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2D Structure
Also known as: 179545-77-8, Bay 12-9566, Bay-12-9566, (s)-4-(4'-chloro-[1,1'-biphenyl]-4-yl)-4-oxo-2-((phenylthio)methyl)butanoic acid, Am1zx94exh, Bay-129566
Molecular Formula
C23H19ClO3S
Molecular Weight
410.9  g/mol
InChI Key
JXAGDPXECXQWBC-LJQANCHMSA-N
FDA UNII
AM1ZX94EXH

Tanomastat 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.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(2S)-4-[4-(4-chlorophenyl)phenyl]-4-oxo-2-(phenylsulfanylmethyl)butanoic acid
2.1.2 InChI
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
2.1.3 InChI Key
JXAGDPXECXQWBC-LJQANCHMSA-N
2.1.4 Canonical SMILES
C1=CC=C(C=C1)SCC(CC(=O)C2=CC=C(C=C2)C3=CC=C(C=C3)Cl)C(=O)O
2.1.5 Isomeric SMILES
C1=CC=C(C=C1)SC[C@@H](CC(=O)C2=CC=C(C=C2)C3=CC=C(C=C3)Cl)C(=O)O
2.2 Other Identifiers
2.2.1 UNII
AM1ZX94EXH
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Bay 12-9566

2. Bay 12-9566n

3. Bay 129566

4. Bay-12-9566

2.3.2 Depositor-Supplied Synonyms

1. 179545-77-8

2. Bay 12-9566

3. Bay-12-9566

4. (s)-4-(4'-chloro-[1,1'-biphenyl]-4-yl)-4-oxo-2-((phenylthio)methyl)butanoic Acid

5. Am1zx94exh

6. Bay-129566

7. Chembl261932

8. (s)-4-[4-(4-chlorophenyl)phenyl]-4-oxo-2-(phenylsulfanylmethyl)butanoic Acid

9. (2s)-4-[4-(4-chlorophenyl)phenyl]-4-oxo-2-(phenylsulfanylmethyl)butanoic Acid

10. [1,1'-biphenyl]-4-butanoic Acid, 4'-chloro-gamma-oxo-alpha-[(phenylthio)methyl]-, (alphas)-

11. C23h19clo3s

12. Tanomastat [usan:inn]

13. Unii-am1zx94exh

14. (1,1'-biphenyl)-4-butanoic Acid, 4'-chloro-gamma-oxo-alpha-((phenylthio)methyl)-, (alphas)-

15. Tanomastat [inn]

16. Tanomastat (usan/inn)

17. Tanomastat [usan]

18. Tanomastat [who-dd]

19. Schembl153066

20. Bay12-9566

21. Gtpl6468

22. Bay 129566

23. Dtxsid60870145

24. Chebi:188765

25. Ex-a7633

26. Bay 12-9566n

27. Bdbm50084661

28. Akos015911399

29. Bay 12-9566 N

30. Db06276

31. (s)-4'-chloro-gamma-oxo-alpha-((phenylthio)methyl)(1,1'-biphenyl)-4-butanoic Acid

32. Hy-12168

33. Cs-0003131

34. Ft-0674808

35. Ns00068311

36. C90420

37. D03802

38. (1,1'-biphenyl)-4-butanoic Acid, 4'-chloro-gamma-oxo-alpha-((phenylthio)methyl)-, (s)-

39. (2s)-4-[4-(4-chlorophenyl)phenyl]-4-oxo-2-(phenylsulanylmethyl)butanoic Acid

40. (s)-3-((4'-chloro-4-biphenylyl)carbonyl)-2-((phenylthio)methyl)propionic Acid

41. (s)-4-(4'-chloro-[1,1'-biphenyl]-4-yl)-4-oxo-2-((phenylthio)methyl)butanoicacid

42. 4-(4''-chloro-biphenyl-4-yl)-4-oxo-2-phenylsulfanylmethyl-butyric Acid(bay-12-9566)

2.4 Create Date
2006-07-28
3 Chemical and Physical Properties
Molecular Weight 410.9 g/mol
Molecular Formula C23H19ClO3S
XLogP35.5
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count4
Rotatable Bond Count8
Exact Mass g/mol
Monoisotopic Mass g/mol
Topological Polar Surface Area79.7
Heavy Atom Count28
Formal Charge0
Complexity504
Isotope Atom Count0
Defined Atom Stereocenter Count1
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Indication

Investigated for use/treatment in pancreatic cancer, lung cancer, ovarian cancer, and osteoarthritis.


5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

Antineoplastic Agents

Substances that inhibit or prevent the proliferation of NEOPLASMS. (See all compounds classified as Antineoplastic Agents.)