| Stereochemistry | ACHIRAL |
| Molecular Formula | C13H7F6NO3S |
| Molecular Weight | 371.255 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
COC1=C(F)C=C(NS(=O)(=O)C2=C(F)C(F)=C(F)C(F)=C2F)C=C1
InChI
InChIKey=ROZCIVXTLACYNY-UHFFFAOYSA-N
InChI=1S/C13H7F6NO3S/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/h2-4,20H,1H3
| Molecular Formula | C13H7F6NO3S |
| Molecular Weight | 371.255 |
| Charge | 0 |
| Count |
MOL RATIO
1 MOL RATIO (average) |
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
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.
CNS Activity
Originator
Approval Year
Doses
AEs
Sourcing
PubMed
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.
