WP-1066

Investigational

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C17H14BrN3O
Molecular Weight	356.217
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C[C@H](NC(=O)C(=C\C1=NC(Br)=CC=C1)\C#N)C2=CC=CC=C2

InChI

InChIKey=VFUAJMPDXIRPKO-LQELWAHVSA-N

InChI=1S/C17H14BrN3O/c1-12(13-6-3-2-4-7-13)20-17(22)14(11-19)10-15-8-5-9-16(18)21-15/h2-10,12H,1H3,(H,20,22)/b14-10+/t12-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C17H14BrN3O
Molecular Weight	356.217
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	1
Optical Activity	UNSPECIFIED

Description
Sources: https://clinicaltrials.gov/ct2/show/NCT01904123 | https://www.ncbi.nlm.nih.gov/pubmed/18245540

WP1066 is a cell-permeable AG490 tyrphostin analog that effectively inhibits the phosphorylation of Janus kinase 2 (JAK2) and its downstream signal transducer and activator of transcription 3 (STAT3) in a dose- and time-dependent manner. As a result, WP1066 concentrations in the low micromolar range induced time- and dose-dependent antiproliferative and proapoptotic effects in cancer cells. WP1066 has been used in Phase I trial studying the treatment of melanoma, brain cancer, solid tumors, and central nervous system neoplasms.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Tyrosine-protein kinase JAK2 59 Target ID: CHEMBL2971 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18245540	Inhibitor 8504		2.3 µM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Brain cancer 10 Sources: https://clinicaltrials.gov/ct2/show/NCT01904123	Primary	Phase I 438	Unknown Approved Use Unknown
Central nervous system neoplasms 4 Sources: https://clinicaltrials.gov/ct2/show/NCT01904123	Primary	Phase I 438	Unknown Approved Use Unknown
Melanoma 88 Sources: https://clinicaltrials.gov/ct2/show/NCT01904123	Primary	Phase I 438	Unknown Approved Use Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
1.5 μg/mL EXPERIMENT https://cancerres.aacrjournals.org/content/75/15_Supplement/4540	200 mg/kg single, oral dose: 200 mg/kg route of administration: Oral experiment type: SINGLE co-administered:		WP 1066 plasma	Mus musculus population: HEALTHY age: ADULT sex: FEMALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
3 h EXPERIMENT https://cancerres.aacrjournals.org/content/75/15_Supplement/4540	200 mg/kg single, oral dose: 200 mg/kg route of administration: Oral experiment type: SINGLE co-administered:		WP 1066 plasma	Mus musculus population: HEALTHY age: ADULT sex: FEMALE food status: FASTED

