ANDROGRAPHOLIDE

Investigational

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

Structure Search

SMILES

C[C@@]1(CO)[C@H](O)CC[C@@]2(C)[C@H](C\C=C3/[C@H](O)COC3=O)C(=C)CC[C@H]12

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

HIDE SMILES / InChI

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

Description
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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Nuclear factor NF-kappa-B complex 11 Target ID: CHEMBL2094258 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15356172 \| https://www.ncbi.nlm.nih.gov/pubmed/27793052	Inhibitor 8504
Interleukin-1 alpha 2 Target ID: P01583 Gene ID: 3552.0 Gene Symbol: IL1A Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/24799081	Inhibitor 8504	0.34 µM [IC50]
Interleukin-1 beta 22 Target ID: CHEMBL1909490 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24799081	Inhibitor 8504	1.52 µM [IC50]
Interleukin-6 4 Target ID: CHEMBL1795129 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24799081	Inhibitor 8504	0.56 µM [IC50]
MCF7 22 Target ID: CHEMBL387 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25506809	Inhibitor 8504	14.87 µM [IC50]
HCT-116 7 Target ID: CHEMBL394 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25506809	Inhibitor 8504	14.18 µM [IC50]
Hepatitis B virus 8 Target ID: CHEMBL613497 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24731274 \| https://www.ncbi.nlm.nih.gov/pubmed/27896563	Inhibitor 8504	54.1 µM [IC50]
DLD-1 1 Target ID: CHEMBL614285 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24875131	Inhibitor 8504	151.4 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Colorectal cancer 102 Sources: https://clinicaltrials.gov/ct2/show/NCT01993472	Primary		Phase II 1147	Unknown Approved Use Unknown
Multiple sclerosis 107 Sources: https://clinicaltrials.gov/ct2/show/NCT02273635	Primary		Phase II 1147	Unknown Approved Use Unknown

C_max

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

T_1/2

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

F_unbound

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
supressor 22 inhibitor 2252	inhibitor 2438	inhibitor 2507 supressor 1	inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 2153 UGT2B4 23 CYP3A4/5 296 OAT1 725 CYP2B6 926 UGT1A3 89 UGT1A8 37 UGT1A6 136 UGT1A10 37 CYP2C 20 UGT2B7 197 UGT1A4 98 UGT1A9 148 UGT1A7 23 CYP2E1 1060 UGT1A1 246 OATP1B1 1079 OATP1B3 961	UGT2B4 278 UGT2B17 237 P-gp 2052 UGT1A3 470 UGT1A6 343 UGT1A8 323 UGT2B7 456 OAT1 395 UGT1A9 423 UGT1A4 399 UGT2B15 236 UGT1A10 331 UGT1A1 479 UGT1A7 249	OAT1 28

Drug as perpetrator

Target	Modality	Activity
CYP1A2 2333	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/18053665/	no [IC50 >100 uM]
CYP2C 37	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/18053665/	no [IC50 >100 uM]
CYP2C9 2497	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/21365364/	no [IC50 >100 uM]
CYP2D6 2546	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/21365364/	no [IC50 >100 uM]
CYP2E1 1146	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/18053665/	no [IC50 >100 uM]
CYP2B6 1160	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/18053665/	no [IC50 >200 uM]
CYP3A4/5 357	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/18053665/	no [IC50 >200 uM]
UGT1A8 49	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/24631340/	no [Inhibition 100 uM]
OAT1 730	inducer 1966 Sources: https://pubmed.ncbi.nlm.nih.gov/30606060/	no
UGT1A10 46	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/24631340/	unlikely [Inhibition 100 uM]
UGT1A4 100	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/24631340/	unlikely [Inhibition 100 uM]
UGT2B4 23	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/24631340/	unlikely [Inhibition 100 uM]
OAT1 730	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/30606060/	unlikely
CYP3A4 2633	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/21365364/	weak [IC50 245.7 uM]
UGT1A1 303	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/24631340/	weak [Inhibition 100 uM]
UGT1A3 99	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/24631340/	weak [Inhibition 100 uM]
UGT1A6 171	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/24631340/	weak [Inhibition 100 uM]
UGT1A7 25	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/24631340/	weak [Inhibition 100 uM]
UGT1A9 155	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/24631340/	weak [Inhibition 100 uM]
OATP1B1 1095	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/23571415/	yes [Inhibition 10 uM]
OATP1B3 970	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/23571415/	yes [Inhibition 10 uM]
UGT2B7 210	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/24631340/	yes [Inhibition 100 uM]
CYP1A2 2333	supressor 160 Sources: https://pubmed.ncbi.nlm.nih.gov/21219911/	yes
CYP2D6 2546	supressor 160 Sources: https://pubmed.ncbi.nlm.nih.gov/21219911/	yes
CYP3A4 2633	supressor 160 Sources: https://pubmed.ncbi.nlm.nih.gov/21925256/	yes

