Gossypol

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

Identification

Generic Name
Gossypol
DrugBank Accession Number
DB13044
Background

Gossypol has been used in trials studying the treatment of Non-small Cell Lung Cancer.

Type
Small Molecule
Groups
Investigational
Structure
Thumb
Weight
Average: 518.5544
Monoisotopic: 518.194067936
Chemical Formula
C30H30O8
Synonyms
Not Available

Pharmacology

Indication

Not Available

Pharmacology
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Contraindications & Blackbox Warnings
Contraindications
Avoid life-threatening adverse drug events
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UBcl-2-like protein 1Not AvailableHumans
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
Adverseeffects
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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.
DrugInteraction
AbciximabThe therapeutic efficacy of Abciximab can be decreased when used in combination with Gossypol.
AcenocoumarolThe therapeutic efficacy of Acenocoumarol can be decreased when used in combination with Gossypol.
AcetaminophenThe metabolism of Gossypol can be increased when combined with Acetaminophen.
AcetazolamideThe metabolism of Gossypol can be increased when combined with Acetazolamide.
AcetohexamideThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Gossypol.
AlpelisibThe metabolism of Gossypol can be increased when combined with Alpelisib.
AlteplaseThe therapeutic efficacy of Alteplase can be decreased when used in combination with Gossypol.
AminoglutethimideThe metabolism of Gossypol can be increased when combined with Aminoglutethimide.
AmobarbitalThe metabolism of Gossypol can be increased when combined with Amobarbital.
AmoxicillinThe therapeutic efficacy of Gossypol can be decreased when used in combination with Amoxicillin.
Interactions
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Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Prenol lipids
Sub Class
Sesquiterpenoids
Direct Parent
Sesquiterpenoids
Alternative Parents
Naphthols and derivatives / Aryl-aldehydes / 1-hydroxy-4-unsubstituted benzenoids / Vinylogous acids / Polyols / Organic oxides / Hydrocarbon derivatives
Substituents
1-hydroxy-4-unsubstituted benzenoid / 1-naphthol / 2-naphthol / Aldehyde / Aromatic homopolycyclic compound / Aryl-aldehyde / Benzenoid / Cadinane sesquiterpenoid / Hydrocarbon derivative / Naphthalene
Molecular Framework
Aromatic homopolycyclic compounds
External Descriptors
polyphenol (CHEBI:28584) / Cadinane sesquiterpenoids, Terpenoids, Cadinanes (C07667) / Cadinane sesquiterpenoids (LMPR0103330002)
Affected organisms
Not Available

Chemical Identifiers

UNII
8DY2X8LXW4
CAS number
303-45-7
InChI Key
QBKSWRVVCFFDOT-UHFFFAOYSA-N
InChI
InChI=1S/C30H30O8/c1-11(2)19-15-7-13(5)21(27(35)23(15)17(9-31)25(33)29(19)37)22-14(6)8-16-20(12(3)4)30(38)26(34)18(10-32)24(16)28(22)36/h7-12,33-38H,1-6H3
IUPAC Name
7-[8-formyl-1,6,7-trihydroxy-3-methyl-5-(propan-2-yl)naphthalen-2-yl]-2,3,8-trihydroxy-6-methyl-4-(propan-2-yl)naphthalene-1-carbaldehyde
SMILES
CC(C)C1=C2C=C(C)C(=C(O)C2=C(C=O)C(O)=C1O)C1=C(O)C2=C(C=O)C(O)=C(O)C(C(C)C)=C2C=C1C

References

General References
Not Available
Human Metabolome Database
HMDB0040723
KEGG Compound
C07667
PubChem Compound
3503
PubChem Substance
347829175
ChemSpider
3383
BindingDB
23223
ChEMBL
CHEMBL51483
ZINC
ZINC000003775575
Wikipedia
Gossypol

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
3Unknown StatusTreatmentNon-Small Cell Lung Carcinoma (NSCLC)1
2CompletedTreatmentExtensive-stage Small Cell Lung Cancer (SCLC) / Recurrent Small Cell Lung Cancer (SCLC)1

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 Solubility0.00385 mg/mLALOGPS
logP4.49ALOGPS
logP8.02ChemAxon
logS-5.1ALOGPS
pKa (Strongest Acidic)7.8ChemAxon
pKa (Strongest Basic)-6.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area155.52 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity147.61 m3·mol-1ChemAxon
Polarizability55.95 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Targets

Drugtargets2
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Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Protein kinase binding
Specific Function
Potent inhibitor of cell death. Inhibits activation of caspases. Appears to regulate cell death by blocking the voltage-dependent anion channel (VDAC) by binding to it and preventing the release of...
Gene Name
BCL2L1
Uniprot ID
Q07817
Uniprot Name
Bcl-2-like protein 1
Molecular Weight
26048.8 Da
References
  1. Bauer JA, Trask DK, Kumar B, Los G, Castro J, Lee JS, Chen J, Wang S, Bradford CR, Carey TE: Reversal of cisplatin resistance with a BH3 mimetic, (-)-gossypol, in head and neck cancer cells: role of wild-type p53 and Bcl-xL. Mol Cancer Ther. 2005 Jul;4(7):1096-104. [Article]

Drug created on October 21, 2016 02:22 / Updated on June 12, 2020 16:53