Tanomastat | BAY12-9566 | CAS#179545-77-8 | MMP Inhibitor

MedKoo Cat#: 202953 | Name: Tanomastat

Description:

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

Tanomastat, also known as BAY 12-9566, is a biphenyl matrix metalloproteinase (MMP) inhibitor (MMPI) with potential antineoplastic activity. Tanomastat inhibits MMP-2, MMP-3, and MMP-9, inhibiting extracellular matrix degradation and potentially inhibiting angiogenesis, tumor growth and invasion, and metastasis. MMPs consist of at least 18 zinc-containing endo-proteinases that are capable of degrading collagen and proteoglycan.

Chemical Structure

Tanomastat

CAS#179545-77-8

Theoretical Analysis

MedKoo Cat#: 202953

Name: Tanomastat

CAS#: 179545-77-8

Chemical Formula: C23H19ClO3S

Exact Mass: 410.0743

Molecular Weight: 410.91

Elemental Analysis: C, 67.23; H, 4.66; Cl, 8.63; O, 11.68; S, 7.80

Price and Availability

Size	Price	Availability	Quantity
5mg	USD 350.00	2 Weeks
10mg	USD 550.00	2 Weeks

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Related CAS #

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Synonym

BAY 12-9566, BAY12-9566, BAY-12-9566, BAY 129566, BAY129566, BAY-129566, Tanomastat

IUPAC/Chemical Name

(S)-4-[4-(4-Chlorophenyl)phenyl]-4-oxo-2-(phenylsulfanylmethyl)butanoic acid

InChi Key

JXAGDPXECXQWBC-LJQANCHMSA-N

InChi Code

InChI=1S/C23H19ClO3S/c24-20-12-10-17(11-13-20)16-6-8-18(9-7-16)22(25)14-19(23(26)27)15-28-21-4-2-1-3-5-21/h1-13,19H,14-15H2,(H,26,27)/t19-/m1/s1

SMILES Code

O=C(O)[C@@H](CSC1=CC=CC=C1)CC(C2=CC=C(C3=CC=C(Cl)C=C3)C=C2)=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

>5 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

Results of phase III clinical trials: This drug, developed by Bayer, was entered into Phase III human clinical trials. However, Bayer decided to stop the trials due to negative results from other phase III trials in pancreatic and small cell lung cancer. It was concluded that BAY 12-9566 was generally well tolerated and at the time of the final analysis, there was no evidence of an impact of BAY 12-9566 on progression-free survival or overall survival . ( source: Gynecol Oncol. 2006 Aug;102(2):300-8. Epub 2006 Jan 25.) .

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 410.91 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.

