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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
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

Piclidenoson

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 Weight 510.3 g/mol
Molecular Formula C18H19IN6O4
XLogP30.9
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count8
Rotatable Bond Count5
Exact Mass510.05125 g/mol
Monoisotopic Mass510.05125 g/mol
Topological Polar Surface Area134 Ų
Heavy Atom Count29
Formal Charge0
Complexity589
Isotope Atom Count0
Defined Atom Stereocenter Count4
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

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.


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Looking for 152918-18-8 / Piclidenoson API manufacturers, exporters & distributors?

Piclidenoson manufacturers, exporters & distributors 1

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PharmaCompass offers a list of Piclidenoson API manufacturers, exporters & distributors, which can be sorted by GMP, USDMF, JDMF, KDMF, CEP (COS), WC, Price,and more, enabling you to easily find the right Piclidenoson manufacturer or Piclidenoson supplier for your needs.

Send us enquiries for free, and we will assist you in establishing a direct connection with your preferred Piclidenoson manufacturer or Piclidenoson supplier.

PharmaCompass also assists you with knowing the Piclidenoson API Price utilized in the formulation of products. Piclidenoson API Price is not always fixed or binding as the Piclidenoson Price is obtained through a variety of data sources. The Piclidenoson Price can also vary due to multiple factors, including market conditions, regulatory modifications, or negotiated pricing deals.

API | Excipient name

Piclidenoson

Synonyms

152918-18-8, Cf-101, 3-ib-meca, Cf 101, N(6)-ibamu, Cf101

Cas Number

152918-18-8

Unique Ingredient Identifier (UNII)

30679UMI0N

About Piclidenoson

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.

Piclidenoson Manufacturers

A Piclidenoson manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of Piclidenoson, including repackagers and relabelers. The FDA regulates Piclidenoson manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. Piclidenoson API Manufacturers are required to adhere to Good Manufacturing Practices (GMP) to ensure that their products are consistently manufactured to meet established quality criteria.

Piclidenoson Suppliers

A Piclidenoson supplier is an individual or a company that provides Piclidenoson active pharmaceutical ingredient (API) or Piclidenoson finished formulations upon request. The Piclidenoson suppliers may include Piclidenoson API manufacturers, exporters, distributors and traders.

Piclidenoson GMP

Piclidenoson Active pharmaceutical ingredient (API) is produced in GMP-certified manufacturing facility.

GMP stands for Good Manufacturing Practices, which is a system used in the pharmaceutical industry to make sure that goods are regularly produced and monitored in accordance with quality standards. The FDA’s current Good Manufacturing Practices requirements are referred to as cGMP or current GMP which indicates that the company follows the most recent GMP specifications. The World Health Organization (WHO) has its own set of GMP guidelines, called the WHO GMP. Different countries can also set their own guidelines for GMP like China (Chinese GMP) or the EU (EU GMP).

PharmaCompass offers a list of Piclidenoson GMP manufacturers, exporters & distributors, which can be sorted by USDMF, JDMF, KDMF, CEP (COS), WC, API price, and more, enabling you to easily find the right Piclidenoson GMP manufacturer or Piclidenoson GMP API supplier for your needs.

Piclidenoson CoA

A Piclidenoson CoA (Certificate of Analysis) is a formal document that attests to Piclidenoson's compliance with Piclidenoson specifications and serves as a tool for batch-level quality control.

Piclidenoson CoA mostly includes findings from lab analyses of a specific batch. For each Piclidenoson CoA document that a company creates, the USFDA specifies specific requirements, such as supplier information, material identification, transportation data, evidence of conformity and signature data.

Piclidenoson may be tested according to a variety of international standards, such as European Pharmacopoeia (Piclidenoson EP), Piclidenoson JP (Japanese Pharmacopeia) and the US Pharmacopoeia (Piclidenoson USP).

Inform the supplier about your product requirements, specifying if you need a product with particular monograph like EP (Ph. Eur.), USP, JP, BP, or any other quality. In addition, clarify whether you need hydrochloride (HCl), anhydricum, base, micronisatum or a specific level of purity. To find reputable suppliers, utilize the filters and select those certified by GMP, FDA, or any other certification as per your requirement.
For your convenience, we have listed synonyms and CAS numbers to help you find the best supplier. The use of synonyms and CAS numbers can be helpful in identifying potential suppliers, but it is crucial to note that they might not always indicate the exact same product. It is important to confirm the product details with the supplier before making a purchase to ensure that it meets your requirements.
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