Brefeldin A
Identification
- Generic Name
- Brefeldin A
- DrugBank Accession Number
- DB07348
- Background
A metabolite from Penicillium brefeldianum that exhibits a wide range of antibiotic activity.
- Type
- Small Molecule
- Groups
- Experimental
- Structure
Structure for Brefeldin A (DB07348)
- Weight
- Average: 280.3594
Monoisotopic: 280.167459256 - Chemical Formula
- C16H24O4
- Synonyms
- (+)-brefeldin A
- Ascotoxin
- Cyanein
- Decumbin
- Nectrolide
- Synergisidin
- External IDs
- NSC-107456
- NSC-244390
- NSC-56310
- NSC-89671
Pharmacology
- Indication
Not Available
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Avoid life-threatening adverse drug eventsImprove clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events & improve clinical decision support.- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UCytohesin-2 Not Available Humans UADP-ribosylation factor 1 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.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.
Drug Interaction Integrate drug-drug
interactions in your softwareAbemaciclib The serum concentration of Abemaciclib can be increased when it is combined with Brefeldin A. Acalabrutinib The metabolism of Acalabrutinib can be decreased when combined with Brefeldin A. Acenocoumarol The serum concentration of Acenocoumarol can be increased when it is combined with Brefeldin A. Acetyldigitoxin The serum concentration of Acetyldigitoxin can be increased when it is combined with Brefeldin A. Afatinib The serum concentration of Afatinib can be increased when it is combined with Brefeldin A. Albendazole The metabolism of Albendazole can be decreased when combined with Brefeldin A. Alectinib The metabolism of Alectinib can be decreased when combined with Brefeldin A. Alfentanil The serum concentration of Alfentanil can be increased when it is combined with Brefeldin A. Alfuzosin The metabolism of Alfuzosin can be decreased when combined with Brefeldin A. Alpelisib The metabolism of Alpelisib can be decreased when combined with Brefeldin A. 
Identify potential medication risksEasily compare up to 40 drugs with our drug interaction checker.Get severity rating, description, and management advice.Learn more - Food Interactions
- Not Available
Categories
- Drug Categories
- Anti-Bacterial Agents
- Anti-Infective Agents
- Cytochrome P-450 CYP3A Inhibitors
- Cytochrome P-450 CYP3A4 Inhibitors
- Cytochrome P-450 CYP3A4 Inhibitors (strength unknown)
- Cytochrome P-450 Enzyme Inhibitors
- Enzyme Inhibitors
- Lactones
- Macrolides
- P-glycoprotein inhibitors
- Polyketides
- Protein Synthesis Inhibitors
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members.
- Kingdom
- Organic compounds
- Super Class
- Phenylpropanoids and polyketides
- Class
- Macrolides and analogues
- Sub Class
- Not Available
- Direct Parent
- Macrolides and analogues
- Alternative Parents
- Enoate esters / Secondary alcohols / Lactones / Cyclic alcohols and derivatives / Oxacyclic compounds / Monocarboxylic acids and derivatives / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
- Substituents
- Alcohol / Aliphatic heteropolycyclic compound / Alpha,beta-unsaturated carboxylic ester / Carbonyl group / Carboxylic acid derivative / Carboxylic acid ester / Cyclic alcohol / Enoate ester / Hydrocarbon derivative / Lactone
- Molecular Framework
- Aliphatic heteropolycyclic compounds
- External Descriptors
- macrolide antibiotic (CHEBI:48080)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- XG0D35F9K6
- CAS number
- 20350-15-6
- InChI Key
- KQNZDYYTLMIZCT-KQPMLPITSA-N
