Chemistry: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;
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)

Short description: Nonsteroidal anti-inflammatory prodrug

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

↑ "Inhibition of human B cell activation by a novel nonsteroidal anti-inflammatory drug, indometacin famesil". Immunopharmacology 44 (3): 245–254. November 1999. doi:10.1016/S0162-3109(99)00084-3. PMID 10598881.
↑ "Infree (indometacin farnesil capsules) Full Prescribing Information". Eisai Co., Ltd.. http://www.eisai.jp/medical/products/di/EPI/INF_C-SC_EPI.pdf. from Eisai Co.

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[1] "Inhibition of human B cell activation by a novel nonsteroidal anti-inflammatory drug, indometacin famesil". Immunopharmacology 44 (3): 245–254. November 1999. doi:10.1016/S0162-3109(99)00084-3. PMID 10598881.

[2] "Infree (indometacin farnesil capsules) Full Prescribing Information". Eisai Co., Ltd.. http://www.eisai.jp/medical/products/di/EPI/INF_C-SC_EPI.pdf. from Eisai Co.

[1]

[2]

v t e Nonsteroidal 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 Bumadizone Bufexamac Diclofenac Difenpiramide Etodolac Felbinac Fenclozic acid Fentiazac Indometacin Indometacin farnesil Isoxepac Ketorolac Lonazolac Oxametacin Prodolic acid Proglumetacin Sulindac Tiopinac Tolmetin Zomepirac^†
Oxicams	Ampiroxicam Droxicam Isoxicam Lornoxicam Meloxicam Piroxicam Tenoxicam
Propionic acid derivatives (profens)	Alminoprofen Benoxaprofen^† Carprofen^‡ Dexibuprofen Dexketoprofen Fenbufen Fenoprofen Flunoxaprofen Flurbiprofen Ibuprofen^# Ibuproxam Indoprofen^† Ketoprofen Loxoprofen Miroprofen Naproxen Oxaprozin Pirprofen Suprofen Tarenflurbil Tepoxalin^‡ Tiaprofenic acid Vedaprofen^‡ Zaltoprofen COX-inhibiting nitric oxide donator: Naproxcinod
N-Arylanthranilic acids (fenamates)	Azapropazone Clonixin Etofenamate Flufenamic acid Flunixin Meclofenamic acid Mefenamic acid Morniflumate Niflumic acid Tolfenamic acid Flutiazin
Coxibs	Apricoxib Celecoxib 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
Items listed in bold indicate initially developed compounds of specific groups. ^#WHO-EM ^†Withdrawn drugs. ^‡Veterinary use medications.

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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^Y
PubChem CID	5282183
ChemSpider	4445378^Y
UNII	MB2386WGG8
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)

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