Fosbretabulin

Fosbretabulin (also known as combretastatin A-4 phosphate or CA4P) is a microtubule destabilizing experimental drug, a type of vascular-targeting agent, a drug designed to damage the vasculature (blood vessels) of cancer tumours causing central necrosis. It is a derivative of combretastatin. It is formulated as the salts fosbretabulin disodium and fosbretabulin tromethamine.^[1]

Fosbretabulin

Clinical data
Other names	Combretastatin A-4 phosphate; CA4P; CA4PD; fosbretabulin disodium; fosbretabulin tromethamine
Legal status
Legal status	Investigational
Identifiers
IUPAC name Phosphoric acid mono-{2-methoxy-5-[(Z)-2-(3,4,5-trimethoxy-phenyl)-vinyl]-phenyl} ester
CAS Number	222030-63-9 Y
PubChem CID	5351387
ChemSpider	4508406
UNII	I5590ES2QZ
CompTox Dashboard (EPA)	DTXSID401028843
Chemical and physical data
Formula	C18H21O8P
Molar mass	396.332 g·mol−1
3D model (JSmol)	Interactive image
SMILES O=P(O)(O)Oc1c(OC)ccc(c1)\C=C/c2cc(OC)c(OC)c(OC)c2
InChI InChI=1S/C18H21O8P/c1-22-14-8-7-12(9-15(14)26-27(19,20)21)5-6-13-10-16(23-2)18(25-4)17(11-13)24-3/h5-11H,1-4H3,(H2,19,20,21)/b6-5- Key:WDOGQTQEKVLZIJ-WAYWQWQTSA-N
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Fosbretabulin is a prodrug. In vivo, it is dephosphorylated to its active metabolite, combretastatin A-4.^[2]

In July 2007, the pharmaceutical company OXiGENE initiated a 180-patient phase III clinical trial of fosbretabulin in combination with carboplatin for the treatment of anaplastic thyroid cancer.^[3] There is currently no fully FDA approved treatment for this form of cancer. By 2017, it had completed multiple clinical trials (e.g. for solid tumours,^[4] non-small cell lung cancer^[5]) with more in progress.^[6]

See also

• Combretastatin, e.g. for the chemical synthesis