Basifungin

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Name
Basifungin
Accession Number
DB14058
Description

Basifungin, also known as aureuobacidin A, is a phosphorylceramide synthase inhibitor 3, 1.

Type
Small Molecule
Groups
Experimental
Structure
Thumb
Weight
Average: 1085.442
Monoisotopic: 1084.693641194
Chemical Formula
C60H92N8O10
Synonyms
  • Aureobasidin A
  • Basifungin
External IDs
  • Antibiotic R106I
  • LY 295337
  • LY295337
  • NK 204
  • R106-1

Pharmacology

Indication
Not Available
Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
Learn More
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
AInositol phosphorylceramide synthase
inhibitor
Yeast
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
Learn about our commercial Adverse Effects data.
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Toxicity
Not Available
Affected organisms
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.
DrugInteraction
AcenocoumarolThe therapeutic efficacy of Acenocoumarol can be increased when used in combination with Basifungin.
DicoumarolThe therapeutic efficacy of Dicoumarol can be increased when used in combination with Basifungin.
FluindioneThe therapeutic efficacy of Fluindione can be increased when used in combination with Basifungin.
PhenindioneThe therapeutic efficacy of Phenindione can be increased when used in combination with Basifungin.
PhenprocoumonThe therapeutic efficacy of Phenprocoumon can be increased when used in combination with Basifungin.
WarfarinThe therapeutic efficacy of Warfarin can be increased when used in combination with Basifungin.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions
Not Available

Products

Categories

Drug Categories
Classification
Not classified

Chemical Identifiers

UNII
VV0USO6I6U
CAS number
127785-64-2
InChI Key
YHSKJPXGXIYLHB-OTNPUQRPSA-N
InChI
InChI=1S/C60H92N8O10/c1-17-39(12)51-55(72)63-47(36(6)7)53(70)61-44(32-41-25-20-18-21-26-41)56(73)65(14)46(33-42-27-22-19-23-28-42)58(75)68-30-24-29-45(68)52(69)64-48(40(13)35(4)5)59(76)66(15)49(37(8)9)54(71)62-43(31-34(2)3)57(74)67(16)50(38(10)11)60(77)78-51/h18-23,25-28,34-40,43-51H,17,24,29-33H2,1-16H3,(H,61,70)(H,62,71)(H,63,72)(H,64,69)/t39-,40-,43+,44+,45+,46+,47?,48-,49+,50+,51+/m1/s1
IUPAC Name
(3R,6S,9S,12S,15S,21S,24S,29aS)-21,24-dibenzyl-15-[(2R)-butan-2-yl]-5,11,23-trimethyl-3-[(2R)-3-methylbutan-2-yl]-9-(2-methylpropyl)-6,12,18-tris(propan-2-yl)-octacosahydropyrrolo[1,2-m]1-oxa-4,7,10,13,16,19,22,25-octaazacycloheptacosane-1,4,7,10,13,16,19,22,25-nonone
SMILES
CC[[email protected]@H](C)[[email protected]@H]1OC(=O)[[email protected]](C(C)C)N(C)C(=O)[[email protected]](CC(C)C)NC(=O)[[email protected]](C(C)C)N(C)C(=O)[[email protected]](NC(=O)[[email protected]@H]2CCCN2C(=O)[[email protected]](CC2=CC=CC=C2)N(C)C(=O)[[email protected]](CC2=CC=CC=C2)NC(=O)C(NC1=O)C(C)C)[[email protected]](C)C(C)C

References

General References
  1. Aeed PA, Young CL, Nagiec MM, Elhammer AP: Inhibition of inositol phosphorylceramide synthase by the cyclic peptide aureobasidin A. Antimicrob Agents Chemother. 2009 Feb;53(2):496-504. doi: 10.1128/AAC.00633-08. Epub 2008 Dec 1. [PubMed:19047657]
  2. Basifungin [Link]
  3. AUR1- Uniprot [Link]
ChemSpider
26332345
ChEBI
61739

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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 Solubility0.00395 mg/mLALOGPS
logP5.14ALOGPS
logP7.02ChemAxon
logS-5.4ALOGPS
pKa (Strongest Acidic)11.76ChemAxon
pKa (Strongest Basic)-2.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area223.94 Å2ChemAxon
Rotatable Bond Count13ChemAxon
Refractivity297.75 m3·mol-1ChemAxon
Polarizability118 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
Not Available

Targets

Kind
Protein
Organism
Yeast
Pharmacological action
Yes
Actions
Inhibitor
General Function
Catalyzes the addition of a phosphorylinositol group onto ceramide to form inositol phosphorylceramide, an essential step in sphingolipid biosynthesis.
Specific Function
Inositol phosphoceramide synthase activity
Gene Name
AUR1
Uniprot ID
O13332
Uniprot Name
Inositol phosphorylceramide synthase
Molecular Weight
53457.9 Da
References
  1. Aeed PA, Young CL, Nagiec MM, Elhammer AP: Inhibition of inositol phosphorylceramide synthase by the cyclic peptide aureobasidin A. Antimicrob Agents Chemother. 2009 Feb;53(2):496-504. doi: 10.1128/AAC.00633-08. Epub 2008 Dec 1. [PubMed:19047657]
  2. aureobasidin A ( Basifungin) [Link]
  3. Basifungin PubChem [Link]

Drug created on June 14, 2018 13:28 / Updated on June 12, 2020 10:53

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