Ombrabulin HCl
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Hodoodo CAT#: H200380

CAS#: 253426-24-3 (HCl)

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.

Chemical Structure

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Ombrabulin HCl
CAS# 253426-24-3 (HCl)
Instruction

Theoretical Analysis

Hodoodo Cat#: H200380
Name: Ombrabulin HCl
CAS#: 253426-24-3 (HCl)
Chemical Formula: C21H27ClN2O6
Exact Mass: 402.18
Molecular Weight: 438.902
Elemental Analysis: C, 57.47; H, 6.20; Cl, 8.08; N, 6.38; O, 21.87

Price and Availability

Size Price Availability Quantity
5mg USD 230 2 Weeks
25mg USD 570 2 Weeks
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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

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

More Info: 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. .

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 438.90 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:
In vitro protocol:
In vivo protocol:

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 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.