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2D Structure
Also known as: 121808-62-6, (r)-3-((s)-5-oxopyrrolidine-2-carbonyl)thiazolidine-4-carboxylic acid, Pidotomod, Pidotimod [inn], Pgt/1a, Pilimod
Molecular Formula
C9H12N2O4S
Molecular Weight
244.27  g/mol
InChI Key
UUTKICFRNVKFRG-WDSKDSINSA-N
FDA UNII
785363R681

Pidotimod is a synthetic dipeptide with immunomodulatory properties.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(4R)-3-[(2S)-5-oxopyrrolidine-2-carbonyl]-1,3-thiazolidine-4-carboxylic acid
2.1.2 InChI
InChI=1S/C9H12N2O4S/c12-7-2-1-5(10-7)8(13)11-4-16-3-6(11)9(14)15/h5-6H,1-4H2,(H,10,12)(H,14,15)/t5-,6-/m0/s1
2.1.3 InChI Key
UUTKICFRNVKFRG-WDSKDSINSA-N
2.1.4 Canonical SMILES
C1CC(=O)NC1C(=O)N2CSCC2C(=O)O
2.1.5 Isomeric SMILES
C1CC(=O)N[C@@H]1C(=O)N2CSC[C@H]2C(=O)O
2.2 Other Identifiers
2.2.1 UNII
785363R681
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 3-((5-oxo-2-pyrrolidinyl)carbonyl)-4-thiazolidinecarboxylic Acid

2. 3-pyroglutamylthiazolidine-4-carboxylic Acid

3. 3-pyroglutamylthiazolidine-4-carboxylic Acid, (r-(r*,s*))-isomer

4. Adimod

5. Pgt-1a

2.3.2 Depositor-Supplied Synonyms

1. 121808-62-6

2. (r)-3-((s)-5-oxopyrrolidine-2-carbonyl)thiazolidine-4-carboxylic Acid

3. Pidotomod

4. Pidotimod [inn]

5. Pgt/1a

6. Pilimod

7. Nsc-759841

8. (r)-3-((s)-5-oxoprolyl)-4-thiazolidinecarboxylic Acid

9. Pidotimod (inn)

10. (4r)-3-[(2s)-5-oxopyrrolidine-2-carbonyl]-1,3-thiazolidine-4-carboxylic Acid

11. Ncgc00160516-01

12. Polimod

13. (4r)-3-{[(2s)-5-oxopyrrolidin-2-yl]carbonyl}-1,3-thiazolidine-4-carboxylic Acid

14. 785363r681

15. Pidotimodum

16. Pigitil

17. Pidotimodum [inn-latin]

18. 4-thiazolidinecarboxylic Acid, 3-[[(2s)-5-oxo-2-pyrrolidinyl]carbonyl]-, (4r)-

19. Smr000466390

20. Ccris 7271

21. Brn 6636310

22. Onaka

23. Thymodolic Acid

24. Axil

25. Timodolic Acid

26. Pilimod (tn)

27. Pidotimod - Bio-x

28. Unii-785363r681

29. Pidotimod [mi]

30. Pidotimod [mart.]

31. (r-(r*,s*))-3-((5-oxo-2-pyrrolidinyl)carbonyl)-4-thiazolidinecarboxylic Acid

32. Pidotimod [who-dd]

33. (4r)-3-[[(2s)-5-oxo-2-pyrrolidinyl]carbonyl]-4-thiazolidinecarboxylic Acid

34. (r)-3-((s)-(5-oxo-2-pyrrolidinyl)carbonyl)-thiazolidin-4-carbonsaeure [german]

35. Dsstox_cid_26199

36. Dsstox_rid_81430

37. Dsstox_gsid_46199

38. Mls000759528

39. Mls001032108

40. Mls001216453

41. Mls001423953

42. Schembl138407

43. Chembl1488165

44. Dtxsid0046199

45. Pidotimod, >=98% (hplc)

46. Chebi:94618

47. Hms2051c04

48. Hms2231m03

49. Hms3715h06

50. Pharmakon1600-01502322

51. Bcp05222

52. Hy-b0944

53. Zinc3781245

54. Tox21_111865

55. Mfcd00867583

56. Nsc759841

57. S3106

58. (r)-3-((s)-(5-oxo-2-pyrrolidinyl)carbonyl)-thiazolidin-4-carbonsaeure

59. Akos015896354

60. Ac-3493

61. Am90280

62. Ccg-100832

63. Db11364

64. Ks-5229

65. Nc00082

66. Nsc 759841

67. (r)-3-[[(s)-5-oxo-2-pyrrolidinyl]carbonyl]-1,3-thiazolidine-4-carboxylic Acid

