Explore a selection of our essential drug information below, or:
Overview
- DrugBank ID
- DB05284
- Type
- Small Molecule
- Clinical Trials
- Phase 0
- 0
- Phase 1
- 0
- Phase 2
- 0
- Phase 3
- 0
- Phase 4
- 0
Identification
- Generic Name
- CA4P
- DrugBank Accession Number
- DB05284
- Background
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.
- 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
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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
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
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
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
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- Not Available
- CAS number
- 222030-63-9
- 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)[C@@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. [Article]
- External Links
- PubChem Compound
- 100154
- PubChem Substance
- 175426964
- ChemSpider
- 90508
- Wikipedia
- Combretastatin
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
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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 splash10-014i-0901000000-03c621320168716f853a Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0gbi-0916000000-a206ba224fd55d0db3b0 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-00lr-0109000000-9ec83915bad8d9d4e220 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-015j-0494000000-ded074375a7823dea480 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0frb-0923000000-93e3dcd3a54a16bf81d4 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-007d-0961000000-39dc21e7e292e03642f2 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0002-0891000000-042447a09ff21bfd0b1c Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 196.0300216 predictedDarkChem Lite v0.1.0 [M-H]- 181.1903 predictedDeepCCS 1.0 (2019) [M+H]+ 194.2110216 predictedDarkChem Lite v0.1.0 [M+H]+ 183.54831 predictedDeepCCS 1.0 (2019) [M+Na]+ 194.0740216 predictedDarkChem Lite v0.1.0 [M+Na]+ 190.67477 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Tubulin is the major constituent of microtubules, a cylinder consisting of laterally associated linear protofilaments composed of alpha- and beta-tubulin heterodimers. Microtubules grow by the addition of GTP-tubulin dimers to the microtubule end, where a stabilizing cap forms. Below the cap, tubulin dimers are in GDP-bound state, owing to GTPase activity of alpha-tubulin
- Specific Function
- GTP binding
- Gene Name
- TUBB
- Uniprot ID
- P07437
- Uniprot Name
- Tubulin beta chain
- Molecular Weight
- 49670.515 Da
Drug created at November 18, 2007 18:23 / Updated at November 03, 2024 03:34