Clonixin: Difference between revisions

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			{{Short description\|Nonsteroidal anti-inflammatory drug (NSAID)}}
	{{chembox
			{{Chembox
⚫	\| UNII_Ref = {{fdacite\|correct\|FDA}}
			\| Verifiedfields = changed
⚫	\| UNII = V7DXN0M42R
			\| Watchedfields = changed
	\| verifiedrevid = ~~444429984~~		\| verifiedrevid = 451725338
	\| ImageFile = Clonixin.png		\| ImageFile = Clonixin.png
			\| ImageClass = skin-invert-image
	\| ImageSize = 200px
	\| ~~IUPACName~~ = 2-(3-~~chloro~~-2-methylanilino)pyridine-3-carboxylic acid		\| PIN = 2-(3-Chloro-2-methylanilino)pyridine-3-carboxylic acid
	\| OtherNames = Clonixic acid; CBA 93626<ref name="Clinical">{{cite ~~web~~\|url=http://~~jcp~~.~~sagepub~~.com/~~cgi~~/~~content~~/~~abstract~~/~~11/5/371~~\|title=Clonixin: A Clinical Evaluation of a New Oral Analgesic \|~~last~~=The Journal of Clinical Pharmacology\|~~accessdate~~=~~2010~~-06-16}}</ref>		\| OtherNames = Clonixic acid; CBA 93626<ref name="Clinical">{{cite journal\|url=http://onlinelibrary.wiley.com/doi/10.1177/009127007101100508/abstract\|title=Clonixin: A Clinical Evaluation of a New Oral Analgesic \|journal=The Journal of Clinical Pharmacology and New Drugs \|volume=11 \|issue=5 \|pages=371–377 \|access-date=2015-05-21\|doi=10.1177/009127007101100508\|pmid=4935715 \|year=1971 \|last1=Finch \|first1=Jay S. \|last2=Dekornfeld \|first2=Thomas J. \|hdl=2027.42/67636 \|s2cid=38883141 \|hdl-access=free }}</ref>
	\| Section1 = {{Chembox Identifiers		\|Section1={{Chembox Identifiers
	\| Abbreviations =		\| Abbreviations =
			\| CASNo_Ref = {{cascite\|correct\|??}}
	\| CASNo = 17737-65-4		\| CASNo = 17737-65-4
		⚫	\| UNII_Ref = {{fdacite\|correct\|FDA}}
		⚫	\| UNII = V7DXN0M42R
	\| PubChem = 28718		\| PubChem = 28718
	\| SMILES = O=C(O)C1=CC=CN=C1NC2=C(C)C(Cl)=CC=C2		\| SMILES = O=C(O)C1=CC=CN=C1NC2=C(C)C(Cl)=CC=C2
	\| MeSHName =		\| MeSHName =
	\| ChemSpiderID_Ref = {{chemspidercite\|~~correct~~\|chemspider}}		\| ChemSpiderID_Ref = {{chemspidercite\|changed\|chemspider}}
	\| ChemSpiderID =		\| ChemSpiderID = 26711
	\| ~~ChEBI_Ref~~ = {{ebicite\|~~correct~~\|EBI}}		\| ChEMBL_Ref = {{ebicite\|changed\|EBI}}
	\| ~~ChEBI~~ =		\| ChEMBL = 1332971
			\| InChI = 1/C13H11ClN2O2/c1-8-10(14)5-2-6-11(8)16-12-9(13(17)18)4-3-7-15-12/h2-7H,1H3,(H,15,16)(H,17,18)
	\| ATCCode_prefix =
			\| InChIKey = CLOMYZFHNHFSIQ-UHFFFAOYAG
	\| ATCCode_suffix =
			\| StdInChI_Ref = {{stdinchicite\|changed\|chemspider}}
	\| ATC_Supplemental =
			\| StdInChI = 1S/C13H11ClN2O2/c1-8-10(14)5-2-6-11(8)16-12-9(13(17)18)4-3-7-15-12/h2-7H,1H3,(H,15,16)(H,17,18)
			\| StdInChIKey_Ref = {{stdinchicite\|changed\|chemspider}}
			\| StdInChIKey = CLOMYZFHNHFSIQ-UHFFFAOYSA-N
			\| ChEBI_Ref = {{ebicite\|changed\|???}}
			\| ChEBI = 76200
	\| DrugBank_Ref = {{drugbankcite\|correct\|drugbank}}		\| DrugBank_Ref = {{drugbankcite\|correct\|drugbank}}
	\| DrugBank =		\| DrugBank =
	\| KEGG_Ref = {{keggcite\|correct\|kegg}}		\| KEGG_Ref = {{keggcite\|correct\|kegg}}
	\| KEGG = D03555		\| KEGG = D03555
		⚫	}}
	\| DCB = 05349 (clonixinato de lisina) <!-- this is brazilian data, pt:Denominação Comum Brasileira //-->
		⚫	\|Section2={{Chembox Properties
	\| Medicamento_de_referência =
⚫	}}
⚫	\| Section2 = {{Chembox Properties
	\| C=13 \| H=11 \| Cl=1 \| N=2 \| O=2		\| C=13 \| H=11 \| Cl=1 \| N=2 \| O=2
	\| Appearance =		\| Appearance =
	\| Density =		\| Density =
	\| MeltingPt =		\| MeltingPt =
	\| ~~Melting_notes~~ =		\| MeltingPt_notes =
	\| BoilingPt =		\| BoilingPt =
	\| ~~Boiling_notes~~ =		\| BoilingPt_notes =
	\| Solubility =		\| Solubility =
	\| SolubleOther =		\| SolubleOther =
	\| Solvent =		\| Solvent =
	}}		}}
	\| Section3 = {{Chembox Pharmacology		\|Section3={{Chembox Pharmacology
	\| AdminRoutes = ]		\| AdminRoutes = ]
	\| Bioavail =		\| Bioavail =
	\| Metabolism =		\| Metabolism = Glucuronidation via UGT2B7
	\| HalfLife =		\| HalfLife =
	\| ProteinBound =		\| ProteinBound =
	\| Excretion =		\| Excretion =
	\| Volume_de_distribuição =
	\| Depuração =
	\| Concentrações_máximas =
	\| Legal_status =		\| Legal_status =
	\| Legal_US =		\| Legal_US = Not sold in the U.S.
			}}
	\| Legal_BR =
		⚫	\|Section4={{Chembox Hazards
		⚫	\| LD50 =
	}}		}}
⚫	\| Section4 = {{Chembox Hazards
	\| RPhrases =
	\| SPhrases =
⚫	\| LD50 = }}
	\|Section5 =
	\|fundo = fármaco
	}}		}}

