Ombrabulin HCl

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

Description: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.

Price and Availability

Ombrabulin HCl, purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received.

Chemical Structure

Theoretical Analysis

MedKoo Cat#: 200380Name: Ombrabulin HClCAS#: 253426-24-3 (HCl)Chemical Formula: C21H27ClN2O6Exact Mass: 402.17909Molecular Weight: 438.90188Elemental Analysis: C, 57.47; H, 6.20; Cl, 8.08; N, 6.38; O, 21.87

Related CAS #:253426-24-3 (HCl); 181816-48-8 (free base);

Synonym:AVE8062; AVE8062; AVE8062; AVE-8062A; AC7700; AC-7700; AC 7700; CS-39-L-Ser.HCl; Ombrabulin; Ombrabulin HCl.

IUPAC/Chemical Name:(2S)-2-amino-3-hydroxy-N-[2-methoxy-5-[(Z)-2-(3,4,5-trimethoxyphenyl)ethenyl]phenyl]propanamide hydrochloride.

InChi Key:UQNRTPFLTRZEIM-MRWUDIQNSA-N

InChi Code:InChI=1S/C21H26N2O6.ClH/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);1H/b6-5-;/t15-;/m0./s1

SMILES Code:O=C(NC1=CC(/C=CC2=CC(OC)=C(OC)C(OC)=C2)=CC=C1OC)[C@@H](N)CO.[H]Cl

Technical Data

Additional Information

Ombrabulin was granted orphan drug status by the European Medicines Agency in April 2011. Ombrabulin is a combretastatin A-4 derivative that exerts its antitumor effect by disrupting the formation of blood vessels needed for tumor growth. .

References

 1: Delmonte A, Sessa C. AVE8062: a newcombretastatin derivative vascular disrupting agent. Expert OpinInvestig Drugs. 2009 Oct;18(10):1541-8. Review. PubMed PMID: 19758109.

2: Hori K, Furumoto S, Kubota K. Tumor blood flow interruption afterradiotherapy strongly inhibits tumor regrowth. Cancer Sci. 2008Jul;99(7):1485-91. Epub 2008 Apr 29. PubMed PMID: 18452559.

3: Cai SX. Small molecule vascular disrupting agents: potential newdrugs for cancer treatment. Recent Pat Anticancer Drug Discov. 2007Jan;2(1):79-101. Review. PubMed PMID: 18221055.

4: Lavisse S, Lejeune P, Rouffiac V, Elie N, Bribes E, Demers B,Vrignaud P, Bissery MC, Brulé A, Koscielny S, Péronneau P, Lassau N.Early quantitative evaluation of a tumor vasculature disruptive agentAVE8062 using dynamic contrast-enhanced ultrasonography. Invest Radiol.2008 Feb;43(2):100-11. PubMed PMID: 18197062.

5: Kim TJ, Ravoori M, Landen CN, Kamat AA, Han LY, Lu C, Lin YG, MerrittWM, Jennings N, Spannuth WA, Langley R, Gershenson DM, Coleman RL,Kundra V, Sood AK. Antitumor and antivascular effects of AVE8062 inovarian carcinoma. Cancer Res. 2007 Oct 1;67(19):9337-45. PubMed PMID:17909042.

6: Lippert JW 3rd. Vascular disrupting agents. Bioorg Med Chem. 2007 Jan15;15(2):605-15. Epub 2006 Oct 27. PubMed PMID: 17070061.

7: Hori K. Antineoplastic strategy: irreversible tumor blood flow stasisinduced by the combretastatin A-4 derivative AVE8062 (AC7700).Chemotherapy. 2005 Oct;51(6):357-60. Epub 2005 Oct 14. Review. PubMedPMID: 16227690.

8: Thorpe PE. Vascular targeting agents as cancer therapeutics. ClinCancer Res. 2004 Jan 15;10(2):415-27. Review. PubMed PMID: 14760060.

9: Hori K, Saito S. Induction of tumour blood flow stasis and necrosis:a new function for epinephrine similar to that of combretastatin A-4derivative AVE8062 (AC7700). Br J Cancer. 2004 Jan 26;90(2):549-53.PubMed PMID: 14735207; PubMed Central PMCID: PMC2409553.

10: Hori K, Saito S. Microvascular mechanisms by which thecombretastatin A-4 derivative AC7700 (AVE8062) induces tumour blood flowstasis. Br J Cancer. 2003 Oct 6;89(7):1334-44. PubMed PMID: 14520469;PubMed Central PMCID: PMC2394288.