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY114882	https://www.001chemical.com/chem/search?q=DY114882
1PlusChem LLC	1P00502F	https://www.1pchem.com/search?query=1P00502F
A2B Chem	AC32567	http://a2bchem.com/prod/AC32567
AK Scientific	X5924	https://aksci.com/item_detail.php?cat=X5924
Ambeed	A203794	http://www.ambeed.com/search/Search.html?keyword=A203794
Angene	AGN-PC-0V1Y8L	http://www.angenechemical.com/productshow/AGN-PC-0V1Y8L.html
AOBIOUS INC	AOB1497	http://aobious.com/aobious/search?search_query=AOB1497
ApexBio Technology	A4140	https://www.apexbt.com/catalogsearch/result/?q=A4140
AstaTech	40618	http://astatechinc.com/CPSResult.php?CRNO=40618
Axon MedChem	2316	https://www.axonmedchem.com/product/2316
BOC Sciences	857064-38-1	http://www.bocsci.com/description.asp?cas=857064-38-1
Cayman Chemical	14736	http://www.caymanchem.com/app/template/Product.vm/catalog/14736
Chem Scene	CS-2736	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-2736
ChemShuttle	104913	https://www.chemshuttle.com/catalogsearch/result/?q=104913
Debye Scientific	DA-41141	https://www.debyesci.com/index.php?id=product&ext[cno]=DA-41141
eMolecules	252325757	https://orderbb.emolecules.com/search/#?query=252325757
eMolecules	26753937	https://orderbb.emolecules.com/search/#?query=26753937
eMolecules	44842169	https://orderbb.emolecules.com/search/#?query=44842169
eMolecules	45915848	https://orderbb.emolecules.com/search/#?query=45915848
Enamine	Z1614810028	https://www.enaminestore.com/blog/real/Z1614810028/
eNovation Chemicals	D383462	https://www.enovationchem.com/Products.asp?SEARCHTEXT=D383462&searchbtn.x=0&searchbtn.y=0
Excenen	EX-A760	http://www.excenen.com/searchresultlist.php?id=EX-A760
Hairui	HR110357	http://www.hairuichem.com/en/product/search.do?q=HR110357
KeyOrganics	AS-19242	http://www.keyorganicsinc.com/bionet/catalogsearch/result?q=AS-19242
Lab Network	LN00199376	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00199376
Matrix Scientific	97109	http://www.matrixscientific.com/097109.html
mcule	MCULE-1376076086	https://mcule.com/MCULE-1376076086/
mcule	MCULE-5124371209	https://mcule.com/MCULE-5124371209/
mcule	MCULE-6286134986	https://mcule.com/MCULE-6286134986/
MedChem Express	HY-15312	https://www.medchemexpress.com/search.html?q=HY-15312&ft=&fa=&fp=
Molcore	MC114882	http://www.molcore.com/CatMC114882.html
Molnova	M16217	https://www.molnova.com/en/serch-list.html?keywords=M16217
MolPort	MolPort-023-219-149	https://www.molport.com/shop/molecule-link/MolPort-023-219-149
MuseChem	I005146	https://www.musechem.com/product/I005146.html
Oakwood	234436	http://www.oakwoodchemical.com/ProductsList.aspx?txtSearch=234436
Otava	7070707057	https://search.otavachemicals.com/#!/search?query=7070707057&type=code
ShangHai Biochempartner	BCP000544	http://www.biochempartner.com/search_BCP000544
TargetMol	T2156	https://www.targetmol.com/search?keyword=T2156
W&J PharmaChem	50C930465	http://wjpharmachem.com/new/searcht.php?keyword=50C930465

PubMed

Title	Date	PubMed
WP1066, a small molecule inhibitor of the JAK/STAT3 pathway, inhibits ceramide glucosyltransferase activity.	2017-09-16	28739255
The evaluation of p,p'-DDT exposure on cell adhesion of hepatocellular carcinoma.	2014-08-01	24820114
Regulation of PSMB5 protein and β subunits of mammalian proteasome by constitutively activated signal transducer and activator of transcription 3 (STAT3): potential role in bortezomib-mediated anticancer therapy.	2014-05-02	24627483
Cucurbitacin B and cucurbitacin I suppress adipocyte differentiation through inhibition of STAT3 signaling.	2014-02	24316209
The tumor microenvironment expression of p-STAT3 influences the efficacy of cyclophosphamide with WP1066 in murine melanoma models.	2012-07-01	21792892
WP1066, a novel JAK2 inhibitor, suppresses proliferation and induces apoptosis in erythroid human cells carrying the JAK2 V617F mutation.	2008-02-01	18245540
WP1066 disrupts Janus kinase-2 and induces caspase-dependent apoptosis in acute myelogenous leukemia cells.	2007-12-01	18056455

Patents

Sample Use Guides

In Vivo Use Guide

6 mg/kg 2 times per day on Monday, Wednesday, and Friday of Weeks 1 and 2 of each 28-day cycle.

Route of Administration: Oral

In Vitro Use Guide

WP1066 was identified as a ceramide glucosyltransferase inhibitor by a screen of known small molecule inhibitors of various enzymes and protein factors. WP1066 inhibited the activity of ceramide glucosyltransferase with an IC50 of 7.2 uM, and that its action was independent of JAK/STAT3 pathway blockade. Moreover, the modes of inhibition of ceramide glucosyltransferase were uncompetitive with respect to both C6-NBD-ceramide and UDP-glucose.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 20:47:43 GMT 2025` Edited by `admin` on `Mon Mar 31 20:47:43 GMT 2025`
Record UNII	63V8AIE65T
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

WP-1066

Code

English

WP 1066

Preferred Name

English

WP1066

Code

English

2-PROPENAMIDE, 3-(6-BROMO-2-PYRIDINYL)-2-CYANO-N-((1S)-1-PHENYLETHYL)-, (2E)-

Systematic Name

English

Classification Tree Code System Code

FDA ORPHAN DRUG

671018