	'''Clonixin''' is a ]. It also has ], ], and ] actions. It is used primarily in the treatment of chronic arthritic conditions and certain soft tissue disorders associated with pain and inflammation.		'''Clonixin''' is a ] (NSAID). It also has ], ], and ] actions. It is used primarily in the treatment of chronic arthritic conditions and certain soft tissue disorders associated with pain and inflammation.

			==Synthesis==
			]).]]

			==Clonixeril==
			The glyceryl ester of clonixin, clonixeril, is also an NSAID. It was prepared by a somewhat roundabout method.
			]
			Clonixin was reacted with ] and ] to give '''2'''. Heating with ] and ] displaced the ] to produce ester '''3''', which was deblocked in ] to produce clonixeril ('''4''').

			==See also==
			*]

	== References ==		== References ==
	{{reflist}}		{{reflist}}

			{{Prostanoidergics}}
	]

⚫	]
	]		]
		⚫	]
			]
	]		]
			]


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

	]

Latest revision as of 23:39, 10 January 2025

Nonsteroidal anti-inflammatory drug (NSAID)

Clonixin
Names

Preferred IUPAC name 2-(3-Chloro-2-methylanilino)pyridine-3-carboxylic acid
Other names Clonixic acid; CBA 93626
Identifiers
CAS Number	17737-65-4
3D model (JSmol)	Interactive image
ChEBI	CHEBI:76200
ChEMBL	ChEMBL1332971
ChemSpider	26711
ECHA InfoCard	100.037.921
KEGG	D03555
PubChem CID	28718
UNII	V7DXN0M42R
CompTox Dashboard (EPA)	DTXSID2046121
InChI InChI=1S/C13H11ClN2O2/c1-8-10(14)5-2-6-11(8)16-12-9(13(17)18)4-3-7-15-12/h2-7H,1H3,(H,15,16)(H,17,18)Key: CLOMYZFHNHFSIQ-UHFFFAOYSA-N InChI=1/C13H11ClN2O2/c1-8-10(14)5-2-6-11(8)16-12-9(13(17)18)4-3-7-15-12/h2-7H,1H3,(H,15,16)(H,17,18)Key: CLOMYZFHNHFSIQ-UHFFFAOYAG
SMILES O=C(O)C1=CC=CN=C1NC2=C(C)C(Cl)=CC=C2
Properties
Chemical formula	C₁₃H₁₁ClN₂O₂
Molar mass	262.69 g·mol
Pharmacology
Routes of administration	per os
Pharmacokinetics:
Metabolism	Glucuronidation via UGT2B7
Legal status	US: Not sold in the U.S.
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). N verify (what is ?) Infobox references

