Ombrabulin | CAS#181816-48-8 | Combretastatin A4 Analogue

MedKoo Cat#: 563933 | Name: Ombrabulin

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Ombrabulin, also known as AVE8062, is a water-soluble analogue of combretastatin A4, inhibiting tubulin polymerization. Ombrabulin induces mitotic arrest and apoptosis in endothelial cells.

Chemical Structure

Ombrabulin

CAS#181816-48-8 (free base)

Theoretical Analysis

MedKoo Cat#: 563933

Name: Ombrabulin

CAS#: 181816-48-8 (free base)

Chemical Formula: C21H26N2O6

Exact Mass: 402.1791

Molecular Weight: 402.45

Elemental Analysis: C, 62.67; H, 6.51; N, 6.96; O, 23.85

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

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Related CAS #

253426-24-3 (HCl) 181816-48-8 (free base)

Synonym

AVE8062; AVE-8062; AVE 8062; Ombrabulin

IUPAC/Chemical Name

(2S)-2-Amino-3-hydroxy-N-[2-methoxy-5-[(Z)-2-(3,4,5-trimethoxyphenyl)ethenyl]phenyl]propanamide

InChi Key

IXWNTLSTOZFSCM-YVACAVLKSA-N

InChi Code

InChI=1S/C21H26N2O6/c1-26-17-8-7-13(9-16(17)23-21(25)15(22)12-24)5-6-14-10-18(27-2)20(29-4)19(11-14)28-3/h5-11,15,24H,12,22H2,1-4H3,(H,23,25)/b6-5-/t15-/m0/s1

SMILES Code

O=C(NC1=CC(/C=C\C2=CC(OC)=C(OC)C(OC)=C2)=CC=C1OC)[C@@H](N)CO

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

Shelf Life

>3 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

2934.99.03.00

More Info

Ombrabulin is a synthetic water-soluble analogue of combretastatin A4, derived from the South African willow bush (Combretum caffrum), with potential vascular-disrupting and antineoplastic activities. Ombrabulin binds to the colchicine binding site of endothelial cell tubulin, inhibiting tubulin polymerization and inducing mitotic arrest and apoptosis in endothelial cells. As apoptotic endothelial cells detach from their substrata, tumor blood vessels collapse; the acute disruption of tumor blood flow may result in tumor necrosis. Ombrabulin has been used in trials studying the treatment of Sarcoma, Neoplasms, Solid Tumor, Neoplasms, Malignant, and Advanced Solid Tumors, among others.

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 402.45 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.

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

1: Nishio M, Satouchi M, Horiike A, Horio Y, Sunaga Y, Ecstein-Fraisse E, Hida T. Phase 1 study of ombrabulin in combination with docetaxel and cisplatin in Japanese patients with advanced solid tumors. Jpn J Clin Oncol. 2018 Apr 1;48(4):322-328. doi: 10.1093/jjco/hyy026. PubMed PMID: 29514256. 2: Takahashi S, Nakano K, Yokota T, Shitara K, Muro K, Sunaga Y, Ecstein-Fraisse E, Ura T. Phase 1 study of ombrabulin in combination with cisplatin (CDDP) in Japanese patients with advanced solid tumors. Jpn J Clin Oncol. 2016 Aug 27. [Epub ahead of print] PubMed PMID: 27566973. 3: Blay JY, Pápai Z, Tolcher AW, Italiano A, Cupissol D, López-Pousa A, Chawla SP, Bompas E, Babovic N, Penel N, Isambert N, Staddon AP, Saâda-Bouzid E, Santoro A, Franke FA, Cohen P, Le-Guennec S, Demetri GD. Ombrabulin plus cisplatin versus placebo plus cisplatin in patients with advanced soft-tissue sarcomas after failure of anthracycline and ifosfamide chemotherapy: a randomised, double-blind, placebo-controlled, phase 3 trial. Lancet Oncol. 2015 May;16(5):531-40. doi: 10.1016/S1470-2045(15)70102-6. Epub 2015 Apr 8. PubMed PMID: 25864104. 4: Bahleda R, Sessa C, Del Conte G, Gianni L, Capri G, Varga A, Oprea C, Daglish B, Hospitel M, Soria JC. Phase I clinical and pharmacokinetic study of ombrabulin (AVE8062) combined with cisplatin/docetaxel or carboplatin/paclitaxel in patients with advanced solid tumors. Invest New Drugs. 2014 Dec;32(6):1188-96. doi: 10.1007/s10637-014-0119-0. Epub 2014 Jun 6. PubMed PMID: 24898305. 5: von Pawel J, Gorbounova V, Reck M, Kowalski DM, Allard A, Chadjaa M, Rey A, Bennouna J, Grossi F; DISRUPT Investigators. DISRUPT: a randomised phase 2 trial of ombrabulin (AVE8062) plus a taxane-platinum regimen as first-line therapy for metastatic non-small cell lung cancer. Lung Cancer. 2014 Aug;85(2):224-9. doi: 10.1016/j.lungcan.2014.05.013. Epub 2014 May 21. PubMed PMID: 24888230. 6: Eskens FA, Tresca P, Tosi D, Van Doorn L, Fontaine H, Van der Gaast A, Veyrat-Follet C, Oprea C, Hospitel M, Dieras V. A phase I pharmacokinetic study of the vascular disrupting agent ombrabulin (AVE8062) and docetaxel in advanced solid tumours. Br J Cancer. 2014 Apr 29;110(9):2170-7. doi: 10.1038/bjc.2014.137. Epub 2014 Apr 8. PubMed PMID: 24714750; PubMed Central PMCID: PMC4007230. 7: Murakami H, Kurata T, Onozawa Y, Watanabe J, Ono A, Takahashi T, Yamamoto N, Fujisaka Y, Kiyota H, Hayashi H, Tanaka K, Nakagawa K, Kuroda S. An open-label, dose-escalation, safety, and pharmacokinetics phase I study of ombrabulin, a vascular disrupting agent, administered as a 30-min intravenous infusion every 3 weeks in Japanese patients with advanced solid tumors. Cancer Chemother Pharmacol. 2014 Mar;73(3):623-30. doi: 10.1007/s00280-014-2388-x. Epub 2014 Jan 30. PubMed PMID: 24477603; PubMed Central PMCID: PMC3931931. 8: Sessa C, Lorusso P, Tolcher A, Farace F, Lassau N, Delmonte A, Braghetti A, Bahleda R, Cohen P, Hospitel M, Veyrat-Follet C, Soria JC. Phase I safety, pharmacokinetic and pharmacodynamic evaluation of the vascular disrupting agent ombrabulin (AVE8062) in patients with advanced solid tumors. Clin Cancer Res. 2013 Sep 1;19(17):4832-42. doi: 10.1158/1078-0432.CCR-13-0427. Epub 2013 Jul 5. PubMed PMID: 23833302. 9: Clémenson C, Jouannot E, Merino-Trigo A, Rubin-Carrez C, Deutsch E. The vascular disrupting agent ombrabulin (AVE8062) enhances the efficacy of standard therapies in head and neck squamous cell carcinoma xenograft models. Invest New Drugs. 2013 Apr;31(2):273-84. doi: 10.1007/s10637-012-9852-4. Epub 2012 Jul 19. PubMed PMID: 22810221.