Details of the Drug

General Information of Drug (ID: DMQ8R4E)

Drug Name
NAFTOPIDIL
Synonyms
naftopidil; 57149-07-2; Flivas; KT-611; Naftopidil [INN]; Avishot; Naftopidilum [Latin]; Naftopidil (Flivas); BM-15275; Naftopidil (unspecified); BRN 0629965; CHEMBL142635; C24H28N2O3; 1-(4-(2-methoxyphenyl)piperazin-1-yl)-3-(naphthalen-1-yloxy)propan-2-ol; NCGC00015718-06; (+-)-1-(4-(2-Methoxyphenyl)piperazinyl)-3-(1-naphthyloxy)propan-2-ol; 4-(2-Methoxyphenyl)-alpha-((1-naphthalenyloxy)methyl)-1-pioerazineethanol; (RS)-1-(4-(2-methoxyphenyl)-1-piperazinyl)-3-(1-naphthyloxy)-2-propanol; DSSTox_RID_80725; DSSTox_CID_25176
Indication
Disease Entry ICD 11 Status REF
Hypertension BA00-BA04 Approved [1]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 392.5
Logarithm of the Partition Coefficient (xlogp) 4.1
Rotatable Bond Count (rotbonds) 7
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 5
ADMET Property
Clearance
The drug present in the plasma can be removed from the body at the rate of 11 mL/min/kg [2]
Half-life
The concentration or amount of drug in body reduced by one-half in 3.3 hours [2]
Unbound Fraction
The unbound fraction of drug in plasma is 0.008% [2]
Chemical Identifiers
Formula
C24H28N2O3
IUPAC Name
1-[4-(2-methoxyphenyl)piperazin-1-yl]-3-naphthalen-1-yloxypropan-2-ol
Canonical SMILES
COC1=CC=CC=C1N2CCN(CC2)CC(COC3=CC=CC4=CC=CC=C43)O
InChI
InChI=1S/C24H28N2O3/c1-28-24-11-5-4-10-22(24)26-15-13-25(14-16-26)17-20(27)18-29-23-12-6-8-19-7-2-3-9-21(19)23/h2-12,20,27H,13-18H2,1H3
InChIKey
HRRBJVNMSRJFHQ-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
4418
ChEBI ID
CHEMBL31891
CAS Number
57149-07-2
UNII
R9PHW59SFN
DrugBank ID
DB12092
TTD ID
D04DKH
INTEDE ID
DR1124
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Drug ADMET Endpoint Profile (DAE)NEW Click to Jump to the Detailed DAE Information of This Drug
Combinatorial Drugs (CBD) Click to Jump to the Detailed CBD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Adrenergic receptor alpha-1A (ADRA1A) TTNGILX ADA1A_HUMAN Inhibitor [3]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 2C9 (CYP2C9) DE5IED8 CP2C9_HUMAN Substrate [4]
Mephenytoin 4-hydroxylase (CYP2C19) DEGTFWK CP2CJ_HUMAN Substrate [4]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Microtubule-associated proteins 1A/1B light chain 3B (MAP1LC3B) OTUYHB84 MLP3B_HUMAN Gene/Protein Processing [5]
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Molecular Expression Atlas of This Drug

The Studied Disease Hypertension
ICD Disease Classification BA00-BA04
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Adrenergic receptor alpha-1A (ADRA1A) DTT ADRA1A 9.43E-01 -0.03 -0.25
Mephenytoin 4-hydroxylase (CYP2C19) DME CYP2C19 7.66E-01 9.19E-03 4.88E-02
Cytochrome P450 2C9 (CYP2C9) DME CYP2C9 7.83E-01 2.32E-03 1.53E-02
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
2 Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
3 Pharmacophore identification of alpha(1A)-adrenoceptor antagonists. Bioorg Med Chem Lett. 2005 Feb 1;15(3):657-64.
4 Identification of human cytochrome P450 isozymes involved in the metabolism of naftopidil enantiomers in vitro. J Pharm Pharmacol. 2014 Nov;66(11):1534-51.
5 Autophagy Induced by Naftopidil Inhibits Apoptosis of Human Gastric Cancer Cells. Anticancer Res. 2018 Feb;38(2):803-809. doi: 10.21873/anticanres.12287.