Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C20H30O5 |
Molecular Weight | 350.4492 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 6 / 6 |
E/Z Centers | 1 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@]12CCC(=C)[C@@H](C\C=C3/[C@H](O)COC3=O)[C@]1(C)CC[C@@H](O)[C@@]2(C)CO
InChI
InChIKey=BOJKULTULYSRAS-OTESTREVSA-N
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
Molecular Formula | C20H30O5 |
Molecular Weight | 350.4492 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 6 / 6 |
E/Z Centers | 1 |
Optical Activity | UNSPECIFIED |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/27896563Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/25553378
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27896563
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/25553378
Andrographolide, a diterpenoid, is known for its anti-inflammatory effects. It can be isolated from various plants of the genus Andrographis, commonly known as 'creat'. Andrographolide has been tested for its anti-inflammatory effects in various stressful conditions, such as ischemia, pyrogenesis, arthritis, hepatic or neural toxicity, carcinoma, and oxidative stress. Apart from its anti-inflammatory effects, andrographolide also exhibits immunomodulatory effects by effectively enhancing cytotoxic T cells, natural killer (NK) cells, phagocytosis, and antibody-dependent cell-mediated cytotoxicity (ADCC). The properties of andrographolide, such as its ability to induce apoptosis of cancer cells and inhibition of DTH, its anti-oxidative and cytoprotective effect, and its ability to enhance CTLs and NK cell activation makes it a potent antiviral agent. Andrographolide inhibited the growth of human breast, prostate, and hepatoma tumors. Andrographolide could be a potent anticancer agent when used in combination with other chemotherapeutic agents.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/20880404
Curator's Comment: Andrographolide was able to cross the brain–blood barrier
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2094258 |
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Target ID: P01583 Gene ID: 3552.0 Gene Symbol: IL1A Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/24799081 |
0.34 µM [IC50] | ||
Target ID: CHEMBL1909490 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24799081 |
1.52 µM [IC50] | ||
Target ID: CHEMBL1795129 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24799081 |
0.56 µM [IC50] | ||
Target ID: CHEMBL387 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25506809 |
14.87 µM [IC50] | ||
Target ID: CHEMBL394 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25506809 |
14.18 µM [IC50] | ||
Target ID: CHEMBL613497 |
54.1 µM [IC50] | ||
Target ID: CHEMBL614285 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24875131 |
151.4 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
141.7 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11081986 |
20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered: |
ANDROGRAPHOLIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1294 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11081986 |
20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered: |
ANDROGRAPHOLIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
3.94 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11081986 |
20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered: |
ANDROGRAPHOLIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
45% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11081986 |
20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered: |
ANDROGRAPHOLIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
moderate to weak [IC50 245.7 uM] | ||||
no [IC50 >100 uM] | ||||
no [IC50 >100 uM] | ||||
no [IC50 >100 uM] | ||||
no [IC50 >100 uM] | ||||
no [IC50 >100 uM] | ||||
no [IC50 >200 uM] | ||||
no [IC50 >200 uM] | ||||
no [Inhibition 100 uM] | ||||
Sources: https://pubmed.ncbi.nlm.nih.gov/30606060/ |
no | |||
unlikely [Inhibition 100 uM] | ||||
unlikely [Inhibition 100 uM] | ||||
unlikely [Inhibition 100 uM] | ||||
unlikely | ||||
weak [Inhibition 100 uM] | ||||
weak [Inhibition 100 uM] | ||||
weak [Inhibition 100 uM] | ||||
weak [Inhibition 100 uM] | ||||
weak [Inhibition 100 uM] | ||||
yes [Inhibition 10 uM] | ||||
yes [Inhibition 10 uM] | ||||
yes [Inhibition 100 uM] | ||||
yes | ||||
yes | ||||
yes |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
major [Km 1.46 uM] | ||||
minor [Km 1020 uM] | ||||
minor | ||||
minor | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
yes |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
PubMed
Title | Date | PubMed |
---|---|---|
Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods. | 2006 Nov |
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Strong synergistic induction of CYP1A1 expression by andrographolide plus typical CYP1A inducers in mouse hepatocytes. | 2007 Oct 15 |
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Synergistic increases of metabolism and oxidation-reduction genes on their expression after combined treatment with a CYP1A inducer and andrographolide. | 2009 Dec 10 |
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Potency of andrographolide as an antitumor compound in BHC-induced liver damage. | 2009 Jun |
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The human bitter taste receptor hTAS2R50 is activated by the two natural bitter terpenoids andrographolide and amarogentin. | 2009 Nov 11 |
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Herb-drug interaction of Andrographis paniculata extract and andrographolide on the pharmacokinetics of theophylline in rats. | 2010 Mar 30 |
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Different AhR binding sites of diterpenoid ligands from Andrographis paniculata caused differential CYP1A1 induction in primary culture in mouse hepatocytes. | 2011 Dec |
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Andrographolide sensitizes the cytotoxicity of human colorectal carcinoma cells toward cisplatin via enhancing apoptosis pathways in vitro and in vivo. | 2014 May |
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Enhanced protective activity of nano formulated andrographolide against arsenic induced liver damage. | 2015 Dec 5 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://clinicaltrials.gov/ct2/show/NCT02273635
Coated tablets containing 140 mg andrographolide twice a day orally administered for a period of 24 months.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27793052
Andrographolide (1-30 uM) significantly decreased the levels of iNOS, COX2, IL-6 and TNF-α in murine bone marrow derived macrophage (BMDM) cells under LPS stimulation
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 16:54:04 GMT 2023
by
admin
on
Fri Dec 15 16:54:04 GMT 2023
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Record UNII |
410105JHGR
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Record Status |
Validated (UNII)
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Record Version |
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DSLD |
2449 (Number of products:2)
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NCI_THESAURUS |
C1327
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100000145625
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5318517
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226-852-5
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383468
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SUB124381
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m1897
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C61637
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5508-58-7
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Andrographolide
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1034862
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C030419
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DB05767
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410105JHGR
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