68. 4-thiazolidinecarboxylic Acid, 3-((5-oxo-2-pyrrolidinyl)carbonyl)-, (r-(r*,s*))-

69. Ncgc00160516-03

70. Bp164260

71. Cas-121808-62-6

72. P2147

73. Sw197462-2

74. D07261

75. Ab00639966-08

76. Ab00639966_10

77. Ab00639966_11

78. 808p626

79. A804790

80. J-502193

81. Q3902720

82. (4r)-3-[(2s)-5-oxopyrrolidine-2-carbonyl]thiazolidine-4-carboxylic Acid;pidotimod

83. (4r)-3-[[(2s)-5-oxo-2-pyrrolidinyl]carbonyl]thiazolidine-4-carboxylic Acid

84. (4r)-3-[oxo-[(2s)-5-oxo-2-pyrrolidinyl]methyl]-4-thiazolidinecarboxylic Acid

2.4 Create Date
2005-08-08
3 Chemical and Physical Properties
Molecular Weight 244.27 g/mol
Molecular Formula C9H12N2O4S
XLogP3-0.7
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count5
Rotatable Bond Count2
Exact Mass244.05177804 g/mol
Monoisotopic Mass244.05177804 g/mol
Topological Polar Surface Area112 Ų
Heavy Atom Count16
Formal Charge0
Complexity346
Isotope Atom Count0
Defined Atom Stereocenter Count2
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

For use as immunostimulant therapy for treatment of cell-mediated immunosuppression with respiratory or urinary infections.


5 Pharmacology and Biochemistry
5.1 Pharmacology

Pidotimod modulates the immune system to induce an immune response against bacterial or viral pathogens


5.2 MeSH Pharmacological Classification

Adjuvants, Immunologic

Substances that augment, stimulate, activate, potentiate, or modulate the immune response at either the cellular or humoral level. The classical agents (Freund's adjuvant, BCG, Corynebacterium parvum, et al.) contain bacterial antigens. Some are endogenous (e.g., histamine, interferon, transfer factor, tuftsin, interleukin-1). Their mode of action is either non-specific, resulting in increased immune responsiveness to a wide variety of antigens, or antigen-specific, i.e., affecting a restricted type of immune response to a narrow group of antigens. The therapeutic efficacy of many biological response modifiers is related to their antigen-specific immunoadjuvanticity. (See all compounds classified as Adjuvants, Immunologic.)


Immunologic Factors

Biologically active substances whose activities affect or play a role in the functioning of the immune system. (See all compounds classified as Immunologic Factors.)


5.3 ATC Code

L - Antineoplastic and immunomodulating agents

L03 - Immunostimulants

L03A - Immunostimulants

L03AX - Other immunostimulants

L03AX05 - Pidotimod


5.4 Absorption, Distribution and Excretion

Absorption

Bioavailability of 45%.


Route of Elimination

95% of intravenous dose is eliminated in the urine as the parent compound.


5.5 Biological Half-Life

Half life of 4 h.


5.6 Mechanism of Action

Pidotimod inhibits tumor necrosis factor (TNF-) induced increases in extracellular signal-related kinase (ERK) phosphorylation. It also increases nuclear factor B (NFB) expression and translocation to the nucleus. It is these to modulatory effects on ERK and NFB signalling which are thought to produce the increase in toll-like receptor expression seen with pidotimod. Pidotimod increase maturation of dendritic cells responsible for presenting antigens to naive Th-cells. It also appears to result in a greater population these cells diiferentiating to Th1 cells which are believed to mediate the immune response to pathogens like bacteria and viruses. Lastly, pidotimod appears to increase antigen-specific antibody titer and cytotoxic response with antigen exposure. The precise mechanism and timeline of events leading to these effects is unknown.