- InChI
- InChI=1S/C16H24O4/c1-11-5-3-2-4-6-12-9-13(17)10-14(12)15(18)7-8-16(19)20-11/h4,6-8,11-15,17-18H,2-3,5,9-10H2,1H3/b6-4+,8-7+/t11-,12+,13-,14+,15+/m0/s1
- IUPAC Name
- (1R,6S,11aS,13S,14aR)-1,13-dihydroxy-6-methyl-1H,4H,6H,7H,8H,9H,11aH,12H,13H,14H,14aH-cyclopenta[f]oxacyclotridecan-4-one
- SMILES
- [H][C@]1(O)C[C@@]2([H])\C=C\CCC[C@]([H])(C)OC(=O)\C=C\[C@@]([H])(O)[C@]2([H])C1
References
- General References
- Not Available
- External Links
- PubChem Compound
- 5287620
- PubChem Substance
- 99443819
- ChemSpider
- 4449949
- BindingDB
- 97307
- ChEBI
- 48080
- ChEMBL
- CHEMBL19980
- ZINC
- ZINC000012371944
- PDBe Ligand
- AFB
- Wikipedia
- Brefeldin_A
- PDB Entries
- 1r8q / 1re0 / 1s9d
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 0.812 mg/mL ALOGPS logP 1.73 ALOGPS logP 2.01 ChemAxon logS -2.5 ALOGPS pKa (Strongest Acidic) 14.42 ChemAxon pKa (Strongest Basic) -2.7 ChemAxon Physiological Charge 0 ChemAxon Hydrogen Acceptor Count 3 ChemAxon Hydrogen Donor Count 2 ChemAxon Polar Surface Area 66.76 Å2 ChemAxon Rotatable Bond Count 0 ChemAxon Refractivity 78.75 m3·mol-1 ChemAxon Polarizability 30.85 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 + 0.9842 Blood Brain Barrier + 0.8777 Caco-2 permeable + 0.6226 P-glycoprotein substrate Substrate 0.635 P-glycoprotein inhibitor I Non-inhibitor 0.9534 P-glycoprotein inhibitor II Non-inhibitor 0.9416 Renal organic cation transporter Non-inhibitor 0.9007 CYP450 2C9 substrate Non-substrate 0.7686 CYP450 2D6 substrate Non-substrate 0.8602 CYP450 3A4 substrate Substrate 0.5245 CYP450 1A2 substrate Inhibitor 0.7107 CYP450 2C9 inhibitor Non-inhibitor 0.9547 CYP450 2D6 inhibitor Non-inhibitor 0.9599 CYP450 2C19 inhibitor Non-inhibitor 0.9054 CYP450 3A4 inhibitor Non-inhibitor 0.8309 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9773 Ames test Non AMES toxic 0.9426 Carcinogenicity Non-carcinogens 0.9598 Biodegradation Ready biodegradable 0.6336 Rat acute toxicity 2.1006 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9471 hERG inhibition (predictor II) Non-inhibitor 0.893
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
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Lipid binding
- Specific Function
- Acts as a guanine-nucleotide exchange factor (GEF). Promotes guanine-nucleotide exchange on ARF1, ARF3 and ARF6. Promotes the activation of ARF factors through replacement of GDP with GTP. The cell...
- Gene Name
- CYTH2
- Uniprot ID
- Q99418
- Uniprot Name
- Cytohesin-2
- Molecular Weight
- 46545.725 Da
References
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Receptor signaling protein activity
- Specific Function
- GTP-binding protein that functions as an allosteric activator of the cholera toxin catalytic subunit, an ADP-ribosyltransferase. Involved in protein trafficking among different compartments. Modula...
- Gene Name
- ARF1
- Uniprot ID
- P84077
- Uniprot Name
- ADP-ribosylation factor 1
- Molecular Weight
- 20696.62 Da
References
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Inhibitor
- General Function
- Vitamin d3 25-hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
- Gene Name
- CYP3A4
- Uniprot ID
- P08684
- Uniprot Name
- Cytochrome P450 3A4
- Molecular Weight
- 57342.67 Da
References
- Kuper JI, D'Aprile M: Drug-Drug interactions of clinical significance in the treatment of patients with Mycobacterium avium complex disease. Clin Pharmacokinet. 2000 Sep;39(3):203-14. doi: 10.2165/00003088-200039030-00003. [Article]
Drug created on September 15, 2010 21:20 / Updated on June 12, 2020 16:52