Brefeldin 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
Thumb
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
TargetActionsOrganism
UCytohesin-2Not AvailableHuman
UADP-ribosylation factor 1Not AvailableHuman
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
DrugInteractionDrug group
AgmatineThe therapeutic efficacy of Brefeldin A can be increased when used in combination with Agmatine.Experimental, Investigational
AmiodaroneThe therapeutic efficacy of Brefeldin A can be increased when used in combination with Amiodarone.Approved, Investigational
AmlodipineThe therapeutic efficacy of Brefeldin A can be increased when used in combination with Amlodipine.Approved
Amphotericin BThe therapeutic efficacy of Amphotericin B can be decreased when used in combination with Brefeldin A.Approved, Investigational
AmrinoneThe therapeutic efficacy of Brefeldin A can be increased when used in combination with Amrinone.Approved
AranidipineThe therapeutic efficacy of Brefeldin A can be increased when used in combination with Aranidipine.Approved, Investigational
AtorvastatinThe risk or severity of rhabdomyolysis can be increased when Brefeldin A is combined with Atorvastatin.Approved
AzelnidipineThe therapeutic efficacy of Brefeldin A can be increased when used in combination with Azelnidipine.Approved, Investigational
AzimilideThe therapeutic efficacy of Brefeldin A can be increased when used in combination with Azimilide.Investigational
BarnidipineThe therapeutic efficacy of Brefeldin A can be increased when used in combination with Barnidipine.Approved
BCG vaccineThe therapeutic efficacy of BCG vaccine can be decreased when used in combination with Brefeldin A.Investigational
BencyclaneThe therapeutic efficacy of Brefeldin A can be increased when used in combination with Bencyclane.Experimental
BenidipineThe therapeutic efficacy of Brefeldin A can be increased when used in combination with Benidipine.Approved, Investigational
BepridilThe therapeutic efficacy of Brefeldin A can be increased when used in combination with Bepridil.Approved, Withdrawn
BioallethrinThe therapeutic efficacy of Brefeldin A can be increased when used in combination with Bioallethrin.Approved, Experimental
BuspironeThe metabolism of Buspirone can be decreased when combined with Brefeldin A.Approved, Investigational
BusulfanThe serum concentration of Busulfan can be increased when it is combined with Brefeldin A.Approved, Investigational
CarboxyamidotriazoleThe therapeutic efficacy of Brefeldin A can be increased when used in combination with Carboxyamidotriazole.Investigational
CaroverineThe therapeutic efficacy of Brefeldin A can be increased when used in combination with Caroverine.Experimental
CerivastatinThe risk or severity of rhabdomyolysis can be increased when Brefeldin A is combined with Cerivastatin.Approved, Withdrawn
CilnidipineThe therapeutic efficacy of Brefeldin A can be increased when used in combination with Cilnidipine.Approved, Investigational
CinnarizineThe therapeutic efficacy of Brefeldin A can be increased when used in combination with Cinnarizine.Approved, Investigational
CisaprideThe serum concentration of Cisapride can be increased when it is combined with Brefeldin A.Approved, Investigational, Withdrawn
ClevidipineThe therapeutic efficacy of Brefeldin A can be increased when used in combination with Clevidipine.Approved, Investigational
CyclandelateThe therapeutic efficacy of Brefeldin A can be increased when used in combination with Cyclandelate.Approved
CyclosporineThe metabolism of Cyclosporine can be decreased when combined with Brefeldin A.Approved, Investigational, Vet Approved
DarodipineThe therapeutic efficacy of Brefeldin A can be increased when used in combination with Darodipine.Experimental
DidanosineDidanosine can cause a decrease in the absorption of Brefeldin A resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
DiltiazemThe therapeutic efficacy of Brefeldin A can be increased when used in combination with Diltiazem.Approved, Investigational
DocetaxelThe metabolism of Docetaxel can be decreased when combined with Brefeldin A.Approved, Investigational
DofetilideThe serum concentration of Dofetilide can be increased when it is combined with Brefeldin A.Approved, Investigational
DotarizineThe therapeutic efficacy of Brefeldin A can be increased when used in combination with Dotarizine.Investigational
EfonidipineThe therapeutic efficacy of Brefeldin A can be increased when used in combination with Efonidipine.Approved, Investigational
EperisoneThe therapeutic efficacy of Brefeldin A can be increased when used in combination with Eperisone.Approved, Investigational
EthosuximideThe therapeutic efficacy of Brefeldin A can be increased when used in combination with Ethosuximide.Approved
EtravirineThe serum concentration of Etravirine can be increased when it is combined with Brefeldin A.Approved
FelodipineThe therapeutic efficacy of Brefeldin A can be increased when used in combination with Felodipine.Approved, Investigational
