Identification

Name
Bafilomycin A1
Accession Number
DB06733
Type
Small Molecule
Groups
Experimental
Description

The bafilomycins are a family of toxic macrolide antibiotic derived from Streptomyces griseus. These compounds all appear in the same fermentation and have quite similar biological activity. Bafilomycins are specific inhibitors of vacuolar-type H+-ATPase. (V-ATPase). The most used bafilomycin is bafilomycin A1. This is a useful tool as it can prevent the re-acidification of synaptic vesicles once they have undergone exocytosis. [Wikipedia]

Structure
Thumb
Synonyms
Not Available
Categories
UNII
Not Available
CAS number
88899-55-2
Weight
Average: 622.84
Monoisotopic: 622.408083448
Chemical Formula
C35H58O9
InChI Key
XDHNQDDQEHDUTM-JQWOJBOSSA-N
InChI
InChI=1S/C35H58O9/c1-19(2)32-24(7)27(36)18-35(40,44-32)26(9)31(38)25(8)33-28(41-10)14-12-13-20(3)15-22(5)30(37)23(6)16-21(4)17-29(42-11)34(39)43-33/h12-14,16-17,19,22-28,30-33,36-38,40H,15,18H2,1-11H3/b14-12+,20-13+,21-16+,29-17-/t22-,23+,24-,25-,26-,27+,28-,30-,31+,32+,33+,35+/m0/s1
IUPAC Name
(3Z,5E,7R,8S,9S,11E,13E,15S,16R)-16-[(2S,3R,4S)-4-[(2R,4R,5S,6R)-2,4-dihydroxy-5-methyl-6-(propan-2-yl)oxan-2-yl]-3-hydroxypentan-2-yl]-8-hydroxy-3,15-dimethoxy-5,7,9,11-tetramethyl-1-oxacyclohexadeca-3,5,11,13-tetraen-2-one
SMILES

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action

The bafilomycins are a family of toxic macrolide antibiotic derived from Streptomyces griseus. These compounds all appear in the same fermentation and have quite similar biological activity. Bafilomycins are specific inhibitors of vacuolar-type H+-ATPase. (V-ATPase).

