NAQUOTINIB MESYLATE

Investigational

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C30H42N8O3.CH4O3S
Molecular Weight	658.812
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CS(O)(=O)=O.CCC1=NC(C(N)=O)=C(NC2=CC=C(C=C2)N3CCC(CC3)N4CCN(C)CC4)N=C1O[C@@H]5CCN(C5)C(=O)C=C

InChI

InChIKey=ALDUQYYVQWGTMR-GJFSDDNBSA-N

InChI=1S/C30H42N8O3.CH4O3S/c1-4-25-30(41-24-12-15-38(20-24)26(39)5-2)34-29(27(33-25)28(31)40)32-21-6-8-22(9-7-21)36-13-10-23(11-14-36)37-18-16-35(3)17-19-37;1-5(2,3)4/h5-9,23-24H,2,4,10-20H2,1,3H3,(H2,31,40)(H,32,34);1H3,(H,2,3,4)/t24-;/m1./s1

HIDE SMILES / InChI

Molecular Formula	C30H42N8O3
Molecular Weight	562.7063
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Molecular Formula	CH4O3S
Molecular Weight	96.106
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/28526474
Curator's Comment: The description was created based on several sources, including https://clinicaltrials.gov/ct2/show/NCT02588261 | https://clinicaltrials.gov/ct2/show/record/NCT03042013 | https://clinicaltrials.gov/ct2/show/record/NCT02674555 | https://www.ncbi.nlm.nih.gov/pubmed/26968253 | http://cancerres.aacrjournals.org/content/74/19_Supplement/1728.short

Naquotinib (ASP8273) is an orally available, irreversible, mutant-selective, epidermal growth factor receptor (EGFR) inhibitor, with potential antineoplastic activity. Naquotinib was found by mass spectrometry to covalently bind to a mutant EGFR (L858R/ T790M) via cysteine residue 797 in the kinase domain of EGFR with long-lasting inhibition of EGFR phosphorylation for 24 h. In the NSCLC cell lines harboring the above EGFR mutations, Naquotinib had IC50 values of 8-33 nM toward EGFR mutants, more potently than that of WT EGFR (IC50 value of 230 nM). In mouse xenograft models, Naquotinib induced complete regression of the tumors after 14 days of treatment. ASP8273 even showed activity in mutant EGFR cell line which is resistant to other EGFR TKIs. Naquotinib is in phase III clinical trials for the oral treatment of EGFR mutated non-small cell lung cancer (NSCLC).

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Epidermal growth factor receptor 49 Target ID: CHEMBL2363049 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26968253	Inhibitor 8504		8.0 nM [IC50]
Epidermal growth factor receptor erbB1 62 Target ID: CHEMBL203 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26968253	Inhibitor 8504		230.0 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Non-small cell lung cancer 211 Sources: https://clinicaltrials.gov/ct2/show/NCT02588261	Primary		Phase II 1147	Unknown Approved Use Unknown
Solid tumors 147 Sources: https://clinicaltrials.gov/ct2/show/NCT02674555	Primary		Phase I 438	Unknown Approved Use Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
629 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29972716/	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:		NAQUOTINIB plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
2790 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/29972716	400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered:		NAQUOTINIB plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

AUC

Value	Dose	Co-administered	Analyte	Population
5610 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29972716/	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:		NAQUOTINIB plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
34600 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/29972716	400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered:		NAQUOTINIB plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
14.3 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29972716/	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:		NAQUOTINIB plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
12.9 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/29972716	400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered:		NAQUOTINIB plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

Sourcing

Vendor/Aggregator	ID	URL
1PlusChem LLC	1P001KO9	https://www.1pchem.com/search?query=1P001KO9
1PlusChem LLC	1P01EOP1	https://www.1pchem.com/search?query=1P01EOP1
AbovChem LLC	HY-19729	http://www.abovchem.com/pc/en/product_list.aspx?wd=HY-19729
AChemBlock	M15696	http://www.achemblock.com/catalogsearch/result/?q=M15696
AstaTech	C91356	http://astatechinc.com/CPSResult.php?CRNO=C91356
BLD Pharm	BD764644	http://www.bldpharm.com/search/Search.html?keyword=BD764644
Chem Scene	CS-5468	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-5468
ChemShuttle	139058	https://www.chemshuttle.com/catalogsearch/result/?q=139058
eMolecules	110118984	https://orderbb.emolecules.com/search/#?query=110118984
eMolecules	275109194	https://orderbb.emolecules.com/search/#?query=275109194
eMolecules	95699478	https://orderbb.emolecules.com/search/#?query=95699478
Hairui	NAJB013	http://www.hairuichem.com/en/product/search.do?q=NAJB013
Hairui	NAJB020	http://www.hairuichem.com/en/product/search.do?q=NAJB020
KeyOrganics	AS-75247	http://www.keyorganicsinc.com/bionet/catalogsearch/result?q=AS-75247
mcule	MCULE-4021911145	https://mcule.com/MCULE-4021911145/
mcule	MCULE-6498314338	https://mcule.com/MCULE-6498314338/
mcule	MCULE-7375839161	https://mcule.com/MCULE-7375839161/
MedChem Express	HY-19803	https://www.medchemexpress.com/search.html?q=HY-19803&ft=&fa=&fp=
Molnova	M11913	https://www.molnova.com/en/serch-list.html?keywords=M11913
Molnova	M11914	https://www.molnova.com/en/serch-list.html?keywords=M11914
MolPort	MolPort-044-830-642	https://www.molport.com/shop/molecule-link/MolPort-044-830-642
MolPort	MolPort-046-418-459	https://www.molport.com/shop/molecule-link/MolPort-046-418-459
MuseChem	I008240	https://www.musechem.com/product/I008240.html
MuseChem	I012076	https://www.musechem.com/product/I012076.html
Selleck Chemicals	S8412	http://www.selleckchem.com/search.html?searchDTO.searchParam=S8412

PubMed

Title	Date	PubMed
Recent progress on third generation covalent EGFR inhibitors.	2016-04-15	26968253

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Oral

In Vitro Use Guide

ASP8273 (Naquotinib ) inhibited the growth of PC-9(del ex19), HCC827(del ex19), NCI-H1975(del ex19/T790M) and PC-9ER(del ex19/T790M) with IC50 values of 8-33 nM

Substance Class	Chemical Created by `admin` on `Mon Mar 31 21:28:59 GMT 2025` Edited by `admin` on `Mon Mar 31 21:28:59 GMT 2025`
Record UNII	12T09LV21O
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NAQUOTINIB MESYLATE

Official Name

English

ASP-8273 MESILATE

Preferred Name

English

ASP-8273 MESYLATE

Code

English

NAQUOTINIB MESYLATE [USAN]

Common Name

English

ASP8273 MESILATE

Code

English

NAQUOTINIB MESILATE [JAN]

Common Name

English

2-PYRAZINECARBOXAMIDE, 6-ETHYL-3-((4-(4-(4-METHYL-1-PIPERAZINYL)-1-PIPERIDINYL)PHENYL)AMINO)-5-(((3R)-1-(1-OXO-2-PROPEN-1-YL)-3-PYRROLIDINYL)OXY)-, METHANESULFONATE (1:1)

Systematic Name

English

Code System Code Type Description

CAS

1448237-05-5