Fosbretabulin tromethamine

For research use only. Not for therapeutic Use.

  • CAT Number: I027711
  • CAS Number: 404886-32-4
  • Molecular Formula: C22H32NO11P
  • Molecular Weight: 517.47
  • Purity: 98%
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Fosbretabulin tromethamine is a biochemical with potential vascular and microtubule disrupting and antineoplastic activities.


Catalog Number I027711
CAS Number 404886-32-4
Synonyms

Fosbretabulin tromethamine; Zybrestat

Molecular Formula C22H32NO11P
Purity 98%
Solubility Soluble in DMSO
Appearance Solid powder
Storage Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
IUPAC Name 2-amino-2-(hydroxymethyl)propane-1,3-diol (Z)-2-methoxy-5-(3,4,5-trimethoxystyryl)phenyl phosphate
InChI InChI=1S/C18H21O8P.C4H11NO3/c1-22-14-8-7-12(9-15(14)26-27(19,20)21)5-6-13-10-16(23-2)18(25-4)17(11-13)24-3;5-4(1-6,2-7)3-8/h5-11H,1-4H3,(H2,19,20,21);6-8H,1-3,5H2/b6-5-;
InChIKey FIDMEHCRMLKKPZ-YSMBQZINSA-N
SMILES COc1ccc(C=C/c2cc(OC)c(OC)c(OC)c2)cc1OP(=O)(O)O.NC(CO)(CO)CO
Reference

1: Sosa JA, Balkissoon J, Lu SP, Langecker P, Elisei R, Jarzab B, Bal CS, Marur S, Gramza A, Ondrey F. Thyroidectomy followed by fosbretabulin (CA4P) combination regimen appears to suggest improvement in patient survival in anaplastic thyroid cancer. Surgery. 2012 Dec;152(6):1078-87. doi: 10.1016/j.surg.2012.08.036. Review. PubMed PMID: 23158178.
2: Venegas B, Zhu W, Haloupek NB, Lee J, Zellhart E, Sugár IP, Kiani MF, Chong PL. Cholesterol superlattice modulates CA4P release from liposomes and CA4P cytotoxicity on mammary cancer cells. Biophys J. 2012 May 2;102(9):2086-94. doi: 10.1016/j.bpj.2012.03.063. PubMed PMID: 22824272; PubMed Central PMCID: PMC3341537.
3: Nathan P, Zweifel M, Padhani AR, Koh DM, Ng M, Collins DJ, Harris A, Carden C, Smythe J, Fisher N, Taylor NJ, Stirling JJ, Lu SP, Leach MO, Rustin GJ, Judson I. Phase I trial of combretastatin A4 phosphate (CA4P) in combination with bevacizumab in patients with advanced cancer. Clin Cancer Res. 2012 Jun 15;18(12):3428-39. doi: 10.1158/1078-0432.CCR-11-3376. Epub 2012 May 29. PubMed PMID: 22645052.
4: Rustin GJ, Shreeves G, Nathan PD, Gaya A, Ganesan TS, Wang D, Boxall J, Poupard L, Chaplin DJ, Stratford MR, Balkissoon J, Zweifel M. A Phase Ib trial of CA4P (combretastatin A-4 phosphate), carboplatin, and paclitaxel in patients with advanced cancer. Br J Cancer. 2010 Apr 27;102(9):1355-60. doi: 10.1038/sj.bjc.6605650. Epub 2010 Apr 13. PubMed PMID: 20389300; PubMed Central PMCID: PMC2865759.
5: Siemann DW, Chaplin DJ, Walicke PA. A review and update of the current status of the vasculature-disabling agent combretastatin-A4 phosphate (CA4P). Expert Opin Investig Drugs. 2009 Feb;18(2):189-97. doi: 10.1517/13543780802691068 . Review. PubMed PMID: 19236265; PubMed Central PMCID: PMC3593193.
6: Siemann DW, Shi W. Dual targeting of tumor vasculature: combining Avastin and vascular disrupting agents (CA4P or OXi4503). Anticancer Res. 2008 Jul-Aug;28(4B):2027-31. PubMed PMID: 18751370; PubMed Central PMCID: PMC2788501.
7: Petit I, Karajannis MA, Vincent L, Young L, Butler J, Hooper AT, Shido K, Steller H, Chaplin DJ, Feldman E, Rafii S. The microtubule-targeting agent CA4P regresses leukemic xenografts by disrupting interaction with vascular cells and mitochondrial-dependent cell death. Blood. 2008 Feb 15;111(4):1951-61. Epub 2007 Nov 16. PubMed PMID: 18024794; PubMed Central PMCID: PMC2234044.
8: Salmon BA, Salmon HW, Siemann DW. Monitoring the treatment efficacy of the vascular disrupting agent CA4P. Eur J Cancer. 2007 Jul;43(10):1622-9. Epub 2007 Apr 23. PubMed PMID: 17451938; PubMed Central PMCID: PMC2962830.
9: Salmon HW, Mladinich C, Siemann DW. Evaluations of vascular disrupting agents CA4P and OXi4503 in renal cell carcinoma (Caki-1) using a silicon based microvascular casting technique. Eur J Cancer. 2006 Nov;42(17):3073-8. Epub 2006 Sep 7. PubMed PMID: 16956760.

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