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
CO[C@H]1\C=C\C=C(C)\C[C@H](C)[C@H](O)[C@H](C)\C=C(/C)\C=C(OC)\C(=O)O[C@@H]1[C@@H](C)[C@@H](O)[C@H](C)[C@@]1(O)C[C@@H](O)[C@H](C)[C@H](O1)C(C)C

Pharmacology

Indication
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
AgmatineThe therapeutic efficacy of Bafilomycin A1 can be increased when used in combination with Agmatine.Experimental, Investigational
AmiodaroneThe therapeutic efficacy of Bafilomycin A1 can be increased when used in combination with Amiodarone.Approved, Investigational
AmlodipineThe therapeutic efficacy of Bafilomycin A1 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 Bafilomycin A1.Approved, Investigational
AmrinoneThe therapeutic efficacy of Bafilomycin A1 can be increased when used in combination with Amrinone.Approved
AranidipineThe therapeutic efficacy of Bafilomycin A1 can be increased when used in combination with Aranidipine.Approved, Investigational
AzelnidipineThe therapeutic efficacy of Bafilomycin A1 can be increased when used in combination with Azelnidipine.Approved, Investigational
AzimilideThe therapeutic efficacy of Bafilomycin A1 can be increased when used in combination with Azimilide.Investigational
BarnidipineThe therapeutic efficacy of Bafilomycin A1 can be increased when used in combination with Barnidipine.Approved
BencyclaneThe therapeutic efficacy of Bafilomycin A1 can be increased when used in combination with Bencyclane.Experimental
BenidipineThe therapeutic efficacy of Bafilomycin A1 can be increased when used in combination with Benidipine.Approved, Investigational
BepridilThe therapeutic efficacy of Bafilomycin A1 can be increased when used in combination with Bepridil.Approved, Withdrawn
BioallethrinThe therapeutic efficacy of Bafilomycin A1 can be increased when used in combination with Bioallethrin.Approved, Experimental
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 therapeutic efficacy of Bafilomycin A1 can be increased when used in combination with Carboxyamidotriazole.Investigational
CaroverineThe therapeutic efficacy of Bafilomycin A1 can be increased when used in combination with Caroverine.Experimental
CilnidipineThe therapeutic efficacy of Bafilomycin A1 can be increased when used in combination with Cilnidipine.Approved, Investigational
CinnarizineThe therapeutic efficacy of Bafilomycin A1 can be increased when used in combination with Cinnarizine.Approved, Investigational
CisaprideThe serum concentration of Cisapride can be increased when it is combined with Bafilomycin A1.Approved, Investigational, Withdrawn
ClevidipineThe therapeutic efficacy of Bafilomycin A1 can be increased when used in combination with Clevidipine.Approved, Investigational
CyclandelateThe therapeutic efficacy of Bafilomycin A1 can be increased when used in combination with Cyclandelate.Approved
CyclosporineThe metabolism of Cyclosporine can be decreased when combined with Bafilomycin A1.Approved, Investigational, Vet Approved
DarodipineThe therapeutic efficacy of Bafilomycin A1 can be increased when used in combination 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 therapeutic efficacy of Bafilomycin A1 can be increased when used in combination with Diltiazem.Approved, Investigational
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, Investigational
DotarizineThe therapeutic efficacy of Bafilomycin A1 can be increased when used in combination with Dotarizine.Investigational
EfonidipineThe therapeutic efficacy of Bafilomycin A1 can be increased when used in combination with Efonidipine.Approved, Investigational
EperisoneThe therapeutic efficacy of Bafilomycin A1 can be increased when used in combination with Eperisone.Approved, Investigational
EthosuximideThe therapeutic efficacy of Bafilomycin A1 can be increased when used in combination with Ethosuximide.Approved
EtravirineThe serum concentration of Etravirine can be increased when it is combined with Bafilomycin A1.Approved
FelodipineThe therapeutic efficacy of Bafilomycin A1 can be increased when used in combination with Felodipine.Approved, Investigational
FendilineThe therapeutic efficacy of Bafilomycin A1 can be increased when used in combination with Fendiline.Withdrawn
Fish oilThe therapeutic efficacy of Bafilomycin A1 can be increased when used in combination with Fish oil.Approved, Nutraceutical
FlunarizineThe therapeutic efficacy of Bafilomycin A1 can be increased when used in combination with Flunarizine.Approved
FluspirileneThe therapeutic efficacy of Bafilomycin A1 can be increased when used in combination with Fluspirilene.Approved, Investigational
FosphenytoinThe serum concentration of Bafilomycin A1 can be decreased when it is combined with Fosphenytoin.Approved, Investigational
GabapentinThe therapeutic efficacy of Bafilomycin A1 can be increased when used in combination with Gabapentin.Approved, Investigational
GallopamilThe therapeutic efficacy of Bafilomycin A1 can be increased when used in combination with Gallopamil.Investigational
IsradipineThe therapeutic efficacy of Bafilomycin A1 can be increased when used in combination with Isradipine.Approved, Investigational
LacidipineThe therapeutic efficacy of Bafilomycin A1 can be increased when used in combination with Lacidipine.Approved, Investigational
LamotrigineThe therapeutic efficacy of Bafilomycin A1 can be increased when used in combination with Lamotrigine.Approved, Investigational
