Details of the Drug

General Information of Drug (ID: DMPBV9D)

Drug Name
Flupirtine
Synonyms
Flupirtine; 56995-20-1; Flupirtine [INN:BAN]; Flupirtinum [INN-Latin]; Flupirtino [INN-Spanish]; UNII-MOH3ET196H; C15H17FN4O2; EINECS 260-503-8; MOH3ET196H; JUUFBMODXQKSTD-UHFFFAOYSA-N; ethyl N-[2-amino-6-[(4-fluorophenyl)methylamino]pyridin-3-yl]carbamate; D 9998; flupirtin maleate; ethyl 2-amino-6-(4-fluorobenzylamino)pyridin-3-ylcarbamate; Flupirtinum; Flupirtino; MLS002153180; Carbamic acid, (2-amino-6-(((4-fluorophenyl)methyl)amino)-3-pyridinyl)-, ethyl ester; NCGC00015451-03; SMR001230672; Flupirtin; Carbamic acid, [2-ami
Indication
Disease Entry ICD 11 Status REF
Cancer related pain MG30 Phase 2 [1]
Fibromyalgia MG30.01 Phase 2 [1]
Affected Organisms
Humans and other mammals
ATC Code
N02BG07: Flupirtine
N02BG: Other analgesics and antipyretics
N02B: OTHER ANALGESICS AND ANTIPYRETICS
N02: ANALGESICS
N: NERVOUS SYSTEM
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 304.32
Logarithm of the Partition Coefficient (xlogp) 2.4
Rotatable Bond Count (rotbonds) 6
Hydrogen Bond Donor Count (hbonddonor) 3
Hydrogen Bond Acceptor Count (hbondacc) 6
ADMET Property
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 1: high solubility and high permeability [2]
Bioavailability
The bioavailability of drug is 90% []
Clearance
The drug present in the plasma can be removed from the body at the rate of 1.6 mL/min/kg [3]
Half-life
The concentration or amount of drug in body reduced by one-half in 6.5 hours [3]
Metabolism
The drug is metabolized via the hepatic []
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 28.1649 micromolar/kg/day [4]
Unbound Fraction
The unbound fraction of drug in plasma is 0.15% [3]
Vd
Fluid volume that would be required to contain the amount of drug present in the body at the same concentration as in the plasma 1.1 L/kg [3]
Chemical Identifiers
Formula
C15H17FN4O2
IUPAC Name
ethyl N-[2-amino-6-[(4-fluorophenyl)methylamino]pyridin-3-yl]carbamate
Canonical SMILES
CCOC(=O)NC1=C(N=C(C=C1)NCC2=CC=C(C=C2)F)N
InChI
InChI=1S/C15H17FN4O2/c1-2-22-15(21)19-12-7-8-13(20-14(12)17)18-9-10-3-5-11(16)6-4-10/h3-8H,2,9H2,1H3,(H,19,21)(H3,17,18,20)
InChIKey
JUUFBMODXQKSTD-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
53276
ChEBI ID
CHEMBL94646
CAS Number
56995-20-1
UNII
MOH3ET196H
DrugBank ID
DB06623
TTD ID
D0SD9V
Drug-Molecule Activity Atlas (DMA)NEW Click to Jump to the Detailed DMA Information of This Drug
Drug Pharmacogenomic Perturbation (DPP)NEW Click to Jump to the Detailed DPP Information of This Drug
Drug ADMET Endpoint Profile (DAE)NEW Click to Jump to the Detailed DAE Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Voltage-gated potassium channel Kv7 (KCNQ) TTQ29KF NOUNIPROTAC Modulator [5]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Bile salt export pump (ABCB11) OTRU7THO ABCBB_HUMAN Gene/Protein Processing [6]
Cytotoxic granule associated RNA binding protein TIA1 (TIA1) OTGPN3P8 TIA1_HUMAN Gene/Protein Processing [7]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Cancer related pain
ICD Disease Classification MG30
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Voltage-gated potassium channel Kv7 (KCNQ) DTT NO-GeName 6.24E-01 0.11 0.85
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 2598).
2 BDDCS predictions, self-correcting aspects of BDDCS assignments, BDDCS assignment corrections, and classification for more than 175 additional drugs
3 Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
4 Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
5 Treatment with the Kv7 potassium channel activator flupirtine is beneficial in two independent mouse models of pulmonary hypertension. Br J Pharmacol. 2009 August; 157(7): 1241-1249.
6 Interference with bile salt export pump function is a susceptibility factor for human liver injury in drug development. Toxicol Sci. 2010 Dec; 118(2):485-500.
7 Melatonin counteracts ischemia-induced apoptosis in human retinal pigment epithelial cells. Invest Ophthalmol Vis Sci. 1998 Nov;39(12):2374-83.