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Details

Stereochemistry ACHIRAL
Molecular Formula C13H6F6NO3S.Na
Molecular Weight 393.237
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BATABULIN SODIUM

SMILES

[Na+].COC1=C(F)C=C([N-]S(=O)(=O)C2=C(F)C(F)=C(F)C(F)=C2F)C=C1

InChI

InChIKey=UWPXRVDIKGZQQW-UHFFFAOYSA-N
InChI=1S/C13H6F6NO3S.Na/c1-23-7-3-2-5(4-6(7)14)20-24(21,22)13-11(18)9(16)8(15)10(17)12(13)19;/h2-4H,1H3;/q-1;+1

HIDE SMILES / InChI
Batabulin or T138067 (2-fluoro-1-methoxy-4-pentafluorophenylsulfonamidobenzene) covalently and selectively modifies the beta1, beta2, and beta4 isotypes of beta-tubulin at a conserved cysteine residue, thereby disrupting microtubule polymerization. Cells exposed to batabulin become altered in shape, indicating a collapse of the cytoskeleton, and show an increase in chromosomal ploidy. Batabulin is equally efficacious in inhibiting the growth of sensitive and multidrug-resistant human tumor xenografts in athymic nude mice. Batabulin has been in clinical trials for the treatment of cancers (breast cancer, colorectal cancer, glioma, hepatocellular carcinoma, non-small cell lung cancer). It does not have clinical activity in the treatment of colorectal cancer and glioma. Batabulin development was discontinued.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P07437
Gene ID: 203068.0
Gene Symbol: TUBB
Target Organism: Homo sapiens (Human)
2.0 µM [IC50]
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
4046 ng/mL
330 mg/m² 1 times / week multiple, intravenous
dose: 330 mg/m²
route of administration: Intravenous
experiment type: MULTIPLE
co-administered:
BREQUINAR plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
9653.7 mg × h/mL
330 mg/m² 1 times / week multiple, intravenous
dose: 330 mg/m²
route of administration: Intravenous
experiment type: MULTIPLE
co-administered:
BREQUINAR plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
0.6 h
330 mg/m² 1 times / week multiple, intravenous
dose: 330 mg/m²
route of administration: Intravenous
experiment type: MULTIPLE
co-administered:
BREQUINAR plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
330 mg/m2 1 times / week multiple, intravenous
Highest studied dose
Dose: 330 mg/m2, 1 times / week
Route: intravenous
Route: multiple
Dose: 330 mg/m2, 1 times / week
Sources:
unhealthy, ADULT
n = 2
Health Status: unhealthy
Condition: hepatocellular carcinoma
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Population Size: 2
Sources:
DLT: Thrombocytopenia...
Dose limiting toxicities:
Thrombocytopenia (grade 1, 100%)
Sources:
330 mg/m2 1 times / week multiple, intravenous
Highest studied dose
Dose: 330 mg/m2, 1 times / week
Route: intravenous
Route: multiple
Dose: 330 mg/m2, 1 times / week
Sources: Page: p.185
unhealthy, ADULT
n = 18
Health Status: unhealthy
Condition: malignant glioma
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Population Size: 18
Sources: Page: p.185
300 mg/m2 1 times / week multiple, intravenous
MTD
Dose: 300 mg/m2, 1 times / week
Route: intravenous
Route: multiple
Dose: 300 mg/m2, 1 times / week
Sources:
unhealthy, ADULT
n = 7
Health Status: unhealthy
Condition: hepatocellular carcinoma
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Population Size: 7
Sources:
DLT: Neutropenia...
Dose limiting toxicities:
Neutropenia (grade 3, 42.9%)
Sources:
AEs

