XL-388 HYDROCHLORIDE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C23H22FN3O4S.ClH
Molecular Weight	491.963
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

Cl.CC1=C(F)C(=CC=C1C(=O)N2CCOC3=CC=C(C=C3C2)C4=CN=C(N)C=C4)S(C)(=O)=O

InChI

InChIKey=XUGXNTJUYGTLLW-UHFFFAOYSA-N

InChI=1S/C23H22FN3O4S.ClH/c1-14-18(5-7-20(22(14)24)32(2,29)30)23(28)27-9-10-31-19-6-3-15(11-17(19)13-27)16-4-8-21(25)26-12-16;/h3-8,11-12H,9-10,13H2,1-2H3,(H2,25,26);1H

HIDE SMILES / InChI

Molecular Formula	C23H22FN3O4S
Molecular Weight	455.502
Charge	0
Count

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

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/800019856
Curator's Comment: Description was created based on several sources, including http://mct.aacrjournals.org/content/8/12_Supplement/B146 | https://www.ncbi.nlm.nih.gov/pubmed/23394126

XL388 is a selective small-molecule ATP-competitive inhibitor of mTOR kinase complexes mTORC1 and mTORC2. XL388 inhibited cellular phosphorylation of mTOR complex 1 (p-p70S6K, pS6, and p-4E-BP1) and mTOR complex 2 (pAKT (S473)) substrates. In vitro, XL388 inhibits the viability of solid and hematopoietic tumor cell lines when assayed as a single agent. XL388 also synergizes with chemotherapeutics in cell‐based assays to block cell viability. When dosed orally once daily in mice, XL388 shows robust anti‐tumor activity in multiple xenograft models. Exelixis has discontinued the development of XL388. The company intends to pursue a collaboration partner or other external opportunities for the development of XL388.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Mammalian target of Rapamycin (mTORC1) 23 Target ID: CHEMBL2221341 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23394126 \| http://mct.aacrjournals.org/content/8/12_Supplement/B146	Inhibitor 8504		8.0 nM [IC50]
TORC2 complex 3 Target ID: GO:0031932 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23394126 \| http://mct.aacrjournals.org/content/8/12_Supplement/B146	Inhibitor 8504		166.0 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Cancer 609 Sources: http://adisinsight.springer.com/drugs/800019856 http://mct.aacrjournals.org/content/8/12_Supplement/B146	Primary		Preclinical	Unknown Approved Use Unknown
Osteosarcoma 22 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27385099	Primary		Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
The anti-cancer activity of the mTORC1/2 dual inhibitor XL388 in preclinical osteosarcoma models.	2016-08-02	27385099
MicroRNA-21 Regulates the Proliferation, Differentiation, and Apoptosis of Human Renal Cell Carcinoma Cells by the mTOR-STAT3 Signaling Pathway.	2016	27712594
Discovery of a novel class of highly potent, selective, ATP-competitive, and orally bioavailable inhibitors of the mammalian target of rapamycin (mTOR).	2013-03-28	23394126

Patents

Sample Use Guides

In Vivo Use Guide

oral administration of XL388 (20 mg/kg body weight, every three days, × 7 times) significantly inhibited U2OS xenograft growth in severe combined immuno-deficient mice.

Route of Administration: Oral

In Vitro Use Guide

XL388 (100 nM) inhibited survival in human osteosarcoma cells

Substance Class	Chemical Created by `admin` on `Mon Mar 31 22:36:48 GMT 2025` Edited by `admin` on `Mon Mar 31 22:36:48 GMT 2025`
Record UNII	I36BZ5F3D1
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

(7-(6-AMINOPYRIDIN-3-YL)-2,3-DIHYDROBENZOL(F)(1,4)OXAZEPIN-4(5H-YL)(3FLUORO-2-METHYL-4-(METHYLSULFONYL)PHENYL)METHANONE HYDROCHLORIDE

Preferred Name

English

XL-388 HYDROCHLORIDE

Code

English

METHANONE, (7-(6-AMINO-3-PYRIDINYL)-2,3-DIHYDRO-1,4-BENZOXAZEPIN-4(5H)-YL)(3-FLUORO-2-METHYL-4-(METHYLSULFONYL)PHENYL)-, HYDROCHLORIDE (1:1)

Systematic Name

English

Code System Code Type Description

CAS

1777807-51-8

Created by admin on Mon Mar 31 22:36:48 GMT 2025 , Edited by admin on Mon Mar 31 22:36:48 GMT 2025

PRIMARY

FDA UNII

I36BZ5F3D1

Created by admin on Mon Mar 31 22:36:48 GMT 2025 , Edited by admin on Mon Mar 31 22:36:48 GMT 2025

PRIMARY

PUBCHEM

131634503

Created by admin on Mon Mar 31 22:36:48 GMT 2025 , Edited by admin on Mon Mar 31 22:36:48 GMT 2025

PRIMARY

Related Record Type Details


					B7I5G3Z7XR

XL-388

ACTIVE MOIETY

Details

SMILES

InChI

DescriptionSources: http://adisinsight.springer.com/drugs/800019856Curator's Comment: Description was created based on several sources, including http://mct.aacrjournals.org/content/8/12_Supplement/B146 | https://www.ncbi.nlm.nih.gov/pubmed/23394126

Originator

Approval Year

Targets

Conditions

Approved Use

Approved Use

PubMed

Patents

Sample Use Guides

Description
Sources: http://adisinsight.springer.com/drugs/800019856
Curator's Comment: Description was created based on several sources, including http://mct.aacrjournals.org/content/8/12_Supplement/B146 | https://www.ncbi.nlm.nih.gov/pubmed/23394126