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
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 |
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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 |
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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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Inhibition of cell-cycle progression in human colorectal carcinoma Lovo cells by andrographolide. | 2008 Aug 11 |
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Andrographolide could inhibit human colorectal carcinoma Lovo cells migration and invasion via down-regulation of MMP-7 expression. | 2009 Aug 14 |
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Effects of Andrographis paniculata extract and Andrographolide on hepatic cytochrome P450 mRNA expression and monooxygenase activities after in vivo administration to rats and in vitro in rat and human hepatocyte cultures. | 2009 May 15 |
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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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Cellular glutathione content modulates the effect of andrographolide on β-naphthoflavone-induced CYP1A1 mRNA expression in mouse hepatocytes. | 2011 Feb 4 |
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Combination therapy with andrographolide and d-penicillamine enhanced therapeutic advantage over monotherapy with d-penicillamine in attenuating fibrogenic response and cell death in the periportal zone of liver in rats during copper toxicosis. | 2011 Jan 1 |
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Andrographolide causes apoptosis via inactivation of STAT3 and Akt and potentiates antitumor activity of gemcitabine in pancreatic cancer. | 2013 Sep 12 |
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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
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Classification Tree | Code System | Code | ||
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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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DTXSID3045980
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C030419
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DB05767
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410105JHGR
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SUBSTANCE RECORD