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    Andrographolide

    ACTIVE PHARMA INGREDIENTS

    REF. STANDARDS & IMPURITIES

    PharmaCompass
    $ API Ref.Price (USD/KG) : 15,860Xls

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    2D Structure
    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

    2D Structure

    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 Weight 350.4 g/mol
    Molecular Formula C20H30O5
    XLogP32.2
    Hydrogen Bond Donor Count3
    Hydrogen Bond Acceptor Count5
    Rotatable Bond Count3
    Exact Mass350.20932405 g/mol
    Monoisotopic Mass350.20932405 g/mol
    Topological Polar Surface Area87 Ų
    Heavy Atom Count25
    Formal Charge0
    Complexity597
    Isotope Atom Count0
    Defined Atom Stereocenter Count6
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count1
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    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.