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Difenamizole

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Difenamizole
Names

IUPAC name 2-(Dimethylamino)-N-(2,5-diphenylpyrazol-3-yl)propanamide
Other names Diphenamizole
Identifiers
CAS Number	20170-20-1^Y
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL2105587
ChemSpider	59123
PubChem CID	65695
UNII	24MR6YLL3W^Y
CompTox Dashboard(EPA)	DTXSID60864923
InChI InChI=1S/C20H22N4O/c1-15(23(2)3)20(25)21-19-14-18(16-10-6-4-7-11-16)22-24(19)17-12-8-5-9-13-17/h4-15H,1-3H3,(H,21,25) Key: PCXMKBOWWVXEDT-UHFFFAOYSA-N
SMILES CC(C(=O)NC1=CC(=NN1C2=CC=CC=C2)C3=CC=CC=C3)N(C)C
Properties
Chemical formula	C₂₀H₂₂N₄O
Molar mass	334.423 g·mol⁻¹
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). Infobox references

Chemical compound

Difenamizole (INN; brand namePasalin; former developmental code nameAP-14) is anonsteroidal anti-inflammatory drug (NSAID) andanalgesic of thepyrazolone group related tometamizole.^[1] It hasmonoaminergic properties, including inhibition ofmonoamine oxidase, augmentation ofpargyline-induced elevation ofstriatal dopamine levels, inhibition ofK⁺-induced striatal dopaminerelease, and inhibition of thereuptake ofdopamine.^[2]^[3]^[4]

^J. Elks (14 November 2014).The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 398–.ISBN 978-1-4757-2085-3.
^Secci, D.; Bolasco, A.; Chimenti, P.; Carradori, S. (2011). "The State of the Art of Pyrazole Derivatives as Monoamine Oxidase Inhibitors and Antidepressant/Anticonvulsant Agents".Current Medicinal Chemistry.18 (33):5114–5144.doi:10.2174/092986711797636090.ISSN 0929-8673.PMID 22050759.
^Kameyama T, Nabeshima T, Yoshida N, Yamaguchi K (1981). "Neurochemical studies of an analgesic, 1,3-diphenyl-5-(2-dimethylaminopropionamide)-pyrazole [difenamizole]".Res. Commun. Chem. Pathol. Pharmacol.31 (1):31–53.PMID 6454942.
^NABESHIMA, Toshitaka; YAMAGUCHI, Kazumasa; KAMEYAMA, Tsutomu (1978)."Effects of Difenamizole on Content of Catecholamines and Metabolites in Mouse Brain".The Japanese Journal of Pharmacology.28 (4):642–646.doi:10.1254/jjp.28.642.ISSN 0021-5198.PMID 732046.

Opiates/opium	Codeine^# +aspirin +paracetamol Morphine^# (+naltrexone) Opium Laudanum Paregoric
Semisynthetic	Acetyldihydrocodeine Benzylmorphine Buprenorphine (+naloxone) Butorphanol Desomorphine Dihydrocodeine (+paracetamol) Dihydromorphine Etorphine Ethylmorphine Hydrocodone (+paracetamol,+ibuprofen,+aspirin) Hydromorphinol Hydromorphone Levorphanol Metopon Nalbuphine Nicocodeine Nicodicodine Nicomorphine Oxycodone (+paracetamol,+aspirin,+ibuprofen,+naloxone,+naltrexone) Oxymorphone Papaveretum Thebacon
Synthetic	Alfentanil Alphaprodine Anileridine Bezitramide Carfentanil Dextromoramide Dextropropoxyphene Dezocine Dimenoxadol Dipipanone Ethoheptazine Fentanyl^# (+fluanisone) Ketobemidone Lofentanil Meptazinol Methadone^# NFEPP Norpipanone Oliceridine Pentazocine Pethidine (meperidine) Phenadoxone Phenazocine Phenoperidine Piminodine Piritramide Proheptazine Propiram Remifentanil Sufentanil Tapentadol Tegileridine Tilidine Tramadol (+celecoxib,+paracetamol) Viminol