FendilineThe therapeutic efficacy of Brefeldin A can be increased when used in combination with Fendiline.Withdrawn
Fish oilThe therapeutic efficacy of Brefeldin A can be increased when used in combination with Fish oil.Approved, Nutraceutical
FlunarizineThe therapeutic efficacy of Brefeldin A can be increased when used in combination with Flunarizine.Approved
FluspirileneThe therapeutic efficacy of Brefeldin A can be increased when used in combination with Fluspirilene.Approved, Investigational
FluvastatinThe risk or severity of rhabdomyolysis can be increased when Brefeldin A is combined with Fluvastatin.Approved
FosphenytoinThe serum concentration of Brefeldin A can be decreased when it is combined with Fosphenytoin.Approved, Investigational
GabapentinThe therapeutic efficacy of Brefeldin A can be increased when used in combination with Gabapentin.Approved, Investigational
GallopamilThe therapeutic efficacy of Brefeldin A can be increased when used in combination with Gallopamil.Investigational
IsradipineThe therapeutic efficacy of Brefeldin A can be increased when used in combination with Isradipine.Approved, Investigational
LacidipineThe therapeutic efficacy of Brefeldin A can be increased when used in combination with Lacidipine.Approved, Investigational
LamotrigineThe therapeutic efficacy of Brefeldin A can be increased when used in combination with Lamotrigine.Approved, Investigational
LercanidipineThe therapeutic efficacy of Brefeldin A can be increased when used in combination with Lercanidipine.Approved, Investigational
LevetiracetamThe therapeutic efficacy of Brefeldin A can be increased when used in combination with Levetiracetam.Approved, Investigational
LidoflazineThe therapeutic efficacy of Brefeldin A can be increased when used in combination with Lidoflazine.Experimental
LoperamideThe therapeutic efficacy of Brefeldin A can be increased when used in combination with Loperamide.Approved
LosartanThe metabolism of Losartan can be decreased when combined with Brefeldin A.Approved
LovastatinThe risk or severity of rhabdomyolysis can be increased when Brefeldin A is combined with Lovastatin.Approved, Investigational
Magnesium sulfateThe therapeutic efficacy of Brefeldin A can be increased when used in combination with Magnesium sulfate.Approved, Investigational, Vet Approved
ManidipineThe therapeutic efficacy of Brefeldin A can be increased when used in combination with Manidipine.Approved, Investigational
MentholThe therapeutic efficacy of Brefeldin A can be increased when used in combination with Menthol.Approved
MethsuximideThe therapeutic efficacy of Brefeldin A can be increased when used in combination with Methsuximide.Approved
MevastatinThe risk or severity of rhabdomyolysis can be increased when Brefeldin A is combined with Mevastatin.Experimental
MibefradilThe therapeutic efficacy of Brefeldin A can be increased when used in combination with Mibefradil.Investigational, Withdrawn
NaftopidilThe therapeutic efficacy of Brefeldin A can be increased when used in combination with Naftopidil.Investigational
NicardipineThe therapeutic efficacy of Brefeldin A can be increased when used in combination with Nicardipine.Approved, Investigational
NifedipineThe therapeutic efficacy of Brefeldin A can be increased when used in combination with Nifedipine.Approved
NiguldipineThe therapeutic efficacy of Brefeldin A can be increased when used in combination with Niguldipine.Experimental
NiludipineThe therapeutic efficacy of Brefeldin A can be increased when used in combination with Niludipine.Experimental
NilvadipineThe therapeutic efficacy of Brefeldin A can be increased when used in combination with Nilvadipine.Approved, Investigational
NimesulideThe therapeutic efficacy of Brefeldin A can be increased when used in combination with Nimesulide.Approved, Investigational, Withdrawn
NimodipineThe therapeutic efficacy of Brefeldin A can be increased when used in combination with Nimodipine.Approved, Investigational
NisoldipineThe therapeutic efficacy of Brefeldin A can be increased when used in combination with Nisoldipine.Approved
NitrendipineThe therapeutic efficacy of Brefeldin A can be increased when used in combination with Nitrendipine.Approved, Investigational
NylidrinThe therapeutic efficacy of Brefeldin A can be increased when used in combination with Nylidrin.Approved
OtiloniumThe therapeutic efficacy of Brefeldin A can be increased when used in combination with Otilonium.Experimental, Investigational
PhenytoinThe serum concentration of Phenytoin can be increased when it is combined with Brefeldin A.Approved, Vet Approved
Picosulfuric acidThe therapeutic efficacy of Picosulfuric acid can be decreased when used in combination with Brefeldin A.Approved
PinaveriumThe therapeutic efficacy of Brefeldin A can be increased when used in combination with Pinaverium.Approved
