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Nifenazone
Clinical data

ATC code	M02AA24 (WHO) N02BB05 (WHO)
Identifiers
IUPAC name N-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)nicotinamide
CAS Number	2139-47-1^Y
PubChem CID	4487
ChemSpider	4332^Y
UNII	8780F0K71U
KEGG	D01437^Y
ChEMBL	ChEMBL1413176^Y
CompTox Dashboard (EPA)	DTXSID7045366
ECHA InfoCard	100.016.716
Chemical and physical data
Formula	C₁₇H₁₆N₄O₂
Molar mass	308.341 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES c1ccccc1N2N(C)C(C)=C(C2=O)NC(=O)c3cccnc3
InChI InChI=1S/C17H16N4O2/c1-12-15(19-16(22)13-7-6-10-18-11-13)17(23)21(20(12)2)14-8-4-3-5-9-14/h3-11H,1-2H3,(H,19,22)^Y Key:BRZANEXCSZCZCI-UHFFFAOYSA-N^Y

Nifenazone is a drug that has been used as an analgesic for a number of rheumatic conditions.^[1]

Synthesis

Nifenazone is the amide formed when ampyrone and the acid chloride of nicotinic acid are combined in a Schotten–Baumann reaction.^[2]^[3]

References

^ Hart FD, Boardman PL (June 1964). "Trial of Nifenazone ("Thylin")". British Medical Journal. 1 (5397): 1553–4. doi:10.1136/bmj.1.5397.1553. PMC 1814611. PMID 14133613.
^ Pongratz A, Zirm L (1957). "Über neue pharmakologisch wirksame Amide und Ester der Nicotinsäure". Monatshefte für Chemie. 88 (3): 330–335. doi:10.1007/BF00901766.
^ "Nifenazone". Pharmaceutical Substances. Georg Thieme Verlag KG. Retrieved 2024-07-16.

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 Meloxicam/rizatriptan 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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Topical products for joint and muscular pain (M02)

Anti-inflammatory
preparations,
non-steroids

Pyrazolidines	Clofezone Mofebutazone Oxyphenbutazone Phenylbutazone
Acetic acid derivatives	Diclofenac Fentiazac Tolmetin
Other	Bendazac Benzydamine Bufexamac Etofenamate Felbinac Feprazone Flurbiprofen Ibuprofen Indometacin Ketoprofen Meclofenamic acid Naproxen Nifenazone Niflumic acid Piketoprofen Piroxicam Suxibuzone

Capsaicin derivatives

Zucapsaicin

Other

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Synthesis

See also

References