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IdentificationPharmacologyInteractionsReferencesTrialsEconomicsPropertiesSpectraTaxonomyBrefeldin A
Identification
- Name
- Brefeldin A
- Accession Number
- DB07348
- Type
- Small Molecule
- Groups
- Experimental
- Description
A metabolite from Penicillium brefeldianum that exhibits a wide range of antibiotic activity.
- Structure
Structure for DB07348 (Brefeldin A)
- Synonyms
- (+)-brefeldin A
- Ascotoxin
- Cyanein
- Decumbin
- Nectrolide
- Synergisidin
- External IDs
- NSC-107456 / NSC-244390 / NSC-56310 / NSC-89671
- Categories
- UNII
- XG0D35F9K6
- CAS number
- 20350-15-6
- Weight
- Average: 280.3594
Monoisotopic: 280.167459256 - Chemical Formula
- C16H24O4
- 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
Pharmacology
- Indication
- Not Available
- Pharmacodynamics
- Not Available
- Mechanism of action
Target Actions Organism UCytohesin-2 Not Available Human UADP-ribosylation factor 1 Not Available Human - 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
- Toxicity
- Not Available
- Affected organisms
- Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
Drug Interaction Drug group Agmatine The therapeutic efficacy of Brefeldin A can be increased when used in combination with Agmatine. Experimental, Investigational Amiodarone The therapeutic efficacy of Brefeldin A can be increased when used in combination with Amiodarone. Approved, Investigational Amlodipine The therapeutic efficacy of Brefeldin A can be increased when used in combination with Amlodipine. Approved Amphotericin B The therapeutic efficacy of Amphotericin B can be decreased when used in combination with Brefeldin A. Approved, Investigational Amrinone The therapeutic efficacy of Brefeldin A can be increased when used in combination with Amrinone. Approved Aranidipine The therapeutic efficacy of Brefeldin A can be increased when used in combination with Aranidipine. Approved, Investigational Atorvastatin The risk or severity of rhabdomyolysis can be increased when Brefeldin A is combined with Atorvastatin. Approved Azelnidipine The therapeutic efficacy of Brefeldin A can be increased when used in combination with Azelnidipine. Approved, Investigational Azimilide The therapeutic efficacy of Brefeldin A can be increased when used in combination with Azimilide. Investigational Barnidipine The therapeutic efficacy of Brefeldin A can be increased when used in combination with Barnidipine. Approved BCG vaccine The therapeutic efficacy of BCG vaccine can be decreased when used in combination with Brefeldin A. Investigational Bencyclane The therapeutic efficacy of Brefeldin A can be increased when used in combination with Bencyclane. Experimental Benidipine The therapeutic efficacy of Brefeldin A can be increased when used in combination with Benidipine. Approved, Investigational Bepridil The therapeutic efficacy of Brefeldin A can be increased when used in combination with Bepridil. Approved, Withdrawn Bioallethrin The therapeutic efficacy of Brefeldin A can be increased when used in combination with Bioallethrin. Approved, Experimental Buspirone The metabolism of Buspirone can be decreased when combined with Brefeldin A. Approved, Investigational Busulfan The serum concentration of Busulfan can be increased when it is combined with Brefeldin A. Approved, Investigational Carboxyamidotriazole The therapeutic efficacy of Brefeldin A can be increased when used in combination with Carboxyamidotriazole. Investigational Caroverine The therapeutic efficacy of Brefeldin A can be increased when used in combination with Caroverine. Experimental Cerivastatin The risk or severity of rhabdomyolysis can be increased when Brefeldin A is combined with Cerivastatin. Approved, Withdrawn Cilnidipine The therapeutic efficacy of Brefeldin A can be increased when used in combination with Cilnidipine. Approved, Investigational Cinnarizine The therapeutic efficacy of Brefeldin A can be increased when used in combination with Cinnarizine. Approved, Investigational Cisapride The serum concentration of Cisapride can be increased when it is combined with Brefeldin A. Approved, Investigational, Withdrawn Clevidipine The therapeutic efficacy of Brefeldin A can be increased when used in combination with Clevidipine. Approved, Investigational Cyclandelate The therapeutic efficacy of Brefeldin A can be increased when used in combination with Cyclandelate. Approved Cyclosporine The metabolism of Cyclosporine can be decreased when combined with Brefeldin A. Approved, Investigational, Vet Approved Darodipine The therapeutic efficacy of Brefeldin A can be increased when used in combination with Darodipine. Experimental Didanosine Didanosine can cause a decrease in the absorption of Brefeldin A resulting in a reduced serum concentration and potentially a decrease in efficacy. Approved Diltiazem The therapeutic efficacy of Brefeldin A can be increased when used in combination with Diltiazem. Approved, Investigational Docetaxel The metabolism of Docetaxel can be decreased when combined with Brefeldin A. Approved, Investigational Dofetilide The serum concentration of Dofetilide can be increased when it is combined with