ABT-751

Investigational

Details

Stereochemistry	ACHIRAL
Molecular Formula	C18H17N3O4S
Molecular Weight	371.41
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC1=CC=C(C=C1)S(=O)(=O)NC2=C(NC3=CC=C(O)C=C3)N=CC=C2

InChI

InChIKey=URCVCIZFVQDVPM-UHFFFAOYSA-N

InChI=1S/C18H17N3O4S/c1-25-15-8-10-16(11-9-15)26(23,24)21-17-3-2-12-19-18(17)20-13-4-6-14(22)7-5-13/h2-12,21-22H,1H3,(H,19,20)

HIDE SMILES / InChI

Molecular Formula	C18H17N3O4S
Molecular Weight	371.41
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/18520803
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/16675578

ABT-751 is an orally bioavailable antimitotic sulfonamide, which binds to the colchicine-binding site on beta-tubulin and inhibits the polymerization of microtubules, leads to a block in the cell cycle at the G2M phase, resulting in cellular apoptosis. ABT-751 had been in phase Ⅱ clinical studies for the treatment of breast cancer; colorectal cancer; non-small cell lung cancer; renal cancer, prostate cancer, but these researches have been discontinued.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Tubulin 69 Target ID: CHEMBL2095182 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9242451	Inhibitor 8297

Conditions

Condition	Modality	Highest Phase	Product
Prostate cancer 178 Sources: https://clinicaltrials.gov/ct2/show/NCT00471718	Primary	Phase II 1132	Unknown Approved Use Unknown
Colorectal cancer 101 Sources: http://ascopubs.org/doi/abs/10.1200/jco.2005.23.16_suppl.3537	Primary	Phase II 1132	Unknown Approved Use Unknown
Renal cell cancer 7 Sources: https://clinicaltrials.gov/ct2/show/NCT00073112	Primary	Phase II 1132	Unknown Approved Use Unknown
Non-small cell lung cancer 206 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18520803	Primary	Phase II 1132	Unknown Approved Use Unknown
Breast cancer 434 Sources: https://clinicaltrials.gov/ct2/show/NCT00063102	Primary	Phase II 1132	Unknown Approved Use Unknown

C_max

Value	Dose	Analyte	Population
5.8 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/16675578	150 mg 2 times / day multiple, oral dose: 150 mg route of administration: Oral experiment type: MULTIPLE co-administered:	ABT-751 plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
9 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/16675578	175 mg 2 times / day multiple, oral dose: 175 mg route of administration: Oral experiment type: MULTIPLE co-administered:	ABT-751 plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
6.6 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/16675578	200 mg 1 times / day multiple, oral dose: 200 mg route of administration: Oral experiment type: MULTIPLE co-administered:	ABT-751 plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
13 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/16675578	300 mg 1 times / day multiple, oral dose: 300 mg route of administration: Oral experiment type: MULTIPLE co-administered:	ABT-751 plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
12.7 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/16675578	250 mg 1 times / day multiple, oral dose: 250 mg route of administration: Oral experiment type: MULTIPLE co-administered:	ABT-751 plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

AUC

Value	Dose	Analyte	Population
31.4 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/16675578	150 mg 2 times / day multiple, oral dose: 150 mg route of administration: Oral experiment type: MULTIPLE co-administered:	ABT-751 plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
43.5 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/16675578	175 mg 2 times / day multiple, oral dose: 175 mg route of administration: Oral experiment type: MULTIPLE co-administered:	ABT-751 plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
42.8 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/16675578	200 mg 1 times / day multiple, oral dose: 200 mg route of administration: Oral experiment type: MULTIPLE co-administered:	ABT-751 plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
50.2 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/16675578	300 mg 1 times / day multiple, oral dose: 300 mg route of administration: Oral experiment type: MULTIPLE co-administered:	ABT-751 plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
60.5 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/16675578	250 mg 1 times / day multiple, oral dose: 250 mg route of administration: Oral experiment type: MULTIPLE co-administered:	ABT-751 plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

