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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
Pharmacology
IndicationNot Available
Structured Indications Not 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).
TargetKindPharmacological actionActionsOrganismUniProt ID
V-type proton ATPase catalytic subunit AProteinyes
inhibitor
HumanP38606 details
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
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
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
BenidipineThe risk or severity of adverse effects can be increased when Bafilomycin A1 is combined with Benidipine.Approved
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
CaiThe risk or severity of adverse effects can be increased when Bafilomycin A1 is combined with Cai.Investigational
CilnidipineThe risk or severity of adverse effects can be increased when Bafilomycin A1 is combined with Cilnidipine.Approved
CinnarizineThe risk or severity of adverse effects can be increased when Bafilomycin A1 is combined with Cinnarizine.Approved
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
ConivaptanThe metabolism of Conivaptan can be decreased when combined with Bafilomycin A1.Approved, Investigational
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 metabolism of Dofetilide can be decreased when 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
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
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
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
MibefradilThe risk or severity of adverse effects can be increased when Bafilomycin A1 is combined with Mibefradil.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
NimesulideThe risk or severity of adverse effects can be increased when Bafilomycin A1 is combined with Nimesulide.Approved, 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
PerhexilineThe risk or severity of adverse effects can be increased when Bafilomycin A1 is combined with Perhexiline.Approved
PhenytoinThe serum concentration of Phenytoin can be increased when it is combined with Bafilomycin A1.Approved, Vet Approved
PimozideBafilomycin A1 may increase the arrhythmogenic activities of Pimozide.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 therapeutic efficacy of Progesterone can be decreased when used in combination with Bafilomycin A1.Approved, Vet Approved
QuinidineThe metabolism of Quinidine can be decreased when combined with Bafilomycin A1.Approved
RanolazineThe metabolism of Ranolazine can be decreased when 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
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
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 InteractionsNot 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)
ADMET
Predicted ADMET featuresNot Available
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
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

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 ]
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Drug created on August 25, 2010 14:38 / Updated on August 17, 2016 12:24