Chemical compound

Clonixin is a nonsteroidal anti-inflammatory drug (NSAID). It also has analgesic, antipyretic, and platelet-inhibitory actions. It is used primarily in the treatment of chronic arthritic conditions and certain soft tissue disorders associated with pain and inflammation.

Synthesis

Clonixeril

The glyceryl ester of clonixin, clonixeril, is also an NSAID. It was prepared by a somewhat roundabout method.

Clonixin was reacted with chloroacetonitrile and triethylamine to give 2. Heating with potassium carbonate and glycerol acetonide displaced the activating group to produce ester 3, which was deblocked in acetic acid to produce clonixeril (4).

References

Finch, Jay S.; Dekornfeld, Thomas J. (1971). "Clonixin: A Clinical Evaluation of a New Oral Analgesic". The Journal of Clinical Pharmacology and New Drugs. 11 (5): 371–377. doi:10.1177/009127007101100508. hdl:2027.42/67636. PMID 4935715. S2CID 38883141. Retrieved 2015-05-21.
M. H. Sherlock, ZA 6802185 (1968); Chem. Abstr., 70: 96640c (1969).
CH 534129 (1973); Chem. Abstr., 79: 18582g (1973).

Prostanoid signaling modulators

Receptor
(ligands)

DP (D₂)Tooltip Prostaglandin D2 receptor

DP₁Tooltip Prostaglandin D2 receptor 1

Agonists: Prostaglandin D₂
Treprostinil

DP₂Tooltip Prostaglandin D2 receptor 2

Agonists: Indometacin
Prostaglandin D₂

EP (E₂)Tooltip Prostaglandin E2 receptor

EP₁Tooltip Prostaglandin EP1 receptor	Agonists: Beraprost Enprostil Iloprost (ciloprost) Latanoprost Lubiprostone Misoprostol Prostaglandin E₁ (alprostadil) Prostaglandin E₂ (dinoprostone) Sulprostone Antagonists: AH-6809 ONO-8130 SC-19220 SC-51089 SC-51322
EP₂Tooltip Prostaglandin EP2 receptor	Agonists: Butaprost Misoprostol Prostaglandin E₁ (alprostadil) Prostaglandin E₂ (dinoprostone) Treprostinil Antagonists: AH-6809 PF-04418948 TG 4-155
EP₃Tooltip Prostaglandin EP3 receptor	Agonists: Beraprost Carbacyclin Cicaprost Enprostil Iloprost (ciloprost) Isocarbacyclin Latanoprost Misoprostol Prostaglandin D₂ Prostaglandin E₁ (alprostadil) Prostaglandin E₂ (dinoprostone) Remiprostol Ricinoleic acid Sulprostone Antagonists: L-798106
EP₄Tooltip Prostaglandin EP4 receptor	Agonists: Lubiprostone Misoprostol Prostaglandin E₁ (alprostadil) Prostaglandin E₂ (dinoprostone) TCS-2510 Antagonists: Grapiprant GW-627368 L-161982 ONO-AE3-208
Unsorted	Agonists: 16,16-Dimethyl Prostaglandin E₂ Aganepag Carboprost Evatanepag Gemeprost Nocloprost Omidenepag Prostaglandin F_2α (dinoprost) Simenepag Taprenepag

FP (F_2α)Tooltip Prostaglandin F receptor

IP (I₂)Tooltip Prostacyclin receptor

Agonists: ACT-333679
AFP-07
Beraprost
BMY-45778
Carbacyclin
Cicaprost
Iloprost (ciloprost)
Isocarbacyclin
MRE-269
NS-304
Prostacyclin (prostaglandin I₂, epoprostenol)
Prostaglandin E₁ (alprostadil)
Ralinepag
Selexipag
Taprostene
TRA-418
Treprostinil

