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NCGC00024978-05

NCGC00024978-05

Synopsis, Chemistry

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Also known as: Piclidenoson, 152918-18-8, Cf-101, 3-ib-meca, Cf 101, N(6)-ibamu

Molecular Formula

C₁₈H₁₉IN₆O₄

Molecular Weight

510.3 g/mol

InChI Key

HUJXGQILHAUCCV-MOROJQBDSA-N

FDA UNII

30679UMI0N

Piclidenoson is an orally bioavailable, adenosine A3 receptor (A3AR) agonist with potential anti-inflammatory activity. Upon administration, piclidenoson selectively targets, binds to and activates the cell surface-expressed A3AR, thereby activating transduction pathways in which A3AR plays a key role. This inhibits nuclear factor-kappa B (NF-kB) signaling and inhibits inflammatory cytokine production, such as tumor necrosis factor (TNF) and several interleukins. A3AR, a G protein-coupled receptor, plays a key role in many inflammatory diseases, and in certain types of cancer.

1 2D Structure

NCGC00024978-05

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2S,3S,4R,5R)-3,4-dihydroxy-5-[6-[(3-iodophenyl)methylamino]purin-9-yl]-N-methyloxolane-2-carboxamide

2.1.2 InChI

InChI=1S/C18H19IN6O4/c1-20-17(28)14-12(26)13(27)18(29-14)25-8-24-11-15(22-7-23-16(11)25)21-6-9-3-2-4-10(19)5-9/h2-5,7-8,12-14,18,26-27H,6H2,1H3,(H,20,28)(H,21,22,23)/t12-,13+,14-,18+/m0/s1

2.1.3 InChI Key

HUJXGQILHAUCCV-MOROJQBDSA-N

2.1.4 Canonical SMILES

CNC(=O)C1C(C(C(O1)N2C=NC3=C(N=CN=C32)NCC4=CC(=CC=C4)I)O)O

2.1.5 Isomeric SMILES

CNC(=O)[C@@H]1[C@H]([C@H]([C@@H](O1)N2C=NC3=C(N=CN=C32)NCC4=CC(=CC=C4)I)O)O

2.2 Other Identifiers

2.2.1 UNII

30679UMI0N

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 3-ib-meca

2. N(6)-(3-iodobenzyl)-5'-n-methylcarboxamidoadenosine

3. N(6)-(3-iodobenzyl)adenosine-5'-n-methyluronamide

4. N(6)-ibamu

2.3.2 Depositor-Supplied Synonyms

1. Piclidenoson

2. 152918-18-8

3. Cf-101

4. 3-ib-meca

5. Cf 101

6. N(6)-ibamu

7. Cf101

8. N(6)-(3-iodobenzyl)-5'-n-methylcarboxamidoadenosine

9. Piclidenoson [usan]

10. 1-deoxy-1-(6-(((3-iodophenyl)methyl)amino)-9h-purin-9-yl)-n-methyl-beta-d-ribofuranuronamide

11. Chembl119709

12. (2s,3s,4r,5r)-3,4-dihydroxy-5-[6-[(3-iodophenyl)methylamino]purin-9-yl]-n-methyloxolane-2-carboxamide

13. Chebi:73286

14. 30679umi0n

15. (2s,3s,4r,5r)-3,4-dihydroxy-5-(6-((3-iodobenzyl)amino)-9h-purin-9-yl)-n-methyltetrahydrofuran-2-carboxamide

16. 3-iodobenzyl-5'-n-methylcarboxamidoadenosine

17. N6-(3-iodobenzyl)adenosine-5'-n-methyluronamide

18. (2s,3s,4r,5r)-3,4-dihydroxy-5-(6-(3-iodobenzylamino)-9h-purin-9-yl)-n-methyltetrahydrofuran-2-carboxamide

19. N(6)-(3-iodo-benzyl)adenosine-5'-n-methyluronamide

20. (2s,3s,4r,5r)-5-{6-[(3-iodobenzyl)amino]-9h-purin-9-yl}-3,4-dihydroxy-n-methyltetrahydrofuran-2-carboxamide

21. N(6)-(3-iodobenzyl)adenosine-5'-n-methyluronamide

22. Unii-30679umi0n

23. Rpr-113090

24. 1-deoxy-1-[6-[[(3-iodophenyl)methyl]amino]-9h-purin-9-yl]-n-methyl-beta-d-ribofuranuronamide

25. Ibmeca

26. Piclidenoson (usan/inn)

27. Piclidenoson [inn]

28. Gtpl422

29. Mls002153391

30. Piclidenoson [who-dd]

31. Schembl465039

32. Regid_for_cid_123683

33. Dtxsid50165158

34. Hms2234i04

35. Hms3412e09

36. Hms3676e09

37. 3,4-dihydroxy-5-[6-(3-iodo-benzylamino)-purin-9-yl]-tetrahydro-furan-2-carboxylic Acid Methylamide