TargetActionsOrganism
AV-type proton ATPase catalytic subunit A
inhibitor
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
DrugInteractionDrug group
AmlodipineThe risk or severity of adverse effects can be increased when Bafilomycin A1 is combined with Amlodipine.Approved
Amphotericin BThe therapeutic efficacy of Amphotericin B can be decreased when used in combination with Bafilomycin A1.Approved, Investigational
AmrinoneThe risk or severity of adverse effects can be increased when Bafilomycin A1 is combined with Amrinone.Approved
AzelnidipineThe risk or severity of adverse effects can be increased when Bafilomycin A1 is combined with Azelnidipine.Approved, Investigational
AzimilideThe risk or severity of adverse effects can be increased when Bafilomycin A1 is combined with Azimilide.Investigational
BarnidipineThe risk or severity of adverse effects can be increased when Bafilomycin A1 is combined with Barnidipine.Approved
BencyclaneThe risk or severity of adverse effects can be increased when Bafilomycin A1 is combined with Bencyclane.Experimental
BenidipineThe risk or severity of adverse effects can be increased when Bafilomycin A1 is combined with Benidipine.Approved, Investigational
BepridilThe risk or severity of adverse effects can be increased when Bafilomycin A1 is combined with Bepridil.Approved, Withdrawn
BuspironeThe metabolism of Buspirone can be decreased when combined with Bafilomycin A1.Approved, Investigational
BusulfanThe serum concentration of Busulfan can be increased when it is combined with Bafilomycin A1.Approved, Investigational
CarboxyamidotriazoleThe risk or severity of adverse effects can be increased when Bafilomycin A1 is combined with Carboxyamidotriazole.Investigational
CaroverineThe risk or severity of adverse effects can be increased when Bafilomycin A1 is combined with Caroverine.Experimental
CilnidipineThe risk or severity of adverse effects can be increased when Bafilomycin A1 is combined with Cilnidipine.Approved, Investigational
CinnarizineThe risk or severity of adverse effects can be increased when Bafilomycin A1 is combined with Cinnarizine.Approved, Investigational
CisaprideThe serum concentration of Cisapride can be increased when it is combined with Bafilomycin A1.Approved, Investigational, Withdrawn
ClevidipineThe risk or severity of adverse effects can be increased when Bafilomycin A1 is combined with Clevidipine.Approved
CyclosporineThe metabolism of Cyclosporine can be decreased when combined with Bafilomycin A1.Approved, Investigational, Vet Approved
DarodipineThe risk or severity of adverse effects can be increased when Bafilomycin A1 is combined with Darodipine.Experimental
DidanosineDidanosine can cause a decrease in the absorption of Bafilomycin A1 resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
DiltiazemThe risk or severity of adverse effects can be increased when Bafilomycin A1 is combined with Diltiazem.Approved
DocetaxelThe metabolism of Docetaxel can be decreased when combined with Bafilomycin A1.Approved, Investigational
DofetilideThe serum concentration of Dofetilide can be increased when it is combined with Bafilomycin A1.Approved
DotarizineThe risk or severity of adverse effects can be increased when Bafilomycin A1 is combined with Dotarizine.Investigational
EfonidipineThe risk or severity of adverse effects can be increased when Bafilomycin A1 is combined with Efonidipine.Approved, Investigational
EperisoneThe risk or severity of adverse effects can be increased when Bafilomycin A1 is combined with Eperisone.Approved, Investigational
EtravirineThe serum concentration of Etravirine can be increased when it is combined with Bafilomycin A1.Approved
FelodipineThe risk or severity of adverse effects can be increased when Bafilomycin A1 is combined with Felodipine.Approved, Investigational
FendilineThe risk or severity of adverse effects can be increased when Bafilomycin A1 is combined with Fendiline.Withdrawn
FlunarizineThe risk or severity of adverse effects can be increased when Bafilomycin A1 is combined with Flunarizine.Approved
FosphenytoinThe serum concentration of Bafilomycin A1 can be decreased when it is combined with Fosphenytoin.Approved
GabapentinThe risk or severity of adverse effects can be increased when Bafilomycin A1 is combined with Gabapentin.Approved, Investigational
GallopamilThe risk or severity of adverse effects can be increased when Bafilomycin A1 is combined with Gallopamil.Investigational
IsradipineThe risk or severity of adverse effects can be increased when Bafilomycin A1 is combined with Isradipine.Approved
LacidipineThe risk or severity of adverse effects can be increased when Bafilomycin A1 is combined with Lacidipine.Approved, Investigational
LamotrigineThe risk or severity of adverse effects can be increased when Bafilomycin A1 is combined with Lamotrigine.Approved, Investigational
LercanidipineThe risk or severity of adverse effects can be increased when Bafilomycin A1 is combined with Lercanidipine.Approved, Investigational
LidoflazineThe risk or severity of adverse effects can be increased when Bafilomycin A1 is combined with Lidoflazine.Experimental
LosartanThe metabolism of Losartan can be decreased when combined with Bafilomycin A1.Approved
Magnesium SulfateThe risk or severity of adverse effects can be increased when Bafilomycin A1 is combined with Magnesium Sulfate.Approved, Vet Approved
ManidipineThe risk or severity of adverse effects can be increased when Bafilomycin A1 is combined with Manidipine.Approved, Investigational
MibefradilThe risk or severity of adverse effects can be increased when Bafilomycin A1 is combined with Mibefradil.Investigational, Withdrawn
NaftopidilThe risk or severity of adverse effects can be increased when Bafilomycin A1 is combined with Naftopidil.Investigational
NicardipineThe risk or severity of adverse effects can be increased when Bafilomycin A1 is combined with Nicardipine.Approved
NifedipineThe risk or severity of adverse effects can be increased when Bafilomycin A1 is combined with Nifedipine.Approved
NiguldipineThe risk or severity of adverse effects can be increased when Bafilomycin A1 is combined with Niguldipine.Experimental
NiludipineThe risk or severity of adverse effects can be increased when Bafilomycin A1 is combined with Niludipine.Experimental
NilvadipineThe risk or severity of adverse effects can be increased when Bafilomycin A1 is combined with Nilvadipine.Approved, Investigational
NimesulideThe risk or severity of adverse effects can be increased when Bafilomycin A1 is combined with Nimesulide.Approved, Investigational, Withdrawn
NimodipineThe risk or severity of adverse effects can be increased when Bafilomycin A1 is combined with Nimodipine.Approved
NisoldipineThe risk or severity of adverse effects can be increased when Bafilomycin A1 is combined with Nisoldipine.Approved
NitrendipineThe risk or severity of adverse effects can be increased when Bafilomycin A1 is combined with Nitrendipine.Approved, Investigational
OtiloniumThe risk or severity of adverse effects can be increased when Bafilomycin A1 is combined with Otilonium.Experimental, Investigational
PerhexilineThe risk or severity of adverse effects can be increased when Bafilomycin A1 is combined with Perhexiline.Approved, Investigational
PhenytoinThe serum concentration of Phenytoin can be increased when it is combined with Bafilomycin A1.Approved, Vet Approved
PinaveriumThe risk or severity of adverse effects can be increased when Bafilomycin A1 is combined with Pinaverium.Approved
PregabalinThe risk or severity of adverse effects can be increased when Bafilomycin A1 is combined with Pregabalin.Approved, Illicit, Investigational
PrenylamineThe risk or severity of adverse effects can be increased when Bafilomycin A1 is combined with Prenylamine.Withdrawn
ProgesteroneThe absorption of Progesterone can be decreased when combined with Bafilomycin A1.Approved, Vet Approved
QuinidineThe serum concentration of Quinidine can be increased when it is combined with Bafilomycin A1.Approved
RanolazineThe serum concentration of Ranolazine can be increased when it is combined with Bafilomycin A1.Approved, Investigational
RifabutinThe serum concentration of Rifabutin can be increased when it is combined with Bafilomycin A1.Approved
RifampicinThe serum concentration of Rifampicin can be increased when it is combined with Bafilomycin A1.Approved
RifapentineThe serum concentration of Rifapentine can be increased when it is combined with Bafilomycin A1.Approved
RifaximinThe serum concentration of Rifaximin can be increased when it is combined with Bafilomycin A1.Approved, Investigational
RisedronateThe risk or severity of adverse effects can be increased when Bafilomycin A1 is combined with Risedronate.Approved, Investigational
SolifenacinThe metabolism of Solifenacin can be decreased when combined with Bafilomycin A1.Approved
SucralfateSucralfate can cause a decrease in the absorption of Bafilomycin A1 resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
SunitinibThe metabolism of Sunitinib can be decreased when combined with Bafilomycin A1.Approved, Investigational
TacrolimusThe metabolism of Tacrolimus can be decreased when combined with Bafilomycin A1.Approved, Investigational
TerodilineThe risk or severity of adverse effects can be increased when Bafilomycin A1 is combined with Terodiline.Experimental
TetrahydropalmatineThe risk or severity of adverse effects can be increased when Bafilomycin A1 is combined with Tetrahydropalmatine.Investigational
Tolfenamic AcidThe risk or severity of adverse effects can be increased when Bafilomycin A1 is combined with Tolfenamic Acid.Approved
TranilastThe risk or severity of adverse effects can be increased when Bafilomycin A1 is combined with Tranilast.Approved, Investigational
VerapamilThe risk or severity of adverse effects can be increased when Bafilomycin A1 is combined with Verapamil.Approved
VinpocetineThe risk or severity of adverse effects can be increased when Bafilomycin A1 is combined with Vinpocetine.Investigational
XylometazolineThe risk or severity of adverse effects can be increased when Bafilomycin A1 is combined with Xylometazoline.Approved
ZiconotideThe risk or severity of adverse effects can be increased when Bafilomycin A1 is combined with Ziconotide.Approved
ZolpidemThe serum concentration of Zolpidem can be increased when it is combined with Bafilomycin A1.Approved
Food Interactions
Not Available