Antagonists: RO1138452

TP (TX_A2)Tooltip Thromboxane receptor

Agonists: Carbocyclic thromboxane A₂
I-BOP
Thromboxane A₂
U-46619
Vapiprost

Unsorted

Enzyme
(inhibitors)

COX (PTGS)	Salicylic acids: Aloxiprin Aspirin (acetylsalicylic acid) Benorilate (benorylate) Carbasalate calcium Diflunisal Dipyrocetyl Ethenzamide Guacetisal Magnesium salicylate Mesalazine (5-aminosalicylic acid) Methyl salicylate Salacetamide Salicin Salicylamide Salicylate (salicylic acid) Salsalate Sodium salicylate Triflusal; Acetic acids: Aceclofenac Acemetacin Aclofenac Amfenac Alclofenac Bendazac Bromfenac Bufexamac Bumadizone Cinmetacin Clometacin Diclofenac Difenpiramide Etodolac Felbinac Fenclofenac Fentiazac Glucametacin Indometacin (indomethacin) Indometacin farnesil Ketorolac Lonazolac Mofezolac Nabumetone Oxametacin Oxindanac Proglumetacin Sulindac Sulindac sulfide Tolmetin Zidometacin Zomepirac; Propionic acids: Alminoprofen Benoxaprofen Bucloxic acid (blucloxate) Butibufen Carprofen Dexibuprofen Dexindoprofen Dexketoprofen Fenbufen Fenoprofen Flunoxaprofen Flurbiprofen Ibuprofen Ibuproxam Indoprofen Ketoprofen Loxoprofen Miroprofen Naproxen Naproxcinod Oxaprozin Pirprofen Pranoprofen Suprofen Tarenflurbil Tepoxalin Tiaprofenic acid (tiaprofenate) Vedaprofen; Anthranilic acids (fenamic acids): Etofenamic acid (etofenamate) Floctafenic acid (floctafenate) Flufenamic acid (flufenamate) Meclofenamic acid (meclofenamate) Mefenamic acid (mefenamate) Morniflumic acid (morniflumate) Niflumic acid (niflumate) Talinflumic acid (talinflumate) Tolfenamic acid (tolfenamate); Pyrazolones: Azapropazone Dipyrone Isopyrin Oxyphenbutazone Phenylbutazone; Enolic acids (oxicams): Ampiroxicam Droxicam Enolicam Isoxicam Lornoxicam Meloxicam Piroxicam Tenoxicam; 4-Aminoquinolines: Antrafenine Floctafenine Glafenine; Quinazolines: Fluproquazone Proquazone; Aminonicotinic acids: Clonixeril Clonixin Flunixin; Sulfonanilides: Flosulide Nimesulide; Aminophenols (anilines): Acetanilide AM-404 (N-arachidonoylaminophenol) Bucetin Paracetamol (acetaminophen) Parapropamol Phenacetin Propacetamol; Selective COX-2 inhibitors (coxibs): Apricoxib Celecoxib Cimicoxib Deracoxib Etoricoxib Firocoxib Lumiracoxib Mavacoxib Parecoxib Polmacoxib Robenacoxib Rofecoxib Tilmacoxib Valdecoxib; Others/unsorted: Anitrazafen Clobuzarit Curcumin DuP-697 FK-3311 Flumizole FR-122047 Glimepiride Hyperforin Itazigrel L-655240 L-670596 Licofelone Menatetrenone (vitamin K₂) NCX-466 NCX-4040 NS-398 Pamicogrel Resveratrol Romazarit Rosmarinic acid Rutecarpine Satigrel SC-236 SC-560 SC-58125 Tenidap Tiflamizole Timegadine Trifenagrel Tropesin
PGD₂STooltip Prostaglandin D synthase	Retinoids Selenium (selenium tetrachloride, sodium selenite, selenium disulfide)
PGESTooltip Prostaglandin E synthase	HQL-79
PGFSTooltip Prostaglandin F synthase	Bimatoprost
PGI₂STooltip Prostacyclin synthase	Tranylcypromine
TXASTooltip Thromboxane A synthase	Camonagrel Dazmegrel Dazoxiben Furegrelate Isbogrel Midazogrel Nafagrel Nicogrelate Ozagrel Picotamide Pirmagrel Ridogrel Rolafagrel Samixogrel Terbogrel U63557A

Others

See also: Receptor/signaling modulators; Leukotriene signaling modulators

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Categories:

Latest revision as of 23:39, 10 January 2025

Synthesis

Clonixeril

See also

References