NAV

Fosbretabulin

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Generic Name
Fosbretabulin
DrugBank Accession Number
DB12577
Background

Fosbretabulin has been investigated for the treatment of Anaplastic Thyroid Cancer.

Type
Small Molecule
Groups
Investigational
Structure
3D
Similar Structures
Weight
Average: 396.332
Monoisotopic: 396.097404634
Chemical Formula
C18H21O8P
Synonyms
  • 2-METHOXY-5-((Z)-2-(3,4,5-TRIMETHOXYPHENYL)VINYL)PHENYL DIHYDROGEN PHOSPHATE
  • Combretastatin A-4 phosphate
  • Combretastatin A4 phosphate
  • Fosbretabulin
  • PHENOL, 2-METHOXY-5-((1Z)-2-(3,4,5-TRIMETHOXYPHENYL)ETHENYL)-,1-(DIHYDROGEN PHOSPHATE)
  • PHENOL, 2-METHOXY-5-((Z)-2-(3,4,5-TRIMETHOXYPHENYL)ETHENYL)-, DIHYDROGEN PHOSPHATE
  • Phosbretabulin
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
Not Available
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
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
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.
DrugInteraction
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interactions in your software
AmbroxolThe risk or severity of methemoglobinemia can be increased when Fosbretabulin is combined with Ambroxol.
ArticaineThe risk or severity of methemoglobinemia can be increased when Fosbretabulin is combined with Articaine.
BenzocaineThe risk or severity of methemoglobinemia can be increased when Fosbretabulin is combined with Benzocaine.
Benzyl alcoholThe risk or severity of methemoglobinemia can be increased when Fosbretabulin is combined with Benzyl alcohol.
BupivacaineThe risk or severity of methemoglobinemia can be increased when Fosbretabulin is combined with Bupivacaine.
Food Interactions
Not Available

Products

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Product Ingredients
IngredientUNIICASInChI Key
Fosbretabulin tromethamineGBW044919E404886-32-4FIDMEHCRMLKKPZ-YSMBQZINSA-N
Active Moieties
NameKindUNIICASInChI Key
Combretastatin A4prodrug16U6OP69RQ117048-59-6HVXBOLULGPECHP-WAYWQWQTSA-N

Categories

Drug Categories
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
Phenyl phosphates / Styrenes / Phenoxy compounds / Methoxybenzenes / Anisoles / Alkyl aryl ethers / Organic oxides / Hydrocarbon derivatives
Substituents
Alkyl aryl ether / Anisole / Aromatic homomonocyclic compound / Aryl phosphate / Aryl phosphomonoester / Benzenoid / Ether / Hydrocarbon derivative / Methoxybenzene / Monocyclic benzene moiety
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
I5590ES2QZ
CAS number
222030-63-9
InChI Key
WDOGQTQEKVLZIJ-WAYWQWQTSA-N
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-
IUPAC Name
{2-methoxy-5-[(Z)-2-(3,4,5-trimethoxyphenyl)ethenyl]phenoxy}phosphonic acid
SMILES
COC1=CC=C(\C=C/C2=CC(OC)=C(OC)C(OC)=C2)C=C1OP(O)(O)=O

References

General References
Not Available
PubChem Compound
5351387
PubChem Substance
347828799
ChemSpider
4508406
ChEMBL
CHEMBL1206232
ZINC
ZINC000001543513
Wikipedia
Fosbretabulin

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
PhaseStatusPurposeConditionsCount
3WithdrawnTreatmentAnaplastic Thyroid Cancer1
2CompletedTreatmentCancer / Tumor1
2CompletedTreatmentHead And Neck Cancer1
2CompletedTreatmentMyopia, Degenerative / Subfoveal Choroidal Neovascularization (CNV)1
2CompletedTreatmentNeuroendocrine Tumors2

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00239 mg/mLALOGPS
logP2.41ALOGPS
logP2.72Chemaxon
logS-5.2ALOGPS
pKa (Strongest Acidic)1.62Chemaxon
pKa (Strongest Basic)-4.3Chemaxon
Physiological Charge-2Chemaxon
Hydrogen Acceptor Count7Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area103.68 Å2Chemaxon
Rotatable Bond Count8Chemaxon
Refractivity100.22 m3·mol-1Chemaxon
Polarizability38.29 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-00kb-0019000000-c28e7a0c2be196011d22
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-9000000000-20877bf3eb810766c71a
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-00kb-5059000000-2f49dc7cb13fcc26d10c
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-9000000000-4f22e414187864965165
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-01t9-9000000000-f2f5cf4bfec67df75922
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0uk9-0196000000-83d8d14f42537f5c3c0d
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-183.7511
predicted
DeepCCS 1.0 (2019)
[M+H]+186.10909
predicted
DeepCCS 1.0 (2019)
[M+Na]+192.73546
predicted
DeepCCS 1.0 (2019)

Drug created at October 20, 2016 22:58 / Updated at July 18, 2023 22:57