ICARITIN

Investigational

Details

Stereochemistry	ACHIRAL
Molecular Formula	C21H20O6
Molecular Weight	368.3799
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC1=CC=C(C=C1)C2=C(O)C(=O)C3=C(O)C=C(O)C(CC=C(C)C)=C3O2

InChI

InChIKey=TUUXBSASAQJECY-UHFFFAOYSA-N

InChI=1S/C21H20O6/c1-11(2)4-9-14-15(22)10-16(23)17-18(24)19(25)20(27-21(14)17)12-5-7-13(26-3)8-6-12/h4-8,10,22-23,25H,9H2,1-3H3

HIDE SMILES / InChI

Molecular Formula	C21H20O6
Molecular Weight	368.3799
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28963488 | https://www.ncbi.nlm.nih.gov/pubmed/21376032 | https://www.ncbi.nlm.nih.gov/pubmed/24064280 | http://adisinsight.springer.com/drugs/800039265

Icaritin is a monoprenylated favonol with 4′-methoxyl from Epimedium Genus. It has been documented to have osteoblastic and neuroprotective activities. It can reduce the incidence of steroid-associated oesteonecrosis in rabbit with inhibition of both intravascular thrombosis and extravascular lipid deposition for maintaining the integrity of intraosseous vasculature. Icaritin shows anti-infammatory activity and inhibitory activities against cancer cells. The phase III clinical trial is planned for the treatment of Hepatocellular carcinoma.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Cytochrome P450 1A2 72 Target ID: CHEMBL1075125 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24791596	Inhibitor 8297
Cytochrome P450 2C9 50 Target ID: CHEMBL3397 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24791596	Inhibitor 8297
IL-6/JAK2/STAT3 signaling 1 Target ID: IL-6/JAK2/STAT3 signaling Sources: https://www.ncbi.nlm.nih.gov/pubmed/25865044	Inhibitor 8297
Sphingosine kinase 1 6 Target ID: CHEMBL4394 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28206952	Inhibitor 8297
Estrogen receptor beta 110 Target ID: CHEMBL242 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28963488 \| http://en.pharmacodia.com/web/drug/1_1836.html	Agonist 2678

Conditions

Condition	Modality	Highest Phase	Product
Hepatocellular carcinoma 83 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28206952 https://www.ncbi.nlm.nih.gov/pubmed/26376676 https://www.ncbi.nlm.nih.gov/pubmed/25434584 http://adisinsight.springer.com/drugs/800039265	Primary	Phase III 656	Unknown Approved Use Unknown
Solid tumors 145 Sources: https://clinicaltrials.gov/ct2/show/NCT02496949 http://adisinsight.springer.com/drugs/800039265	Primary	Phase I 428	Unknown Approved Use Unknown
Multiple myeloma 159 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25865044	Primary	Preclinical	Unknown Approved Use Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
7.89 ng/mL EXPERIMENT https://link.springer.com/content/pdf/10.1365/s10337-008-0685-4.pdf	80 mg single, oral dose: 80 mg route of administration: Oral experiment type: SINGLE co-administered:		ICARIIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
10.08 ng/mL EXPERIMENT https://link.springer.com/content/pdf/10.1365/s10337-008-0685-4.pdf	80 mg single, oral dose: 80 mg route of administration: Oral experiment type: SINGLE co-administered:		ICARISIDE II plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
279 ng × h/mL EXPERIMENT https://link.springer.com/content/pdf/10.1365/s10337-008-0685-4.pdf	80 mg single, oral dose: 80 mg route of administration: Oral experiment type: SINGLE co-administered:		ICARIIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
255 mg × h/mL EXPERIMENT https://link.springer.com/content/pdf/10.1365/s10337-008-0685-4.pdf	80 mg single, oral dose: 80 mg route of administration: Oral experiment type: SINGLE co-administered:		ICARISIDE II plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
3.16 h EXPERIMENT https://link.springer.com/content/pdf/10.1365/s10337-008-0685-4.pdf	80 mg single, oral dose: 80 mg route of administration: Oral experiment type: SINGLE co-administered:		ICARIIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
2.21 h EXPERIMENT https://link.springer.com/content/pdf/10.1365/s10337-008-0685-4.pdf	80 mg single, oral dose: 80 mg route of administration: Oral experiment type: SINGLE co-administered:		ICARISIDE II plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

