You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on DrugBank.
Identification
NameBafilomycin A1
Accession NumberDB06733
TypeSmall Molecule
GroupsExperimental
DescriptionThe 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
SynonymsNot Available
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNIINot Available
CAS number88899-55-2
WeightAverage: 622.84
Monoisotopic: 622.408083448
Chemical FormulaC35H58O9
InChI KeyXDHNQDDQEHDUTM-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
CO[[email protected]]1\C=C\C=C(C)\C[[email protected]](C)[[email protected]](O)[[email protected]](C)\C=C(/C)\C=C(OC)\C(=O)O[C@@H]1[C@@H](C)[C@@H](O)[[email protected]](C)[C@@]1(O)C[C@@H](O)[[email protected]](C)[[email protected]](O1)C(C)C
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassMacrolides and analogues
Sub ClassNot Available
Direct ParentMacrolides and analogues
Alternative Parents
Substituents
  • Macrolide
  • Oxane
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Carboxylic acid ester
  • Hemiacetal
  • Lactone
  • Secondary alcohol
  • Carboxylic acid derivative
  • Dialkyl ether
  • Ether
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Organoheterocyclic compound
  • Carbonyl group
  • Organic oxide
  • Hydrocarbon derivative
  • Alcohol
  • Organic oxygen compound
  • Organooxygen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionThe 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).
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal AbsorptionNot AvailableNot Available
Blood Brain BarrierNot AvailableNot Available
Caco-2 permeableNot AvailableNot Available
P-glycoprotein substrateNot AvailableNot Available
P-glycoprotein inhibitor INot AvailableNot Available
P-glycoprotein inhibitor IINot AvailableNot Available
Renal organic cation transporterNot AvailableNot Available
CYP450 2C9 substrateNot AvailableNot Available
CYP450 2D6 substrateNot AvailableNot Available
CYP450 3A4 substrateNot AvailableNot Available
CYP450 1A2 substrateNot AvailableNot Available
CYP450 2C9 inhibitorNot AvailableNot Available
CYP450 2D6 inhibitorNot AvailableNot Available
CYP450 2C19 inhibitorNot AvailableNot Available
CYP450 3A4 inhibitorNot AvailableNot Available
CYP450 inhibitory promiscuityNot AvailableNot Available
Ames testNot AvailableNot Available
CarcinogenicityNot AvailableNot Available
BiodegradationNot AvailableNot Available
Rat acute toxicityNot AvailableNot applicable
hERG inhibition (predictor I)Not AvailableNot Available
hERG inhibition (predictor II)Not AvailableNot Available
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot 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 FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (48 KB)
Interactions
Drug Interactions
Drug
AmlodipineThe risk or severity of adverse effects can be increased when Bafilomycin A1 is combined with Amlodipine.
Amphotericin BThe therapeutic efficacy of Amphotericin B can be decreased when used in combination with Bafilomycin A1.
AmrinoneThe risk or severity of adverse effects can be increased when Bafilomycin A1 is combined with Amrinone.
AzelnidipineThe risk or severity of adverse effects can be increased when Bafilomycin A1 is combined with Azelnidipine.
AzimilideThe risk or severity of adverse effects can be increased when Bafilomycin A1 is combined with Azimilide.
BarnidipineThe risk or severity of adverse effects can be increased when Bafilomycin A1 is combined with Barnidipine.
BenidipineThe risk or severity of adverse effects can be increased when Bafilomycin A1 is combined with Benidipine.
BepridilThe risk or severity of adverse effects can be increased when Bafilomycin A1 is combined with Bepridil.
BuspironeThe metabolism of Buspirone can be decreased when combined with Bafilomycin A1.
BusulfanThe serum concentration of Busulfan can be increased when it is combined with Bafilomycin A1.
CilnidipineThe risk or severity of adverse effects can be increased when Bafilomycin A1 is combined with Cilnidipine.
CinnarizineThe risk or severity of adverse effects can be increased when Bafilomycin A1 is combined with Cinnarizine.
CisaprideThe serum concentration of Cisapride can be increased when it is combined with Bafilomycin A1.
ConivaptanThe metabolism of Conivaptan can be decreased when combined with Bafilomycin A1.
CyclosporineThe metabolism of Cyclosporine can be decreased when combined with Bafilomycin A1.
DarodipineThe risk or severity of adverse effects can be increased when Bafilomycin A1 is combined with Darodipine.
DidanosineDidanosine can cause a decrease in the absorption of Bafilomycin A1 resulting in a reduced serum concentration and potentially a decrease in efficacy.
DiltiazemThe risk or severity of adverse effects can be increased when Bafilomycin A1 is combined with Diltiazem.
DocetaxelThe metabolism of Docetaxel can be decreased when combined with Bafilomycin A1.
DofetilideThe metabolism of Dofetilide can be decreased when combined with Bafilomycin A1.
DotarizineThe risk or severity of adverse effects can be increased when Bafilomycin A1 is combined with Dotarizine.
EfonidipineThe risk or severity of adverse effects can be increased when Bafilomycin A1 is combined with Efonidipine.
