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CA4P
Identification
- Name
- CA4P
- Accession Number
- DB05284
- Description
CA4P (Combretastatin)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.
- Type
- Small Molecule
- Groups
- Investigational
- Structure
Structure for CA4P (DB05284)
- Weight
- Average: 334.3637
Monoisotopic: 334.141638436 - Chemical Formula
- C18H22O6
- Synonyms
- Not Available
Pharmacology
- Indication
- Not Available
- Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
Learn More- Pharmacodynamics
- Not Available
- 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.
Target Actions Organism UTubulin beta chain Not Available Humans - Absorption
- Not Available
- Volume of distribution
- Not Available
- Protein binding
- Not Available
- Metabolism
- Not Available
- Route of elimination
- Not Available
- Half-life
- Not Available
- Clearance
- Not Available
- Adverse Effects
Learn about our commercial Adverse Effects data.
Learn More- Toxicity
- Not Available
- Affected organisms
- Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.Not Available
- Food Interactions
- Not Available
Products
Categories
- Drug Categories
- Not Available
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids.
- Kingdom
- Organic compounds
- Super Class
- Phenylpropanoids and polyketides
- Class
- Stilbenes
- Sub Class
- Not Available
- Direct Parent
- Stilbenes
- Alternative Parents
- Methoxyphenols / Phenoxy compounds / Methoxybenzenes / Anisoles / Alkyl aryl ethers / 1-hydroxy-4-unsubstituted benzenoids / 1-hydroxy-2-unsubstituted benzenoids / Secondary alcohols / Hydrocarbon derivatives / Aromatic alcohols
- Substituents
- 1-hydroxy-2-unsubstituted benzenoid / 1-hydroxy-4-unsubstituted benzenoid / Alcohol / Alkyl aryl ether / Anisole / Aromatic alcohol / Aromatic homomonocyclic compound / Benzenoid / Ether / Hydrocarbon derivative
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- Not Available
Chemical Identifiers
- UNII
- Not Available
- CAS number
- Not Available
- InChI Key
- LGZKGOGODCLQHG-ZDUSSCGKSA-N
- InChI
- InChI=1S/C18H22O6/c1-21-15-6-5-11(8-14(15)20)7-13(19)12-9-16(22-2)18(24-4)17(10-12)23-3/h5-6,8-10,13,19-20H,7H2,1-4H3/t13-/m0/s1
- IUPAC Name
- 5-[(2S)-2-hydroxy-2-(3,4,5-trimethoxyphenyl)ethyl]-2-methoxyphenol
- SMILES
- COC1=CC(=CC(OC)=C1OC)[[email protected]@H](O)CC1=CC(O)=C(OC)C=C1
References
- General References
- Petit I, Karajannis MA, Vincent L, Young L, Butler J, Hooper AT, Shido K, Steller H, Chaplin DJ, Feldman E, Rafii S: The microtubule-targeting agent CA4P regresses leukemic xenografts by disrupting interaction with vascular cells and mitochondrial-dependent cell death. Blood. 2008 Feb 15;111(4):1951-61. Epub 2007 Nov 16. [PubMed:18024794]
- External Links
- PubChem Compound
- 100154
- PubChem Substance
- 175426964
- ChemSpider
- 90508
- Wikipedia
- Combretastatin
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.0545 mg/mL ALOGPS logP 2.23 ALOGPS logP 2.34 ChemAxon logS -3.8 ALOGPS pKa (Strongest Acidic) 9.99 ChemAxon pKa (Strongest Basic) -3.1 ChemAxon Physiological Charge 0 ChemAxon Hydrogen Acceptor Count 6 ChemAxon Hydrogen Donor Count 2 ChemAxon Polar Surface Area 77.38 Å2 ChemAxon Rotatable Bond Count 7 ChemAxon Refractivity 89.75 m3·mol-1 ChemAxon Polarizability 34.48 Å3 ChemAxon Number of Rings 2 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule No ChemAxon MDDR-like Rule No ChemAxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.8812 Blood Brain Barrier + 0.623 Caco-2 permeable + 0.6844 P-glycoprotein substrate Substrate 0.5603 P-glycoprotein inhibitor I Non-inhibitor 0.6316 P-glycoprotein inhibitor II Inhibitor 0.5186 Renal organic cation transporter Non-inhibitor 0.8798 CYP450 2C9 substrate Non-substrate 0.7495 CYP450 2D6 substrate Non-substrate 0.7875 CYP450 3A4 substrate Substrate 0.5304 CYP450 1A2 substrate Inhibitor 0.645 CYP450 2C9 inhibitor Non-inhibitor 0.8555 CYP450 2D6 inhibitor Non-inhibitor 0.5144 CYP450 2C19 inhibitor Inhibitor 0.7786 CYP450 3A4 inhibitor Non-inhibitor 0.7694 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.5604 Ames test Non AMES toxic 0.8759 Carcinogenicity Non-carcinogens 0.8488 Biodegradation Not ready biodegradable 0.9737 Rat acute toxicity 2.5923 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9438 hERG inhibition (predictor II) Non-inhibitor 0.8336
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Ubiquitin protein ligase binding
- Specific Function
- Tubulin is the major constituent of microtubules. It binds two moles of GTP, one at an exchangeable site on the beta chain and one at a non-exchangeable site on the alpha chain.
- Gene Name
- TUBB
- Uniprot ID
- P07437
- Uniprot Name
- Tubulin beta chain
- Molecular Weight
- 49670.515 Da
Drug created on November 18, 2007 11:23 / Updated on June 12, 2020 10:52
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