Drug as victim

Target	Modality	Activity
UGT2B7 456	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/25204783/	major [Km 1.46 uM]
UGT1A4 399	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/25204783/	minor [Km 1020 uM]
UGT1A3 470	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/25204783/	minor
UGT2B4 278	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/25204783/	minor
OAT1 395	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/30606060/	no
UGT1A1 479	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/25204783/	no
UGT1A10 331	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/25204783/	no
UGT1A6 343	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/25204783/	no
UGT1A7 249	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/25204783/	no
UGT1A8 323	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/25204783/	no
UGT1A9 423	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/25204783/	no
UGT2B15 236	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/25204783/	no
UGT2B17 237	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/25204783/	no
P-gp 2052	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/21721007/	yes

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://pubmed.ncbi.nlm.nih.gov/34075974/

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	NO22456	https://www.001chemical.com/chem/search?q=NO22456
1PlusChem LLC	1P003OCV	https://www.1pchem.com/search?query=1P003OCV
A2B Chem	AB70735	http://a2bchem.com/prod/AB70735
AK Scientific	J10022	https://aksci.com/item_detail.php?cat=J10022
AK Scientific	J92516	https://aksci.com/item_detail.php?cat=J92516
AK Scientific	L973	https://aksci.com/item_detail.php?cat=L973
Ambeed	A108018	http://www.ambeed.com/search/Search.html?keyword=A108018
AstaTech	33684	http://astatechinc.com/CPSResult.php?CRNO=33684
Biopurify Phytochemicals	BP0164	https://www.phytopurify.com/search.do?a=s&searchtype=3&psize=10&q=BP0164&searchhtmp=simplesearch&t=1
BioSynth	Q-100624	https://www.biosynth.com/en/products/life-science/other-biochemicals/products/Q-100624
BOC Sciences	5508-58-7	http://www.bocsci.com/description.asp?cas=5508-58-7
Cayman Chemical	11679	http://www.caymanchem.com/app/template/Product.vm/catalog/11679
Chem Scene	CS-3334	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-3334
Chem4Pharma	C4PN20	https://www.chem4pharma.com/product-page/C4PN20
ChemDiv	BB01-8144	http://chemistryondemand.com:8080/eShop/search_results.jsp?idnumber=BB01-8144
ChemShuttle	151608	https://www.chemshuttle.com/catalogsearch/result/?q=151608
Combi-Blocks	QA-8068	http://www.combi-blocks.com/cgi-bin/find.cgi?QA-8068
eMolecules	1935749	https://orderbb.emolecules.com/search/#?query=1935749
eMolecules	29909141	https://orderbb.emolecules.com/search/#?query=29909141
eMolecules	46012953	https://orderbb.emolecules.com/search/#?query=46012953
eMolecules	49265809	https://orderbb.emolecules.com/search/#?query=49265809
eNovation Chemicals	D378929	https://www.enovationchem.com/Products.asp?SEARCHTEXT=D378929&searchbtn.x=0&searchbtn.y=0
Frontier Scientific Services	501003435	http://orders.frontierssi.com/fssionline32/public/product.aspx?cat=501003435&type=hts
Indofine	A-003	https://indofinechemical.com/details.aspx?Sku=A-003
KeyOrganics	AS-13637	http://www.keyorganicsinc.com/bionet/catalogsearch/result?q=AS-13637
KeyOrganics	VS-02751	http://www.keyorganicsinc.com/bionet/catalogsearch/result?q=VS-02751
Lab Network	LN01040476	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN01040476
Lab Seeker	SC-46922	http://www.labseeker.com/search.php?keywords=SC-46922&category=0
LabSeeker	SC-46922	http://www.labseeker.com/search.php?keywords=SC-46922&category=0
Matrix Scientific	75423	http://www.matrixscientific.com/075423.html
mcule	MCULE-5521128905	https://mcule.com/MCULE-5521128905/
mcule	MCULE-7580934560	https://mcule.com/MCULE-7580934560/
mcule	MCULE-8461763255	https://mcule.com/MCULE-8461763255/
MedChem Express	HY-N0191	https://www.medchemexpress.com/search.html?q=HY-N0191&ft=&fa=&fp=
Molcore	CS22456	http://www.molcore.com/CatCS22456.html
MolPort	MolPort-001-741-138	https://www.molport.com/shop/molecule-link/MolPort-001-741-138
MolPort	MolPort-002-507-305	https://www.molport.com/shop/molecule-link/MolPort-002-507-305
MolPort	MolPort-003-931-008	https://www.molport.com/shop/molecule-link/MolPort-003-931-008
Oakwood	78895	http://www.oakwoodchemical.com/ProductsList.aspx?txtSearch=078895
PI Chemicals	PI-28635	http://www.pipharm.com/catalog_products/PI-28635.html
Princeton BioMolecular Research	OSSL_331483	http://www.princetonbio.com/order_online?common_id=OSSL_331483
Selleck Chemicals	S2261	http://www.selleckchem.com/search.html?searchDTO.searchParam=S2261
TargetMol	BBP60056	https://www.targetmol.com/search?keyword=BBP60056
TargetMol	T2898	https://www.targetmol.com/search?keyword=T2898
Tetrahedron	TS59635	http://www.thsci.com/search.do?q=TS59635
Vitas-M Laboratory	BBL010924	http://www.vitasmlab.biz/search/BBL010924
Vitas-M Laboratory	STK801912	http://www.vitasmlab.biz/search/STK801912

