Niflumic acid

Niflumic acid
Clinical data
AHFS/Drugs.com	International Drug Names
ATC code	M01AX02 (WHO) M02AA17 (WHO);
Pharmacokinetic data
Elimination half-life	2.5 hr
Identifiers
	IUPAC name 2-{[3-(trifluoromethyl)phenyl]amino}nicotinic acid;
CAS Number	4394-00-7 ;
PubChem CID	4488;
IUPHAR/BPS	2439;
ChemSpider	4333 ;
UNII	4U5MP5IUD8;
KEGG	D08275 ;
ChEMBL	ChEMBL63323 ;
CompTox Dashboard (EPA)	DTXSID1023368 ;
ECHA InfoCard	100.022.289
Chemical and physical data
Formula	C13H9F3N2O2
Molar mass	282.222 g·mol−1
3D model (JSmol)	Interactive image;
Melting point	204 °C (399 °F)
	SMILES C1=CC(=CC(=C1)NC2=C(C=CC=N2)C(=O)O)C(F)(F)F;
	InChI InChI=1S/C13H9F3N2O2/c14-13(15,16)8-3-1-4-9(7-8)18-11-10(12(19)20)5-2-6-17-11/h1-7H,(H,17,18)(H,19,20) ; Key:JZFPYUNJRRFVQU-UHFFFAOYSA-N ;
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Niflumic acid is a drug used for joint and muscular pain. It is categorized as an inhibitor of cyclooxygenase-2. In experimental biology, it has been employed to inhibit chloride channels.^[2] It has also been reported to act on GABA-A^[3] and NMDA channels^[4] and to block T-type calcium channels.^[5]

References

^ "Half life". Drug Bank. Retrieved 15 July 2011.
^ Knauf PA, Mann NA (May 1984). "Use of niflumic acid to determine the nature of the asymmetry of the human erythrocyte anion exchange system". The Journal of General Physiology. 83 (5): 703–25. doi:10.1085/jgp.83.5.703. PMC 2215658. PMID 6736917.
^ Sinkkonen ST, Mansikkamäki S, Möykkynen T, Lüddens H, Uusi-Oukari M, Korpi ER (September 2003). "Receptor subtype-dependent positive and negative modulation of GABA(A) receptor function by niflumic acid, a nonsteroidal anti-inflammatory drug". Molecular Pharmacology. 64 (3): 753–63. doi:10.1124/mol.64.3.753. PMID 12920213.
^ Lerma J, Martín del Río R (February 1992). "Chloride transport blockers prevent N-methyl-D-aspartate receptor-channel complex activation". Molecular Pharmacology. 41 (2): 217–22. PMID 1371581.
^ Balderas E, Ateaga-Tlecuitl R, Rivera M, Gomora JC, Darszon A (June 2012). "Niflumic acid blocks native and recombinant T-type channels". Journal of Cellular Physiology. 227 (6): 2542–55. doi:10.1002/jcp.22992. PMC 4146346. PMID 21898399.

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[1] "Half life". Drug Bank. Retrieved 15 July 2011.

[2] Knauf PA, Mann NA (May 1984). "Use of niflumic acid to determine the nature of the asymmetry of the human erythrocyte anion exchange system". The Journal of General Physiology. 83 (5): 703–25. doi:10.1085/jgp.83.5.703. PMC 2215658. PMID 6736917.

[3] Sinkkonen ST, Mansikkamäki S, Möykkynen T, Lüddens H, Uusi-Oukari M, Korpi ER (September 2003). "Receptor subtype-dependent positive and negative modulation of GABA(A) receptor function by niflumic acid, a nonsteroidal anti-inflammatory drug". Molecular Pharmacology. 64 (3): 753–63. doi:10.1124/mol.64.3.753. PMID 12920213.

[4] Lerma J, Martín del Río R (February 1992). "Chloride transport blockers prevent N-methyl-D-aspartate receptor-channel complex activation". Molecular Pharmacology. 41 (2): 217–22. PMID 1371581.

[5] Balderas E, Ateaga-Tlecuitl R, Rivera M, Gomora JC, Darszon A (June 2012). "Niflumic acid blocks native and recombinant T-type channels". Journal of Cellular Physiology. 227 (6): 2542–55. doi:10.1002/jcp.22992. PMC 4146346. PMID 21898399.

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v t e Non-steroidal anti-inflammatory drugs (NSAIDs) (primarily M01A and M02A, also N02BA)
pyrazolones / pyrazolidines	Aminophenazone Ampyrone Azapropazone Clofezone Difenamizole Famprofazone Feprazone Kebuzone Metamizole Mofebutazone Morazone Nifenazone Oxyphenbutazone Phenazone Phenylbutazone Propyphenazone Sulfinpyrazone Suxibuzone^‡
salicylates	Aspirin (acetylsalicylic acid)^# Aloxiprin Benorylate Carbasalate calcium Diflunisal Dipyrocetyl Ethenzamide Guacetisal Magnesium salicylate Methyl salicylate Salsalate Salicin Salicylamide Salicylic acid (salicylate) Sodium salicylate
acetic acid derivatives and related substances	Aceclofenac Acemetacin Alclofenac Amfenac Bendazac Bromfenac Bufexamac Bumadizone Diclofenac Difenpiramide Etodolac Felbinac Fenclozic acid Fentiazac Indometacin Indometacin farnesil Isoxepac Ketorolac Lonazolac Mofezolac Oxametacin Prodolic acid Proglumetacin Sulindac Tiopinac Tolmetin Zomepirac^†
oxicams	Ampiroxicam Droxicam Isoxicam Lornoxicam Meloxicam Piroxicam Pivoxicam Tenoxicam
propionic acid derivatives (profens)	Alminoprofen Benoxaprofen^† Carprofen^‡ Dexibuprofen Dexketoprofen Fenbufen Fenoprofen Flunoxaprofen Flurbiprofen Ibuprofen^# Ibuproxam Indoprofen^† Ketoprofen Loxoprofen Miroprofen Naproxen Oxaprozin Pelubiprofen Piketoprofen Pirprofen Suprofen Tarenflurbil Tepoxalin^‡ Tiaprofenic acid Vedaprofen^‡ Zaltoprofen COX-inhibiting nitric oxide donator: Naproxcinod
n-arylanthranilic acids (fenamates)	Azapropazone Clonixin Etofenamate Floctafenine Flufenamic acid Flunixin Flutiazin Glafenine^† Meclofenamic acid Mefenamic acid Morniflumate Niflumic acid Tolfenamic acid
COX-2 inhibitors (coxibs)	Apricoxib Celecoxib (+tramadol) Cimicoxib^‡ Deracoxib^‡ Etoricoxib Firocoxib^‡ Lumiracoxib^† Mavacoxib^‡ Parecoxib Robenacoxib^‡ Rofecoxib^† Valdecoxib^†
other	Aminopropionitrile Benzydamine Chondroitin sulfate Diacerein Fluproquazone Glucosamine Glycosaminoglycan Hyperforin Nabumetone Nimesulide Oxaceprol Proquazone Superoxide dismutase / orgotein Tenidap
NSAID combinations	Ibuprofen/famotidine Ibuprofen/hydrocodone Ibuprofen/oxycodone Ibuprofen/paracetamol Meloxicam/bupivacaine Naproxen/diphenhydramine Naproxen/esomeprazole
Key: underline indicates initially developed first-in-class compound of specific group; ^#WHO-Essential Medicines; ^†withdrawn drugs; ^‡veterinary use.
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