Combretastatin A-1
{{Use dmy dates|date=August 2024}}
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| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 460120971
| Name = Combretastatin A-1
| ImageFile = Combretastatin A-1.svg
| ImageSize = 200px
| PIN = 3-Methoxy-6-[(E)-2-(3,4,5-trimethoxyphenyl)ethen-1-yl]benzene-1,2-diol
| OtherNames = Combretastatin A1; OXi4500
|Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 109971-63-3
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 2222ATS339
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 520204
| PubChem = 6078282
| SMILES = COC1=C(C(=C(C=C1)C=CC2=CC(=C(C(=C2)OC)OC)OC)O)O
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 4800178
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = YUSYSJSHVJULID-AATRIKPKSA-N
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI=1S/C18H20O6/c1-21-13-8-7-12(16(19)17(13)20)6-5-11-9-14(22-2)18(24-4)15(10-11)23-3/h5-10,19-20H,1-4H3/b6-5+
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|Section2={{Chembox Properties
| C=18 | H=20 | O=6
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|Section3={{Chembox Hazards
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Combretastatin A-1 is a combretastatin and a stilbenoid. It can be found in Combretum afrum, the Eastern Cape South African Bushwillow tree.{{Cite journal | last1 = Pettit | first1 = G. R. | last2 = Singh | first2 = S. B. | last3 = Niven | first3 = M. L. | last4 = Hamel | first4 = E. | last5 = Schmidt | first5 = J. M. | title = Isolation, Structure, and Synthesis of Combretastatins A-1 and B-1, Potent New Inhibitors of Microtubule Assembly, Derived from Combretum caffrum | doi = 10.1021/np50049a016 | journal = Journal of Natural Products | volume = 50 | issue = 1 | pages = 119–131 | year = 1987 | pmid = 3598594}}
Biological effects in mammals
It is an antiangiogenic agent acting by destabilizing tubulin, which induces cell apoptosis of proliferating endothelial cells.
Derivatives as drugs
Currently designated an orphan drug by the FDA, combretastatin A1 diphosphate (OXi4503 or CA1P) is in Phase I clinical trials for relapsed and refractory acute myeloid leukemia and myelodysplastic syndrome.{{Cite web|url=http://clinicaltrials.gov/ct2/show/NCT01085656|title = A Phase I Clinical Trial of OXi4503 for Relapsed and Refractory Acute Myelogenous Leukemia (AML) and Myelodysplastic Syndromes (MDS)|date = 7 August 2017}}