ULIXERTINIB HYDROCHLORIDE

Investigational

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C21H22Cl2N4O2.ClH
Molecular Weight	469.792
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

Cl.CC(C)NC1=NC=C(Cl)C(=C1)C2=CNC(=C2)C(=O)N[C@H](CO)C3=CC=CC(Cl)=C3

InChI

InChIKey=DKGYQCPFBWFTHM-FSRHSHDFSA-N

InChI=1S/C21H22Cl2N4O2.ClH/c1-12(2)26-20-8-16(17(23)10-25-20)14-7-18(24-9-14)21(29)27-19(11-28)13-4-3-5-15(22)6-13;/h3-10,12,19,24,28H,11H2,1-2H3,(H,25,26)(H,27,29);1H/t19-;/m1./s1

HIDE SMILES / InChI

Molecular Formula	C21H22Cl2N4O2
Molecular Weight	433.331
Charge	0
Count

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

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count

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

Description
Sources: http://adisinsight.springer.com/drugs/800037542
Curator's Comment: Description was created based on several sources, including http://cancerres.aacrjournals.org/content/75/15_Supplement/4693 |https://biomed-valley.com/portfolio/bvd-523

BVD-523 potently and selectively inhibits ERK1 and ERK2 kinases in a reversible, ATP-competitive fashion. Consistent with its mechanism of action, BVD-523 inhibits signal transduction, cell proliferation, and cell survival, most potently in cell lines bearing mutations that activate MAPK pathway signaling. Similarly, single-agent BVD-523 inhibits tumor growth in vivo in BRAF-mutant melanoma and colorectal xenografts as well as in KRAS-mutant colorectal and pancreatic models. BioMed Valley Discoveries is developing ulixertinib, a potent and selective small molecule inhibitor of ERK 1 and 2 kinases, as an oral treatment for cancers harbouring mutations in the MAPK signaling pathway. Phase I/II development of the drug for advanced cancers including, acute myeloid leukaemia and myelodysplastic syndromes is underway in the US. A phase I trial is underway in the US for pancreatic cancer.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
MAP kinase ERK1 5 Target ID: CHEMBL3385 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25977981	Inhibitor 8504
MAP kinase ERK2 7 Target ID: CHEMBL4040 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25977981	Inhibitor 8504		0.3 nM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Pancreatic cancer 98 Sources: http://adisinsight.springer.com/drugs/800037542	Primary	Phase I 438	Unknown Approved Use Unknown
Acute myeloid leukemia 141 Sources: http://adisinsight.springer.com/drugs/800037542	Primary	Phase II 1147	Unknown Approved Use Unknown
Myelodysplastic syndromes 61 Sources: http://adisinsight.springer.com/drugs/800037542	Primary	Phase II 1147	Unknown Approved Use Unknown
Solid tumors 147 Sources: http://adisinsight.springer.com/drugs/800037542	Primary	Phase II 1147	Unknown Approved Use Unknown

C_max

Value	Dose	Analyte	Population
1136.39 ng/mL CLINICAL TRIAL https://clinicaltrials.gov/study/NCT04488003	600 mg 2 times / day steady-state, oral dose: 600 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	BVD-523 plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
982 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29247021/	600 mg 2 times / day multiple, oral dose: 600 mg route of administration: Oral experiment type: MULTIPLE co-administered:	ULIXERTINIB plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
2.12 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29247021/	600 mg 2 times / day steady-state, oral dose: 600 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	ULIXERTINIB plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

AUC

Value	Dose	Co-administered	Analyte	Population
8.2 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29247021/	600 mg 2 times / day multiple, oral dose: 600 mg route of administration: Oral experiment type: MULTIPLE co-administered:		ULIXERTINIB plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
19.93 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29247021/	600 mg 2 times / day steady-state, oral dose: 600 mg route of administration: Oral experiment type: STEADY-STATE co-administered:		ULIXERTINIB plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
21.7 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29247021/	600 mg 2 times / day multiple, oral dose: 600 mg route of administration: Oral experiment type: MULTIPLE co-administered:		ULIXERTINIB plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
0.05% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29603015/			ULIXERTINIB plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