PubMed

Title	Date	PubMed
Enhanced protective activity of nano formulated andrographolide against arsenic induced liver damage.	2015-12-05	26485141
Bioavailability of andrographolide and protection against carbon tetrachloride-induced oxidative damage in rats.	2014-10-01	25110055
Andrographolide inhibits tumor angiogenesis via blocking VEGFA/VEGFR2-MAPKs signaling cascade.	2014-07-25	24814888
Andrographolide sensitizes the cytotoxicity of human colorectal carcinoma cells toward cisplatin via enhancing apoptosis pathways in vitro and in vivo.	2014-05	24563380
Andrographolide causes apoptosis via inactivation of STAT3 and Akt and potentiates antitumor activity of gemcitabine in pancreatic cancer.	2013-09-12	23845849
Different AhR binding sites of diterpenoid ligands from Andrographis paniculata caused differential CYP1A1 induction in primary culture in mouse hepatocytes.	2011-12	21963808
Stage of action of naturally occurring andrographolides and their semisynthetic analogues against herpes simplex virus type 1 in vitro.	2011-06	21259187
Cellular glutathione content modulates the effect of andrographolide on β-naphthoflavone-induced CYP1A1 mRNA expression in mouse hepatocytes.	2011-02-04	21094198
Andrographolide down-regulates hypoxia-inducible factor-1α in human non-small cell lung cancer A549 cells.	2011-02-01	21134392
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.	2011-01-01	20946909
Herb-drug interaction of Andrographis paniculata extract and andrographolide on the pharmacokinetics of theophylline in rats.	2010-03-30	20096675
Synergistic increases of metabolism and oxidation-reduction genes on their expression after combined treatment with a CYP1A inducer and andrographolide.	2009-12-10	19737545
The human bitter taste receptor hTAS2R50 is activated by the two natural bitter terpenoids andrographolide and amarogentin.	2009-11-11	19817411
Andrographolide could inhibit human colorectal carcinoma Lovo cells migration and invasion via down-regulation of MMP-7 expression.	2009-08-14	19426720
Potency of andrographolide as an antitumor compound in BHC-induced liver damage.	2009-06	19679627
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.	2009-05-15	19041297
Andrographolide enhances 5-fluorouracil-induced apoptosis via caspase-8-dependent mitochondrial pathway involving p53 participation in hepatocellular carcinoma (SMMC-7721) cells.	2009-04-18	19097688
Inhibition of cell-cycle progression in human colorectal carcinoma Lovo cells by andrographolide.	2008-08-11	18619950
Strong synergistic induction of CYP1A1 expression by andrographolide plus typical CYP1A inducers in mouse hepatocytes.	2007-10-15	17825862
Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods.	2006-11	16497524
Steroid hormone activity of flavonoids and related compounds.	2000-07	10989984
Dehydroandrographolide succinic acid monoester as an inhibitor against the human immunodeficiency virus.	1991-05	1708503

Patents

Sample Use Guides

In Vivo Use Guide

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

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 `Mon Mar 31 18:37:52 GMT 2025` Edited by `admin` on `Mon Mar 31 18:37:52 GMT 2025`
Record UNII	410105JHGR
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

HMPL004

Preferred Name

English

ANDROGRAPHOLIDE

Official Name

English

NSC-383468

Code

English

Andrographolide [WHO-DD]

Common Name

English

ANDROGRAPHOLIDE [MI]

Common Name

English

ANDROGRAPHOLIDE (CONSTITUENT OF ANDROGRAPHIS) [DSC]

Common Name

English

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)-

Systematic Name

English

(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

Systematic Name

English

ANDROGRAPHOLIDE [USP-RS]

Common Name

English

3.ALPHA.,14,15,18-TETRAHYDROXY-5.BETA.,9.BETA.H,10.ALPHA.-LABDA-8(20),12-DIEN-16-OIC ACID .GAMMA.-LACTONE

Common Name

English

Classification Tree Code System Code

DSLD

2449 (Number of products:2)