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Indometacin farnesil

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From Wikipedia, the free encyclopedia

Nonsteroidal anti-inflammatory prodrug

Pharmaceutical compound

Indometacin farnesil
Clinical data

AHFS/Drugs.com	International Drug Names
Routes of administration	Oral
ATC code	None
Legal status
Legal status	In general: ℞ (Prescription only)
Pharmacokinetic data
Metabolism	Toindometacin
Eliminationhalf-life	1.5 hours
Excretion	Renal
Identifiers
IUPAC name (2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl [1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetate
CAS Number	85801-02-1^Y
PubChemCID	5282183
ChemSpider	4445378^Y
UNII	MB2386WGG8
CompTox Dashboard(EPA)	DTXSID9057844
ECHA InfoCard	100.242.585
Chemical and physical data
Formula	C₃₄H₄₀ClNO₄
Molar mass	562.15 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CC1=C(C2=C(N1C(=O)C3=CC=C(C=C3)Cl)C=CC(=C2)OC)CC(=O)OCC=C(C)CCC=C(C)CCC=C(C)C
InChI InChI=1S/C34H40ClNO4/c1-23(2)9-7-10-24(3)11-8-12-25(4)19-20-40-33(37)22-30-26(5)36(32-18-17-29(39-6)21-31(30)32)34(38)27-13-15-28(35)16-14-27/h9,11,13-19,21H,7-8,10,12,20,22H2,1-6H3/b24-11+,25-19+^Y Key:CFIGYZZVJNJVDQ-LMJOQDENSA-N^Y
(verify)

Indometacin farnesil (INN) is aprodrug of thenonsteroidal anti-inflammatory drug (NSAID)indometacin,^[1] designed to reduce the occurrence of side-effects by esterification of the carboxyl group on indometacin withfarnesol. Indometacin farnesil was first approved inJapan in 1991, and is available in Japan^[2] andIndonesia, under the trade namesInfree andDialon, respectively.

References

[edit]

^Hirohata S, Yanagida T, Kawai M, Kikuchi H (November 1999). "Inhibition of human B cell activation by a novel nonsteroidal anti-inflammatory drug, indometacin famesil".Immunopharmacology.44 (3):245–254.doi:10.1016/S0162-3109(99)00084-3.PMID 10598881.
^"Infree (indometacin farnesil capsules) Full Prescribing Information"(PDF).Eisai Co., Ltd. Archived fromthe original(PDF) on 2010-12-03. fromEisai Co.

v t e Non-steroidal anti-inflammatory drugs (NSAIDs) (primarilyM01A andM02A, alsoN02BA)
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 Grapiprant^‡ 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.
category commons portal

Prostanoid signaling modulators

Receptor
(ligands)

DP (D₂)Tooltip Prostaglandin D2 receptor

DP₁Tooltip Prostaglandin D2 receptor 1	Agonists:Prostaglandin D₂ Treprostinil Antagonists:Asapiprant Laropiprant Vidupiprant
DP₂Tooltip Prostaglandin D2 receptor 2	Agonists:Indometacin Prostaglandin D₂ Antagonists:ADC-3680 AZD-1981 Bay U3405 Fevipiprant MK-1029 MK-7246 QAV-680 Ramatroban Setipiprant Timapiprant TM30089 Vidupiprant

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

Antagonists:RO1138452

TP (TX_A2)Tooltip Thromboxane receptor

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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