LOMEGUATRIB

Details

Stereochemistry	ACHIRAL
Molecular Formula	C10H8BrN5OS
Molecular Weight	326.172
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

NC1=NC2=C(NC=N2)C(OCC3=CC(Br)=CS3)=N1

InChI

InChIKey=JUJPKFNFCWJBCX-UHFFFAOYSA-N

InChI=1S/C10H8BrN5OS/c11-5-1-6(18-3-5)2-17-9-7-8(14-4-13-7)15-10(12)16-9/h1,3-4H,2H2,(H3,12,13,14,15,16)

HIDE SMILES / InChI

Molecular Formula	C10H8BrN5OS
Molecular Weight	326.172
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/16533784
Curator's Comment: description was created based on several sources, including https://www.astrazeneca.com/content/dam/az/our-company/investor-relations/presentations-and-webcast/Annual-Reports/2005-Annual_Report.pdf

Lomeguatrib is a O6-methylguanine-DNA-methyl-transferase inhibitor which was developed by AstraZeneca for the treatment of cancer. It was tested in phase I and II of clinical trials for the treatment of colorectal cancer, melanoma and other solid tumors.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Methylated-DNA--protein-cysteine methyltransferase 2 Target ID: P16455 Gene ID: 4255.0 Gene Symbol: MGMT Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/16533784	Inhibitor 8504		5.0 nM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Metastatic cutaneous melanoma 1 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19367282	Primary	Phase I 438	Unknown Approved Use Unknown
Metastatic colorectal cancer 14 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18475294	Primary	Phase II 1147	Unknown Approved Use Unknown
Solid tumors 147 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21811257	Primary	Phase II 1147	Unknown Approved Use Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
35.2 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/18475294	40 mg 1 times / day multiple, oral dose: 40 mg route of administration: Oral experiment type: MULTIPLE co-administered: TEMOZOLOMIDE	TEMOZOLOMIDE	LOMEGUATRIB blood	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
104.4 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/18475294	40 mg 1 times / day multiple, oral dose: 40 mg route of administration: Oral experiment type: MULTIPLE co-administered: TEMOZOLOMIDE	TEMOZOLOMIDE	LOMEGUATRIB blood	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
1.4 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/18475294	40 mg 1 times / day multiple, oral dose: 40 mg route of administration: Oral experiment type: MULTIPLE co-administered: TEMOZOLOMIDE	TEMOZOLOMIDE	LOMEGUATRIB blood	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

Sourcing

Vendor/Aggregator	ID	URL
1PlusChem LLC	1P002GFC	https://www.1pchem.com/search?query=1P002GFC
A2B Chem	AB13800	http://a2bchem.com/prod/AB13800
AChemBlock	M15128	http://www.achemblock.com/catalogsearch/result/?q=M15128
AK Scientific	Z6198	https://aksci.com/item_detail.php?cat=Z6198
AKOS	AKOS028109340	http://akoscompounds.de/catalogue/AKosSamplesiSSretrieval.php?GUID=4e4caa52-3dca-4da0-b75a-caeae59e1096&IDNUMBERS=AKOS028109340
Angene	AGN-PC-0KO1R0	http://www.angenechemical.com/productshow/AGN-PC-0KO1R0.html
AOBIOUS INC	AOB5936	http://aobious.com/aobious/search?search_query=AOB5936
ApexBio Technology	A1912	https://www.apexbt.com/catalogsearch/result/?q=A1912
AstaTech	41281	http://astatechinc.com/CPSResult.php?CRNO=41281
Axon MedChem	2223	https://www.axonmedchem.com/product/2223
BLD Pharm	BD305667	http://www.bldpharm.com/search/Search.html?keyword=BD305667
BOC Sciences	192441-08-0	http://www.bocsci.com/description.asp?cas=192441-08-0
Cayman Chemical	11732	http://www.caymanchem.com/app/template/Product.vm/catalog/11732
Chem Scene	CS-1385	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-1385
ChemShuttle	111979	https://www.chemshuttle.com/catalogsearch/result/?q=111979
eMolecules	44466280	https://orderbb.emolecules.com/search/#?query=44466280
eMolecules	45925053	https://orderbb.emolecules.com/search/#?query=45925053
eNovation Chemicals	D372527	https://www.enovationchem.com/Products.asp?SEARCHTEXT=D372527&searchbtn.x=0&searchbtn.y=0
Excenen	EX-A661	http://www.excenen.com/searchresultlist.php?id=EX-A661
Fluorochem	468340	http://www.fluorochem.co.uk/Products/Product?code=468340
KeyOrganics	GS-1303	http://www.keyorganicsinc.com/bionet/catalogsearch/result?q=GS-1303
Lab Network	LN00334879	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00334879
Lab Seeker	SC-94262	http://www.labseeker.com/search.php?keywords=SC-94262&category=0
LabSeeker	SC-94262	http://www.labseeker.com/search.php?keywords=SC-94262&category=0
Matrix Scientific	147294	http://www.matrixscientific.com/147294.html
mcule	MCULE-3927136716	https://mcule.com/MCULE-3927136716/
MedChem Express	HY-13668	https://www.medchemexpress.com/search.html?q=HY-13668&ft=&fa=&fp=
MolPort	MolPort-023-277-162	https://www.molport.com/shop/molecule-link/MolPort-023-277-162
MolPort	MolPort-035-936-422	https://www.molport.com/shop/molecule-link/MolPort-035-936-422
MuseChem	I002464	https://www.musechem.com/product/I002464.html
Princeton BioMolecular Research	PBMR221981	http://www.princetonbio.com/order_online?common_id=PBMR221981
Ryan Scientific	101-94182	https://ryansci.com/products?q=101-94182&list_q=&search_type=exact
Selleck Chemicals	S8056	http://www.selleckchem.com/search.html?searchDTO.searchParam=S8056
ShangHai Biochempartner	BCP000917	http://www.biochempartner.com/search_BCP000917
ShangHai Biochempartner	BCP07818	http://www.biochempartner.com/search_BCP07818
Tocris	4359	https://www.tocris.com/search.php?Type=QuickSearch&Value=4359