LercanidipineThe therapeutic efficacy of Bafilomycin A1 can be increased when used in combination with Lercanidipine.Approved, Investigational
LevetiracetamThe therapeutic efficacy of Bafilomycin A1 can be increased when used in combination with Levetiracetam.Approved, Investigational
LidoflazineThe therapeutic efficacy of Bafilomycin A1 can be increased when used in combination with Lidoflazine.Experimental
LoperamideThe therapeutic efficacy of Bafilomycin A1 can be increased when used in combination with Loperamide.Approved
LosartanThe metabolism of Losartan can be decreased when combined with Bafilomycin A1.Approved
Magnesium sulfateThe therapeutic efficacy of Bafilomycin A1 can be increased when used in combination with Magnesium sulfate.Approved, Investigational, Vet Approved
ManidipineThe therapeutic efficacy of Bafilomycin A1 can be increased when used in combination with Manidipine.Approved, Investigational
MentholThe therapeutic efficacy of Bafilomycin A1 can be increased when used in combination with Menthol.Approved
MethsuximideThe therapeutic efficacy of Bafilomycin A1 can be increased when used in combination with Methsuximide.Approved
MibefradilThe therapeutic efficacy of Bafilomycin A1 can be increased when used in combination with Mibefradil.Investigational, Withdrawn
NaftopidilThe therapeutic efficacy of Bafilomycin A1 can be increased when used in combination with Naftopidil.Investigational
NicardipineThe therapeutic efficacy of Bafilomycin A1 can be increased when used in combination with Nicardipine.Approved, Investigational
NifedipineThe therapeutic efficacy of Bafilomycin A1 can be increased when used in combination with Nifedipine.Approved
NiguldipineThe therapeutic efficacy of Bafilomycin A1 can be increased when used in combination with Niguldipine.Experimental
NiludipineThe therapeutic efficacy of Bafilomycin A1 can be increased when used in combination with Niludipine.Experimental
NilvadipineThe therapeutic efficacy of Bafilomycin A1 can be increased when used in combination with Nilvadipine.Approved, Investigational
NimesulideThe therapeutic efficacy of Bafilomycin A1 can be increased when used in combination with Nimesulide.Approved, Investigational, Withdrawn
NimodipineThe therapeutic efficacy of Bafilomycin A1 can be increased when used in combination with Nimodipine.Approved, Investigational
NisoldipineThe therapeutic efficacy of Bafilomycin A1 can be increased when used in combination with Nisoldipine.Approved
NitrendipineThe therapeutic efficacy of Bafilomycin A1 can be increased when used in combination with Nitrendipine.Approved, Investigational
NylidrinThe therapeutic efficacy of Bafilomycin A1 can be increased when used in combination with Nylidrin.Approved
OtiloniumThe therapeutic efficacy of Bafilomycin A1 can be increased when used in combination with Otilonium.Experimental, Investigational
PhenytoinThe serum concentration of Phenytoin can be increased when it is combined with Bafilomycin A1.Approved, Vet Approved
PinaveriumThe therapeutic efficacy of Bafilomycin A1 can be increased when used in combination with Pinaverium.Approved
PrenylamineThe therapeutic efficacy of Bafilomycin A1 can be increased when used in combination 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, Investigational
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, Investigational
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, Investigational
RifaximinThe serum concentration of Rifaximin can be increased when it is combined with Bafilomycin A1.Approved, Investigational
SeletracetamThe therapeutic efficacy of Bafilomycin A1 can be increased when used in combination with Seletracetam.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 therapeutic efficacy of Bafilomycin A1 can be increased when used in combination with Terodiline.Experimental
TetrahydropalmatineThe therapeutic efficacy of Bafilomycin A1 can be increased when used in combination with Tetrahydropalmatine.Investigational
Tolfenamic AcidThe therapeutic efficacy of Bafilomycin A1 can be increased when used in combination with Tolfenamic Acid.Approved, Investigational
TranilastThe therapeutic efficacy of Bafilomycin A1 can be increased when used in combination with Tranilast.Approved, Investigational
TrimebutineThe therapeutic efficacy of Bafilomycin A1 can be increased when used in combination with Trimebutine.Approved
TrimethadioneThe therapeutic efficacy of Bafilomycin A1 can be increased when used in combination with Trimethadione.Approved
VerapamilThe therapeutic efficacy of Bafilomycin A1 can be increased when used in combination with Verapamil.Approved
VinpocetineThe therapeutic efficacy of Bafilomycin A1 can be increased when used in combination with Vinpocetine.Investigational
WIN 55212-2The therapeutic efficacy of Bafilomycin A1 can be increased when used in combination with WIN 55212-2.Experimental
ZiconotideThe therapeutic efficacy of Bafilomycin A1 can be increased when used in combination with Ziconotide.Approved
ZolpidemThe serum concentration of Zolpidem can be increased when it is combined with Bafilomycin A1.Approved
ZonisamideThe therapeutic efficacy of Bafilomycin A1 can be increased when used in combination with Zonisamide.Approved, Investigational
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 June 02, 2018 07:45