BMS-690514

Investigational

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C19H24N6O2
Molecular Weight	368.4329
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC1=CC=CC(NC2=NC=NN3C=CC(CN4CC[C@@H](N)[C@H](O)C4)=C23)=C1

InChI

InChIKey=CSGQVNMSRKWUSH-IAGOWNOFSA-N

InChI=1S/C19H24N6O2/c1-27-15-4-2-3-14(9-15)23-19-18-13(5-8-25(18)22-12-21-19)10-24-7-6-16(20)17(26)11-24/h2-5,8-9,12,16-17,26H,6-7,10-11,20H2,1H3,(H,21,22,23)/t16-,17-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C19H24N6O2
Molecular Weight	368.4329
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/20166197
Curator's Comment: Description was created based on several sources, including http://adisinsight.springer.com/drugs/800025400 https://www.ncbi.nlm.nih.gov/pubmed/23490650

BMS-690514 is a potent, reversible oral inhibitor of epidermal growth factor receptor (EGFR/HER-1), HER-2 and -4, and vascular endothelial growth factor receptors (VEGFRs)-1 to -3 offering targeted inhibition of tumour growth and vascularisation in a single agent. Bristol-Myers Squibb was developing BMS 690514, as an oral treatment for cancer. BMS-690514 had being in phase II for the treatment of breast cancer; non-small cell lung cancer, but later these studies were discontinued.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
PC-9 3 Target ID: CHEMBL614102 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23490650 \| https://www.ncbi.nlm.nih.gov/pubmed/21531814	Inhibitor 8504	9.0 nM [IC50]
Receptor protein-tyrosine kinase erbB-4 12 Target ID: CHEMBL3009 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21531814	Inhibitor 8504	60.0 nM [IC50]
Receptor protein-tyrosine kinase erbB-2 35 Target ID: CHEMBL1824 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21531814	Inhibitor 8504	19.0 nM [IC50]
Vascular endothelial growth factor receptor 1 44 Target ID: CHEMBL1868 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21531814	Inhibitor 8504	50.0 nM [IC50]
Vascular endothelial growth factor receptor 2 112 Target ID: CHEMBL279 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21531814	Inhibitor 8504	50.0 nM [IC50]
Vascular endothelial growth factor receptor 3 41 Target ID: CHEMBL1955 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21531814 \| http://clincancerres.aacrjournals.org/content/clincanres/suppl/2011/06/17/1078-0432.CCR-10-3417.DC1/T3.FL1-6.pdf	Inhibitor 8504	25.0 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Non small cell lung cancer 7 Sources: https://clinicaltrials.gov/ct2/show/NCT00743938	Primary		Phase II 1147	Unknown Approved Use Unknown
Breast cancer 432 Sources: https://clinicaltrials.gov/ct2/show/NCT01068704	Primary		Phase II 1147	Unknown Approved Use Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
203.77 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/22878519	200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered:		BMS-690514 plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
207.8 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/22878519	200 mg 1 times / day multiple, oral dose: 200 mg route of administration: Oral experiment type: MULTIPLE co-administered:		BMS-690514 plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

AUC

Value	Dose	Co-administered	Analyte	Population
1205.81 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/22878519	200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered:		BMS-690514 plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
1349.77 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/22878519	200 mg 1 times / day multiple, oral dose: 200 mg route of administration: Oral experiment type: MULTIPLE co-administered:		BMS-690514 plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
12.17 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/22878519	200 mg 1 times / day multiple, oral dose: 200 mg route of administration: Oral experiment type: MULTIPLE co-administered:		BMS-690514 plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inducer 1087 substrate 1946	inhibitor 2438 substrate 1193	inhibitor 2507 substrate 1388

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
P-gp 1741 CYP2C19 2057 CYP2C8 1057 CYP1A2 2153 CYP2B6 926 CYP3A4/5 296 CYP2A6 879	UGT 219 CYP2C19 1119 CYP1A2 1197 UGT1A10 331 UGT2B4/7 1 UGT2B15 236 CYP2E1 729 UGT2B17 237 UGT1A3 470 CYP3A5 446 UGT1A4 399 CYP1B1 104 UGT1A6 343 CYP2A6 626 UGT1A7 249 CYP2B6 776 UGT1A8 323 UGT1A9 423 CYP2C8 810 P-gp 2052 UGT1A1 479	CYP2B6 669 CYP1A2 832 UGT1A1 78 CYP1A1 151

