Indometacin farnesil

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	To indometacin
Elimination half-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 ;
PubChem CID	5282183;
ChemSpider	4445378 ;
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+ ; Key:CFIGYZZVJNJVDQ-LMJOQDENSA-N ;
	(verify)

Indometacin farnesil (INN) is a prodrug of the nonsteroidal anti-inflammatory drug (NSAID) indometacin,^[1] designed to reduce the occurrence of side-effects by esterification of the carboxyl group on indometacin with farnesol. Indometacin farnesil was first approved in Japan in 1991, and is available in Japan^[2] and Indonesia, under the trade names Infree and Dialon, respectively.

References

^ 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 from the original (PDF) on 2010-12-03. from Eisai Co.

[1] 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.

[2] "Infree (indometacin farnesil capsules) Full Prescribing Information" (PDF). Eisai Co., Ltd. Archived from the original (PDF) on 2010-12-03. from Eisai Co.

[1]

[2]

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 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.
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