NAV

Flupirtine

Identification

Generic Name
Flupirtine
DrugBank Accession Number
DB06623
Background

Flupirtine is a pyridine derivative that is in clinical use as a nonopioid analgesic. It was approved for the treatment of pain in 1984 in Europe. It is not approved for use in the U.S. or Canada, but is currently in phase II trials for the treatment of fibromyalgia.

Type
Small Molecule
Groups
Investigational
Structure
3D
Similar Structures
Weight
Average: 304.3195
Monoisotopic: 304.133554013
Chemical Formula
C15H17FN4O2
Synonyms
  • Flupirtine
  • Flupirtino
  • Flupirtinum
Poor quality drug data slowing you down?
Unlock 38% more drug discovery time and eliminate decision-making doubts with this one-stop guide to quality drug data.
Download eBook
Poor quality drug data slowing you down?
Download eBook

Pharmacology

Indication

Investigated for use/treatment in fibromyalgia.

Reduce drug development failure rates
Build, train, & validate machine-learning models
with evidence-based and structured datasets.
See how
Build, train, & validate predictive machine-learning models with structured datasets.
See how
Contraindications & Blackbox Warnings
Prevent Adverse Drug Events Today
Tap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.
Learn more
Avoid life-threatening adverse drug events with our Clinical API
Learn more
Pharmacodynamics

Not Available

Mechanism of action

Flupirtine upregulates Bcl-2, increases glutathione levels, activates an inwardly rectifying potassium channel, and delays loss of intermitochondrial membrane calcium retention capacity. Flupirtine acts like a NMDA receptor antagonists, but does not bind to the receptor. One study concluded that the discriminative effects of flupirtine are neither of opioid nor of alpha-1 adrenergic type, but are primarily mediated through alpha-2 adrenergic mechanisms [PMID: 2901483].

TargetActionsOrganism
UAlpha-2A adrenergic receptorNot AvailableHumans
Absorption

Bioavailability: 90% (oral), 70% (rectal)

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism

Hepatic to 2-amino-3-acetylamino-6-(para-fluorobenzylamino) pyridine (which has 20-30% the analgesic potential of its parent compound) and Para-fluorohippuric acid.

Route of elimination

72% of flupirtine and its metabolites appear in urine and 18% appear in faeces.

Half-life

6.5 hrs (average), 11.2-16.8 hrs (average 14 hrs) (elderly), 8.7-10.9 hrs (average 9.8 hrs) (in those with moderate-level renal impairment).

Clearance

Not Available

Adverse Effects
Improve decision support & research outcomes
With structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!
See the data
Improve decision support & research outcomes with our structured adverse effects data.
See a data sample
Toxicity

Oral, mouse: LD50 = 300 mg/kg; Oral, rabbit: LD50 = 3200 mg/kg; Oral, rat: LD50 = 980 mg/kg.

Pathways
Not Available
Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
Integrate drug-drug
interactions in your software
AbacavirAbacavir may decrease the excretion rate of Flupirtine which could result in a higher serum level.
AceclofenacAceclofenac may decrease the excretion rate of Flupirtine which could result in a higher serum level.
AcemetacinAcemetacin may decrease the excretion rate of Flupirtine which could result in a higher serum level.
AcetaminophenAcetaminophen may decrease the excretion rate of Flupirtine which could result in a higher serum level.
AcetazolamideAcetazolamide may increase the excretion rate of Flupirtine which could result in a lower serum level and potentially a reduction in efficacy.
Food Interactions
Not Available

Products

Drug product information from 10+ global regions
Our datasets provide approved product information including:
dosage, form, labeller, route of administration, and marketing period.
Access now
Access drug product information from over 10 global regions.
Access now
Product Ingredients
IngredientUNIICASInChI Key
Flupirtine gluconateD7NP6CR89M815586-85-7KTUKTXYTLNEYHO-IFWQJVLJSA-N
Flupirtine maleate0VCI53PK4A75507-68-5DPYIXBFZUMCMJM-BTJKTKAUSA-N
International/Other Brands
Awegal / Effirma / Efiret / Katadolon / Metanor / Trancolong

Categories

ATC Codes
N02BG07 — Flupirtine
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as 2-benzylaminopyridines. These are aromatic compounds containing pyridine ring substituted at the 2-position by a benzylamine group.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Benzylamines
Direct Parent
2-benzylaminopyridines
Alternative Parents
Secondary alkylarylamines / Fluorobenzenes / Aminopyridines and derivatives / Imidolactams / Aryl fluorides / Heteroaromatic compounds / Carbamate esters / Organic carbonic acids and derivatives / Azacyclic compounds / Primary amines
show 5 more
Substituents
2-benzylaminopyridine / Amine / Aminopyridine / Aromatic heteromonocyclic compound / Aryl fluoride / Aryl halide / Azacycle / Carbamic acid ester / Carbonic acid derivative / Carbonyl group
show 18 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
MOH3ET196H
CAS number
56995-20-1
InChI Key
JUUFBMODXQKSTD-UHFFFAOYSA-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)
IUPAC Name
ethyl N-(2-amino-6-{[(4-fluorophenyl)methyl]amino}pyridin-3-yl)carbamate
SMILES
CCOC(=O)NC1=C(N)N=C(NCC2=CC=C(F)C=C2)C=C1

