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Taurolidine

Taurolidine

Synopsis, Chemistry

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Also known as: 19388-87-5, Taurolidin, Taurolin, Cyclo-taurolidine, (cyclo)-taurolidine, 4-[(1,1-dioxo-1,2,4-thiadiazinan-4-yl)methyl]-1,2,4-thiadiazinane 1,1-dioxide

Molecular Formula

C₇H₁₆N₄O₄S₂

Molecular Weight

284.4 g/mol

InChI Key

AJKIRUJIDFJUKJ-UHFFFAOYSA-N

FDA UNII

8OBZ1M4V3V

Taurolidine is a synthetic broad-spectrum antibiotic with antibacterial, anticoagulant and potential antiangiogenic activities. Taurolidine, derived from the amino acid taurine, binds to and neutralizes bacterial exotoxins and endotoxins, or lipopolysaccharides (LPS). Taurolidine binding to LPS prevents bacterial adherence to host epithelial cells, thereby prevents bacterial invasion of uninfected host cells. Although the mechanism underlying its antineoplastic activity has not been fully elucidated, it may be related to this agent's anti-adherence property. In addition, taurolidine also promotes apoptosis by inducing various apoptotic factors and suppresses the production of vascular endothelial growth factor (VEGF), a protein that plays an important role in angiogenesis.

1 2D Structure

Taurolidine

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

4-[(1,1-dioxo-1,2,4-thiadiazinan-4-yl)methyl]-1,2,4-thiadiazinane 1,1-dioxide

2.1.2 InChI

InChI=1S/C7H16N4O4S2/c12-16(13)3-1-10(5-8-16)7-11-2-4-17(14,15)9-6-11/h8-9H,1-7H2

2.1.3 InChI Key

AJKIRUJIDFJUKJ-UHFFFAOYSA-N

2.1.4 Canonical SMILES

C1CS(=O)(=O)NCN1CN2CCS(=O)(=O)NC2

2.2 Other Identifiers

2.2.1 UNII

8OBZ1M4V3V

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 4,4'-methylenebis-(tetrahydro-1,2,4-thiadiazine- 1,1-dioxide)

2. Bis(1,1-dioxo-perhydro-1,2,4-thiadiazinyl-4)methane

3. Bis- (1,1-dioxoperhydro-1,2,4-thiadiazinyl-4)methane

4. Tauroflex

5. Taurolin

6. Tauroline

2.3.2 Depositor-Supplied Synonyms

1. 19388-87-5

2. Taurolidin

3. Taurolin

4. Cyclo-taurolidine

5. (cyclo)-taurolidine

6. 4-[(1,1-dioxo-1,2,4-thiadiazinan-4-yl)methyl]-1,2,4-thiadiazinane 1,1-dioxide

7. 8obz1m4v3v

8. 4,4'-methylenebis(1,2,4-thiadiazinane 1,1-dioxide)

9. Tauroline

10. 4,4'-methylenebis(tetrahydro-1,2,4-thiadiazine 1,1-dioxide)

11. Taurolidine (inn)

12. W-3100m

13. Taurolidine [inn]

14. Taurolidina

15. Taurolidinum

16. Taurolidinum [inn-latin]

17. Taurolidina [inn-spanish]

18. Taurolidine [inn:ban]

19. Einecs 243-016-5

20. Unii-8obz1m4v3v

21. Taurolidine [mi]

22. Taurolidine [mart.]

23. Schembl65313

24. Taurolidine [who-dd]

25. Chembl2105420

26. Dtxsid00173001

27. Chebi:135173

28. Amy28822

29. S4885

30. Taurolidine, >97% (nmr), Powder

31. Zinc19322537

32. Taurolock Component Taurolidine

33. 2h-1,2,4-thiadiazine, 4,4'-methylenebis[tetrahydro-, 1,1,1',1'-tetraoxide

34. Akos015896472

35. Ac-1423

36. Ccg-267310

37. Cs-w012238

38. Db12473

39. Hy-w011522

40. Ls-13376

41. Ft-0617113

42. T3980

43. D07146

44. D78247

45. 388t875

46. A813672

47. Sr-01000872621

48. Q3981568

49. Sr-01000872621-2

50. W-107711

51. 4,4'-methylenebis(1,2,4-thiadiazinane) 1,1,1',1'-tetraoxide

52. 4,4'-methylene-bis(tetrahydro-1,2,4-thiadiazine-1,1-dioxide)

53. 4-[(1,1-dioxido-1,2,4-thiadiazinan-4-yl)methyl]-1,2,4-thiadiazinane 1,1-dioxide #

2.4 Create Date

2005-03-27

3 Chemical and Physical Properties

Molecular Formula	C₇H₁₆N₄O₄S₂
Molecular Weight	284.4 g/mol
XLogP3	-1.7
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	8
Rotatable Bond Count	2
Exact Mass	284.06129735 g/mol
Monoisotopic Mass	284.06129735 g/mol
Topological Polar Surface Area	116 Å²
Heavy Atom Count	17
Formal Charge	0
Complexity	419
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Pharmacology and Biochemistry

4.1 MeSH Pharmacological Classification

Antineoplastic Agents

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

Anti-Infective Agents

Substances that prevent infectious agents or organisms from spreading or kill infectious agents in order to prevent the spread of infection. (See all compounds classified as Anti-Infective Agents.)

Anti-Infective Agents, Local

Substances used on humans and other animals that destroy harmful microorganisms or inhibit their activity. They are distinguished from DISINFECTANTS, which are used on inanimate objects. (See all compounds classified as Anti-Infective Agents, Local.)

4.2 ATC Code

B - Blood and blood forming organs

B05 - Blood substitutes and perfusion solutions

B05C - Irrigating solutions

B05CA - Antiinfectives

B05CA05 - Taurolidine