GANDOTINIB

Details

Stereochemistry	ACHIRAL
Molecular Formula	C23H25ClFN7O
Molecular Weight	469.942
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC1=CC(NC2=NN3C(CC4=C(F)C=C(Cl)C=C4)=C(C)N=C3C(CN5CCOCC5)=C2)=NN1

InChI

InChIKey=SQSZANZGUXWJEA-UHFFFAOYSA-N

InChI=1S/C23H25ClFN7O/c1-14-9-21(29-28-14)27-22-11-17(13-31-5-7-33-8-6-31)23-26-15(2)20(32(23)30-22)10-16-3-4-18(24)12-19(16)25/h3-4,9,11-12H,5-8,10,13H2,1-2H3,(H2,27,28,29,30)

HIDE SMILES / InChI

Description
Sources: https://www.cancer.gov/publications/dictionaries/cancer-drug?cdrid=682801
Curator's Comment: description was created based on several sources, including: http://www.pharmacodia.com/yaodu/html/v1/chemicals/6eab78f10219a83895b2e2d71dc0656e.html | https://www.ncbi.nlm.nih.gov/pubmed/23317159 | https://www.ncbi.nlm.nih.gov/pubmed/22227528

An orally bioavailable imidazopyridazine and inhibitor of Janus kinase 2 mutant V617F (JAK2V617F), with potential antineoplastic activity. Upon oral administration, gandotinib selectively and competitively inhibits the activation of JAK2V617F, which may result in the inhibition of the JAK-STAT signaling pathway and the induction of apoptosis in JAK2V617F-expressing tumor cells. Gandotinib is in phase II clinical trials by Lilly for the treatment of myeloproliferative disorders.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Tyrosine-protein kinase JAK2 55 Target ID: CHEMBL2971 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22227528	Inhibitor 8297		0.055 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
African trypanosomiasis 12 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27626104	Curative		Basic research	Unknown Approved Use Unknown
Myeloproliferative disorders 2 Sources: http://adisinsight.springer.com/drugs/800032290	Primary		Phase II 1132	Unknown Approved Use Unknown

Sourcing

Vendor/Aggregator	ID	URL
1PlusChem LLC	1P000K91	https://www.1pchem.com/search?query=1P000K91
AChemBlock	L14811	http://www.achemblock.com/catalogsearch/result/?q=L14811
AK Scientific	SYN1196	https://aksci.com/item_detail.php?cat=SYN1196
AK Scientific	X7498	https://aksci.com/item_detail.php?cat=X7498
AOBIOUS INC	AOB87108	http://aobious.com/aobious/search?search_query=AOB87108
Aceschem	ACF021704	https://www.aceschem.com/catalog/search.do?q=ACF021704
Ambeed	A315267	http://www.ambeed.com/search/Search.html?keyword=A315267
Angene	AGN-PC-0WH9IZ	http://www.angenechemical.com/productshow/AGN-PC-0WH9IZ.html
ApexBio Technology	A4147	https://www.apexbt.com/catalogsearch/result/?q=A4147
AstaTech	42560	http://astatechinc.com/CPSResult.php?CRNO=42560
Axon MedChem	2554	https://www.axonmedchem.com/product/2554
BLD Pharm	BD243877	http://www.bldpharm.com/search/Search.html?keyword=BD243877
BOC Sciences	1229236-86-5	http://www.bocsci.com/description.asp?cas=1229236-86-5
Capot Chemical	22469	https://www.capotchem.com/search.do?q=22469
Cayman Chemical	16705	http://www.caymanchem.com/app/template/Product.vm/catalog/16705
Chem Scene	CS-0426	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-0426
ChemShuttle	104778	https://www.chemshuttle.com/catalogsearch/result/?q=104778
Excenen	EX-A1114	http://www.excenen.com/searchresultlist.php?id=EX-A1114
KeyOrganics	AS-16329	http://www.keyorganicsinc.com/bionet/catalogsearch/result?q=AS-16329
Lab Seeker	SC-85765	http://www.labseeker.com/search.php?keywords=SC-85765&category=0
LabSeeker	SC-85765	http://www.labseeker.com/search.php?keywords=SC-85765&category=0
Matrix Scientific	145184	http://www.matrixscientific.com/145184.html
MedChem Express	HY-13034	https://www.medchemexpress.com/search.html?q=HY-13034&ft=&fa=&fp=
MolPort	MolPort-016-633-296	https://www.molport.com/shop/molecule-link/MolPort-016-633-296
MolPort	MolPort-042-652-644	https://www.molport.com/shop/molecule-link/MolPort-042-652-644
Molnova	M10896	https://www.molnova.com/en/serch-list.html?keywords=M10896
MuseChem	I000902	https://www.musechem.com/product/I000902.html
Ryan Scientific	TAK901	https://ryansci.com/products?q=TAK901&list_q=&search_type=exact
Selleck Chemicals	S2179	http://www.selleckchem.com/search.html?searchDTO.searchParam=S2179
ShangHai Biochempartner	BCP000303	http://www.biochempartner.com/search_BCP000303
ShangHai Biochempartner	BCP02309	http://www.biochempartner.com/search_BCP02309
Toronto Research Chemicals	L486570	https://www.trc-canada.com/product-detail/?CatNum=L486570
eMolecules	36516774	https://orderbb.emolecules.com/search/#?query=36516774
eMolecules	48670923	https://orderbb.emolecules.com/search/#?query=48670923
eNovation Chemicals	D572647	https://www.enovationchem.com/Products.asp?SEARCHTEXT=D572647&searchbtn.x=0&searchbtn.y=0
mcule	MCULE-1937502358	https://mcule.com/MCULE-1937502358/

PubMed

Title	Date	PubMed
Discovery and characterization of LY2784544, a small-molecule tyrosine kinase inhibitor of JAK2V617F.	2013 Apr 12	23584399

Patents

Sample Use Guides

In Vivo Use Guide

120 mg administered once daily for 6 cycles (168 days).

Route of Administration: Oral

In Vitro Use Guide

LY2784544 effectively inhibited JAK2V617F-driven signaling and cell proliferation in Ba/F3 cells (IC50=20 and 55 nM, respectively). In comparison, LY2784544 was much less potent at inhibiting interleukin-3-stimulated wild-type JAK2-mediated signaling and cell proliferation (IC50=1183 and 1309 nM, respectively).

Name

Type

Language

GANDOTINIB

Official Name

English

Gandotinib [WHO-DD]

Common Name

English

3-(4-CHLORO-2-FLUOROBENZYL)-2-METHYL-N-(5-METHYL-1H-PYRAZOL-3-YL)-8- (MORPHOLINOMETHYL)IMIDAZO(1,2-B)PYRIDAZIN-6-AMINE

Systematic Name

English

IMIDAZO(1,2-B)PYRIDAZIN-6-AMINE, 3-((4-CHLORO-2-FLUOROPHENYL)METHYL)-2-METHYL-N-(5- METHYL-1H-PYRAZOL-3-YL)-8-(4-MORPHOLINYLMETHYL)-

Common Name

English

gandotinib [INN]

Common Name

English

LY2784544

Code

English

GANDOTINIB [USAN]

Common Name

English

3-((4-CHLORO-2-FLUOROPHENYL)METHYL)-2-METHYL-N-(5-METHYL-1H-PYRAZOL-3-YL)-8- (MORPHOLIN-4-YLMETHYL)IMIDAZO(1,2-B)PYRIDAZIN-6-AMINE

Systematic Name

English

LY-2784544

Code

English

Classification Tree Code System Code

FDA ORPHAN DRUG

334211