References

General References
  1. Muller WE, Laplanche JL, Ushijima H, Schroder HC: Novel approaches in diagnosis and therapy of Creutzfeldt-Jakob disease. Mech Ageing Dev. 2000 Jul 31;116(2-3):193-218. [Article]
  2. Dhar S, Bitting RL, Rylova SN, Jansen PJ, Lockhart E, Koeberl DD, Amalfitano A, Boustany RM: Flupirtine blocks apoptosis in batten patient lymphoblasts and in human postmitotic CLN3- and CLN2-deficient neurons. Ann Neurol. 2002 Apr;51(4):448-66. [Article]
  3. Swedberg MD, Shannon HE, Nickel B, Goldberg SR: Pharmacological mechanisms of action of flupirtine: a novel, centrally acting, nonopioid analgesic evaluated by its discriminative effects in the rat. J Pharmacol Exp Ther. 1988 Sep;246(3):1067-74. [Article]
  4. Abrams SM, Baker LR, Crome P, White AS, Johnston A, Ankier SI, Warrington SJ, Turner P, Niebch G: Pharmacokinetics of flupirtine in elderly volunteers and in patients with moderate renal impairment. Postgrad Med J. 1988 May;64(751):361-3. [Article]
  5. Narang PK, Tourville JF, Chatterji DC, Gallelli JF: Quantitation of flupirtine and its active acetylated metabolite by reversed-phase high-performance liquid chromatography using fluorometric detection. J Chromatogr. 1984 Jan 13;305(1):135-43. [Article]
KEGG Drug
D07978
PubChem Compound
53276
PubChem Substance
175427080
ChemSpider
48119
BindingDB
81199
RxNav
25193
ChEBI
94646
ChEMBL
CHEMBL255044
ZINC
ZINC000000001473
PharmGKB
PA166152829
Wikipedia
Flupirtine
MSDS
Download (568 KB)

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
PhaseStatusPurposeConditionsCount
2TerminatedTreatmentRelapsing Remitting Multiple Sclerosis (RRMS)1
1CompletedNot AvailableAxonal Change, Neuronal / Pain1
1CompletedBasic ScienceFlupirtine / Pain / Pharmacokinetics1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
Capsule
Suppository
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)115.5 °CPhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.0732 mg/mLALOGPS
logP2.61ALOGPS
logP2.67Chemaxon
logS-3.6ALOGPS
pKa (Strongest Acidic)12.9Chemaxon
pKa (Strongest Basic)7.5Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area89.27 Å2Chemaxon
Rotatable Bond Count6Chemaxon
Refractivity85.49 m3·mol-1Chemaxon
Polarizability31.37 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9873
Blood Brain Barrier+0.9373
Caco-2 permeable-0.5757
P-glycoprotein substrateSubstrate0.5425
P-glycoprotein inhibitor INon-inhibitor0.8064
P-glycoprotein inhibitor IINon-inhibitor0.959
Renal organic cation transporterNon-inhibitor0.8922
CYP450 2C9 substrateNon-substrate0.8747
CYP450 2D6 substrateNon-substrate0.8227
CYP450 3A4 substrateNon-substrate0.6669
CYP450 1A2 substrateInhibitor0.7646
CYP450 2C9 inhibitorNon-inhibitor0.7681
CYP450 2D6 inhibitorInhibitor0.8931
CYP450 2C19 inhibitorNon-inhibitor0.5559
CYP450 3A4 inhibitorInhibitor0.7559
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.5155
Ames testNon AMES toxic0.6798
CarcinogenicityNon-carcinogens0.8404
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.5191 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9762
hERG inhibition (predictor II)Non-inhibitor0.5543
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-053r-0094000000-816e5b614d4cddc83185
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0fb9-0093000000-a73a5fefd3ea3bfc9cd5
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-001i-0190000000-f635e09a20fdde0c7ff9
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0036-0190000000-1641ecc7ea843e0cce0d
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0bti-0951000000-4fe414a26363bd5f9949
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-00dl-6940000000-dc2b1ced624663368490
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-174.14136
predicted
DeepCCS 1.0 (2019)
[M+H]+176.49937
predicted
DeepCCS 1.0 (2019)
[M+Na]+182.59251
predicted
DeepCCS 1.0 (2019)

Targets

Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock new
insights and accelerate drug research.
Learn more
Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
Learn more
Details1. Alpha-2A adrenergic receptor
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Thioesterase binding
Specific Function
Alpha-2 adrenergic receptors mediate the catecholamine-induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is oxymetazo...
Gene Name
ADRA2A
Uniprot ID
P08913
Uniprot Name
Alpha-2A adrenergic receptor
Molecular Weight
48956.275 Da
References
  1. Swedberg MD, Shannon HE, Nickel B, Goldberg SR: Pharmacological mechanisms of action of flupirtine: a novel, centrally acting, nonopioid analgesic evaluated by its discriminative effects in the rat. J Pharmacol Exp Ther. 1988 Sep;246(3):1067-74. [Article]

Drug created at March 19, 2008 16:41 / Updated at December 02, 2023 06:59