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]
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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)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

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: CHEBI:94646
CAS Number: 56995-20-1
DrugBank ID: DB06623
TTD ID: D0SD9V

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]

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Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
Apoptosis regulator Bcl-2 (BCL2)	OT9DVHC0	BCL2_HUMAN	Gene/Protein Processing	[6]
Bile salt export pump (ABCB11)	OTRU7THO	ABCBB_HUMAN	Gene/Protein Processing	[7]
Caspase-2 (CASP2)	OTUDYSPP	CASP2_HUMAN	Gene/Protein Processing	[6]
Cytotoxic granule associated RNA binding protein TIA1 (TIA1)	OTGPN3P8	TIA1_HUMAN	Gene/Protein Processing	[6]

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Molecular Interaction Atlas (MIA)

MIA Detail

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)

MEA Detail

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	Melatonin counteracts ischemia-induced apoptosis in human retinal pigment epithelial cells. Invest Ophthalmol Vis Sci. 1998 Nov;39(12):2374-83.
7	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.