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MedKoo Cat#: 319597 | Name: Tetomilast (OPC6535)

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Tetomilast, also known as OPC6535, is a novel thiazole phosphodiesterase-4 (PDE-4) inhibitor, which may prove useful in both the treatment of inflammatory bowel disease (IBD) and chronic obstructive pulmonary disease (COPD). Tetomilast attenuates elastase-induced pulmonary emphysema through inhibition of oxidative stress in rabbits. Tetomilast suppressed production of proinflammatory cytokines from human monocytes and ameliorated chronic colitis in IL-10-deficient mice.

Chemical Structure

Tetomilast (OPC6535)
CAS#145739-56-6

Theoretical Analysis

MedKoo Cat#: 319597

Name: Tetomilast (OPC6535)

CAS#: 145739-56-6

Chemical Formula: C19H18N2O4S

Exact Mass: 370.0987

Molecular Weight: 370.42

Elemental Analysis: C, 61.61; H, 4.90; N, 7.56; O, 17.28; S, 8.65

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
OPC6535; OPC-6535; OPC 6535; Tetomilast
IUPAC/Chemical Name
6-[2-(3,4-diethoxyphenyl)-1,3-thiazol-4-yl]pyridine-2-carboxylic acid
InChi Key
XDBHURGONHZNJF-UHFFFAOYSA-N
InChi Code
InChI=1S/C19H18N2O4S/c1-3-24-16-9-8-12(10-17(16)25-4-2)18-21-15(11-26-18)13-6-5-7-14(20-13)19(22)23/h5-11H,3-4H2,1-2H3,(H,22,23)
SMILES Code
O=C(C1=NC(C2=CSC(C3=CC=C(OCC)C(OCC)=C3)=N2)=CC=C1)O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO, not in water
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 370.42 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Mulhall AM, Droege CA, Ernst NE, Panos RJ, Zafar MA. Phosphodiesterase 4 inhibitors for the treatment of chronic obstructive pulmonary disease: a review of current and developing drugs. Expert Opin Investig Drugs. 2015 Dec;24(12):1597-611. doi: 10.1517/13543784.2015.1094054. Epub 2015 Sep 30. PubMed PMID: 26419847. 2: Song SD, Tang HF. [Progress in PDE4 targeted therapy for inflammatory diseases]. Zhejiang Da Xue Xue Bao Yi Xue Ban. 2014 May;43(3):353-8. Review. Chinese. PubMed PMID: 24998661. 3: Bickston SJ, Snider KR, Kappus MR. Tetomilast: new promise for phosphodiesterase-4 inhibitors? Expert Opin Investig Drugs. 2012 Dec;21(12):1845-9. doi: 10.1517/13543784.2012.732065. Epub 2012 Oct 8. Review. PubMed PMID: 23043390. 4: Baila B, Ohno Y, Nagamoto H, Kotosai K, Yabuuchi Y, Funaguchi N, Ito F, Endo J, Mori H, Takemura G, Fujiwara T, Fujiwara H, Minatoguchi S. Tetomilast attenuates elastase-induced pulmonary emphysema through inhibition of oxidative stress in rabbits. Biol Pharm Bull. 2012;35(4):494-502. PubMed PMID: 22466552. 5: Salari P, Abdollahi M. Phosphodiesterase inhibitors in inflammatory bowel disease. Expert Opin Investig Drugs. 2012 Mar;21(3):261-4. doi: 10.1517/13543784.2012.658915. Epub 2012 Feb 6. PubMed PMID: 22303952. 6: Salari-Sharif P, Abdollahi M. Phosphodiesterase 4 inhibitors in inflammatory bowel disease: a comprehensive review. Curr Pharm Des. 2010;16(33):3661-7. Review. PubMed PMID: 21128899. 7: Giembycz MA. Can the anti-inflammatory potential of PDE4 inhibitors be realized: guarded optimism or wishful thinking? Br J Pharmacol. 