Batabulin sodium
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MedKoo CAT#: 200440

CAS#: 195533-98-3 (sodium)

Description: Batabulin, also known as T138067, 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.


Chemical Structure

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Batabulin sodium
CAS# 195533-98-3 (sodium)

Theoretical Analysis

MedKoo Cat#: 200440
Name: Batabulin sodium
CAS#: 195533-98-3 (sodium)
Chemical Formula: C13H6F6NNaO3S
Exact Mass:
Molecular Weight: 393.2352
Elemental Analysis: C, 39.71; H, 1.54; F, 28.99; N, 3.56; Na, 5.85; O, 12.21; S, 8.15

Price and Availability

Size Price Availability Quantity
5.0mg USD 250.0 2 Weeks
10.0mg USD 410.0 2 Weeks
25.0mg USD 730.0 2 Weeks
50.0mg USD 1060.0 2 Weeks
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Related CAS #: 195533-98-3 (sodium)   195533-53-0 (free)  

Synonym: Batabulin sodium; Batabulin; T138067; T-138067; T 138067;

IUPAC/Chemical Name: sodium (3-fluoro-4-methoxyphenyl)-(2,3,4,5,6-pentafluorophenyl)sulfonylazanide

InChi Key: UWPXRVDIKGZQQW-UHFFFAOYSA-N

InChi Code: 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

SMILES Code: O=S([N-]C1=CC=C(OC)C(F)=C1)(C2=C(F)C(F)=C(F)C(F)=C2F)=O.[Na+]

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >5 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Product Data:

Biological target: Batabulin sodium (T138067 sodium) is an antitumor agent which binds covalently and selectively to a subset of the β-tubulin isotypes, thereby disrupting microtubule polymerization.
In vitro activity: To measure the effects of T138067 on microtubule formation, two types of in vitro tubulin polymerization assays were used. In a sedimentation assay, the polymerization reaction was performed in the absence or presence of T138067 (Fig. 3A). The reaction products were size-fractionated by spinning the mixture through a glycerol cushion. Heterodimeric tubulin remains primarily in the cushion, whereas larger molecules (microtubules) sediment through the cushion and form a pellet at the bottom of the tube. In the absence of any agent, a substantial reduction in the amount of tubulin in the cushion fraction was observed in a polymerization reaction that was incubated at 37°C, in comparison to one that was kept at 0°C, indicating the formation of microtubules (Fig. 3A, compare lanes 1 and 2). However, increasing concentrations of T138067 at 37°C increased the amount of tubulin in the cushion fraction to levels comparable to those derived from the control reaction at 0°C (Fig. 3A, compare lanes 1 and 3 to 5). When the pellet fractions were analyzed, a strong reduction of tubulin was observed in reactions containing T138067 in comparison to reactions that were incubated in the absence of the drug. In summary, these results indicate that T138067 prevents microtubule formation. Reference: Proc Natl Acad Sci U S A. 1999 May 11;96(10):5686-91. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC21921/
In vivo activity: The antitumor efficacies of T138067, paclitaxel, and vinblastine were evaluated in mouse xenograft models. Drug-sensitive, human T cell leukemia CCRF-CEM cells, and their vinblastine/paclitaxel-resistant subline (CCRF-CEM/VBL100) were grafted separately into athymic nude mice. Animals were dosed i.p. at the maximally tolerated doses of paclitaxel (30 mg/kg), vinblastine (1 mg/kg), and T138067 (40 mg/kg) once per week. After a single i.p. dose, all three drugs impaired the growth of the drug-sensitive CCRF-CEM tumors (Fig. 5A). Two additional weekly doses of each drug further impeded tumor growth, resulting in similar antitumor efficacies for all three drugs. T138067 showed the same degree of efficacy when tested against the MDR subline (Fig. 5B). In contrast, paclitaxel and vinblastine showed approximately 50% reduced efficacy against the MDR tumors (Fig. 5B). Thus, T138067 may be clinically useful for the treatment of human cancers that have developed resistance to standard chemotherapeutic agents. Reference: Proc Natl Acad Sci U S A. 1999 May 11;96(10):5686-91. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC21921/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMF 30.0 76.29
DMSO 30.0 76.29
Ethanol 30.0 76.29
Ethanol:PBS (pH 7.2) (1:3) 0.25 0.64