Propionates	Benoxaprofen^‡ Fenoprofen Flurbiprofen Ibuprofen^# (Dexibuprofen) (+paracetamol) Ketoprofen (Dexketoprofen) Loxoprofen Naproxen Oxaprozin Suprofen Tiaprofenic acid Zaltoprofen
Oxicams	Isoxicam Lornoxicam Meloxicam Piroxicam Tenoxicam
Acetates	Acemetacin Bromfenac Diclofenac Etodolac Indometacin (Indometacin farnesil) Ketorolac Sulindac Tolmetin Zomepirac^‡
COX-2 inhibitors	Celecoxib (+tramadol) Etoricoxib Lumiracoxib^‡ Parecoxib Rofecoxib^‡ Valdecoxib^‡
Fenamates	Flufenamic acid Meclofenamic acid Mefenamic acid Tolfenamic acid
Salicylates	Aspirin (acetylsalicylic acid)^# (+paracetamol/caffeine) Aloxiprin Benorylate Carbasalate calcium Choline salicylate Diflunisal Dipyrocetyl Ethenzamide Guacetisal Imidazole salicylate Magnesium salicylate Morpholine salicylate Potassium salicylate Salicin Salicylamide Salsalate Sodium salicylate Wintergreen (methyl salicylate)
Pyrazolones	Aminophenazone^‡ Ampyrone Metamizole (dipyrone) Nifenazone Phenazone Propyphenazone (+paracetamol/caffeine)
Others	Benzydamine Floctafenine Glafenine Nabumetone Nimesulide Proquazone

Calcium blockers	Alcohol (ethanol) Gabapentin Gabapentin enacarbil Leconotide Mirogabalin Pregabalin Ziconotide
Sodium blockers	Carbamazepine Lacosamide Local anesthetics (e.g.,cocaine,lidocaine) Mexiletine Nefopam Tricyclic antidepressants (e.g.,amitriptyline^#) Na_v1.7/1.8-selective:DSP-2230^§ Funapide^§ PF-05089771^§ Suzetrigine
Potassium openers	Flupirtine^‡

Others

Agonists	Benzazepines:6-Br-APB Fenoldopam SKF-38,393 SKF-77,434 SKF-81,297 SKF-82,958 SKF-83,959 Trepipam Zelandopam Ergolines:Cabergoline CY-208,243 Dihydroergocryptine LEK-8829 Lisuride Pergolide Terguride Dihydrexidine derivatives:A-77636 A-86929 Adrogolide (ABT-431, DAS-431) Dihydrexidine Dinapsoline Dinoxyline Doxanthrine Phenethylamines:BCO-001 Deoxyepinephrine (N-methyldopamine, epinine) Dipropyldopamine (DPDA) Dopamine Dopexamine Etilevodopa Ibopamine L-DOPA (levodopa) Lu AE04621 Melevodopa L-Phenylalanine L-Tyrosine XP21279 Others:A-68930 Apomorphine Isocorypalmine Lu AF28996 Nuciferine PF-06412562 PF-6649751 PF 6669571 Propylnorapomorphine Rotigotine SKF-89,145 SKF-89,626 Stepholidine Tavapadon Tetrahydropalmatine
PAMs	Tetrahydroisoquinolines:DETQ DPTQ Glovadalen Mevidalen
Antagonists	Typical antipsychotics:Butaclamol Chlorpromazine Chlorprothixene Flupentixol (flupenthixol) (+melitracen) Fluphenazine Loxapine Perphenazine (+amitriptyline) Pifluthixol Thioridazine Thiothixene Trifluoperazine (+tranylcypromine) Zuclopenthixol Atypical antipsychotics:Asenapine Clorotepine Clotiapine Clozapine DHA-clozapine Fluperlapine Iloperidone Norclozapine Norquetiapine Olanzapine (+fluoxetine) Paliperidone Quetiapine Risperidone Tefludazine Zicronapine Ziprasidone Zotepine Others:Berupipam Ecopipam EEDQ Metitepine (methiothepin) Odapipam Perlapine SCH-23390