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Andrographolide

Andrographolide

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Also known as: 5508-58-7, Chebi:65408, (s,e)-4-hydroxy-3-(2-((1r,4as,5r,6r,8as)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylenedecahydronaphthalen-1-yl)ethylidene)dihydrofuran-2(3h)-one, Hmpl004, Andro, 410105jhgr

Molecular Formula

C₂₀H₃₀O₅

Molecular Weight

350.4 g/mol

InChI Key

BOJKULTULYSRAS-OTESTREVSA-N

FDA UNII

410105JHGR

Andrographolide is a labdane diterpenoid that is produced by the Andrographis paniculata plant, which has a broad range of therapeutic applications including anti-inflammatory and anti-platelet aggregation activities and potential antineoplastic properties. Since andrographolide has multiple therapeutic activities there are several proposed mechanisms of action for this agent. The anti-inflammatory effects of this agent appear to be related to the inhibition of nitric oxide (NO) production by macrophages. This agent may activate the NO/cyclic GMP pathway and inhibit both the phospholipase C gamma 2 (PLC gamma2)/protein kinase C (PKC) and PI3K/AKT-MAPK signaling pathways in activated platelets to inhibit platelet aggregation. In activated platelets, these three signaling pathways are downstream of integrin activation mediated by collagen binding and influence the association of fibrinogen with its receptors. Additionally, andrographolide may exert its anti-cancer activity through the induction of cell cycle arrest at G0/G1 phase and the stimulation of lymphocyte proliferation and activation. These processes could result in decreased proliferation of and increased immunocytotoxicity against tumor cells.

1 2D Structure

Andrographolide

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(3E,4S)-3-[2-[(1R,4aS,5R,6R,8aS)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]ethylidene]-4-hydroxyoxolan-2-one

2.1.2 InChI

InChI=1S/C20H30O5/c1-12-4-7-16-19(2,9-8-17(23)20(16,3)11-21)14(12)6-5-13-15(22)10-25-18(13)24/h5,14-17,21-23H,1,4,6-11H2,2-3H3/b13-5+/t14-,15-,16+,17-,19+,20+/m1/s1

2.1.3 InChI Key

BOJKULTULYSRAS-OTESTREVSA-N

2.1.4 Canonical SMILES

CC12CCC(C(C1CCC(=C)C2CC=C3C(COC3=O)O)(C)CO)O

2.1.5 Isomeric SMILES

C[C@@]12CC[C@H]([C@@]([C@H]1CCC(=C)[C@H]2C/C=C/3\[C@@H](COC3=O)O)(C)CO)O

2.2 Other Identifiers

2.2.1 UNII

410105JHGR

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 17-hydro-9-dehydro-andrographolide

2. Isoandrographolide

2.3.2 Depositor-Supplied Synonyms

1. 5508-58-7

2. Chebi:65408

3. (s,e)-4-hydroxy-3-(2-((1r,4as,5r,6r,8as)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylenedecahydronaphthalen-1-yl)ethylidene)dihydrofuran-2(3h)-one

4. Hmpl004

5. Andro

6. 410105jhgr

7. Nsc-383468

8. 3alpha,14,15,18-tetrahydroxy-5b,9bh,10a-labda-8(20),12-dien-16-oic Acid Gamma-lactone

9. (3e,4s)-3-[2-[(1r,4as,5r,6r,8as)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1h-naphthalen-1-yl]ethylidene]-4-hydroxyoxolan-2-one

10. 3-(2-(decahydro-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylenenaphthyl)ethylidene)dihydro-4-hydroxyfuran-2(3h)-one

11. (1r-(1-alpha(e(s)),4abeta,5alpha,6alpha,8aalpha))-3-(2-(decahydro-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylene-1-naphthalenyl)ethylidene)dihydro-4-hydroxy-2(3h)-furanone

12. (3e,4s)-3-{2-[(1r,4as,5r,6r,8as)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-decahydronaphthalen-1-yl]ethylidene}-4-hydroxyoxolan-2-one

13. (3e,4s)-4-hydroxy-3-{2-[(1r,4as,5r,6r,8as)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidenedecahydronaphthalen-1-yl]ethylidene}dihydrofuran-2(3h)-one

14. 2(3h)-furanone, 3-[2-[(1r,4as,5r,6r,8as)-decahydro-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylene-1-naphthalenyl]ethylidene]dihydro-4-hydroxy-, (3e,4s)-

15. Unii-410105jhgr

16. Hmpl-004

17. Nsc383468

18. Ncgc00095597-01

19. 2(3h)-furanone, 3-(2-((1r,4as,5r,6r,8as)-decahydro-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylene-1-naphthalenyl)ethylidene)dihydro-4-hydroxy-, (3e,4s)-

