Infree

• CAT Number: I029363
• CAS Number: 85801-02-1
• Molecular Formula: C34H40ClNO4
• Molecular Weight: 562.14
• Purity: 98%
• Synonyms: Infree; INF; Indomethacin farnesil; Indometacin farnesil
• Solubility: Soluble in DMSO
• Appearance: Solid powder
• Storage: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
• IUPAC Name: 3,7,11-Trimethyldodeca-2,6,10-trien-1-yl 2-(1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl)acetate
• 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+
• InChIKey: CFIGYZZVJNJVDQ-LMJOQDENSA-N
• SMILES: O=C(OC/C=C(C)/CC/C=C(C)/CC/C=C(C)/C)CC1=C(C)N(C(C2=CC=C(Cl)C=C2)=O)C3=C1C=C(OC)C=C3

Infree (CAT: I029363) is a prodrug of indomethacin, a nonsteroidal anti-inflammatory drug (NSAID). Indomethacin is known for its anti-inflammatory, analgesic, and antipyretic properties. Infree is specifically designed to undergo enzymatic conversion into indomethacin after administration, allowing for targeted delivery and improved pharmacokinetics. As an NSAID, Infree works by inhibiting the production of prostaglandins, which are responsible for inflammation and pain.

Reference

1: Ono K, Hashimoto T, Satoh T. Eosinophilic pustular folliculitis clinically presenting as orofacial granuloma: successful treatment with indomethacin, but not ibuprofen. Acta Derm Venereol. 2015 Mar;95(3):361-2. doi: 10.2340/00015555-1926. PubMed PMID: 24979363.
2: Hakozaki M, Kikuchi S, Otani K, Tajino T, Konno S. Pseudogout of the acromioclavicular joint: report of two cases and review of the literature. Mod Rheumatol. 2011 Aug;21(4):440-3. doi: 10.1007/s10165-011-0417-8. Epub 2011 Feb 5. Review. PubMed PMID: 21298395.
3: Satoh K, Takano S, Kobayashi T. Keishikajutsubuto (Guizhi-shu-fu-tang) treatment for refractory accumulation of synovial fluid in a patient with pustulotic arthro-osteitis. Fukushima J Med Sci. 2007 Jun;53(1):33-8. PubMed PMID: 17957964.
4: Fujita Y, Fujii T, Takeda N, Tanaka M, Mimori T. Successful treatment of primary Sjögren’s syndrome with chronic natural killer lymphocytosis by high-dose prednisolone and indomethacin farnesil. Intern Med. 2007;46(5):251-4. Epub 2007 Mar 1. PubMed PMID: 17329922.
5: Hirohata S, Yanagida T, Kawai M, Kikuchi H. Inhibition of human B cell activation by a novel nonsteroidal anti-inflammatory drug, indometacin famesil. Immunopharmacology. 1999 Nov;44(3):245-54. PubMed PMID: 10598881.
6: Sekine K, Nakajima Y, Sawamoto S, Yamada K, Nakajima M, Miyasaka T, Arioka H, Nakano J, Yamashita N, Ohta K, Mano K. [Vasculo-Behcet’s disease with fatal massive hemoptysis]. Nihon Kokyuki Gakkai Zasshi. 1999 Feb;37(2):135-9. Japanese. PubMed PMID: 10214043.
7: Takayama F, Miyazaki T, Aoyama I, Tsukushi S, Sato M, Yamazaki C, Shimokata K, Niwa T. Involvement of interleukin-8 in dialysis-related arthritis. Kidney Int. 1998 Apr;53(4):1007-13. PubMed PMID: 9551411.
8: Hirohata S, Konuma K, Inoue T, Ito K. Interaction of indometacin farnesil, a new nonsteroidal antiinflammatory drug with peripheral blood mononuclear cells from patients with rheumatoid arthritis. Nihon Rinsho Meneki Gakkai Kaishi. 1996 Apr;19(2):136-44. PubMed PMID: 8705690.
9: Nomura K, Sasaki C, Murai T, Mitsuhashi Y, Sato S. Angiolymphoid hyperplasia with eosinophilia: successful treatment with indomethacin farnesil. Br J Dermatol. 1996 Jan;134(1):189-90. PubMed PMID: 8745919.
10: Arakawa T, Fukuda T, Nakagawa K, Higuchi K, Watanabe T, Tominaga K, Kobayashi K. Ulcerogenicity and effect on inhibition of prostaglandin generation of indometacin farnesil, a prodrug of indomethacin, in rat gastric mucosa: comparison with indomethacin or loxoprofen. Drugs Exp Clin Res. 1995;21(3):85-8. PubMed PMID: 7555616.
11: Mishima M, Kobayashi S, Hashida R, Yuzuriha T, Sato T, Satoh T. Enzymatic hydrolysis of indometacin farnesil, a prodrug of indomethacin, by carboxylesterase in cultured synovial cells. Res Commun Chem Pathol Pharmacol. 1991 May;72(2):183-90. PubMed PMID: 1876749.
12: Kumakura S, Mishima M, Kobayashi S, Shirota H, Abe S, Yamada K, Tsurufuji S. Inhibitory effect of indomethacin farnesil, a novel antiinflammatory prodrug, on carrageenin-induced inflammation in rats. Agents Actions. 1990 Mar;29(3-4):286-91. PubMed PMID: 2339670.
13: Mishima M, Kobayashi S, Abe S, Yamato C. Metabolic fate of indometacin farnesil, a prodrug of indomethacin: characteristic biotransformation of indometacin farnesil in rats. Xenobiotica. 1990 Feb;20(2):135-46. PubMed PMID: 2333710.
14: Hara K, Akiyama Y, Kato Y, Orikasa E, Takahira H, Tajima T. [Influence of indometacin farnesil on blood coagulation. Comparison with indomethacin in normal rats and warfarin induced hypoprothrombinemic rats]. Nihon Yakurigaku Zasshi. 1988 Dec;92(6):365-73. Japanese. PubMed PMID: 3250914.