Sourcing

Vendor/Aggregator	ID	URL
1PlusChem LLC	1P006YRX	https://www.1pchem.com/search?query=1P006YRX
AK Scientific	X7522	https://aksci.com/item_detail.php?cat=X7522
Angene	AGN-PC-0PQSM0	http://www.angenechemical.com/productshow/AGN-PC-0PQSM0.html
ApexBio Technology	A1493	https://www.apexbt.com/catalogsearch/result/?q=A1493
AstaTech	62303	http://astatechinc.com/CPSResult.php?CRNO=62303
BLD Pharm	BD448852	http://www.bldpharm.com/search/Search.html?keyword=BD448852
BOC Sciences	141430-65-1	http://www.bocsci.com/description.asp?cas=141430-65-1
Chem Scene	CS-0495	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-0495
ChemShuttle	141357	https://www.chemshuttle.com/catalogsearch/result/?q=141357
Excenen	EX-A517	http://www.excenen.com/searchresultlist.php?id=EX-A517
KeyOrganics	AS-55908	http://www.keyorganicsinc.com/bionet/catalogsearch/result?q=AS-55908
Lab Network	LN00333102	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00333102
MedChem Express	HY-13270	https://www.medchemexpress.com/search.html?q=HY-13270&ft=&fa=&fp=
MolPort	MolPort-009-679-422	https://www.molport.com/shop/molecule-link/MolPort-009-679-422
Molnova	M11717	https://www.molnova.com/en/serch-list.html?keywords=M11717
MuseChem	I001578	https://www.musechem.com/product/I001578.html
Princeton BioMolecular Research	PBMR221751	http://www.princetonbio.com/order_online?common_id=PBMR221751
Ryan Scientific	Obeticholic_Acid	https://ryansci.com/products?q=Obeticholic_Acid&list_q=&search_type=exact
Selleck Chemicals	S1165	http://www.selleckchem.com/search.html?searchDTO.searchParam=S1165
ShangHai Biochempartner	BCP000236	http://www.biochempartner.com/search_BCP000236
ShangHai Biochempartner	BCP02079	http://www.biochempartner.com/search_BCP02079
TargetMol	T1758	https://www.targetmol.com/search?keyword=T1758
Tocris	4138	https://www.tocris.com/search.php?Type=QuickSearch&Value=4138
Toronto Research Chemicals	A112620	https://www.trc-canada.com/product-detail/?CatNum=A112620
Toronto Research Chemicals	B809593	https://www.trc-canada.com/product-detail/?CatNum=B809593
eMolecules	32176497	https://orderbb.emolecules.com/search/#?query=32176497
eMolecules	36772270	https://orderbb.emolecules.com/search/#?query=36772270
eNovation Chemicals	D480464	https://www.enovationchem.com/Products.asp?SEARCHTEXT=D480464&searchbtn.x=0&searchbtn.y=0
mcule	MCULE-1224707126	https://mcule.com/MCULE-1224707126/
mcule	MCULE-4261213773	https://mcule.com/MCULE-4261213773/

PubMed

Title	Date	PubMed
Array-based structure and gene expression relationship study of antitumor sulfonamides including N-[2-[(4-hydroxyphenyl)amino]-3-pyridinyl]-4-methoxybenzenesulfonamide and N-(3-chloro-7-indolyl)-1,4-benzenedisulfonamide.	2002 Oct 24	12383017
Sulfonamide drugs binding to the colchicine site of tubulin: thermodynamic analysis of the drug-tubulin interactions by isothermal titration calorimetry.	2005 Jan 27	15658868

Patents

Sample Use Guides

In Vivo Use Guide

ABT-751 was administered on a daily (q.d.) or twice daily (b.i.d.) oral schedule for 7 days every 3 weeks to 39 patients with refractory solid tumors.

Route of Administration: Oral

In Vitro Use Guide

It was evaluated in vitro cytotoxicity of ABT-751. The cytotoxicity profiles were evaluated in each pediatric tumor cell lines (Neuroblastoma (SK-N-AS, SK-N-DZ), rhabdomyosarcoma (RD), Ewing sarcoma (TC-71), medulloblastoma (HTB-186 Daoy) and osteosarcoma (HOS) pediatric tumor cell lines by ACEA RT-CES with hourly cell index measurements. The ABT-751 IC(50) was 0.6-2.6 uM in neuroblastoma and 0.7-4.6 uM in other solid tumor cell lines. Following drug exposure, polymerized tubulin decreased in a concentration- and time-dependent manner in cell lines.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 05:42:59 GMT 2023` Edited by `admin` on `Sat Dec 16 05:42:59 GMT 2023`
Record UNII	WDT5V5OB9F
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

ABT-751

Common Name

English

E-7010

Common Name

English

NSC-742134

Code

English

E 7010 [WHO-DD]

Common Name

English

E 7010

Common Name

English

BENZENESULFONAMIDE, N-(2-((4-HYDROXYPHENYL)AMINO)-3-PYRIDINYL)-4-METHOXY-

Systematic Name

English

Classification Tree Code System Code

FDA ORPHAN DRUG

188604