38. Cf-101; Ib-meca; Piclidenoson

39. Ex-a2514

40. Zinc3811810

41. Bdbm50118812

42. Mfcd00671785

43. Si-615

44. Akos024456363

45. Cs-5048

46. Db05511

47. Ib-meca, Solid, >=98% (hplc)

48. Ncgc00024978-02

49. Ncgc00024978-03

50. Ncgc00024978-04

51. Ncgc00024978-05

52. Ncgc00024978-09

53. Ac-36111

54. As-16876

55. Beta-d-ribofuranuronamide, 1-deoxy-1-(6-(((3-iodophenyl)methyl)amo)-9h-purin-9-yl)-n-methyl-

56. Hy-13591

57. Smr001230772

58. D10971

59. A848868

60. J-008958

61. N6-(3-iodobenzyl)-5''-n-methylcarboxamidoadenosine

62. (n-6-(3-iodobenzyl)adenosine-5''-n-methyluronamide

63. Q27088384

64. Adenosine, N(6)-[3-iodobenzyl]-4'-methylcarbamoyl-4'-dehydroxymethyl-

65. 1-deoxy-1-[6-[[(3-iodophenyl)methyl]amino]-9h-purin-9-yl]-n-methyl-?-d-ribofuranuronamide

66. (2r,3r,4s,5s)-5-(6-(3-iodobenzylamino)-9h-purin-9-yl)-3,4-dihydroxy-n-methyl-tetrahydrofuran-2-carboxamide;cf 101

67. (2s,3s,4r,5r)-3,4-dihydroxy-5-[6-(3-iodo-benzylamino)-purin-9-yl]-tetrahydro-furan-2-carboxylic Acid Methylamide

68. (2s,3s,4r,5r)-5-(6-(3-iodobenzylamino)-9h-purin-9-yl)-3,4-dihydroxy-n-methyl-tetrahydrofuran-2-carboxamide

69. (3r,4s,5r)-3,4-dihydroxy-5-[6-(3-iodo-benzylamino)-purin-9-yl]-tetrahydro-furan-2-carboxylic Acid Methylamide

70. (3s,4r,5r)-3,4-dihydroxy-5-[6-(3-iodo-benzylamino)-purin-9-yl]-tetrahydro-furan-2-carboxylic Acid Methylamide

71. .beta.-d-ribofuranuronamide, 1-deoxy-1-(6-(((3-iodophenyl)methyl)amino)-9h-purin-9-yl)-n-methyl-

72. 1-deoxy-1-[6-[[(3-iodophenyl)methyl]amino]-9h-purin-9-yl]-n-methyl-beta-d-ribofuranuronamide;n6-(3-iodobenzyl)adenosine-5'-n-methyluronamide;(2r,3r,4s,5s)-5-(6-(3-iodobenzylamino)-9h-purin-9-yl)-3,4-dihydroxy-n-methyl-tetrahydrofuran-2-carboxamide;cf 101

2.4 Create Date

2005-08-08

3 Chemical and Physical Properties

Molecular Formula	C₁₈H₁₉IN₆O₄
Molecular Weight	510.3 g/mol
XLogP3	0.9
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	8
Rotatable Bond Count	5
Exact Mass	510.05125 g/mol
Monoisotopic Mass	510.05125 g/mol
Topological Polar Surface Area	134 Å²
Heavy Atom Count	29
Formal Charge	0
Complexity	589
Isotope Atom Count	0
Defined Atom Stereocenter Count	4
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

Investigated for use/treatment in cancer/tumors (unspecified), eye disorders/infections, psoriasis and psoriatic disorders, and rheumatoid arthritis. Can-Fite BioPharma has reported that by targeting the adenosine A3-receptor, CF101 may also be used to treat Crohn's disease, a serious gastrointestinal disorder.

5 Pharmacology and Biochemistry

5.1 Pharmacology

CF-101 is an adenoside A3 agonist for the treatment of a variety of autoimmune-inflammatory disorders, particularly rhematoid arthritis. In clinical trials, it was found to be safe, well tolerated and showed strong evidence of an anti-inflammatory effect in rheumatoid arthritis patients. In this trial, a statistically significant correlation was found between A(3)AR expression level and response to the drug, so A(3)AR expression may serve as a biopredictor of patient response.

5.2 Mechanism of Action

CF 101 is an A(3)AR agonist. A(3)AR is highly expressed in inflammatory cells and overexpressed in peripheral blood mononuclear cells, reflecting its role in the remote inflammatory process. In normal tissues, there is low adenoside A3 receptor expression. A(3)AR activation with a specific agonist deregulates the NF-kappaB signaling pathway in inflammatory cells and initiates immunomodulatory effects.