20. Einecs 226-852-5

21. Nsc 383468

22. Andrographolide, 98%

23. Andrographolide [mi]

24. Dsstox_cid_25980

25. Dsstox_rid_81270

26. Dsstox_gsid_45980

27. Andrographolide [inci]

28. Bidd:er0530

29. Chembl186141

30. Gtpl9675

31. Megxp0_000978

32. Andrographolide [usp-rs]

33. Andrographolide [who-dd]

34. Dtxsid3045980

35. Schembl12056309

36. Acon1_002113

37. (3e,4s)-3-(2-((1r,4as,5r,6r,8as)-decahydro-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylene-1-naphthalenyl)ethylidene)dihydro-4-hydroxy-2(3h)-furanone

38. 869807-57-8

39. Act03252

40. Andrographolide, Analytical Standard

41. Hy-n0191

42. Zinc3881797

43. Tox21_111508

44. Bdbm50084419

45. Mfcd07778082

46. Akos015920075

47. Ccg-208428

48. Cs-3334

49. Db05767

50. Ncgc00179817-01

51. Ncgc00179817-02

52. As-13637

53. Cas-5508-58-7

54. C20214

55. 508a587

56. A830479

57. Q-100624

58. Q4759444

59. Brd-k89282837-001-01-0

60. Andrographolide (constituent Of Andrographis) [dsc]

61. Andrographolide, United States Pharmacopeia (usp) Reference Standard

62. (3e)-3-[2-[(1r,8as)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylene-decalin-1-yl]ethylidene]-4-hydroxy-tetrahydrofuran-2-one;andrographolide

63. (3e,4s)-3-[2-[(1r,4as,5r,6r,8as)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylene-decalin-1-yl]ethylidene]-4-hydroxy-tetrahydrofuran-2-one

64. (5beta,9r,10alpha,14s)-3alpha,14,15,18-tetrahydroxylabdane-8(20),12-diene-16-oic Acid Gamma-lactone

65. (s,e)-4-hydroxy-3-(2-((1r,4as,5r,6r,8as)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylenedecahydronaphthalen-1-yl)ethylidene)dihydrofuran-2

66. 2(3h)-furanone, 3-(2-(decahydro-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylene-1-naphthalenyl)ethylidene)dihydro-4-hydroxy-, (1r-(1-alpha(e(s*)),4a-beta,5-alpha,6-alpha,8a-alpha))-

67. 2(3h)-furanone,3-[2-[(1r,4as,5r,6r,8as)-decahydro-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylene-1-naphthalenyl]ethylidene]dihydro-4-hydroxy-,(3e,4s)-

68. 3.alpha.,14,15,18-tetrahydroxy-5.beta.,9.beta.h,10.alpha.-labda-8(20),12-dien-16-oic Acid .gamma.-lactone

2.4 Create Date

2006-01-18

3 Chemical and Physical Properties

Molecular Formula	C₂₀H₃₀O₅
Molecular Weight	350.4 g/mol
XLogP3	2.2
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	3
Exact Mass	350.20932405 g/mol
Monoisotopic Mass	350.20932405 g/mol
Topological Polar Surface Area	87 Å²
Heavy Atom Count	25
Formal Charge	0
Complexity	597
Isotope Atom Count	0
Defined Atom Stereocenter Count	6
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	1
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

Investigated for use/treatment in ulcerative colitis.

5 Pharmacology and Biochemistry

5.1 MeSH Pharmacological Classification

Antiprotozoal Agents

Substances that are destructive to protozoans. (See all compounds classified as Antiprotozoal Agents.)

Anti-Inflammatory Agents

Substances that reduce or suppress INFLAMMATION. (See all compounds classified as Anti-Inflammatory Agents.)

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.)

Antiviral Agents

Agents used in the prophylaxis or therapy of VIRUS DISEASES. Some of the ways they may act include preventing viral replication by inhibiting viral DNA polymerase; binding to specific cell-surface receptors and inhibiting viral penetration or uncoating; inhibiting viral protein synthesis; or blocking late stages of virus assembly. (See all compounds classified as Antiviral Agents.)

Platelet Aggregation Inhibitors

Drugs or agents which antagonize or impair any mechanism leading to blood platelet aggregation, whether during the phases of activation and shape change or following the dense-granule release reaction and stimulation of the prostaglandin-thromboxane system. (See all compounds classified as Platelet Aggregation Inhibitors.)

5.2 Mechanism of Action

HMPL-004 acts on multiple cellular targets in the inflammatory signal transduction pathways resulting in suppressed inflammation cytokine expression including TNF-, IL-1 and IL-6. HMPL-004 was demonstrated to inhibit TNF- and IL-1 production in cell-based assays. HMPL-004 is also able to inhibit NF-kB activation. NF-kB is a family of transcriptional factors that regulate a wide spectrum of genes critically involved in host defence and inflammation. The mechanism of action of HMPL-004 was further supported in laboratory IBD animal models. Treatment of IBD rats with HMPL-004 caused a significant drop in plasma cytokine concentrations, including TNF- and IL-1.