Brefeldin A. Approved, Investigational Dotarizine The therapeutic efficacy of Brefeldin A can be increased when used in combination with Dotarizine. Investigational Efonidipine The therapeutic efficacy of Brefeldin A can be increased when used in combination with Efonidipine. Approved, Investigational Eperisone The therapeutic efficacy of Brefeldin A can be increased when used in combination with Eperisone. Approved, Investigational Ethosuximide The therapeutic efficacy of Brefeldin A can be increased when used in combination with Ethosuximide. Approved Etravirine The serum concentration of Etravirine can be increased when it is combined with Brefeldin A. Approved Felodipine The therapeutic efficacy of Brefeldin A can be increased when used in combination with Felodipine. Approved, Investigational Fendiline The therapeutic efficacy of Brefeldin A can be increased when used in combination with Fendiline. Withdrawn Fish oil The therapeutic efficacy of Brefeldin A can be increased when used in combination with Fish oil. Approved, Nutraceutical Flunarizine The therapeutic efficacy of Brefeldin A can be increased when used in combination with Flunarizine. Approved Fluspirilene The therapeutic efficacy of Brefeldin A can be increased when used in combination with Fluspirilene. Approved, Investigational Fluvastatin The risk or severity of rhabdomyolysis can be increased when Brefeldin A is combined with Fluvastatin. Approved Fosphenytoin The serum concentration of Brefeldin A can be decreased when it is combined with Fosphenytoin. Approved, Investigational Gabapentin The therapeutic efficacy of Brefeldin A can be increased when used in combination with Gabapentin. Approved, Investigational Gallopamil The therapeutic efficacy of Brefeldin A can be increased when used in combination with Gallopamil. Investigational Isradipine The therapeutic efficacy of Brefeldin A can be increased when used in combination with Isradipine. Approved, Investigational Lacidipine The therapeutic efficacy of Brefeldin A can be increased when used in combination with Lacidipine. Approved, Investigational Lamotrigine The therapeutic efficacy of Brefeldin A can be increased when used in combination with Lamotrigine. Approved, Investigational Lercanidipine The therapeutic efficacy of Brefeldin A can be increased when used in combination with Lercanidipine. Approved, Investigational Levetiracetam The therapeutic efficacy of Brefeldin A can be increased when used in combination with Levetiracetam. Approved, Investigational Lidoflazine The therapeutic efficacy of Brefeldin A can be increased when used in combination with Lidoflazine. Experimental Loperamide The therapeutic efficacy of Brefeldin A can be increased when used in combination with Loperamide. Approved Losartan The metabolism of Losartan can be decreased when combined with Brefeldin A. Approved Lovastatin The risk or severity of rhabdomyolysis can be increased when Brefeldin A is combined with Lovastatin. Approved, Investigational Magnesium sulfate The therapeutic efficacy of Brefeldin A can be increased when used in combination with Magnesium sulfate. Approved, Investigational, Vet Approved Manidipine The therapeutic efficacy of Brefeldin A can be increased when used in combination with Manidipine. Approved, Investigational Menthol The therapeutic efficacy of Brefeldin A can be increased when used in combination with Menthol. Approved Methsuximide The therapeutic efficacy of Brefeldin A can be increased when used in combination with Methsuximide. Approved Mevastatin The risk or severity of rhabdomyolysis can be increased when Brefeldin A is combined with Mevastatin. Experimental Mibefradil The therapeutic efficacy of Brefeldin A can be increased when used in combination with Mibefradil. Investigational, Withdrawn Naftopidil The therapeutic efficacy of Brefeldin A can be increased when used in combination with Naftopidil. Investigational Nicardipine The therapeutic efficacy of Brefeldin A can be increased when used in combination with Nicardipine. Approved, Investigational Nifedipine The therapeutic efficacy of Brefeldin A can be increased when used in combination with Nifedipine. Approved Niguldipine The therapeutic efficacy of Brefeldin A can be increased when used in combination with Niguldipine. Experimental Niludipine The therapeutic efficacy of Brefeldin A can be increased when used in combination with Niludipine. Experimental Nilvadipine The therapeutic efficacy of Brefeldin A can be increased when used in combination with Nilvadipine. Approved, Investigational Nimesulide The therapeutic efficacy of Brefeldin A can be increased when used in combination with Nimesulide. Approved, Investigational, Withdrawn Nimodipine The therapeutic efficacy of Brefeldin A can be increased when used in combination with Nimodipine. Approved, Investigational Nisoldipine The therapeutic efficacy of Brefeldin A can be increased when used in combination with Nisoldipine. Approved Nitrendipine The therapeutic efficacy of Brefeldin A can be increased when used in combination with Nitrendipine. Approved, Investigational Nylidrin The therapeutic efficacy of Brefeldin A can be increased when used in combination