SAPITINIB DIFUMURATE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C23H25ClFN5O3.2C4H4O4
Molecular Weight	706.072
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	2
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC(=O)\C=C\C(O)=O.OC(=O)\C=C\C(O)=O.CNC(=O)CN1CCC(CC1)OC2=CC3=C(NC4=CC=CC(Cl)=C4F)N=CN=C3C=C2OC

InChI

InChIKey=LSXKPHWAKWZIKV-LVEZLNDCSA-N

InChI=1S/C23H25ClFN5O3.2C4H4O4/c1-26-21(31)12-30-8-6-14(7-9-30)33-20-10-15-18(11-19(20)32-2)27-13-28-23(15)29-17-5-3-4-16(24)22(17)25;2*5-3(6)1-2-4(7)8/h3-5,10-11,13-14H,6-9,12H2,1-2H3,(H,26,31)(H,27,28,29);2*1-2H,(H,5,6)(H,7,8)/b;2*2-1+

HIDE SMILES / InChI

Molecular Formula	C23H25ClFN5O3
Molecular Weight	473.928
Charge	0
Count

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

Molecular Formula	C4H4O4
Molecular Weight	116.0722
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	1
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/20145185 | https://clinicaltrials.gov/ct2/show/NCT01862003 | https://www.ncbi.nlm.nih.gov/pubmed/27654971 | https://www.ncbi.nlm.nih.gov/pubmed/25007130

Sapitinib is an oral, reversible and equipotent inhibitor of EGFR, HER2 and HER3 signalling. The drug was tested in phase II of clinical trials in patients with breast cancer, colorectal cancer, gastric cancer and NSCL carcinoma, however its development for breast cancer therapy seems to be terminated. Sapitinib absorption is rapid and the drug is totally cleared by metabolism with the major routes being oxidation and amine or ether cleavage around the piperidine ring with subsequent glucuronide or sulphate conjugation.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Epidermal growth factor receptor erbB1 58 Target ID: CHEMBL203 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20145185	Inhibitor 8297	4.0 nM [IC50]
Receptor protein-tyrosine kinase erbB-2 35 Target ID: CHEMBL1824 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20145185	Inhibitor 8297	3.0 nM [IC50]
Receptor tyrosine-protein kinase erbB-3 4 Target ID: CHEMBL5838 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20145185	Inhibitor 8297	4.0 nM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Breast cancer 434 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27654971	Primary	Phase II 1132	Unknown Approved Use Unknown
Non-small cell lung cancer 2 Sources: https://clinicaltrials.gov/ct2/show/NCT02117167	Primary	Phase II 1132	Unknown Approved Use Unknown
Colorectal cancer 101 Sources: https://clinicaltrials.gov/ct2/show/NCT01862003	Primary	Phase II 1132	Unknown Approved Use Unknown
Gastric cancer 53 Sources: https://clinicaltrials.gov/ct2/show/NCT01579578	Primary	Phase II 1132	Unknown Approved Use Unknown

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY443108	https://www.001chemical.com/chem/search?q=DY443108
1PlusChem LLC	1P00G487	https://www.1pchem.com/search?query=1P00G487
AChemBlock	M15332	http://www.achemblock.com/catalogsearch/result/?q=M15332
AK Scientific	SYN5767	https://aksci.com/item_detail.php?cat=SYN5767
AOBIOUS INC	AOB87778	http://aobious.com/aobious/search?search_query=AOB87778
Aceschem	ACF019996	https://www.aceschem.com/catalog/search.do?q=ACF019996
Angene	AGN-PC-00A3ZY	http://www.angenechemical.com/productshow/AGN-PC-00A3ZY.html
ApexBio Technology	A8375	https://www.apexbt.com/catalogsearch/result/?q=A8375
AstaTech	42509	http://astatechinc.com/CPSResult.php?CRNO=42509
BLD Pharm	BD304648	http://www.bldpharm.com/search/Search.html?keyword=BD304648
Capot Chemical	34105	https://www.capotchem.com/search.do?q=34105
Chem Scene	CS-3951	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-3951
ChemShuttle	111923	https://www.chemshuttle.com/catalogsearch/result/?q=111923
Combi-Blocks	QJ-2458	http://www.combi-blocks.com/cgi-bin/find.cgi?QJ-2458
Debye Scientific	DA-35304	https://www.debyesci.com/index.php?id=product&ext[cno]=DA-35304
Excenen	EX-A036	http://www.excenen.com/searchresultlist.php?id=EX-A036
Hairui	HR33145	http://www.hairuichem.com/en/product/search.do?q=HR33145
KeyOrganics	AS-17066	http://www.keyorganicsinc.com/bionet/catalogsearch/result?q=AS-17066
Lab Seeker	SC-94600	http://www.labseeker.com/search.php?keywords=SC-94600&category=0
LabSeeker	SC-94600	http://www.labseeker.com/search.php?keywords=SC-94600&category=0
Matrix Scientific	147255	http://www.matrixscientific.com/147255.html
MedChem Express	HY-13050	https://www.medchemexpress.com/search.html?q=HY-13050&ft=&fa=&fp=
MolPort	MolPort-016-633-303	https://www.molport.com/shop/molecule-link/MolPort-016-633-303
Molcore	MC443108	http://www.molcore.com/CatMC443108.html
Molnova	M16163	https://www.molnova.com/en/serch-list.html?keywords=M16163
MuseChem	I005089	https://www.musechem.com/product/I005089.html
Selleck Chemicals	S2192	http://www.selleckchem.com/search.html?searchDTO.searchParam=S2192
ShangHai Biochempartner	BCP000459	http://www.biochempartner.com/search_BCP000459
ShangHai Biochempartner	BCP02835	http://www.biochempartner.com/search_BCP02835
TargetMol	T6092	https://www.targetmol.com/search?keyword=T6092
eMolecules	261437794	https://orderbb.emolecules.com/search/#?query=261437794
eMolecules	32278235	https://orderbb.emolecules.com/search/#?query=32278235
eNovation Chemicals	D388308	https://www.enovationchem.com/Products.asp?SEARCHTEXT=D388308&searchbtn.x=0&searchbtn.y=0
eNovation Chemicals	D628723	https://www.enovationchem.com/Products.asp?SEARCHTEXT=D628723&searchbtn.x=0&searchbtn.y=0
mcule	MCULE-9860747204	https://mcule.com/MCULE-9860747204/

