Tanomastat
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MedKoo CAT#: 202953

CAS#: 179545-77-8

Description: 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.


Price and Availability

Size
Price

5mg
USD 300
Size
Price

10mg
USD 525
Size
Price

Tanomastat purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 202953
Name: Tanomastat
CAS#: 179545-77-8
Chemical Formula: C23H19ClO3S
Exact Mass: 410.07434
Molecular Weight: 410.91
Elemental Analysis: C, 67.23; H, 4.66; Cl, 8.63; O, 11.68; S, 7.80


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


Technical Data

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).

Harmonized System Code:
293490


Additional Information

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.) .
 
 


References

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18: Oettle H. [Adjuvant treatment of pancreatic cancer]. Zentralbl Chir. 2003 May;128(5):411-8. Review. German. PubMed PMID: 12813641.

19: Leff RL, Elias I, Ionescu M, Reiner A, Poole AR. Molecular changes in human osteoarthritic cartilage after 3 weeks of oral administration of BAY 12-9566, a matrix metalloproteinase inhibitor. J Rheumatol. 2003 Mar;30(3):544-9. PubMed PMID: 12610815.

20: Heinemann V. Gemcitabine in the treatment of advanced pancreatic cancer: a comparative analysis of randomized trials. Semin Oncol. 2002 Dec;29(6 Suppl 20):9-16. Review. PubMed PMID: 12577228.

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27: Billinghurst RC, Buxton EM, Edwards MG, McGraw MS, McIlwraith CW. Use of an antineoepitope antibody for identification of type-II collagen degradation in equine articular cartilage. Am J Vet Res. 2001 Jul;62(7):1031-9. PubMed PMID: 11453476.

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29: Zucker S, Cao J, Chen WT. Critical appraisal of the use of matrix metalloproteinase inhibitors in cancer treatment. Oncogene. 2000 Dec 27;19(56):6642-50. Review. PubMed PMID: 11426650.

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33: Shah A, Woodruff M, Agarwal V, Liu P, Sundaresan P. Pharmacokinetics, safety, and tolerability of BAY 12-9566 and nonsteroidal anti-inflammatory agents (naproxen, ibuprofen) during coadministration in patients with osteoarthritis. J Clin Pharmacol. 2001 Mar;41(3):330-9. PubMed PMID: 11269574.

34: Hirte H, Goel R, Major P, Seymour L, Huan S, Stewart D, Yau J, Arnold A, Holohan S, Waterfield B, Bates S, Bennett K, Walsh W, Elias I. A phase I dose escalation study of the matrix metalloproteinase inhibitor BAY 12-9566 administered orally in patients with advanced solid tumours. Ann Oncol. 2000 Dec;11(12):1579-84. PubMed PMID: 11205466.

35: Hidalgo M, Eckhardt SG. Development of matrix metalloproteinase inhibitors in cancer therapy. J Natl Cancer Inst. 2001 Feb 7;93(3):178-93. Review. PubMed PMID: 11158186.

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38: Zucker S, Eckhardt SG, Rowinsky EK. Plasma MMPs as surrogates of BAY 12-9566. J Clin Oncol. 2000 Apr;18(8):1805-6. PubMed PMID: 10764446.

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