PubMed

Title	Date	PubMed
Tumor O(6)-methylguanine-DNA methyltransferase inactivation by oral lomeguatrib.	2010-01-15	20068091
O(6)-methylguanine-DNA methyltransferase depletion and DNA damage in patients with melanoma treated with temozolomide alone or with lomeguatrib.	2009-04-21	19367283
Novel role of triazenes in haematological malignancies: pilot study of Temozolomide, Lomeguatrib and IL-2 in the chemo-immunotherapy of acute leukaemia.	2007-08-01	17500047
O6-(4-bromothenyl)guanine (PaTrin-2), a novel inhibitor of O6-alkylguanine DNA alkyl-transferase, increases the inhibitory activity of temozolomide against human acute leukaemia cells in vitro.	2006-04	16412662
O6-(4-bromothenyl)guanine reverses temozolomide resistance in human breast tumour MCF-7 cells and xenografts.	2005-11-14	16278661
Quantitative trait locus analysis reveals two intragenic sites that influence O6-alkylguanine-DNA alkyltransferase activity in peripheral blood mononuclear cells.	2005-08	15831531
Effect of O6-(4-bromothenyl)guanine on different temozolomide schedules in a human melanoma xenograft model.	2002-08-10	12124813

Sample Use Guides

In Vivo Use Guide

In metastatic colorectal cancer: lomeguatrib (40 mg) is given together with temozolomide (50-200 mg m(-2)) orally for 5 consecutive days every 4 weeks. Advanced melanoma: lomeguatrib is given at dose of 40 mg, b.i.d. for 10 or 14 days and temozolomide 75-100 mg m(-2) on days 1-5. Drugs are administered orally with cycles repeated every 28 days, for up to six cycles. Advanced solid tumors: lomeguatrib is administered at dose levels of 10 to 40 mg/m2 (orally or intravenously) days 1 to 5, as a single agent, and also in combination with temozolomide.

Route of Administration: Other

In Vitro Use Guide

Anaplastic astrocytoma cell lines were treated with a temozolomide-lomeguatrib combination at concentration of 50 uM.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:07:56 GMT 2025` Edited by `admin` on `Mon Mar 31 18:07:56 GMT 2025`
Record UNII	S79265T71M
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

LOMEGUATRIB

Official Name

English

Lomeguatrib [WHO-DD]

Preferred Name

English

lomeguatrib [INN]

Common Name

English

O6-(4-Bromothenyl)guanine

Common Name

English

6-((4-BROMO-2-THIENYL)METHOXYL)PURIN-2-AMINE

Systematic Name

English

PaTrin-2

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C2134