PubMed

Title	Date	PubMed
AZD8931, an equipotent, reversible inhibitor of signaling by epidermal growth factor receptor, ERBB2 (HER2), and ERBB3: a unique agent for simultaneous ERBB receptor blockade in cancer.	2010 Feb 15	20145185
Discovery of AZD8931, an Equipotent, Reversible Inhibitor of Signaling by EGFR, HER2, and HER3 Receptors.	2013 Aug 8	24900741

Sample Use Guides

In Vivo Use Guide

Colorectal cancer: Patients were receiving 160 mg sapitinib tablets, twice daily on days 1-4 of each 2-weekly cycle + FOLFIRI. Breast cancer: Patients were receiving daily anastrozole (1 mg) in combination with sapitinib 20 mg twice daily (bid) or sapitinib 40 mg bid.

Route of Administration: Oral

In Vitro Use Guide

MCF7 and T47D breast cancer cells were treated with sapitinib (1 uM) in combination with estradiol (10−9 M), estrogen deprivation, tamoxifen (10−7 M), or ICI 182,78 (10−7 M).

Substance Class	Chemical Created by `admin` on `Sat Dec 16 14:13:19 UTC 2023` Edited by `admin` on `Sat Dec 16 14:13:19 UTC 2023`
Record UNII	RD1QAE9R4N
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

SAPITINIB DIFUMURATE

Common Name

English

1-PIPERIDINEACETAMIDE, 4-((4-((3-CHLORO-2-FLUOROPHENYL)AMINO)-7-METHOXY-6-QUINAZOLINYL)OXY)-N-METHYL-, (2E)-2-BUTENEDIOATE (1:2)

Systematic Name

English

AZD8931 DIFUMARICACID

Code

English

AZD-8931 DIFUMARICACID

Common Name

English

Code System Code Type Description

CAS

1196531-39-1

Created by admin on Sat Dec 16 14:13:19 UTC 2023 , Edited by admin on Sat Dec 16 14:13:19 UTC 2023

PRIMARY

FDA UNII

RD1QAE9R4N

Created by admin on Sat Dec 16 14:13:19 UTC 2023 , Edited by admin on Sat Dec 16 14:13:19 UTC 2023

PRIMARY

PUBCHEM

44470103

Created by admin on Sat Dec 16 14:13:19 UTC 2023 , Edited by admin on Sat Dec 16 14:13:19 UTC 2023

PRIMARY

Related Record Type Details

3499328002

SAPITINIB

PARENT -> SALT/SOLVATE

Related Record Type Details

3499328002

SAPITINIB

ACTIVE MOIETY

Details

SMILES

InChI

DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/20145185 | https://clinicaltrials.gov/ct2/show/NCT01862003 | https://www.ncbi.nlm.nih.gov/pubmed/27654971 | https://www.ncbi.nlm.nih.gov/pubmed/25007130

CNS Activity

Originator

Approval Year

Targets

Conditions

Approved Use

Approved Use

Approved Use

Approved Use

Sourcing

PubMed

Sample Use Guides

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/20145185 | https://clinicaltrials.gov/ct2/show/NCT01862003 | https://www.ncbi.nlm.nih.gov/pubmed/27654971 | https://www.ncbi.nlm.nih.gov/pubmed/25007130