Sourcing

Vendor/Aggregator	ID	URL
1PlusChem LLC	1P008U2S	https://www.1pchem.com/search?query=1P008U2S
A2B Chem	AE11428	http://a2bchem.com/prod/AE11428
AK Scientific	Y0107	https://aksci.com/item_detail.php?cat=Y0107
Ambeed	A172681	http://www.ambeed.com/search/Search.html?keyword=A172681
AstaTech	42940	http://astatechinc.com/CPSResult.php?CRNO=42940
BLD Pharm	BD298185	http://www.bldpharm.com/search/Search.html?keyword=BD298185
BOC Sciences	118525-40-9	http://www.bocsci.com/description.asp?cas=118525-40-9
Biopurify Phytochemicals	BP0759	https://www.phytopurify.com/search.do?a=s&searchtype=3&psize=10&q=BP0759&searchhtmp=simplesearch&t=1
Capot Chemical	44957	https://www.capotchem.com/search.do?q=44957
Cayman Chemical	20236	http://www.caymanchem.com/app/template/Product.vm/catalog/20236
Chem Scene	CS-3679	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-3679
Hairui	HR108322	http://www.hairuichem.com/en/product/search.do?q=HR108322
KeyOrganics	AS-55987	http://www.keyorganicsinc.com/bionet/catalogsearch/result?q=AS-55987
Lab Network	LN01294415	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN01294415
MedChem Express	HY-N0678	https://www.medchemexpress.com/search.html?q=HY-N0678&ft=&fa=&fp=
MolPort	MolPort-020-006-012	https://www.molport.com/shop/molecule-link/MolPort-020-006-012
Molnova	M17860	https://www.molnova.com/en/serch-list.html?keywords=M17860
PI Chemicals	PI-38827	http://www.pipharm.com/catalog_products/PI-38827.html
Selleck Chemicals	S9080	http://www.selleckchem.com/search.html?searchDTO.searchParam=S9080
TargetMol	BBP03005	https://www.targetmol.com/search?keyword=BBP03005
TargetMol	T3398	https://www.targetmol.com/search?keyword=T3398
Toronto Research Chemicals	D465854	https://www.trc-canada.com/product-detail/?CatNum=D465854
Toronto Research Chemicals	I163700	https://www.trc-canada.com/product-detail/?CatNum=I163700
W&J PharmaChem	50C1004425	http://wjpharmachem.com/new/searcht.php?keyword=50C1004425
eMolecules	31592912	https://orderbb.emolecules.com/search/#?query=31592912
eNovation Chemicals	D761959	https://www.enovationchem.com/Products.asp?SEARCHTEXT=D761959&searchbtn.x=0&searchbtn.y=0
mcule	MCULE-1362839244	https://mcule.com/MCULE-1362839244/

PubMed

Title	Date	PubMed
Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods.	2006 Nov	16497524

Patents

Sample Use Guides

In Vivo Use Guide

600 mg/time, 2 times/day

Route of Administration: Oral

In Vitro Use Guide

Icaritin strongly inhibited the growth of breast cancer MDA-MB-453 and MCF7 cells. At concentrations of 2-3 uM, icaritin induced cell cycle arrest at the G(2)/M phase accompanied by a down-regulation of the expression levels of the G(2)/M regulatory proteins such as cyclinB, cdc2 and cdc25C. Icaritin at concentrations of 4-5 uM, however, induced apoptotic cell death characterized by the accumulation of the annexin V- and propidium iodide-positive cells, cleavage of poly ADP-ribose polymerase (PARP) and down-regulation of the Bcl-2 expression.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 08:13:46 GMT 2023` Edited by `admin` on `Sat Dec 16 08:13:46 GMT 2023`
Record UNII	UFE666UELY
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ICARITIN

Common Name

English

SGN-162

Code

English

Icaritin [WHO-DD]

Common Name

English

4H-1-BENZOPYRAN-4-ONE, 3,5,7-TRIHYDROXY-2-(4-METHOXYPHENYL)-8-(3-METHYL-2-BUTEN-1-YL)-

Systematic Name

English

SGN162

Code

English

Code System Code Type Description

DRUG BANK

DB12672