EperisoneThe risk or severity of adverse effects can be increased when Bafilomycin A1 is combined with Eperisone.
EtravirineThe serum concentration of Etravirine can be increased when it is combined with Bafilomycin A1.
FelodipineThe risk or severity of adverse effects can be increased when Bafilomycin A1 is combined with Felodipine.
FendilineThe risk or severity of adverse effects can be increased when Bafilomycin A1 is combined with Fendiline.
FlunarizineThe risk or severity of adverse effects can be increased when Bafilomycin A1 is combined with Flunarizine.
FosphenytoinThe serum concentration of Bafilomycin A1 can be decreased when it is combined with Fosphenytoin.
GabapentinThe risk or severity of adverse effects can be increased when Bafilomycin A1 is combined with Gabapentin.
IsradipineThe risk or severity of adverse effects can be increased when Bafilomycin A1 is combined with Isradipine.
LacidipineThe risk or severity of adverse effects can be increased when Bafilomycin A1 is combined with Lacidipine.
LamotrigineThe risk or severity of adverse effects can be increased when Bafilomycin A1 is combined with Lamotrigine.
LercanidipineThe risk or severity of adverse effects can be increased when Bafilomycin A1 is combined with Lercanidipine.
LosartanThe metabolism of Losartan can be decreased when combined with Bafilomycin A1.
Magnesium SulfateThe risk or severity of adverse effects can be increased when Bafilomycin A1 is combined with Magnesium Sulfate.
ManidipineThe risk or severity of adverse effects can be increased when Bafilomycin A1 is combined with Manidipine.
MibefradilThe risk or severity of adverse effects can be increased when Bafilomycin A1 is combined with Mibefradil.
NicardipineThe risk or severity of adverse effects can be increased when Bafilomycin A1 is combined with Nicardipine.
NifedipineThe risk or severity of adverse effects can be increased when Bafilomycin A1 is combined with Nifedipine.
NiguldipineThe risk or severity of adverse effects can be increased when Bafilomycin A1 is combined with Niguldipine.
NiludipineThe risk or severity of adverse effects can be increased when Bafilomycin A1 is combined with Niludipine.
NilvadipineThe risk or severity of adverse effects can be increased when Bafilomycin A1 is combined with Nilvadipine.
NimesulideThe risk or severity of adverse effects can be increased when Bafilomycin A1 is combined with Nimesulide.
NimodipineThe risk or severity of adverse effects can be increased when Bafilomycin A1 is combined with Nimodipine.
NisoldipineThe risk or severity of adverse effects can be increased when Bafilomycin A1 is combined with Nisoldipine.
NitrendipineThe risk or severity of adverse effects can be increased when Bafilomycin A1 is combined with Nitrendipine.
PerhexilineThe risk or severity of adverse effects can be increased when Bafilomycin A1 is combined with Perhexiline.
PhenytoinThe serum concentration of Phenytoin can be increased when it is combined with Bafilomycin A1.
PimozideBafilomycin A1 may increase the arrhythmogenic activities of Pimozide.
PinaveriumThe risk or severity of adverse effects can be increased when Bafilomycin A1 is combined with Pinaverium.
PregabalinThe risk or severity of adverse effects can be increased when Bafilomycin A1 is combined with Pregabalin.
PrenylamineThe risk or severity of adverse effects can be increased when Bafilomycin A1 is combined with Prenylamine.
ProgesteroneThe therapeutic efficacy of Progesterone can be decreased when used in combination with Bafilomycin A1.
QuinidineThe metabolism of Quinidine can be decreased when combined with Bafilomycin A1.
RanolazineThe metabolism of Ranolazine can be decreased when combined with Bafilomycin A1.
RisedronateThe risk or severity of adverse effects can be increased when Bafilomycin A1 is combined with Risedronate.
SolifenacinThe metabolism of Solifenacin can be decreased when combined with Bafilomycin A1.
SucralfateSucralfate can cause a decrease in the absorption of Bafilomycin A1 resulting in a reduced serum concentration and potentially a decrease in efficacy.
SunitinibThe metabolism of Sunitinib can be decreased when combined with Bafilomycin A1.
TacrolimusThe metabolism of Tacrolimus can be decreased when combined with Bafilomycin A1.
Tolfenamic AcidThe risk or severity of adverse effects can be increased when Bafilomycin A1 is combined with Tolfenamic Acid.
TranilastThe risk or severity of adverse effects can be increased when Bafilomycin A1 is combined with Tranilast.
VerapamilThe risk or severity of adverse effects can be increased when Bafilomycin A1 is combined with Verapamil.
XylometazolineThe risk or severity of adverse effects can be increased when Bafilomycin A1 is combined with Xylometazoline.
ZiconotideThe risk or severity of adverse effects can be increased when Bafilomycin A1 is combined with Ziconotide.
ZolpidemThe serum concentration of Zolpidem can be increased when it is combined with Bafilomycin A1.
Food InteractionsNot Available

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
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 ]
Comments
comments powered by Disqus
Drug created on August 25, 2010 14:38 / Updated on August 17, 2016 12:24