Feprazone: Difference between revisions

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			{{Short description\|NSAID analgesic drug}}
	{{drugbox
			{{Drugbox
⚫	\| UNII_Ref = {{fdacite\|correct\|FDA}}
			\| Watchedfields = changed
⚫	\| UNII = 7BVX6J0CGR
	\| verifiedrevid = ~~437279023~~		\| verifiedrevid = 444188860
	\| IUPAC_name = 4-(3-methylbut-2-enyl)-1,2-di(phenyl)pyrazolidine-3,5-dione		\| IUPAC_name = 4-(3-methylbut-2-enyl)-1,2-di(phenyl)pyrazolidine-3,5-dione
	\| image = feprazone.png		\| image = feprazone.png
			\| image_class = skin-invert-image

			<!--Clinical data-->
			\| tradename =
			\| Drugs.com = {{drugs.com\|international\|feprazone}}
		⚫	\| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
		⚫	\| pregnancy_US = <!-- A / B / C / D / X -->
		⚫	\| pregnancy_category =
		⚫	\| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
		⚫	\| legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII -->
		⚫	\| legal_UK = <!-- GSL / P / POM / CD / Class A, B, C -->
		⚫	\| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->
		⚫	\| legal_status =
		⚫	\| routes_of_administration =

			<!--Pharmacokinetic data-->
		⚫	\| bioavailability =
		⚫	\| protein_bound =
		⚫	\| metabolism =
		⚫	\| elimination_half-life =
		⚫	\| excretion =

			<!--Identifiers-->
			\| CAS_number_Ref = {{cascite\|correct\|CAS}}
		⚫	\| CAS_number = 30748-29-9
		⚫	\| ATC_prefix = M02
		⚫	\| ATC_suffix = AA16
		⚫	\| PubChem = 35455
		⚫	\| DrugBank_Ref = {{drugbankcite\|correct\|drugbank}}
		⚫	\| DrugBank =
	\| ChemSpiderID_Ref = {{chemspidercite\|correct\|chemspider}}		\| ChemSpiderID_Ref = {{chemspidercite\|correct\|chemspider}}
	\| ChemSpiderID = 32612		\| ChemSpiderID = 32612
		⚫	\| UNII_Ref = {{fdacite\|correct\|FDA}}
	\| InChI = 1/C20H20N2O2/c1-15(2)13-14-18-19(23)21(16-9-5-3-6-10-16)22(20(18)24)17-11-7-4-8-12-17/h3-13,18H,14H2,1-2H3
		⚫	\| UNII = 7BVX6J0CGR
	\| InChIKey = RBBWCVQDXDFISW-UHFFFAOYAV
		⚫	\| KEGG_Ref = {{keggcite\|correct\|kegg}}
		⚫	\| KEGG = D01305

			<!--Chemical data-->
		⚫	\| C=20 \| H=20 \| N=2 \| O=2
	\| smiles = O=C2N(c1ccccc1)N(C(=O)C2C\C=C(/C)C)c3ccccc3		\| smiles = O=C2N(c1ccccc1)N(C(=O)C2C\C=C(/C)C)c3ccccc3
	\| StdInChI_Ref = {{stdinchicite\|correct\|chemspider}}		\| StdInChI_Ref = {{stdinchicite\|correct\|chemspider}}
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	\| StdInChIKey_Ref = {{stdinchicite\|correct\|chemspider}}		\| StdInChIKey_Ref = {{stdinchicite\|correct\|chemspider}}
	\| StdInChIKey = RBBWCVQDXDFISW-UHFFFAOYSA-N		\| StdInChIKey = RBBWCVQDXDFISW-UHFFFAOYSA-N
⚫	\| CAS_number =
⚫	\| ATC_prefix = M02
⚫	\| ATC_suffix = AA16
⚫	\| PubChem = 35455
⚫	\| DrugBank_Ref = {{drugbankcite\|correct\|drugbank}}
⚫	\| DrugBank =
⚫	\| KEGG_Ref = {{keggcite\|correct\|kegg}}
⚫	\| KEGG = D01305
⚫	\| C=20\|H=20\|N=2\|O=2
	\| molecular_weight = 320.385 g/mol
⚫	\| bioavailability =
⚫	\| protein_bound =
⚫	\| metabolism =
⚫	\| elimination_half-life =
⚫	\| excretion =
⚫	\| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
⚫	\| pregnancy_US = <!-- A / B / C / D / X -->
⚫	\| pregnancy_category=
⚫	\| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
⚫	\| legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII -->
⚫	\| legal_UK = <!-- GSL / P / POM / CD / Class A, B, C -->
⚫	\| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->
⚫	\| legal_status =
⚫	\| routes_of_administration =
	}}		}}

			'''Feprazone''' (or '''prenazone''') is a drug used for joint and muscular ].<ref>{{cite journal \| vauthors = Koyama T, Izawa Y, Wada H, Makita T, Hashimoto Y, Enomoto M \| title = Toxicological aspects of feprazone, a new nonsteroidal anti-inflammatory drug \| journal = Toxicology and Applied Pharmacology \| volume = 64 \| issue = 2 \| pages = 255–70 \| date = June 1982 \| pmid = 7123554 \| doi = 10.1016/0041-008X(82)90222-8 \| bibcode = 1982ToxAP..64..255K }}</ref>
	'''Feprazone''' (or '''prenazone''') is a drug used for joint and muscular ].

			It is an analog of ] but instead of a ''n''-butyl group it is ].

			== References ==
			{{reflist}}

	{{Anti-inflammatory and antirheumatic products}}		{{Anti-inflammatory and antirheumatic products}}
	{{Topical products for joint and muscular pain}}		{{Topical products for joint and muscular pain}}

	]		]
	]		]


	{{musculoskeletal-drug-stub}}		{{musculoskeletal-drug-stub}}

	]

Latest revision as of 23:12, 10 January 2025

NSAID analgesic drug Pharmaceutical compound

Feprazone
Clinical data

AHFS/Drugs.com	International Drug Names
ATC code	M02AA16 (WHO)
Identifiers
IUPAC name 4-(3-methylbut-2-enyl)-1,2-di(phenyl)pyrazolidine-3,5-dione
CAS Number	30748-29-9
PubChem CID	35455
ChemSpider	32612
UNII	7BVX6J0CGR
KEGG	D01305
CompTox Dashboard (EPA)	DTXSID3023051
ECHA InfoCard	100.045.735
Chemical and physical data
Formula	C₂₀H₂₀N₂O₂
Molar mass	320.392 g·mol
3D model (JSmol)	Interactive image
SMILES O=C2N(c1ccccc1)N(C(=O)C2C\C=C(/C)C)c3ccccc3
InChI InChI=1S/C20H20N2O2/c1-15(2)13-14-18-19(23)21(16-9-5-3-6-10-16)22(20(18)24)17-11-7-4-8-12-17/h3-13,18H,14H2,1-2H3 Key:RBBWCVQDXDFISW-UHFFFAOYSA-N
(verify)

Feprazone (or prenazone) is a drug used for joint and muscular pain.

It is an analog of phenylbutazone but instead of a n-butyl group it is prenylated.

References

Koyama T, Izawa Y, Wada H, Makita T, Hashimoto Y, Enomoto M (June 1982). "Toxicological aspects of feprazone, a new nonsteroidal anti-inflammatory drug". Toxicology and Applied Pharmacology. 64 (2): 255–70. Bibcode:1982ToxAP..64..255K. doi:10.1016/0041-008X(82)90222-8. PMID 7123554.

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.
category [REDACTED] commons portal

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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