NAV

Nigericin

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

Identification

Generic Name
Nigericin
DrugBank Accession Number
DB14056
Background

A polyether antibiotic which affects ion transport and ATPase activity in mitochondria. It is produced by Streptomyces hygroscopicus. (From Merck Index, 11th ed)

Type
Small Molecule
Groups
Experimental
Structure
Similar Structures
Weight
Average: 724.973
Monoisotopic: 724.47616301
Chemical Formula
C40H68O11
Synonyms
  • Azalomycin M
  • Helixin C
  • Polyetherin A
External IDs
  • Antibiotic K 178
  • Antibiotic X-464
  • BRN 1696755
  • X-464
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
Not Available
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
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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.
DrugInteraction
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interactions in your software
AcenocoumarolThe risk or severity of bleeding can be increased when Nigericin is combined with Acenocoumarol.
AmbroxolThe risk or severity of methemoglobinemia can be increased when Nigericin is combined with Ambroxol.
ArticaineThe risk or severity of methemoglobinemia can be increased when Nigericin is combined with Articaine.
BCG vaccineThe therapeutic efficacy of BCG vaccine can be decreased when used in combination with Nigericin.
BenzocaineThe risk or severity of methemoglobinemia can be increased when Nigericin is combined with Benzocaine.
Food Interactions
Not Available

Products

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Product Ingredients
IngredientUNIICASInChI Key
Nigericin sodiumDGN38HI97628643-80-3MOYOTUKECQMGHE-PDEFJWSRSA-M

Categories

Drug Categories
Classification
Not classified
Affected organisms
Not Available

Chemical Identifiers

UNII
RRU6GY95IS
CAS number
28380-24-7
InChI Key
DANUORFCFTYTSZ-SJSJOXFOSA-N
InChI
InChI=1S/C40H68O11/c1-21-11-12-28(46-33(21)26(6)36(42)43)17-29-18-30(45-10)27(7)40(48-29)25(5)19-38(9,51-40)32-13-14-37(8,49-32)35-23(3)16-31(47-35)34-22(2)15-24(4)39(44,20-41)50-34/h21-35,41,44H,11-20H2,1-10H3,(H,42,43)/t21-,22-,23-,24+,25+,26+,27+,28+,29+,30+,31+,32+,33+,34-,35+,37-,38-,39-,40+/m0/s1
IUPAC Name
(2R)-2-[(2R,3S,6R)-6-{[(2S,4R,5R,7R,9R,10R)-2-[(2S,2'R,3'S,5R,5'R)-5'-[(2S,3S,5R,6R)-6-hydroxy-6-(hydroxymethyl)-3,5-dimethyloxan-2-yl]-2,3'-dimethyl-[2,2'-bioxolan]-5-yl]-9-methoxy-2,4,10-trimethyl-1,6-dioxaspiro[4.5]decan-7-yl]methyl}-3-methyloxan-2-yl]propanoic acid
SMILES
[H][C@@]1(C[C@H](C)[C@@]([H])(O1)[C@]1(C)CC[C@@]([H])(O1)[C@]1(C)C[C@@H](C)[C@]2(O1)O[C@]([H])(C[C@@]1([H])CC[C@H](C)[C@@]([H])(O1)[C@@H](C)C(O)=O)C[C@@H](OC)[C@H]2C)[C@@]1([H])O[C@@](O)(CO)[C@H](C)C[C@@H]1C

References

General References
  1. Steinrauf LK, Pinkerton M, Chamberlin JW: The structure of nigericin. Biochem Biophys Res Commun. 1968 Oct 10;33(1):29-31. [Article]
KEGG Compound
C11609
ChemSpider
10196461
ChEBI
7569
ChEMBL
CHEMBL405862
ZINC
ZINC000085552063
Wikipedia
Nigericin

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 Solubility0.00137 mg/mLALOGPS
logP4.09ALOGPS
logP6.11Chemaxon
logS-5.7ALOGPS
pKa (Strongest Acidic)4.07Chemaxon
pKa (Strongest Basic)-3.4Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count11Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area142.37 Å2Chemaxon
Rotatable Bond Count9Chemaxon
Refractivity189.1 m3·mol-1Chemaxon
Polarizability81.84 Å3Chemaxon
Number of Rings6Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
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/MSsplash10-056r-0100002900-314b8e54aed8cef6f80f
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-00di-0000001900-79e804f3051fc9dc8b62
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a6s-0301126900-a38ccd9fb0e238e36b9d
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-01xt-0000209200-44366740ff3d73809c30
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-00di-3400045900-ee4927cf3ff0d734adb2
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-002u-0209110200-08650be5828bbe353920
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-295.0097537
predicted
DarkChem Lite v0.1.0
[M-H]-300.7427537
predicted
DarkChem Lite v0.1.0
[M+H]+296.2937537
predicted
DarkChem Lite v0.1.0
[M+H]+299.7199537
predicted
DarkChem Lite v0.1.0
[M+Na]+292.5317537
predicted
DarkChem Lite v0.1.0

Drug created at June 12, 2018 20:54 / Updated at June 12, 2020 16:53