Fluproquazone

Fluproquazone
Clinical data
ATC code	none;
Identifiers
	IUPAC name 4-(4-fluorophenyl)-7-methyl-1-propan-2-ylquinazolin-2-one;
CAS Number	40507-23-1;
PubChem CID	38503;
ChemSpider	35289 ;
UNII	U4K85O58HD;
KEGG	D04229 ;
CompTox Dashboard (EPA)	DTXSID70193519 ;
Chemical and physical data
Formula	C18H17FN2O
Molar mass	296.345 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES Fc3ccc(C/1=N/C(=O)N(c2cc(ccc\12)C)C(C)C)cc3;
	InChI InChI=1S/C18H17FN2O/c1-11(2)21-16-10-12(3)4-9-15(16)17(20-18(21)22)13-5-7-14(19)8-6-13/h4-11H,1-3H3 ; Key:ZWOUXWWGKJBAHQ-UHFFFAOYSA-N ;
	(verify)

Fluproquazone (trade name Tormosyl, RF 46-790 ) was a quinazolinone derivative with potent analgesic, antipyretic, and anti-inflammatory effects discovered by Sandoz.[1][2][3][4] It was withdrawn during development due to liver toxicity.[5]^:370[6]^:520

References

Haanaes HR, Benterud UJ, Skoglund LA (November 1986). "RF 46-790 versus paracetamol: effect on post-operative pain". International Journal of Clinical Pharmacology, Therapy, and Toxicology. 24 (11): 598–601. PMID 3491794.
Mohing W, Suckert R, Lataste X (1981). "Comparative study of fluproquazone in the management of post-operative pain". Arzneimittel-Forschung. 31 (5a): 918–20. PMID 6973986.
Wheatley D (May 1982). "Analgesic properties of fluproquazone". Rheumatology and Rehabilitation. 21 (2): 98–100. doi:10.1093/rheumatology/21.2.98. PMID 7043713.
Fankhauser S, Laube W, Marti HR, Schultheiss HR, Vögtlin J, von Graffenried B (1981). "Antipyretic activity of fluproquazone in man". Arzneimittel-Forschung. 31 (5a): 934–5. PMID 6973990.
Lewis JH, Stine JG (2013). "Nonsteroidal Antiinflammatory Drugs and Leukotriene Receptor Antagonists". In Kaplowitz N, DeLeve LD (eds.). Drug-induced Liver Disease (third ed.). Elsevier Inc. ISBN 9780123878175.
Zimmerman HJ (1999). Hepatotoxicity: The Adverse Effects of Drugs and Other Chemicals on the Liver. Lippincott Williams & Wilkins. ISBN 9780781719520.

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[1] Haanaes HR, Benterud UJ, Skoglund LA (November 1986). "RF 46-790 versus paracetamol: effect on post-operative pain". International Journal of Clinical Pharmacology, Therapy, and Toxicology. 24 (11): 598–601. PMID 3491794.

[pmid6973986-2] Mohing W, Suckert R, Lataste X (1981). "Comparative study of fluproquazone in the management of post-operative pain". Arzneimittel-Forschung. 31 (5a): 918–20. PMID 6973986.

[pmid7043713-3] Wheatley D (May 1982). "Analgesic properties of fluproquazone". Rheumatology and Rehabilitation. 21 (2): 98–100. doi:10.1093/rheumatology/21.2.98. PMID 7043713.

[pmid6973990-4] Fankhauser S, Laube W, Marti HR, Schultheiss HR, Vögtlin J, von Graffenried B (1981). "Antipyretic activity of fluproquazone in man". Arzneimittel-Forschung. 31 (5a): 934–5. PMID 6973990.

[5] Lewis JH, Stine JG (2013). "Nonsteroidal Antiinflammatory Drugs and Leukotriene Receptor Antagonists". In Kaplowitz N, DeLeve LD (eds.). Drug-induced Liver Disease (third ed.). Elsevier Inc. ISBN 9780123878175.

[6] Zimmerman HJ (1999). Hepatotoxicity: The Adverse Effects of Drugs and Other Chemicals on the Liver. Lippincott Williams & Wilkins. ISBN 9780781719520.

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 Bumadizone Bufexamac Diclofenac Difenpiramide Etodolac Felbinac Fenclozic acid Fentiazac Indometacin Indometacin farnesil Isoxepac Ketorolac Lonazolac Oxametacin Prodolic acid Proglumetacin Sulindac Tiopinac Tolmetin Zomepirac^†
Oxicams	Ampiroxicam Droxicam Isoxicam Lornoxicam Meloxicam Piroxicam Tenoxicam
Propionic acid derivatives (profens)	Alminoprofen Benoxaprofen^† Carprofen^‡ Dexibuprofen Dexketoprofen Fenbufen Fenoprofen Flunoxaprofen Flurbiprofen Ibuprofen^# Ibuproxam Indoprofen^† Ketoprofen Loxoprofen Miroprofen Naproxen Oxaprozin Pirprofen Suprofen Tarenflurbil Tepoxalin^‡ Tiaprofenic acid Vedaprofen^‡ Zaltoprofen COX-inhibiting nitric oxide donator: Naproxcinod
N-Arylanthranilic acids (fenamates)	Azapropazone Clonixin Etofenamate Flufenamic acid Flunixin Meclofenamic acid Mefenamic acid Morniflumate Niflumic acid Tolfenamic acid Flutiazin
Coxibs	Apricoxib Celecoxib 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
Combinations	Ibuprofen/paracetamol Meloxicam/bupivacaine
Items listed in bold indicate initially developed compounds of specific groups. ^#WHO-EM ^†Withdrawn drugs. ^‡Veterinary use medications.