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    Bucillamine

    ACTIVE PHARMA INGREDIENTS

    DEVELOPMENTS

    FINISHED DOSAGE FORMULATIONS

    DIGITAL CONTENT

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    2D Structure
    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

    2D Structure

    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 Weight 223.3 g/mol
    Molecular Formula C7H13NO3S2
    XLogP30.4
    Hydrogen Bond Donor Count4
    Hydrogen Bond Acceptor Count5
    Rotatable Bond Count4
    Exact Mass223.03368562 g/mol
    Monoisotopic Mass223.03368562 g/mol
    Topological Polar Surface Area68.4 Ų
    Heavy Atom Count13
    Formal Charge0
    Complexity218
    Isotope Atom Count0
    Defined Atom Stereocenter Count1
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    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