2008 Oct;155(3):288-90. doi: 10.1038/bjp.2008.297. Epub 2008 Jul 28. PubMed PMID: 18660832; PubMed Central PMCID: PMC2567889. 8: Ichikawa H, Okamoto S, Kamada N, Nagamoto H, Kitazume MT, Kobayashi T, Chinen H, Hisamatsu T, Hibi T. Tetomilast suppressed production of proinflammatory cytokines from human monocytes and ameliorated chronic colitis in IL-10-deficient mice. Inflamm Bowel Dis. 2008 Nov;14(11):1483-90. doi: 10.1002/ibd.20524. PubMed PMID: 18618633. 9: Bayes M, Rabasseda X, Prous JR. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2007 Sep;29(7):467-509. PubMed PMID: 17982511. 10: Keshavarzian A, Mutlu E, Guzman JP, Forsyth C, Banan A. Phosphodiesterase 4 inhibitors and inflammatory bowel disease: emerging therapies in inflammatory bowel disease. Expert Opin Investig Drugs. 2007 Sep;16(9):1489-506. Review. PubMed PMID: 17714033. 11: Schreiber S, Keshavarzian A, Isaacs KL, Schollenberger J, Guzman JP, Orlandi C, Hanauer SB. A randomized, placebo-controlled, phase II study of tetomilast in active ulcerative colitis. Gastroenterology. 2007 Jan;132(1):76-86. Epub 2006 Nov 18. PubMed PMID: 17241861. 12: O'Mahony S. Tetomilast. IDrugs. 2005 Jun;8(6):502-7. PubMed PMID: 15906198. 13: Bayés M, Rabasseda X, Prous JR. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2004 Dec;26(10):801-27. PubMed PMID: 15672123. 14: Ross AS, Cohen RD. Medical therapy for ulcerative colitis: the state of the art and beyond. Curr Gastroenterol Rep. 2004 Dec;6(6):488-95. Review. PubMed PMID: 15527679. 15: Gotham S. Digestive Disease Week 2004. Bowel inflammation. IDrugs. 2004 Jun;7(6):516-9. PubMed PMID: 15197649. 16: Hasegawa T, Sakurai K, Kambayashi Y, Saniabadi AR, Nagamoto H, Tsukada K, Takahashi A, Kuwano H, Nakano M. Effects of OPC-6535 on lipopolysaccharide-induced acute liver injury in the rat: involvement of superoxide and tumor necrosis factor-alpha from hepatic macrophages. Surgery. 2003 Nov;134(5):818-26. PubMed PMID: 14639361. 17: Aki S, Fujioka T, Ishigami M, Minamikawa J. A practical synthesis of 3,4-diethoxybenzthioamide based on Friedel-Crafts reaction with potassium thiocyanate in methanesulfonic acid. Bioorg Med Chem Lett. 2002 Sep 2;12(17):2317-20. PubMed PMID: 12161124. 18: Banan A, Fitzpatrick L, Zhang Y, Keshavarzian A. OPC-compounds prevent oxidant-induced carbonylation and depolymerization of the F-actin cytoskeleton and intestinal barrier hyperpermeability. Free Radic Biol Med. 2001 Feb 1;30(3):287-98. PubMed PMID: 11165875. 19: Ejiri S, Eguchi Y, Kishida A, Kurumi Y, Tani T, Kodama M. Protective effect of OPC-6535, a superoxide anion production inhibitor, on liver grafts subjected to warm ischemia during porcine liver transplantation. Transplant Proc. 2000 Mar;32(2):318-21. PubMed PMID: 10715428. 20: Cheng XS, Shimokawa H, Momii H, Oyama J, Fukuyama N, Egashira K, Nakazawa H, Takeshita A. Role of superoxide anion in the pathogenesis of cytokine-induced myocardial dysfunction in dogs in vivo. Cardiovasc Res. 1999 Jun;42(3):651-9. PubMed PMID: 10533605.