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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 of ABT-751

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
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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: CHEMBL2095182
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
5.8 μg/mL
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
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
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
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
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

AUC

ValueDoseCo-administeredAnalytePopulation
31.4 ng × h/mL
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
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
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
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
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

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
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
Sulfonamide drugs binding to the colchicine site of tubulin: thermodynamic analysis of the drug-tubulin interactions by isothermal titration calorimetry.
2005 Jan 27
Patents

Patents

Sample Use Guides

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
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
WHO-DD  
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
Created by admin on Sat Dec 16 05:42:59 GMT 2023 , Edited by admin on Sat Dec 16 05:42:59 GMT 2023
NCI_THESAURUS C67421
Created by admin on Sat Dec 16 05:42:59 GMT 2023 , Edited by admin on Sat Dec 16 05:42:59 GMT 2023
Code System Code Type Description
SMS_ID
100000175291
Created by admin on Sat Dec 16 05:42:59 GMT 2023 , Edited by admin on Sat Dec 16 05:42:59 GMT 2023
PRIMARY
CAS
141430-65-1
Created by admin on Sat Dec 16 05:42:59 GMT 2023 , Edited by admin on Sat Dec 16 05:42:59 GMT 2023
PRIMARY
NSC
742134
Created by admin on Sat Dec 16 05:42:59 GMT 2023 , Edited by admin on Sat Dec 16 05:42:59 GMT 2023
PRIMARY
DRUG BANK
DB12254
Created by admin on Sat Dec 16 05:42:59 GMT 2023 , Edited by admin on Sat Dec 16 05:42:59 GMT 2023
PRIMARY
PUBCHEM
3035714
Created by admin on Sat Dec 16 05:42:59 GMT 2023 , Edited by admin on Sat Dec 16 05:42:59 GMT 2023
PRIMARY
FDA UNII
WDT5V5OB9F
Created by admin on Sat Dec 16 05:42:59 GMT 2023 , Edited by admin on Sat Dec 16 05:42:59 GMT 2023
PRIMARY
NCI_THESAURUS
C2679
Created by admin on Sat Dec 16 05:42:59 GMT 2023 , Edited by admin on Sat Dec 16 05:42:59 GMT 2023
PRIMARY
EPA CompTox
DTXSID60869913
Created by admin on Sat Dec 16 05:42:59 GMT 2023 , Edited by admin on Sat Dec 16 05:42:59 GMT 2023
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR
Binds to the colchicine site on β-tubulin that leads to a block in the cell cycle at the G2M phase, resulting in cellular apoptosis
Related Record Type Details
ACTIVE MOIETY