MedKoo Cat#: 200380
Name: Ombrabulin HCl
CAS#: 253426-24-3 (HCl)
Chemical Formula: C21H27ClN2O6
Exact Mass: 402.17909
Molecular Weight: 438.90188
Elemental 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=C\C2=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 new combretastatin derivative vascular disrupting agent. Expert Opin Investig Drugs. 2009 Oct;18(10):1541-8. Review. PubMed PMID: 19758109.
2: Hori K, Furumoto S, Kubota K. Tumor blood flow interruption after radiotherapy strongly inhibits tumor regrowth. Cancer Sci. 2008 Jul;99(7):1485-91. Epub 2008 Apr 29. PubMed PMID: 18452559.
3: Cai SX. Small molecule vascular disrupting agents: potential new drugs for cancer treatment. Recent Pat Anticancer Drug Discov. 2007 Jan;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 agent AVE8062 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, Merritt WM, Jennings N, Spannuth WA, Langley R, Gershenson DM, Coleman RL, Kundra V, Sood AK. Antitumor and antivascular effects of AVE8062 in ovarian carcinoma. Cancer Res. 2007 Oct 1;67(19):9337-45. PubMed PMID: 17909042.
6: Lippert JW 3rd. Vascular disrupting agents. Bioorg Med Chem. 2007 Jan 15;15(2):605-15. Epub 2006 Oct 27. PubMed PMID: 17070061.
7: Hori K. Antineoplastic strategy: irreversible tumor blood flow stasis induced by the combretastatin A-4 derivative AVE8062 (AC7700). Chemotherapy. 2005 Oct;51(6):357-60. Epub 2005 Oct 14. Review. PubMed PMID: 16227690.
8: Thorpe PE. Vascular targeting agents as cancer therapeutics. Clin Cancer 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-4 derivative 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 the combretastatin A-4 derivative AC7700 (AVE8062) induces tumour blood flow stasis. Br J Cancer. 2003 Oct 6;89(7):1334-44. PubMed PMID: 14520469; PubMed Central PMCID: PMC2394288.