PitavastatinThe risk or severity of rhabdomyolysis can be increased when Brefeldin A is combined with Pitavastatin.Approved
PravastatinThe risk or severity of rhabdomyolysis can be increased when Brefeldin A is combined with Pravastatin.Approved
PrenylamineThe therapeutic efficacy of Brefeldin A can be increased when used in combination with Prenylamine.Withdrawn
ProgesteroneThe absorption of Progesterone can be decreased when combined with Brefeldin A.Approved, Vet Approved
QuinidineThe serum concentration of Quinidine can be increased when it is combined with Brefeldin A.Approved, Investigational
RanolazineThe serum concentration of Ranolazine can be increased when it is combined with Brefeldin A.Approved, Investigational
RifabutinThe serum concentration of Rifabutin can be increased when it is combined with Brefeldin A.Approved, Investigational
RifampicinThe serum concentration of Rifampicin can be increased when it is combined with Brefeldin A.Approved
RifapentineThe serum concentration of Rifapentine can be increased when it is combined with Brefeldin A.Approved, Investigational
RifaximinThe serum concentration of Rifaximin can be increased when it is combined with Brefeldin A.Approved, Investigational
RosuvastatinThe risk or severity of rhabdomyolysis can be increased when Brefeldin A is combined with Rosuvastatin.Approved
SeletracetamThe therapeutic efficacy of Brefeldin A can be increased when used in combination with Seletracetam.Investigational
SimvastatinThe risk or severity of rhabdomyolysis can be increased when Brefeldin A is combined with Simvastatin.Approved
SolifenacinThe metabolism of Solifenacin can be decreased when combined with Brefeldin A.Approved
SucralfateSucralfate can cause a decrease in the absorption of Brefeldin A resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
SunitinibThe metabolism of Sunitinib can be decreased when combined with Brefeldin A.Approved, Investigational
TacrolimusThe metabolism of Tacrolimus can be decreased when combined with Brefeldin A.Approved, Investigational
TerodilineThe therapeutic efficacy of Brefeldin A can be increased when used in combination with Terodiline.Experimental
TetrahydropalmatineThe therapeutic efficacy of Brefeldin A can be increased when used in combination with Tetrahydropalmatine.Investigational
Tolfenamic AcidThe therapeutic efficacy of Brefeldin A can be increased when used in combination with Tolfenamic Acid.Approved, Investigational
TranilastThe therapeutic efficacy of Brefeldin A can be increased when used in combination with Tranilast.Approved, Investigational
TrimebutineThe therapeutic efficacy of Brefeldin A can be increased when used in combination with Trimebutine.Approved
TrimethadioneThe therapeutic efficacy of Brefeldin A can be increased when used in combination with Trimethadione.Approved
VerapamilThe therapeutic efficacy of Brefeldin A can be increased when used in combination with Verapamil.Approved
VinpocetineThe therapeutic efficacy of Brefeldin A can be increased when used in combination with Vinpocetine.Investigational
WIN 55212-2The therapeutic efficacy of Brefeldin A can be increased when used in combination with WIN 55212-2.Experimental
ZiconotideThe therapeutic efficacy of Brefeldin A can be increased when used in combination with Ziconotide.Approved
ZolpidemThe serum concentration of Zolpidem can be increased when it is combined with Brefeldin A.Approved
ZonisamideThe 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

Clinical Trials
Not Available

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
PropertyValueSource
Water Solubility0.812 mg/mLALOGPS
logP1.73ALOGPS
logP2.01ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)14.42ChemAxon
pKa (Strongest Basic)-2.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity78.75 m3·mol-1ChemAxon
Polarizability30.85 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9842
Blood Brain Barrier+0.8777
Caco-2 permeable+0.6226
P-glycoprotein substrateSubstrate0.635
P-glycoprotein inhibitor INon-inhibitor0.9534
P-glycoprotein inhibitor IINon-inhibitor0.9416
Renal organic cation transporterNon-inhibitor0.9007
CYP450 2C9 substrateNon-substrate0.7686
CYP450 2D6 substrateNon-substrate0.8602
CYP450 3A4 substrateSubstrate0.5245
CYP450 1A2 substrateInhibitor0.7107
CYP450 2C9 inhibitorNon-inhibitor0.9547
CYP450 2D6 inhibitorNon-inhibitor0.9599
CYP450 2C19 inhibitorNon-inhibitor0.9054
CYP450 3A4 inhibitorNon-inhibitor0.8309
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9773
Ames testNon AMES toxic0.9426
CarcinogenicityNon-carcinogens0.9598
BiodegradationReady biodegradable0.6336
Rat acute toxicity2.1006 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9471
hERG inhibition (predictor II)Non-inhibitor0.893
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

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

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
  1. 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
  1. 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