AEs

AESignificanceDosePopulation
Thrombocytopenia grade 1, 100%
DLT
330 mg/m2 1 times / week multiple, intravenous
Highest studied dose
Dose: 330 mg/m2, 1 times / week
Route: intravenous
Route: multiple
Dose: 330 mg/m2, 1 times / week
Sources:
unhealthy, ADULT
n = 2
Health Status: unhealthy
Condition: hepatocellular carcinoma
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Population Size: 2
Sources:
Neutropenia grade 3, 42.9%
DLT
300 mg/m2 1 times / week multiple, intravenous
MTD
Dose: 300 mg/m2, 1 times / week
Route: intravenous
Route: multiple
Dose: 300 mg/m2, 1 times / week
Sources:
unhealthy, ADULT
n = 7
Health Status: unhealthy
Condition: hepatocellular carcinoma
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Population Size: 7
Sources:
PubMed

PubMed

TitleDatePubMed
Selective, covalent modification of beta-tubulin residue Cys-239 by T138067, an antitumor agent with in vivo efficacy against multidrug-resistant tumors.
1999 May 11
Hydrophilic, pro-drug analogues of T138067 are efficacious in controlling tumor growth in vivo and show a decreased ability to cross the blood brain barrier.
2001 Oct 25
Phase 2 study of T138067-sodium in patients with malignant glioma: Trial of the National Cancer Institute of Canada Clinical Trials Group.
2005 Apr
Patents

Sample Use Guides

In clinical trials, patients with recurrent anaplastic astrocytoma or glioblastoma multiforme were treated intravenously with 330 mg/m^2 of batabulin (T138067-sodium) weekly. Treatment was continued until the patient experienced either unacceptable toxicity or progressive disease.
Route of Administration: Intravenous
The effects of batabulin (T138067) on the cytoskeleton and morphology of MCF7 cells were investigated. In the absence of batabulin, cells showed the typical morphology of adherent growing cells. However, in the presence of 100 nM batabulin for 9 hr, approximately 40% of the cells adopted a rounded morphology and became detached from the plate surface. At slightly higher drug concentrations (300 nM), almost all cells showed these morphological changes.
Name Type Language
BATABULIN SODIUM
USAN   WHO-DD  
USAN  
Official Name English
BATABULIN SODIUM [USAN]
Common Name English
BENZENESULFONAMIDE, 2,3,4,5,6-PENTAFLUORO-N-(3-FLUORO-4-METHOXYPHENYL)-, SODIUM SALT
Common Name English
2-FLUORO-1-METHOXY-4-PENTAFLUOROPHENYLSULFONAMIDOBENZENE, SODIUM SALT
Common Name English
Sodium 2,3,4,5,6-pentafluoro-N-(3-fluoro-4-methoxyphenyl)benzenesulfonamidate
Systematic Name English
T-138067 SODIUM
Code English
T138067-SODIUM
Code English
Batabulin sodium [WHO-DD]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C67421
Created by admin on Fri Dec 15 16:10:09 GMT 2023 , Edited by admin on Fri Dec 15 16:10:09 GMT 2023
Code System Code Type Description
EPA CompTox
DTXSID30173231
Created by admin on Fri Dec 15 16:10:09 GMT 2023 , Edited by admin on Fri Dec 15 16:10:09 GMT 2023
PRIMARY
NCI_THESAURUS
C1835
Created by admin on Fri Dec 15 16:10:09 GMT 2023 , Edited by admin on Fri Dec 15 16:10:09 GMT 2023
PRIMARY
FDA UNII
G04B77F772
Created by admin on Fri Dec 15 16:10:09 GMT 2023 , Edited by admin on Fri Dec 15 16:10:09 GMT 2023
PRIMARY
USAN
PP-06
Created by admin on Fri Dec 15 16:10:09 GMT 2023 , Edited by admin on Fri Dec 15 16:10:09 GMT 2023
PRIMARY
CAS
195533-98-3
Created by admin on Fri Dec 15 16:10:09 GMT 2023 , Edited by admin on Fri Dec 15 16:10:09 GMT 2023
PRIMARY
PUBCHEM
23669770
Created by admin on Fri Dec 15 16:10:09 GMT 2023 , Edited by admin on Fri Dec 15 16:10:09 GMT 2023
PRIMARY
ChEMBL
CHEMBL79280
Created by admin on Fri Dec 15 16:10:09 GMT 2023 , Edited by admin on Fri Dec 15 16:10:09 GMT 2023
PRIMARY