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CHEMISTRY
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DEVELOPMENTS

2 Drugs in Development

2 Drugs in Development

Synopsis

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Chemistry

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Also known as: 16208-51-8, Tavocept, Sodium 2,2'-disulfanediyldiethanesulfonate, Dimesna [inn], Dimesna-d8, Bnp-7787

Molecular Formula

C₄H₈Na₂O₆S₄

Molecular Weight

326.4 g/mol

InChI Key

KQYGMURBTJPBPQ-UHFFFAOYSA-L

FDA UNII

230R951Y4D

Dimesna is a synthetic derivative of dithio-ethane sulfonate with uroprotective properties. In the kidney, dimesna undergoes reduction to the free thiol compound, mesna, which reacts chemically with the urotoxic ifosfamide metabolites acrolein and 4-hydroxy-ifosfamide, resulting in their detoxification. This agent also inhibits cyclophosphamide-induced hemorrhagic cystitis.

1 2D Structure

Dimesna

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

disodium;2-(2-sulfonatoethyldisulfanyl)ethanesulfonate

2.1.2 InChI

InChI=1S/C4H10O6S4.2Na/c5-13(6,7)3-1-11-12-2-4-14(8,9)10;;/h1-4H2,(H,5,6,7)(H,8,9,10);;/q;2*+1/p-2

2.1.3 InChI Key

KQYGMURBTJPBPQ-UHFFFAOYSA-L

2.1.4 Canonical SMILES

C(CS(=O)(=O)[O-])SSCCS(=O)(=O)[O-].[Na+].[Na+]

2.2 Other Identifiers

2.2.1 UNII

230R951Y4D

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 2,2'-dithiodiethanesulfonic Acid

2. 2,2'-dithiodiethanesulfonic Acid, Ammonium Salt

3. 2,2'-dithiodiethanesulfonic Acid, Disodium Salt

4. Bnp7787

5. Disodium 2,2'-dithio-bis-ethane Sulfonate

6. Tavocept

2.3.2 Depositor-Supplied Synonyms

1. 16208-51-8

2. Tavocept

3. Sodium 2,2'-disulfanediyldiethanesulfonate

4. Dimesna [inn]

5. Dimesna-d8

6. Bnp-7787

7. Ethanesulfonic Acid, 2,2'-dithiobis-, Disodium Salt

8. Bis(2-sulfoethyl)disulfide Disodium Salt

9. 1189975-43-6

10. Disodium 2,2'-dithiodiethanesulfonate

11. Disodium 2,2'-dithio-bis-ethane Sulfonate

12. Bnp7787

13. Disodium;2-(2-sulfonatoethyldisulfanyl)ethanesulfonate

14. 230r951y4d

15. Nsc-716976

16. Nsc-760345

17. Ethanesulfonic Acid, 2,2'-dithiobis-, Sodium Salt (1:2)

18. Dimesnum

19. Dimesnum [inn-latin]

20. Ccris 5852

21. Bnp 7787

22. Einecs 240-337-2

23. Nsc 716976

24. Bionumerik

25. Disodium 2,2'-dithiobis(ethanesulfonate)

26. Beta,beta'-sulfoethyldisulfide, Disodium Salt

27. Unii-230r951y4d

28. 2,2'-dithiodi-1-ethanesulfonic Acid Disodium Salt

29. Tavocept;bnp7787

30. Dinatrium 3,4-dithiahexan-1,6-disulfonat

31. Dimesna [usan]

32. Dimesna [mi]

33. Dimesna [mart.]

34. Dimesna [who-dd]

35. Schembl18847

36. Dinatrium 3,4-dithiahexan-1,6-disulfonat [iupac]

37. Ethanesulfonic Acid, 2,2'-dithiodi-, Disodium Salt

38. Chembl2104318

39. Dtxsid6066024

40. Hms3264g13

41. Hms3654m20

42. Hms3867m13

43. Hms3884k05

44. Bcp21002

45. Mfcd00868218

46. Akos015833466

47. Ac-1240

48. As-2006

49. Ccg-213814

50. Disodium 2,2'-dithiobisethane Sulfonate

51. Disodium 2,2'-dithiobis-ethane Sulfonate

52. Db-064437

53. Ft-0601551

54. Ft-0667231

55. Sw220298-1

56. Disodium 2,2'-dithiodiethanesulphonate

57. C73103

58. A883003

59. J-009892

60. Q27253698

2.4 Create Date

2005-08-08

3 Chemical and Physical Properties

Molecular Formula	C₄H₈Na₂O₆S₄
Molecular Weight	326.4 g/mol
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	8
Rotatable Bond Count	5
Exact Mass	325.89991123 g/mol
Monoisotopic Mass	325.89991123 g/mol
Topological Polar Surface Area	182 Å²
Heavy Atom Count	16
Formal Charge	0
Complexity	268
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	3

4 Pharmacology and Biochemistry

4.1 MeSH Pharmacological Classification

Protective Agents

Synthetic or natural substances which are given to prevent a disease or disorder or are used in the process of treating a disease or injury due to a poisonous agent. (See all compounds classified as Protective Agents.)

Drugs in Development