 CP2B6_HUMAN Gene/Protein Processing [5]
Cytochrome P450 2C19 (CYP2C19) OTFMJYYE CP2CJ_HUMAN Gene/Protein Processing [5]
Cytochrome P450 2C9 (CYP2C9) OTGLBN29 CP2C9_HUMAN Gene/Protein Processing [5]
Cytochrome P450 2D6 (CYP2D6) OTZJC802 CP2D6_HUMAN Gene/Protein Processing [5]
Cytochrome P450 2J2 (CYP2J2) OTJBTEH8 CP2J2_HUMAN Gene/Protein Processing [6]
Cytochrome P450 3A4 (CYP3A4) OTQGYY83 CP3A4_HUMAN Gene/Protein Processing [5]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 Malhotra HS, Plosker GL: Barnidipine. Drugs. 2001;61(7):989-96; discussion 997-8.
2 Vasexten (barnidipine hydrochloride modified release capsules) Summary of Product Characteristics
3 Chan NC, Bhagirath V, Eikelboom JW: Profile of betrixaban and its potential in the prevention and treatment of venous thromboembolism. Vasc Health Risk Manag. 2015 Jun 26;11:343-51. doi: 10.2147/VHRM.S63060. eCollection 2015.
4 Examination of metabolic pathways and identification of human liver cytochrome P450 isozymes responsible for the metabolism of barnidipine, a calcium channel blocker. Xenobiotica. 1997 Sep;27(9):885-900.
5 Inhibition of human cytochrome P450 enzymes by 1,4-dihydropyridine calcium antagonists: prediction of in vivo drug-drug interactions. Eur J Clin Pharmacol. 2000 Feb-Mar;55(11-12):843-52.
6 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.