Sourcing

Vendor/Aggregator	ID	URL
1PlusChem LLC	1P00GUNZ	https://www.1pchem.com/search?query=1P00GUNZ
1PlusChem LLC	1P01ENK4	https://www.1pchem.com/search?query=1P01ENK4
AChemBlock	H-8856	http://www.achemblock.com/catalogsearch/result/?q=H-8856
AChemBlock	M22598	http://www.achemblock.com/catalogsearch/result/?q=M22598
Ambeed	A162263	http://www.ambeed.com/search/Search.html?keyword=A162263
Angene	AGN-PC-0WAFGZ	http://www.angenechemical.com/productshow/AGN-PC-0WAFGZ.html
AstaTech	40612	http://astatechinc.com/CPSResult.php?CRNO=40612
BLD Pharm	BD304093	http://www.bldpharm.com/search/Search.html?keyword=BD304093
BLD Pharm	BD517941	http://www.bldpharm.com/search/Search.html?keyword=BD517941
Cayman Chemical	18298	http://www.caymanchem.com/app/template/Product.vm/catalog/18298
Chem Scene	CS-0093706	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-0093706
Chem Scene	CS-2115	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-2115
ChemShuttle	150956	https://www.chemshuttle.com/catalogsearch/result/?q=150956
Combi-Blocks	QV-3688	http://www.combi-blocks.com/cgi-bin/find.cgi?QV-3688
Combi-Blocks	QW-7165	http://www.combi-blocks.com/cgi-bin/find.cgi?QW-7165
Debye Scientific	DA-41038	https://www.debyesci.com/index.php?id=product&ext[cno]=DA-41038
eMolecules	195278582	https://orderbb.emolecules.com/search/#?query=195278582
eMolecules	300936835	https://orderbb.emolecules.com/search/#?query=300936835
eMolecules	300937091	https://orderbb.emolecules.com/search/#?query=300937091
eMolecules	46339049	https://orderbb.emolecules.com/search/#?query=46339049
eMolecules	50282375	https://orderbb.emolecules.com/search/#?query=50282375
eNovation Chemicals	D586758	https://www.enovationchem.com/Products.asp?SEARCHTEXT=D586758&searchbtn.x=0&searchbtn.y=0
KeyOrganics	AS-56114	http://www.keyorganicsinc.com/bionet/catalogsearch/result?q=AS-56114
KeyOrganics	DS-18785	http://www.keyorganicsinc.com/bionet/catalogsearch/result?q=DS-18785
mcule	MCULE-1866531685	https://mcule.com/MCULE-1866531685/
mcule	MCULE-2624959223	https://mcule.com/MCULE-2624959223/
mcule	MCULE-4284628079	https://mcule.com/MCULE-4284628079/
mcule	MCULE-4935852054	https://mcule.com/MCULE-4935852054/
MedChem Express	HY-15816	https://www.medchemexpress.com/search.html?q=HY-15816A&ft=&fa=&fp=
MedChem Express	HY-15816A	https://www.medchemexpress.com/search.html?q=HY-15816A&ft=&fa=&fp=
MolPort	MolPort-023-219-147	https://www.molport.com/shop/molecule-link/MolPort-023-219-147
MolPort	MolPort-028-720-815	https://www.molport.com/shop/molecule-link/MolPort-028-720-815
MuseChem	I005233	https://www.musechem.com/product/I005233.html
MuseChem	I009947	https://www.musechem.com/product/I009947.html
MuseChem	R065757	https://www.musechem.com/product/R065757.html
Selleck Chemicals	S7854	http://www.selleckchem.com/search.html?searchDTO.searchParam=S7854
ShangHai Biochempartner	BCP000545	http://www.biochempartner.com/search_BCP000545
ShangHai Biochempartner	BCP04232	http://www.biochempartner.com/search_BCP04232
Toronto Research Chemicals	U700835	https://www.trc-canada.com/product-detail/?CatNum=U700835
W&J PharmaChem	50C9001989	http://wjpharmachem.com/new/searcht.php?keyword=50C9001989

PubMed

Title	Date	PubMed
Determination of ulixertinib in mice plasma by LC-MS/MS and its application to a pharmacokinetic study in mice.	2016-06-05	27017572
Structure-Guided Design of Highly Selective and Potent Covalent Inhibitors of ERK1/2.	2015-06-11	25977981

Patents

Sample Use Guides

In Vivo Use Guide

In March 2016, BioMed Valley Discoveries, in collaboration with Washington University School of Medicine, initiated a phase Ib trial to evaluate the safety and efficacy of ulixertinib 600 mg bid at the RP2D in combination with nab-paclitaxel 125 mg/m2 plus gemcitabine 1000 mg/m2 in patients with newly diagnosed metastatic pancreatic cancer (15-x384; NCT02608229)

Route of Administration: Oral

In Vitro Use Guide

In an A375 melanoma cell line containing a b-RAFV600E mutation, Ulixertinib reduces the levels of phosphorylated ERK2 (pERK) and of the phosphorylation of the downstream kinase RSK (pRSK) with IC50 of 4.1/0.14 μM, respectively. Ulixertinib also inhibits A375 cell proliferation with IC50 of 180 nM.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 21:36:57 GMT 2025` Edited by `admin` on `Mon Mar 31 21:36:57 GMT 2025`
Record UNII	3K792HRQ8B
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ULIXERTINIB HYDROCHLORIDE

Common Name

English

(S)-4-(5-CHLORO-2-(ISOPROPYLAMINO)PYRIDIN-4-YL)-N-(1-(3-CHLOROPHENYL)-2-HYDROXYETHYL)-1H-PYRROLE-2-CARBOXAMIDE HYDROCHLORIDE

Preferred Name

English

1H-PYRROLE-2-CARBOXAMIDE, 4-(5-CHLORO-2-((1-METHYLETHYL)AMINO)-4-PYRIDINYL)-N-((1S)-1-(3-CHLOROPHENYL)-2-HYDROXYETHYL)-, HYDROCHLORIDE (1:1)

Systematic Name

English

Classification Tree Code System Code

FDA ORPHAN DRUG

398213