Explore a selection of our essential drug information below, or:
Overview
- DrugBank ID
- DB06733
- Type
- Small Molecule
- Clinical Trials
- Phase 0
- 0
- Phase 1
- 0
- Phase 2
- 0
- Phase 3
- 0
- Phase 4
- 0
- Mechanism of Action
Identification
- Generic Name
- Bafilomycin A1
- DrugBank Accession Number
- DB06733
- Background
The bafilomycins refer to a category of toxic macrolide antibiotics that are derivatives of Streptomyces griseus. These compounds all appear in the same fermentation and have similar biological activity. Bafilomycins are specific inhibitors of vacuolar-type H+-ATPase. (V-ATPase). The most commonly utilized bafilomycin is bafilomycin A1. This is a useful tool as it can prevent the re-acidification of synaptic vesicles once they have undergone exocytosis.
- Type
- Small Molecule
- Groups
- Experimental
- Structure
Structure for Bafilomycin A1 (DB06733)
- Weight
- Average: 622.84
Monoisotopic: 622.408083448 - Chemical Formula
- C35H58O9
- Synonyms
- Not Available
Pharmacology
- Indication
Not Available
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- 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).
Target Actions Organism AV-type proton ATPase catalytic subunit A inhibitorHumans - 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
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAcenocoumarol The therapeutic efficacy of Acenocoumarol can be increased when used in combination with Bafilomycin A1. Dicoumarol The therapeutic efficacy of Dicoumarol can be increased when used in combination with Bafilomycin A1. Fluindione The therapeutic efficacy of Fluindione can be increased when used in combination with Bafilomycin A1. Phenindione The therapeutic efficacy of Phenindione can be increased when used in combination with Bafilomycin A1. Phenprocoumon The therapeutic efficacy of Phenprocoumon can be increased when used in combination with Bafilomycin A1. - Food Interactions
- Not Available
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- 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
- Alcohol / Aliphatic heteromonocyclic compound / Alpha,beta-unsaturated carboxylic ester / Carbonyl group / Carboxylic acid derivative / Carboxylic acid ester / Dialkyl ether / Enoate ester / Ether / Hemiacetal show 11 more
- Molecular Framework
- Aliphatic heteromonocyclic compounds
- External Descriptors
- macrolide antibiotic, cyclic hemiketal, oxanes (CHEBI:22689)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- Not Available
- CAS number
- 88899-55-2
- 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
References
- General References
- Not Available
- External Links
- PubChem Compound
- 6436223
- PubChem Substance
- 347827783
- ChemSpider
- 4642865
- BindingDB
- 50064186
- ChEBI
- 22689
- ChEMBL
- CHEMBL290814
- ZINC
- ZINC000169647947
- Wikipedia
- Bafilomycin
- MSDS
- Download (48 KB)
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
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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
Property Value Source Water Solubility 0.0155 mg/mL ALOGPS logP 3.89 ALOGPS logP 5.08 Chemaxon logS -4.6 ALOGPS pKa (Strongest Acidic) 11.69 Chemaxon pKa (Strongest Basic) -0.73 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 8 Chemaxon Hydrogen Donor Count 4 Chemaxon Polar Surface Area 134.91 Å2 Chemaxon Rotatable Bond Count 7 Chemaxon Refractivity 174.53 m3·mol-1 Chemaxon Polarizability 69.33 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 255.57016 predictedDeepCCS 1.0 (2019) [M+H]+ 257.29388 predictedDeepCCS 1.0 (2019) [M+Na]+ 263.62283 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Catalytic subunit of the V1 complex of vacuolar(H+)-ATPase (V-ATPase), a multisubunit enzyme composed of a peripheral complex (V1) that hydrolyzes ATP and a membrane integral complex (V0) that translocates protons (PubMed:8463241). V-ATPase is responsible for acidifying and maintaining the pH of intracellular compartments and in some cell types, is targeted to the plasma membrane, where it is responsible for acidifying the extracellular environment (PubMed:32001091). In aerobic conditions, involved in intracellular iron homeostasis, thus triggering the activity of Fe(2+) prolyl hydroxylase (PHD) enzymes, and leading to HIF1A hydroxylation and subsequent proteasomal degradation (PubMed:28296633). May play a role in neurite development and synaptic connectivity (PubMed:29668857)
- Specific Function
- ATP binding
- Gene Name
- ATP6V1A
- Uniprot ID
- P38606
- Uniprot Name
- V-type proton ATPase catalytic subunit A
- Molecular Weight
- 68303.5 Da
References
- 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. [Article]
Drug created at August 25, 2010 20:38 / Updated at June 12, 2020 16:52