Fenclozic acid

Fenclozic acid
Clinical data
Trade names	Myalex
Identifiers
	IUPAC name [2-(4-Chlorophenyl)-1,3-thiazol-4-yl]acetic acid;
CAS Number	17969-20-9 ;
PubChem CID	28858;
ChemSpider	26843 ;
UNII	58SRQ4DV53;
CompTox Dashboard (EPA)	DTXSID4046157 ;
Chemical and physical data
Formula	C11H8ClNO2S
Molar mass	253.70 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES c1cc(ccc1c2nc(cs2)CC(=O)O)Cl;
	InChI InChI=1S/C11H8ClNO2S/c12-8-3-1-7(2-4-8)11-13-9(6-16-11)5-10(14)15/h1-4,6H,5H2,(H,14,15) ; Key:APBSKHYXXKHJFK-UHFFFAOYSA-N ;
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Fenclozic acid (proposed brand name Myalex) is a nonsteroidal anti-inflammatory drug (NSAID) with analgesic, antipyretic, and anti-inflammatory properties developed in the 1960s by ICI Pharmaceuticals.^[1]^[2] It failed to pass the Phase III clinical trial, and was withdrawn from clinical development in 1971 due to severe dose-related hepatotoxicity and jaundice in humans, despite showing an excellent preclinical safety profile and promising clinical efficacy in animal testing.^[3]^[4] It is considered a classic example of human-specific drug induced liver injury linked to unique metabolic activation in humans.^[4]^[5]

References

↑ Newbould BB (March 1969). "The pharmacology of fenclozic acid (2-(4-chlorophenyl)-thiazol-4-ylacetic acid; I.C.I. 54,450; 'Myalex'); a new compound with anti-inflammatory, analgesic and antipyretic activityl". British Journal of Pharmacology. 35 (3): 487–497. doi:10.1111/j.1476-5381.1969.tb08290.x. PMC 1703354. PMID 5809740.
↑ US 3538107, Hepworth W, Stacey GJ, "Aryl-thiazolyl-acetic acid derivatives", issued 1970, assigned to Imperial Chemical Industries Ltd
↑ Hart FD, Bain LS, Huskisson EC, Littler TR, Taylor RT (November 1970). "Hepatic effects of fenzlozic acid". Annals of the Rheumatic Diseases. 29 (6): 684. doi:10.1136/ard.29.6.684. PMC 1010604. PMID 5496073.
1 2 Rodrigues AV, Rollison HE, Martin S, Sarda S, Schulz-Utermoehl T, Stahl S, et al. (August 2013). "In vitro exploration of potential mechanisms of toxicity of the human hepatotoxic drug fenclozic acid". Archives of Toxicology. 87 (8): 1569–1579. doi:10.1007/s00204-013-1056-y. PMID 23609606.
↑ Pickup K, Martin S, Partridge EA, Jones HB, Wills J, Schulz-Utermoehl T, et al. (July 2017). "Acute liver effects, disposition and metabolic fate of [¹⁴C]-fenclozic acid following oral administration to normal and bile-cannulated male C57BL/6J mice". Archives of Toxicology. 91 (7): 2643–2653. doi:10.1007/s00204-016-1894-5. PMC 5489613. PMID 27896398.

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[Newbould_1969-1] Newbould BB (March 1969). "The pharmacology of fenclozic acid (2-(4-chlorophenyl)-thiazol-4-ylacetic acid; I.C.I. 54,450; 'Myalex'); a new compound with anti-inflammatory, analgesic and antipyretic activityl". British Journal of Pharmacology. 35 (3): 487–497. doi:10.1111/j.1476-5381.1969.tb08290.x. PMC 1703354. PMID 5809740.

[2] US 3538107, Hepworth W, Stacey GJ, "Aryl-thiazolyl-acetic acid derivatives", issued 1970, assigned to Imperial Chemical Industries Ltd

[Hart_1970-3] Hart FD, Bain LS, Huskisson EC, Littler TR, Taylor RT (November 1970). "Hepatic effects of fenzlozic acid". Annals of the Rheumatic Diseases. 29 (6): 684. doi:10.1136/ard.29.6.684. PMC 1010604. PMID 5496073.

[Rodrigues_2013-4] 1 2 Rodrigues AV, Rollison HE, Martin S, Sarda S, Schulz-Utermoehl T, Stahl S, et al. (August 2013). "In vitro exploration of potential mechanisms of toxicity of the human hepatotoxic drug fenclozic acid". Archives of Toxicology. 87 (8): 1569–1579. doi:10.1007/s00204-013-1056-y. PMID 23609606.

[Pickup_2017-5] Pickup K, Martin S, Partridge EA, Jones HB, Wills J, Schulz-Utermoehl T, et al. (July 2017). "Acute liver effects, disposition and metabolic fate of [¹⁴C]-fenclozic acid following oral administration to normal and bile-cannulated male C57BL/6J mice". Archives of Toxicology. 91 (7): 2643–2653. doi:10.1007/s00204-016-1894-5. PMC 5489613. PMID 27896398.

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v t e Nonsteroidal 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 Grapiprant^‡ Hyperforin Nabumetone Nimesulide Oxaceprol Proquazone Superoxide dismutase / orgotein Tenidap
NSAID combinations	Ibuprofen/famotidine Ibuprofen/hydrocodone Ibuprofen/oxycodone Ibuprofen/paracetamol Meloxicam/bupivacaine Meloxicam/rizatriptan Naproxen/diphenhydramine Naproxen/esomeprazole Naproxen/paracetamol
Key: underline indicates initially developed first-in-class compound of specific group; ^#WHO-Essential Medicines; ^†withdrawn drugs; ^‡veterinary use.
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