NAV

Talniflumate

Identification

Generic Name
Talniflumate
DrugBank Accession Number
DB09295
Background

Talniflumate, is an anti-inflammatory molecule studied and used as a mucin regulator in the treatment of cystic fibrosis, chronic obstructive pulmonary disease (COPD) and asthma 5. In addition, it is used in inflammatory conditions such as rheumatoid arthritis. Phase I trials with talniflumate for the treatment of cystic fibrosis and COPD were completed in August 2001, and phase II trials were performed in Ireland for the treatment of cystic fibrosis but this research has now been discontinued 7,10. Talniflumate has been approved for approximately 20 years in Argentina other countries (excluding the United States, Europe, and Japan) 10.

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 414.34
Monoisotopic: 414.082741396
Chemical Formula
C21H13F3N2O4
Synonyms
  • Talniflumate
  • Talniflumato
  • Talniflumatum
External IDs
  • BA 7602-06
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Pharmacology

Indication

Talnifumate is a phthalidyl ester of nifumic acid, which has potent analgesic and anti-inflammatory effects and is widely used to treat inflammatory disorders, such as rheumatoid arthritis and osteoarthritis 13, and has also been studied for the management of cystic fibrosis 8.

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Talniflumate is metabolized to its prodrug, niflumic acid, which has several pharmacodynamic effects. Firstly, it blocks synthesis of mucin. Secondly, talniflumate blocks prostaglandin synthesis by cyclooxygenases, which aids in pain and inflammation management.

Mechanism of action

Talniflumate is a strong and selective inhibitor of core mucin-synthesizing enzyme GCNT3 (core 2 b-1,6 N-acetylglucosaminyltransferase). Talniflumate decreases gene expression of GCNT3 and production of mucins in vivo and in vitro. Talniflumate improves response of pancreatic tumors to gefitinib (chemotherapy drug). Talniflumate is a strong calcium-activated chloride channel (CaCC) blocker.

TargetActionsOrganism
UProstaglandin G/H synthase 1
antagonist
Humans
UProstaglandin G/H synthase 2
antagonist
Humans
UChloride channel protein ClC-Ka
antagonist
Humans
Absorption

Not Available

Volume of distribution

In 12 subjects after a single oral administration, total plasma clearance of the main metabolite, niflumic acid, averaged 45 ml/min giving a distribution volume of 0.12 l/kg on average 3.

Protein binding

Niflumic acid, the active form of Talniflumate, is weak acid that is strongly bound to plasma proteins. Bioavailability was 100% in a study of 12 volunteers. It is a weak acid, strongly bound to plasma proteins 3.

Metabolism

Extensive liver metabolism.

Route of elimination

Not Available

Half-life

Approximately 2h in 12 subjects 3

Clearance

This drug undergoes extensive first pass effect.

Adverse Effects
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Toxicity

LD50 orally in rats: 12000 mg/kg 14

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
AbacavirTalniflumate may decrease the excretion rate of Abacavir which could result in a higher serum level.
AbciximabThe risk or severity of bleeding and hemorrhage can be increased when Talniflumate is combined with Abciximab.
AcebutololTalniflumate may decrease the antihypertensive activities of Acebutolol.
AceclofenacThe risk or severity of adverse effects can be increased when Aceclofenac is combined with Talniflumate.
AcemetacinThe risk or severity of adverse effects can be increased when Talniflumate is combined with Acemetacin.
Food Interactions
Not Available

Products

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International/Other Brands
Huluma (Myungmoon) / Somalgen / Stofen (Shin poong) / Talmain (Korea United Pharm) / Talmen (Daewoo) / Talniflumate Hanall (Hanall Biopharma) / Talumat (Taiguk) / Tariful (KWANG DONG)

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as benzofuranones. These are organic compounds containing a benzene ring fused to a furanone.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Benzofurans
Sub Class
Benzofuranones
Direct Parent
Benzofuranones
Alternative Parents
Trifluoromethylbenzenes / Phthalides / Pyridinecarboxylic acids / Aniline and substituted anilines / Aminopyridines and derivatives / Dicarboxylic acids and derivatives / Imidolactams / Vinylogous amides / Heteroaromatic compounds / Amino acids and derivatives
show 11 more
Substituents
Acetal / Alkyl fluoride / Alkyl halide / Amine / Amino acid or derivatives / Aminopyridine / Aniline or substituted anilines / Aromatic heteropolycyclic compound / Azacycle / Benzenoid
show 27 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
JFK78S0U9S
CAS number
66898-62-2
InChI Key
ANMLJLFWUCQGKZ-UHFFFAOYSA-N
InChI
InChI=1S/C21H13F3N2O4/c22-21(23,24)12-5-3-6-13(11-12)26-17-16(9-4-10-25-17)19(28)30-20-15-8-2-1-7-14(15)18(27)29-20/h1-11,20H,(H,25,26)
IUPAC Name
3-oxo-1,3-dihydro-2-benzofuran-1-yl 2-{[3-(trifluoromethyl)phenyl]amino}pyridine-3-carboxylate
SMILES
FC(F)(F)C1=CC(NC2=C(C=CC=N2)C(=O)OC2OC(=O)C3=CC=CC=C23)=CC=C1

