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Bucillamine

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Chemistry

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Also known as: 65002-17-7, Tiobutarit, Rimatil, N-(2-mercapto-2-methylpropionyl)-l-cysteine, Thiobutarit, Bucilant

Molecular Formula

C₇H₁₃NO₃S₂

Molecular Weight

223.3 g/mol

InChI Key

VUAFHZCUKUDDBC-BYPYZUCNSA-N

FDA UNII

R80LRA5WTF

Bucillamine is an orally bioavailable derivative of the endogenous amino acid cysteine with two donatable thiol groups, with potential antioxidant and anti-inflammatory activities. Upon oral administration, bucillamine enters cells rapidly via the same pathway as cysteine and replenishes the thiol group in glutathione (GSH), thereby increasing intracellular GSH levels and GSH activity. GSH is an antioxidant and plays an important protective role in oxidative stress and injury. Bucillamine may have additional anti-inflammatory effects, though the mechanisms of action have yet to be fully elucidated.

1 2D Structure

Bucillamine

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2R)-2-[(2-methyl-2-sulfanylpropanoyl)amino]-3-sulfanylpropanoic acid

2.1.2 InChI

InChI=1S/C7H13NO3S2/c1-7(2,13)6(11)8-4(3-12)5(9)10/h4,12-13H,3H2,1-2H3,(H,8,11)(H,9,10)/t4-/m0/s1

2.1.3 InChI Key

VUAFHZCUKUDDBC-BYPYZUCNSA-N

2.1.4 Canonical SMILES

CC(C)(C(=O)NC(CS)C(=O)O)S

2.1.5 Isomeric SMILES

CC(C)(C(=O)N[C@@H](CS)C(=O)O)S

2.2 Other Identifiers

2.2.1 UNII

R80LRA5WTF

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 2-mercapto-2-methylpropanoyl-l-cysteine

2. De-019

3. De019

4. L-cysteine, N-(2-mercapto-2-methyl-1-oxopropyl)-

5. N-(2-mercapto-2-methylpropionyl)-l-cysteine

6. Rimatil

7. Sa 96

8. Sa-96

9. Tiobutarit

2.3.2 Depositor-Supplied Synonyms

1. 65002-17-7

2. Tiobutarit

3. Rimatil

4. N-(2-mercapto-2-methylpropionyl)-l-cysteine

5. Thiobutarit

6. Bucilant

7. De-019

8. (r)-3-mercapto-2-(2-mercapto-2-methylpropanamido)propanoic Acid

9. (2r)-2-[(2-methyl-2-sulfanylpropanoyl)amino]-3-sulfanylpropanoic Acid

10. N-(2-mercapto-2-methylpropanoyl)-l-cysteine

11. R80lra5wtf

12. Chembl80830

13. L-cysteine, N-(2-mercapto-2-methyl-1-oxopropyl)-

14. Dsstox_cid_28513

15. Dsstox_rid_82785

16. Dsstox_gsid_48587

17. Sa96

18. Bucilamina

19. Bucillaminum

20. (r)-3-mercapto-2-(2-mercapto-2-methylpropanamido)-propanoic Acid

21. Cas-65002-17-7

22. Bucilamina [spanish]

23. Bucillaminum [latin]

24. Bucillamine [inn:jan]

25. Unii-r80lra5wtf

26. N-(2-mercapto-2-methyl-1-oxopropyl)-l-cysteine

27. Ccris 5260

28. Sa-96

29. Ncgc00182062-02

30. Ncgc00183271-01

31. Bucilant (tn)

32. N-(2-mercaptoisobutyryl)-l-cysteine

33. Bucillamine [mi]

34. Bucillamine [inn]

35. Bucillamine [jan]

36. Bucillamine (jp17/inn)

37. Bucillamine [mart.]

38. Bucillamine [who-dd]

39. Mls006010100

40. Schembl121965

41. Dtxsid2048587

42. Chebi:31312

43. Zinc20222

44. Bcp12127

45. Tox21_112916

46. Tox21_113147

47. Bdbm50406934

48. Mfcd00867570

49. Rb3025

50. Akos015841445

51. Akos015895462

52. Am62722

53. Db12160

54. Ks-1449

55. Ac-32465

56. Smr004701240

57. Hy-118530

58. D01809

59. 002b177

60. A834941

61. Sr-01000883966

62. Q-101254

63. Q4982752

64. Sr-01000883966-1

65. (2r)-2-[(2-methyl-2-sulfanyl-propanoyl)amino]-3-sulfanyl-propanoic Acid

66. (2r)-3-mercapto-2-[(2-mercapto-2-methyl-1-oxopropyl)amino]propanoic Acid

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₇H₁₃NO₃S₂
Molecular Weight	223.3 g/mol
XLogP3	0.4
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	4
Exact Mass	223.03368562 g/mol
Monoisotopic Mass	223.03368562 g/mol
Topological Polar Surface Area	68.4 Å²
Heavy Atom Count	13
Formal Charge	0
Complexity	218
Isotope Atom Count	0
Defined Atom Stereocenter Count	1
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

Anti-Inflammatory Agents, Non-Steroidal

Anti-inflammatory agents that are non-steroidal in nature. In addition to anti-inflammatory actions, they have analgesic, antipyretic, and platelet-inhibitory actions. They act by blocking the synthesis of prostaglandins by inhibiting cyclooxygenase, which converts arachidonic acid to cyclic endoperoxides, precursors of prostaglandins. Inhibition of prostaglandin synthesis accounts for their analgesic, antipyretic, and platelet-inhibitory actions; other mechanisms may contribute to their anti-inflammatory effects. (See all compounds classified as Anti-Inflammatory Agents, Non-Steroidal.)

Antioxidants

Naturally occurring or synthetic substances that inhibit or retard oxidation reactions. They counteract the damaging effects of oxidation in animal tissues. (See all compounds classified as Antioxidants.)

4.2 ATC Code

M - Musculo-skeletal system

M01 - Antiinflammatory and antirheumatic products

M01C - Specific antirheumatic agents

M01CC - Penicillamine and similar agents

M01CC02 - Bucillamine

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