Drug as perpetrator

Target	Modality	Activity
P-gp 1932	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/20166197/	likely [Inhibition 10 uM]
CYP2B6 1160	inducer 1966 Sources: https://pubmed.ncbi.nlm.nih.gov/21673131/	likely
CYP3A4 2633	inducer 1966 Sources: https://pubmed.ncbi.nlm.nih.gov/21673131/	likely
UGT1A1 303	inducer 1966 Sources: https://pubmed.ncbi.nlm.nih.gov/21673131/	no
CYP1A2 2333	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/20166197/	weak [IC50 >40 uM]
CYP2C19 2141	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/20166197/ \| https://pubmed.ncbi.nlm.nih.gov/21673131/	weak [IC50 >40 uM]
CYP2C8 1117	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/20166197/	weak [IC50 >40 uM]
CYP2C9 2497	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/20166197/ \| https://pubmed.ncbi.nlm.nih.gov/21673131/	weak [IC50 >40 uM]
CYP2D6 2546	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/20166197/	weak [IC50 >40 uM]
CYP3A4/5 357	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/20166197/ \| https://pubmed.ncbi.nlm.nih.gov/21673131/	weak [IC50 >40 uM]
CYP2A6 911	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/21673131/	weak [IC50 >45 uM]
CYP2B6 1160	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/21673131/	weak [IC50 >45 uM]
CYP1A1 272	inducer 1966 Sources: https://pubmed.ncbi.nlm.nih.gov/21673131/	yes
CYP1A2 2333	inducer 1966 Sources: https://pubmed.ncbi.nlm.nih.gov/21673131/	yes

Drug as victim

Target	Modality	Activity	Clinical evidence
CYP2D6 1388	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/20668249/ \| https://pubmed.ncbi.nlm.nih.gov/20166197/	major [Km >= 1 uM]	no (pharmacogenomic study) Comment: No clinically relevant differences between poor and extensive metabolizers Sources: https://pubmed.ncbi.nlm.nih.gov/20668249/ \| https://pubmed.ncbi.nlm.nih.gov/20166197/
CYP3A4 1946	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/20668249/ \| https://pubmed.ncbi.nlm.nih.gov/20166197/ \| https://pubmed.ncbi.nlm.nih.gov/23436267/	major [Km >= 23 uM]	yes (co-administration study) Comment: Ketoconazole increased dose-normalized Cmax and AUCinf by 55% and 127%. Sources: https://pubmed.ncbi.nlm.nih.gov/20668249/ \| https://pubmed.ncbi.nlm.nih.gov/20166197/ \| https://pubmed.ncbi.nlm.nih.gov/23436267/
CYP2C9 1193	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/21673131/	major
CYP1A2 1197	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/20166197/	no
CYP2C19 1119	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/20166197/	no
UGT1A1 479	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/21673131/	no
UGT1A10 331	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/21673131/	no
UGT1A3 470	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/21673131/	no
UGT1A4 399	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/21673131/	no
UGT1A6 343	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/21673131/	no
UGT1A7 249	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/21673131/	no
UGT1A8 323	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/21673131/	no
UGT1A9 423	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/21673131/	no
UGT2B15 236	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/21673131/	no
UGT2B17 237	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/21673131/	no
CYP1B1 104	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/21673131/	unlikely
CYP2A6 626	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/21673131/	unlikely
CYP2B6 776	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/21673131/	unlikely
CYP2C8 810	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/21673131/	unlikely
CYP2E1 729	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/21673131/	unlikely
CYP3A5 446	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/21673131/	unlikely
UGT 219	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/20668249/ \| https://pubmed.ncbi.nlm.nih.gov/20166197/	yes
UGT2B4/7 1	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/21673131/	yes
P-gp 2052	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/20166197/ \| https://pubmed.ncbi.nlm.nih.gov/23436267/	yes	yes (co-administration study) Comment: Ketoconazole increased dose-normalized Cmax and AUCinf by 55% and 127%. Sources: https://pubmed.ncbi.nlm.nih.gov/20166197/ \| https://pubmed.ncbi.nlm.nih.gov/23436267/