References

General References
  1. Knight D: Talniflumate (Genaera). Curr Opin Investig Drugs. 2004 May;5(5):557-62. [Article]
  2. Rao CV, Janakiram NB, Madka V, Kumar G, Scott EJ, Pathuri G, Bryant T, Kutche H, Zhang Y, Biddick L, Gali H, Zhao YD, Lightfoot S, Mohammed A: Small-Molecule Inhibition of GCNT3 Disrupts Mucin Biosynthesis and Malignant Cellular Behaviors in Pancreatic Cancer. Cancer Res. 2016 Apr 1;76(7):1965-74. doi: 10.1158/0008-5472.CAN-15-2820. Epub 2016 Feb 15. [Article]
  3. Houin G, Tremblay D, Bree F, Dufour A, Ledudal P, Tillement JP: The pharmacokinetics and availability of niflumic acid in humans. Int J Clin Pharmacol Ther Toxicol. 1983 Mar;21(3):130-4. [Article]
  4. Talniflumate [Link]
  5. Screening study for genetic polymorphisms af­fecting pharmacokinetics of talnifumate [Link]
  6. Pharmacokinetics of talniflumate, a prodrug of niflumic acid, following oral administration to man [Link]
  7. Talniflumate (Genaera) [Link]
  8. Talniflunate [Link]
  9. Chemistry Dashboard: Talniflumate [Link]
  10. TALNIFLUMATE [Link]
  11. Talniflumate Increases Survival in a Cystic Fibrosis Mouse Model of Distal Intestinal Obstructive Syndrome [Link]
  12. TALNIFLUMATE [Link]
  13. KWANG DONG TARIFUL TAB [Link]
  14. Talniflumate [Link]
KEGG Drug
D02701
PubChem Compound
48229
PubChem Substance
310265187
ChemSpider
43868
BindingDB
50239971
RxNav
236770
ChEBI
91991
ChEMBL
CHEMBL1081506
Drugs.com
Drugs.com Drug Page

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)177[L1404]
boiling point (°C)454[L1404]
water solubility5 mg/mL clear[L1399]
logP4.47[L1404]
Predicted Properties
PropertyValueSource
Water Solubility0.00417 mg/mLALOGPS
logP4ALOGPS
logP6.65Chemaxon
logS-5ALOGPS
pKa (Strongest Acidic)13.33Chemaxon
pKa (Strongest Basic)3.5Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area77.52 Å2Chemaxon
Rotatable Bond Count6Chemaxon
Refractivity100.11 m3·mol-1Chemaxon
Polarizability37.83 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-014i-0090200000-300841dbed583b710ac4
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-03yr-0094700000-696ffb93d4e73ec93bda
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-014i-0090200000-f5934cdb7c676f3b2b56
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-03ei-0293200000-06168dd06782a53903cc
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-0930000000-e81324fde1377dcb51e5
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-0950000000-93c095635f3247bb674f
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]-189.6018
predicted
DeepCCS 1.0 (2019)
[M+H]+191.95981
predicted
DeepCCS 1.0 (2019)
[M+Na]+198.05295
predicted
DeepCCS 1.0 (2019)

Targets

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insights and accelerate drug research.
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Details1. Prostaglandin G/H synthase 1
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Antagonist
General Function
Prostaglandin-endoperoxide synthase activity
Specific Function
Converts arachidonate to prostaglandin H2 (PGH2), a committed step in prostanoid synthesis. Involved in the constitutive production of prostanoids in particular in the stomach and platelets. In gas...
Gene Name
PTGS1
Uniprot ID
P23219
Uniprot Name
Prostaglandin G/H synthase 1
Molecular Weight
68685.82 Da
References
  1. TALNIFLUMATE [Link]
Details2. Prostaglandin G/H synthase 2
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Antagonist
General Function
Prostaglandin-endoperoxide synthase activity
Specific Function
Converts arachidonate to prostaglandin H2 (PGH2), a committed step in prostanoid synthesis. Constitutively expressed in some tissues in physiological conditions, such as the endothelium, kidney and...
Gene Name
PTGS2
Uniprot ID
P35354
Uniprot Name
Prostaglandin G/H synthase 2
Molecular Weight
68995.625 Da
References
  1. TALNIFLUMATE [Link]
Details3. Chloride channel protein ClC-Ka
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Antagonist
General Function
Voltage-gated chloride channel activity
Specific Function
Voltage-gated chloride channel. Chloride channels have several functions including the regulation of cell volume; membrane potential stabilization, signal transduction and transepithelial transport...
Gene Name
CLCNKA
Uniprot ID
P51800
Uniprot Name
Chloride channel protein ClC-Ka
Molecular Weight
75284.08 Da
References
  1. TALNIFLUMATE [Link]

Enzymes

Details1. Prostaglandin G/H synthase 1
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Prostaglandin-endoperoxide synthase activity
Specific Function
Converts arachidonate to prostaglandin H2 (PGH2), a committed step in prostanoid synthesis. Involved in the constitutive production of prostanoids in particular in the stomach and platelets. In gas...
Gene Name
PTGS1
Uniprot ID
P23219
Uniprot Name
Prostaglandin G/H synthase 1
Molecular Weight
68685.82 Da
References
  1. TALNIFLUMATE [Link]
Details2. Prostaglandin G/H synthase 2
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Prostaglandin-endoperoxide synthase activity
Specific Function
Converts arachidonate to prostaglandin H2 (PGH2), a committed step in prostanoid synthesis. Constitutively expressed in some tissues in physiological conditions, such as the endothelium, kidney and...
Gene Name
PTGS2
Uniprot ID
P35354
Uniprot Name
Prostaglandin G/H synthase 2
Molecular Weight
68995.625 Da
References
  1. TALNIFLUMATE [Link]

Drug created at October 30, 2015 15:27 / Updated at February 21, 2021 18:52