Preparing Stock Solutions

The following data is based on the product molecular weight 393.2352 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Shan B, Medina JC, Santha E, Frankmoelle WP, Chou TC, Learned RM, Narbut MR, Stott D, Wu P, Jaen JC, Rosen T, Timmermans PB, Beckmann H. Selective, covalent modification of beta-tubulin residue Cys-239 by T138067, an antitumor agent with in vivo efficacy against multidrug-resistant tumors. Proc Natl Acad Sci U S A. 1999 May 11;96(10):5686-91. doi: 10.1073/pnas.96.10.5686. PMID: 10318945; PMCID: PMC21921.
In vitro protocol: 1. Shan B, Medina JC, Santha E, Frankmoelle WP, Chou TC, Learned RM, Narbut MR, Stott D, Wu P, Jaen JC, Rosen T, Timmermans PB, Beckmann H. Selective, covalent modification of beta-tubulin residue Cys-239 by T138067, an antitumor agent with in vivo efficacy against multidrug-resistant tumors. Proc Natl Acad Sci U S A. 1999 May 11;96(10):5686-91. doi: 10.1073/pnas.96.10.5686. PMID: 10318945; PMCID: PMC21921.
In vivo protocol: 1. Shan B, Medina JC, Santha E, Frankmoelle WP, Chou TC, Learned RM, Narbut MR, Stott D, Wu P, Jaen JC, Rosen T, Timmermans PB, Beckmann H. Selective, covalent modification of beta-tubulin residue Cys-239 by T138067, an antitumor agent with in vivo efficacy against multidrug-resistant tumors. Proc Natl Acad Sci U S A. 1999 May 11;96(10):5686-91. doi: 10.1073/pnas.96.10.5686. PMID: 10318945; PMCID: PMC21921.

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 1: Ling X, He X, Apontes P, Cao F, Azrak RG, Li F. Enhancing effectiveness of the MDR-sensitive compound T138067 using advanced treatment with negative modulators of the drug-resistant protein survivin. Am J Transl Res. 2009 Jul 15;1(4):393-405. PubMed PMID: 19956451; PubMed Central PMCID: PMC2780039.

2: Berlin JD, Venook A, Bergsland E, Rothenberg M, Lockhart AC, Rosen L. Phase II trial of T138067, a novel microtubule inhibitor, in patients with metastatic, refractory colorectal carcinoma. Clin Colorectal Cancer. 2008 Jan;7(1):44-7. PubMed PMID: 18279576.

3: Kirby S, Gertler SZ, Mason W, Watling C, Forsyth P, Aniagolu J, Stagg R, Wright M, Powers J, Eisenhauer EA. Phase 2 study of T138067-sodium in patients with malignant glioma: Trial of the National Cancer Institute of Canada Clinical Trials Group. Neuro Oncol. 2005 Apr;7(2):183-8. PubMed PMID: 15831236; PubMed Central PMCID: PMC1871890.

4: Banerjee M, Poddar A, Mitra G, Surolia A, Owa T, Bhattacharyya B. Sulfonamide drugs binding to the colchicine site of tubulin: thermodynamic analysis of the drug-tubulin interactions by isothermal titration calorimetry. J Med Chem. 2005 Jan 27;48(2):547-55. PubMed PMID: 15658868.

5: Kim YJ, Pannell LK, Sackett DL. Mass spectrometric measurement of differential reactivity of cysteine to localize protein-ligand binding sites. Application to tubulin-binding drugs. Anal Biochem. 2004 Sep 15;332(2):376-83. PubMed PMID: 15325307.

6: Fei X, Zheng QH, Wang JQ, Stone KL, Martinez TD, Miller KD, Sledge GW, Hutchins GD. Synthesis, biodistribution and micro-PET imaging of radiolabeled antimitotic agent T138067 analogues. Bioorg Med Chem Lett. 2004 Mar 8;14(5):1247-51. PubMed PMID: 14980675.

7: Bayes M, Rabasseda X, Prous JR. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2003 Nov;25(9):747-71. PubMed PMID: 14685303.

8: Bayés M, Rabasseda X, Prous JR. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2003 Jan-Feb;25(1):53-76. PubMed PMID: 12690708.

9: Rubenstein SM, Baichwal V, Beckmann H, Clark DL, Frankmoelle W, Roche D, Santha E, Schwender S, Thoolen M, Ye Q, Jaen JC. 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. J Med Chem. 2001 Oct 25;44(22):3599-605. PubMed PMID: 11606124.

10: von Angerer E. Tubulin as a target for anticancer drugs. Curr Opin Drug Discov Devel. 2000 Sep;3(5):575-84. PubMed PMID: 19649885.



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