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: Lim TYM, Jaladanki CK, Wong YH, Yogarajah T, Fan H, Chu JJH. Tanomastat exerts multi-targeted inhibitory effects on viral capsid dissociation and RNA replication in human enteroviruses. EBioMedicine. 2024 Sep;107:105277. doi: 10.1016/j.ebiom.2024.105277. Epub 2024 Sep 2. PMID: 39226680; PMCID: PMC11419895. 2: Baidya SK, Amin SA, Jha T. Outline of gelatinase inhibitors as anti-cancer agents: A patent mini-review for 2010-present. Eur J Med Chem. 2021 Mar 5;213:113044. doi: 10.1016/j.ejmech.2020.113044. Epub 2020 Nov 24. PMID: 33279289. 3: Denlinger CE. Matrix metalloproteinases and bronchiolitis obliterans: Wrapping the enigma in a riddle. J Thorac Cardiovasc Surg. 2015 Apr;149(4):1203-4. doi: 10.1016/j.jtcvs.2014.12.051. Epub 2014 Dec 29. PMID: 25618413. 4: Krenn K, Gmeiner M, Paulus P, Sela N, Torres L, Zins K, Dekan G, Aharinejad S. Effects of azithromycin and tanomastat on experimental bronchiolitis obliterans. J Thorac Cardiovasc Surg. 2015 Apr;149(4):1194-202. doi: 10.1016/j.jtcvs.2014.11.088. Epub 2014 Dec 4. PMID: 25595376. 5: Saif MW. Advanced stage pancreatic cancer: novel therapeutic options. Expert Rev Clin Pharmacol. 2014 Jul;7(4):487-98. doi: 10.1586/17512433.2014.910451. PMID: 24939470. 6: Wong MS, Sidik SM, Mahmud R, Stanslas J. Molecular targets in the discovery and development of novel antimetastatic agents: current progress and future prospects. Clin Exp Pharmacol Physiol. 2013 May;40(5):307-19. doi: 10.1111/1440-1681.12083. PMID: 23534409. 7: Chaudhary AK, Pandya S, Ghosh K, Nadkarni A. Matrix metalloproteinase and its drug targets therapy in solid and hematological malignancies: an overview. Mutat Res. 2013 Jul-Sep;753(1):7-23. doi: 10.1016/j.mrrev.2013.01.002. Epub 2013 Jan 28. PMID: 23370482. 8: Iatropoulos MJ, Cerven DR, de George G, von Keutz E, Williams GM. Reduction by dietary matrix metalloproteinase inhibitor BAY 12-9566N of neoplastic development induced by diethylnitrosamine, N-nitrosodimethylamine, or 7,12-dimethylbenz(a)anthracene in rats. Drug Chem Toxicol. 2008;31(3):305-16. doi: 10.1080/01480540701873350. PMID: 18622867. 9: Auranen A, Grénman S. Radiation therapy and biological compounds for consolidation therapy in advanced ovarian cancer. Int J Gynecol Cancer. 2008 Mar-Apr;18 Suppl 1:44-6. doi: 10.1111/j.1525-1438.2007.01105.x. PMID: 18336400. 10: Cosgrove D, Meehan DT, Delimont D, Pozzi A, Chen X, Rodgers KD, Tempero RM, Zallocchi M, Rao VH. Integrin alpha1beta1 regulates matrix metalloproteinases via P38 mitogen-activated protein kinase in mesangial cells: implications for Alport syndrome. Am J Pathol. 2008 Mar;172(3):761-73. doi: 10.2353/ajpath.2008.070473. Epub 2008 Feb 7. PMID: 18258846; PMCID: PMC2258247. 11: Moore AS, Dernell WS, Ogilvie GK, Kristal O, Elmslie R, Kitchell B, Susaneck S, Rosenthal R, Klein MK, Obradovich J, Legendre A, Haddad T, Hahn K, Powers BE, Warren D. Doxorubicin and BAY 12-9566 for the treatment of osteosarcoma in dogs: a randomized, double-blind, placebo-controlled study. J Vet Intern Med. 2007 Jul-Aug;21(4):783-90. doi: 10.1892/0891-6640(2007)21[783:dabftt]2.0.co;2. PMID: 17708400. 12: Howes JM, Theakston RD, Laing GD. Neutralization of the haemorrhagic activities of viperine snake venoms and venom metalloproteinases using synthetic peptide inhibitors and chelators. Toxicon. 2007 Apr;49(5):734-9. doi: 10.1016/j.toxicon.2006.11.020. Epub 2006 Nov 30. PMID: 17196631. 13: Narazaki M, Tosato G. Conflicting results from clinical observations and murine models: what is the role of plasminogen activators in tumor growth? J Natl Cancer Inst. 2006 Jun 7;98(11):726-7. doi: 10.1093/jnci/djj227. PMID: 16757692. 14: Saif MW. Anti-angiogenesis therapy in pancreatic carcinoma. JOP. 2006 Mar 9;7(2):163-73. PMID: 16525200. 15: Hirte H, Vergote IB, Jeffrey JR, Grimshaw RN, Coppieters S, Schwartz B, Tu D, Sadura A, Brundage M, Seymour L. A phase III randomized trial of BAY 12-9566 (tanomastat) as maintenance therapy in patients with advanced ovarian cancer responsive to primary surgery and paclitaxel/platinum containing chemotherapy: a National Cancer Institute of Canada Clinical Trials Group Study. Gynecol Oncol. 2006 Aug;102(2):300-8. doi: 10.1016/j.ygyno.2005.12.020. Epub 2006 Jan 25. PMID: 16442153. 16: Molina JR, Reid JM, Erlichman C, Sloan JA, Furth A, Safgren SL, Lathia CD, Alberts SR. A phase I and pharmacokinetic study of the selective, non-peptidic inhibitor of matrix metalloproteinase BAY 12-9566 in combination with etoposide and carboplatin. Anticancer Drugs. 2005 Oct;16(9):997-1002. doi: 10.1097/01.cad.0000176504.86551.5c. PMID: 16162976. 17: Hirte H, Stewart D, Goel R, Chouinard E, Huan S, Stafford S, Waterfield B, Matthews S, Lathia C, Schwartz B, Agarwal V, Humphrey R, Seymour AL. An NCIC-CTG phase I dose escalation pharmacokinetic study of the matrix metalloproteinase inhibitor BAY 12-9566 in combination with doxorubicin. Invest New Drugs. 2005 Oct;23(5):437-43. doi: 10.1007/s10637-005-2903-3. PMID: 16133795. 18: Bayés M, Rabasseda X, Prous JR. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2005 Jun;27(5):331-72. PMID: 16082422. 19: Lutz J, Yao Y, Song E, Antus B, Hamar P, Liu S, Heemann U. Inhibition of matrix metalloproteinases during chronic allograft nephropathy in rats. Transplantation. 2005 Mar 27;79(6):655-61. doi: 10.1097/01.tp.0000151644.85832.b5. PMID: 15785371. 20: Stanciūte D, Didziapetriene J, Kadziauskas J. Matrikso metaloproteinazes sergant piktybiniais navikais [Expression of matrix metalloproteinases in patients with malignant tumors]. 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