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY100111	https://www.001chemical.com/chem/search?q=DY100111
1PlusChem LLC	1P00GUIN	https://www.1pchem.com/search?query=1P00GUIN
AChemBlock	C-2973	http://www.achemblock.com/catalogsearch/result/?q=C-2973
AK Scientific	0913AF	https://aksci.com/item_detail.php?cat=0913AF
AstaTech	C13451	http://astatechinc.com/CPSResult.php?CRNO=C13451
AstaTech	P12423	http://astatechinc.com/CPSResult.php?CRNO=P12423
BioSynth	J-501257	https://www.biosynth.com/en/products/life-science/other-biochemicals/products/J-501257
BLD Pharm	BD301507	http://www.bldpharm.com/search/Search.html?keyword=BD301507
BOC Sciences	859853-30-8	http://www.bocsci.com/description.asp?cas=859853-30-8
Chem Scene	CS-M1183	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-M1183
ChemShuttle	101178	https://www.chemshuttle.com/catalogsearch/result/?q=101178
Combi-Blocks	QM-7559	http://www.combi-blocks.com/cgi-bin/find.cgi?QM-7559
eMolecules	275181491	https://orderbb.emolecules.com/search/#?query=275181491
eMolecules	300607242	https://orderbb.emolecules.com/search/#?query=300607242
eMolecules	36553283	https://orderbb.emolecules.com/search/#?query=36553283
eMolecules	50285824	https://orderbb.emolecules.com/search/#?query=50285824
eNovation Chemicals	D500114	https://www.enovationchem.com/Products.asp?SEARCHTEXT=D500114&searchbtn.x=0&searchbtn.y=0
Fluorochem	502781	http://www.fluorochem.co.uk/Products/Product?code=502781
KeyOrganics	CS-15397	http://www.keyorganicsinc.com/bionet/catalogsearch/result?q=CS-15397
Lab Network	LN00169691	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00169691
Matrix Scientific	69274	http://www.matrixscientific.com/069274.html
mcule	MCULE-1050657001	https://mcule.com/MCULE-1050657001/
mcule	MCULE-6012766942	https://mcule.com/MCULE-6012766942/
mcule	MCULE-8033837307	https://mcule.com/MCULE-8033837307/
MedChem Express	HY-10333	https://www.medchemexpress.com/search.html?q=HY-10333&ft=&fa=&fp=
Molcore	MC100111	http://www.molcore.com/CatMC100111.html
Molnova	M16232	https://www.molnova.com/en/serch-list.html?keywords=M16232
MolPort	MolPort-020-393-325	https://www.molport.com/shop/molecule-link/MolPort-020-393-325
MolPort	MolPort-046-593-158	https://www.molport.com/shop/molecule-link/MolPort-046-593-158
ShangHai Biochempartner	BCP000362	http://www.biochempartner.com/search_BCP000362
Synthonix	1197	https://synthonix.com/catalogsearch/result/?q=1197
Synthonix	A65740	https://synthonix.com/catalogsearch/result/?q=A65740
Synthonix	SL100047	http://www.synthon-lab.com/search.php?cas_or_id=SL100047&cas_id_field=1
Tetrahedron	TS86847	http://www.thsci.com/search.do?q=TS86847

PubMed

Title	Date	PubMed
Mechanistic studies on a P450-mediated rearrangement of BMS-690514: conversion of a pyrrolotriazine to a hydroxypyridotriazine.	2011-01-14	21080678
Preclinical pharmacokinetics and in vitro metabolism of BMS-690514, a potent inhibitor of EGFR and VEGFR2.	2010-08	20166197
A novel epidermal growth factor receptor inhibitor promotes apoptosis in non-small cell lung cancer cells resistant to erlotinib.	2007-07-01	17616683

Patents

Sample Use Guides

In Vivo Use Guide

Tablets, Oral, 200 mg, once daily,

Route of Administration: Oral

In Vitro Use Guide

Non–small cell lung tumor cells with exon 19 deletion (HCC4006, HCC827, and PC9) were highly sensitive to BMS-690514, which inhibits their proliferation with IC50 values of 2 to 35 nmol/L. Breast and gastric tumor cell lines that have HER2 gene amplification (N87, SNU-216, AU565, BT474, KPL4, and HCC202) were inhibited with IC50 values of 20 to 60 nmol/L

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:12:23 GMT 2025` Edited by `admin` on `Mon Mar 31 18:12:23 GMT 2025`
Record UNII	VKU5X213Q7
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

BMS-690514

Common Name

English

BMS 6690514

Preferred Name

English

3-PIPERIDINOL, 4-AMINO-1-((4-((3-METHOXYPHENYL)AMINO)PYRROLO(2,1-F)(1,2,4)TRIAZIN-5-YL)METHYL)-, (3R,4R)-

Systematic Name

English

BMS 690514

Common Name

English

BMS 690514 [WHO-DD]

Common Name

English

(3R,4R)-4-AMINO-1-((4-((3-METHOXYPHENYL)AMINO)PYRROLO(2,1-F)(1,2,4)TRIAZIN-5-YL)METHYL)-3-PIPERIDINOL

Systematic Name

English

Code System Code Type Description

PUBCHEM

11349170