Basic information
- CAS
222030-63-9- Standard SMILES
COc1ccc(C[C@H](O)c2cc(OC)c(OC)c(OC)c2)cc1O- InChIKey
LGZKGOGODCLQHG-ZDUSSCGKSA-N- Molecular formula
- C18H22O6
- Average molar mass
- 334.4 g/mol
- Monoisotopic mass
- 334.14163842
Overview
CA4P has been shown in the laboratory to shut down the blood supply to tumours. It is one of the first vascular targeting drugs to be tested in patients. This drug was originally isolated from the African Bush Willow. The first studies in patients with this drug were aimed at finding out whether it can be safely given to patients, what side effects it produces and whether it can actually shut down the blood supply to human tumours.
Names & identifiers
- Preferred name
- 5-[(2S)-2-hydroxy-2-(3,4,5-trimethoxyphenyl)ethyl]-2-methoxyphenol
- IUPAC
- 5-[(2S)-2-hydroxy-2-(3,4,5-trimethoxyphenyl)ethyl]-2-methoxyphenol
- English name
- [2-methoxy-5-[(Z)-2-(3,4,5-trimethoxyphenyl)ethenyl]phenoxy]phosphonic acid
- Molecular formula
- C18H21O8P
- Molecular weight
- 396.33
Names & synonyms
CA4P5-[(2S)-2-hydroxy-2-(3,4,5-trimethoxyphenyl)ethyl]-2-methoxyphenolSCHEMBL29356562LGZKGOGODCLQHG-ZDUSSCGKSA-NAKOS015967221DB05284Q27095579(R,S)-5-[2-Hydroxy-2-(3,4,5-trimethoxy-phenyl)-ethyl]-2-methoxy-phenolFosbretabulinCA 4DPFosbretabulin [free base]CoMbretastatin A4 disodiuM phosphate(CA4P)
Show more names
combretastatin A-4 phosphate, Fosbretabulin(Z)-2-Methoxy-5-(3,4,5-trimethoxystyryl)phenyl dihydrogen phosphate2-Methoxy-5-[2-(3,4,5-trimethoxyphenyl)ethenyl]phenyl dihydrogen phosphate[2-methoxy-5-[(Z)-2-(3,4,5-trimethoxyphenyl)ethenyl]phenoxy]phosphonic acidPhenol, 2-methoxy-5-[(1Z)-2-(3,4,5-trimethoxyphenyl)ethenyl]-, 1-(dihydrogen phosphate)
Database identifiers
- CAS
222030-63-9
Properties
Computed structural properties
- XLogP
- 2.6
- Topological polar surface area
- 77.4 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 7
- Heavy atoms
- 24
- Formal charge
- 0
- Complexity
- 351
Experimental & physicochemical properties
SpringerMaterials PropertiesChemical shift
Physicochemical properties
- Boiling point
- 611.8 · 611.8±65.0 °C(Predicted)
- Density
- 1.342 · 1.342±0.06 g/cm3(Predicted)
- pka
- 1.17 · 1.17±0.50(Predicted)
- FDA UNII
- 5590 ES2QZ · I5590ES2QZ
Chemistry & industry
Pharmacology
Mechanism of Action
CA4P binds tubulin with a higher efficacy than colchicines, and was therefore initially investigated as an anti-mitotic agent. However, it was later observed to also induce vascular shutdown and necrosis in tumours. Clinical trials have revealed its positive effects, either as a single agent or in combination with chemotherapy, in patients with ovarian, lung or anaplastic thyroid cancer. Biochemical analyses revealed that CA4P rapidly diminished the tyrosine phosphorylation of VE-cadherin and beta-catenin, thereby blocking the endothelial signalling pathway that is necessary for maintaining a functional endothelial cell structure and survival.
Applications
UsesFosbretabulin (Combretastatin A4 phosphate) is a vascular disruptor with antitumor activity against atypical thyroid carcinoma (ATC) cell lines and xenografts. Fosbretabulin inhibits tumor growth by inhibiting microtubule polymerization, inducing apoptosis, and suppressing angiogenesis in tumors[1].
Upstream & downstream products
Downstream products
Suppliers12 total
Career Henan Chemica Co+86-0371-86658258 +86-13203830695 · [email protected]
杭州摩库生物医药科技有限公司+86-057181025280; +8617767106207 · [email protected]
Wuhan NCE Biomedical Co.,Ltd.4000-027-021 |24 +86-13986109188 | +86-15623472865 | +81-08033611988
BOC Sciences16314854226; +8616314854226 · [email protected]
Related reactions
1 records
Compound notes
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