Batabulin sodium

• CAT Number: I003955
• CAS Number: 195533-53-0
• Molecular Formula: C13H7F6NO3S
• Molecular Weight: 371.26
• Purity: ≥95%
• Synonyms: T138067 sodiumT138067sodiumT 138067 sodiumT 67D03059.;sodium (3-fluoro-4-methoxyphenyl)-(2,3,4,5,6-pentafluorophenyl)sulfonylazanide
• Solubility: Soluble in DMSO, not in water
• Storage: store at -20°C
• IUPAC Name: 2,3,4,5,6-pentafluoro-N-(3-fluoro-4-methoxyphenyl)benzenesulfonamide
• InChI: 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
• InChIKey: ROZCIVXTLACYNY-UHFFFAOYSA-N
• SMILES: COC1=C(C=C(C=C1)NS(=O)(=O)C2=C(C(=C(C(=C2F)F)F)F)F)F

Batabulin sodium (Cat.No:I003955) is a synthetic pentafluorophenylsulfonamide with potential antineoplastic activity. T138067 covalently binds to and selectively modifies the beta 1, beta 2, beta 3, and beta 4 isotypes of beta tubulin at a conserved cysteine residue, resulting in disruption of microtubule polymerization, collapse of the cytoskeleton, an increase in chromosomal ploidy, cell cycle arrest, and tumor cell apoptosis.

Reference

1:Neuro Oncol. 2005 Apr;7(2):183-8. Phase 2 study of T138067-sodium in patients with malignant glioma: Trial of the National Cancer Institute of Canada Clinical Trials Group.Kirby S,Gertler SZ,Mason W,Watling C,Forsyth P,Aniagolu J,Stagg R,Wright M,Powers J,Eisenhauer EA, PMID: 15831236 PMCID: PMC1871890 DOI: 10.1215/S1152851704000602 Abstract: We studied the activity of T138067-sodium in patients with malignant gliomas. T138067-sodium is a unique new chemotherapy agent that inhibits microtubule formation by binding irreversibly and specifically to beta(1), beta(2)and beta(4) isotypes of 3-tubulin, causing cell arrest at G(2)/M and inducing apoptosis. Patients with recurrent anaplastic astrocytoma or glioblastoma multiforme were treated intravenously with 330 mg/m(2) of T138067-sodium weekly. Treatment was continued until the patient experienced either unacceptable toxicity or progressive disease. Patients had to have histologically proven glioma, have bidimensionally measurable disease at least 1 cm x 1 cm, and have received no more than one prior adjuvant chemotherapy. No chemotherapy or radiotherapy for recurrent disease was permitted. Nineteen patients entered the trial. One patient was found to be ineligible. There were two patients with anaplastic astrocytoma and 16 with glioblastoma multiforme. Only two patients had received prior adjuvant chemotherapy. The first seven patients had full pharmacokinetic sampling. No dose-limiting toxicity was seen, and pharmacokinetic results were consistent with those from nonglioma patients. The most common drug-related effects were fatigue (33%), nausea (28%), neutropenia (28%), and anorexia (17%). No patients stopped the study because of toxicity. No responses were seen in the 15 eligible patients who completed at least one cycle. Three patients had stable disease with a median duration of 2.6 months. Our results suggest that given in this dose and schedule T138067-sodium does not have activity in this population of anaplastic astrocytoma and glioblastoma multiforme.