References

General References
Not Available
External Links
PubChem Compound
6436223
PubChem Substance
347827783
ChemSpider
4642865
BindingDB
50064186
ChEBI
22689
ChEMBL
CHEMBL290814
Wikipedia
Bafilomycin
MSDS
Download (48 KB)

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 Solubility0.0155 mg/mLALOGPS
logP3.89ALOGPS
logP5.08ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)11.69ChemAxon
pKa (Strongest Basic)-0.73ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area134.91 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity174.53 m3·mol-1ChemAxon
Polarizability69.33 Å3ChemAxon
Number of Rings2ChemAxon
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 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
Oxanes / Enoate esters / Secondary alcohols / Lactones / Hemiacetals / Oxacyclic compounds / Monocarboxylic acids and derivatives / Dialkyl ethers / Organic oxides / Hydrocarbon derivatives
show 1 more
Substituents
Macrolide / Oxane / Alpha,beta-unsaturated carboxylic ester / Enoate ester / Carboxylic acid ester / Hemiacetal / Lactone / Secondary alcohol / Carboxylic acid derivative / Dialkyl ether
show 11 more
Molecular Framework
Aliphatic heteromonocyclic compounds
External Descriptors
macrolide antibiotic, cyclic hemiketal, oxanes (CHEBI:22689)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Inhibitor
General Function
Proton-transporting atpase activity, rotational mechanism
Specific Function
Catalytic subunit of the peripheral V1 complex of vacuolar ATPase. V-ATPase vacuolar ATPase is responsible for acidifying a variety of intracellular compartments in eukaryotic cells.
Gene Name
ATP6V1A
Uniprot ID
P38606
Uniprot Name
V-type proton ATPase catalytic subunit A
Molecular Weight
68303.5 Da
References
  1. Takami M, Suda K, Sahara T, Itoh K, Nagai K, Sasaki T, Udagawa N, Takahashi N: Involvement of vacuolar H+ -ATPase in incorporation of risedronate into osteoclasts. Bone. 2003 Apr;32(4):341-9. [PubMed:12689676]

Drug created on August 25, 2010 14:38 / Updated on December 01, 2017 15:41