with Nylidrin. Approved Otilonium The therapeutic efficacy of Brefeldin A can be increased when used in combination with Otilonium. Experimental, Investigational Phenytoin The serum concentration of Phenytoin can be increased when it is combined with Brefeldin A. Approved, Vet Approved Picosulfuric acid The therapeutic efficacy of Picosulfuric acid can be decreased when used in combination with Brefeldin A. Approved Pinaverium The therapeutic efficacy of Brefeldin A can be increased when used in combination with Pinaverium. Approved Pitavastatin The risk or severity of rhabdomyolysis can be increased when Brefeldin A is combined with Pitavastatin. Approved Pravastatin The risk or severity of rhabdomyolysis can be increased when Brefeldin A is combined with Pravastatin. Approved Prenylamine The therapeutic efficacy of Brefeldin A can be increased when used in combination with Prenylamine. Withdrawn Progesterone The absorption of Progesterone can be decreased when combined with Brefeldin A. Approved, Vet Approved Quinidine The serum concentration of Quinidine can be increased when it is combined with Brefeldin A. Approved, Investigational Ranolazine The serum concentration of Ranolazine can be increased when it is combined with Brefeldin A. Approved, Investigational Rifabutin The serum concentration of Rifabutin can be increased when it is combined with Brefeldin A. Approved, Investigational Rifampicin The serum concentration of Rifampicin can be increased when it is combined with Brefeldin A. Approved Rifapentine The serum concentration of Rifapentine can be increased when it is combined with Brefeldin A. Approved, Investigational Rifaximin The serum concentration of Rifaximin can be increased when it is combined with Brefeldin A. Approved, Investigational Rosuvastatin The risk or severity of rhabdomyolysis can be increased when Brefeldin A is combined with Rosuvastatin. Approved Seletracetam The therapeutic efficacy of Brefeldin A can be increased when used in combination with Seletracetam. Investigational Simvastatin The risk or severity of rhabdomyolysis can be increased when Brefeldin A is combined with Simvastatin. Approved Solifenacin The metabolism of Solifenacin can be decreased when combined with Brefeldin A. Approved Sucralfate Sucralfate can cause a decrease in the absorption of Brefeldin A resulting in a reduced serum concentration and potentially a decrease in efficacy. Approved Sunitinib The metabolism of Sunitinib can be decreased when combined with Brefeldin A. Approved, Investigational Tacrolimus The metabolism of Tacrolimus can be decreased when combined with Brefeldin A. Approved, Investigational Terodiline The therapeutic efficacy of Brefeldin A can be increased when used in combination with Terodiline. Experimental Tetrahydropalmatine The therapeutic efficacy of Brefeldin A can be increased when used in combination with Tetrahydropalmatine. Investigational Tolfenamic Acid The therapeutic efficacy of Brefeldin A can be increased when used in combination with Tolfenamic Acid. Approved, Investigational Tranilast The therapeutic efficacy of Brefeldin A can be increased when used in combination with Tranilast. Approved, Investigational Trimebutine The therapeutic efficacy of Brefeldin A can be increased when used in combination with Trimebutine. Approved Trimethadione The therapeutic efficacy of Brefeldin A can be increased when used in combination with Trimethadione. Approved Verapamil The therapeutic efficacy of Brefeldin A can be increased when used in combination with Verapamil. Approved Vinpocetine The therapeutic efficacy of Brefeldin A can be increased when used in combination with Vinpocetine. Investigational WIN 55212-2 The therapeutic efficacy of Brefeldin A can be increased when used in combination with WIN 55212-2. Experimental Ziconotide The therapeutic efficacy of Brefeldin A can be increased when used in combination with Ziconotide. Approved Zolpidem The serum concentration of Zolpidem can be increased when it is combined with Brefeldin A. Approved Zonisamide The therapeutic efficacy of Brefeldin A can be increased when used in combination with Zonisamide. Approved, Investigational - Food Interactions
- Not Available
References
- General References
- Not Available
- External Links
- PubChem Compound
- 5287620
- PubChem Substance
- 99443819
- ChemSpider
- 4449949
- BindingDB
- 97307
- ChEBI
- 48080
- ChEMBL
- CHEMBL19980
- HET
- 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
Taxonomy
- 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
- Macrolide / Cyclic alcohol / Alpha,beta-unsaturated carboxylic ester / Enoate ester / Carboxylic acid ester / Lactone / Secondary alcohol / Carboxylic acid derivative / Oxacycle / Monocarboxylic acid or derivatives
- Molecular Framework
- Aliphatic heteropolycyclic compounds
- External Descriptors
- macrolide antibiotic (CHEBI:48080)
Targets
- Kind
- Protein
- Organism
- Human
- 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. [PubMed:10592235]
- Kind
- Protein
- Organism
- Human
- 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. [PubMed:10592235]
Drug created on September 15, 2010 15:20 / Updated on June 02, 2018 07:52