NIGERICIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C40H68O11
Molecular Weight	724.9613
Optical Activity	UNSPECIFIED
Defined Stereocenters	19 / 19
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CO[C@@H]1C[C@@H](C[C@H]2CC[C@H](C)[C@@H](O2)[C@@H](C)C(O)=O)O[C@]3(O[C@@](C)(C[C@H]3C)[C@H]4CC[C@](C)(O4)[C@@H]5O[C@H](C[C@@H]5C)[C@H]6O[C@@](O)(CO)[C@H](C)C[C@@H]6C)[C@@H]1C

InChI

InChIKey=DANUORFCFTYTSZ-SJSJOXFOSA-N

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

HIDE SMILES / InChI

Molecular Formula	C40H68O11
Molecular Weight	724.9613
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	19 / 19
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27519418 | https://www.ncbi.nlm.nih.gov/pubmed/9092947 | https://www.ncbi.nlm.nih.gov/pubmed/15595852 | DOI: 10.1007/978-3-642-46051-7_45

Nigericin is an antibiotic derived from Streptomyces “Nig-1”. It is the potassium ionophore and H+/K+ exchanger. It is shown to be highly effective as an ionophore for Pb(2+). Thus, nigericin may be more useful than monensin in the treatment of Pb intoxication. Nigericin induced mitochondrial membrane hyperpolarization. Malignant characteristics of human glioma cells were markedly suppressed by nigericin treatment in vivo. Nigericin induces cell death and promotes the maturation and release of IL-1beta in lipopolysaccharide (LPS)-primed monocytes and macrophages. The mechanism of induction of apoptosis by nigericin is most probably to decrease intracellular pH.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
intracellular pH reduction 2 Target ID: GO:0051452 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9092947	Activator 1447
Apoptosis 156 Target ID: WP1254 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9092947	Activator 1447
cellular potassium ion homeostasis 2 Target ID: GO:0030007 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12934070 \| https://www.ncbi.nlm.nih.gov/pubmed/9092947	Modulator 846
lead ion transport 2 Target ID: GO:0015692 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15595852	Modulator 846
Apoptosis 156 Target ID: WP1254 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9092947	Activator 1447
cellular potassium ion homeostasis 2 Target ID: GO:0030007 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12934070 \| https://www.ncbi.nlm.nih.gov/pubmed/9092947	Modulator 846
lead ion transport 2 Target ID: GO:0015692 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15595852	Modulator 846
intracellular pH reduction 2 Target ID: GO:0051452 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9092947	Activator 1447

Conditions

Condition	Modality	Highest Phase	Product
Lead intoxication 2 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15595852	Curative	Basic research	Unknown Approved Use Unknown
Coccidiosis 45 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1539028 https://www.google.com/patents/US3555150	Curative	Not Provided 511	Unknown Approved Use Unknown
Glioma 25 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27519418	Primary	Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Intracellular pH homeostasis in cultured human placental syncytiotrophoblast cells: recovery from acidification.	2005-04	15601755
Characterization of inorganic phosphate transport in osteoclast-like cells.	2005-04	15601753
Role of H+-ATPase-mediated acidification in sorting and release of the regulated secretory protein chromogranin A: evidence for a vesiculogenic function.	2005-02-04	15542860
Characterization of photosynthetic electron transport in bundle sheath cells of maize. I. Ascorbate effectively stimulates cyclic electron flow around PSI.	2005-02	15449056
Determination of the ionophoric coccidiostats narasin, monensin, lasalocid and salinomycin in eggs by liquid chromatography/tandem mass spectrometry.	2005	15655792
Efficient and sensitive detection of residues of nine coccidiostats in egg and muscle by liquid chromatography-electrospray tandem mass spectrometry.	2004-12-25	15556532
The ionophore nigericin transports Pb2+ with high activity and selectivity: a comparison to monensin and ionomycin.	2004-12-21	15595852
Regulated overexpression of CDR1 in Candida albicans confers multidrug resistance.	2004-12	15486081
Effects of 25-hydroxycholesterol on cholesterol esterification and sterol regulatory element-binding protein processing are dissociable: implications for cholesterol movement to the regulatory pool in the endoplasmic reticulum.	2004-11-05	15317807
P2X7 receptor polymorphism impairs extracellular adenosine 5'-triphosphate-induced interleukin-18 release from human monocytes.	2004-11	15306849
Human platelet dense granules contain polyphosphate and are similar to acidocalcisomes of bacteria and unicellular eukaryotes.	2004-10-22	15308650
A dynamic phase microscopic study of optical characteristics of individual chloroplasts.	2004-10-11	15471571
Mitochondrial toxicity detected in a health product with a boar spermatozoan bioassay.	2004-10	15651926
Evaluation of the presence of a thapsigargin-sensitive calcium store in trypanosomatids using Trypanosoma evansi as a model.	2004-10	15562626
Flow cytometric kinetic assay of the activity of Na+/H+ antiporter in mammalian cells.	2004-10	15382148
Top-down control analysis of the effect of temperature on ectotherm oxidative phosphorylation.	2004-10	15191905
Superoxide production by NADH:ubiquinone oxidoreductase (complex I) depends on the pH gradient across the mitochondrial inner membrane.	2004-09-01	15175007
Membrane potential and endocytic activity control disintegration of cell-cell adhesion and cell fusion in vinculin-injected MDBK cells.	2004-09	15254970
Effects of freezing on thermoluminescence in various plant species.	2004-08-25	15323581
Fluorescence measurements of free [Mg2+] by use of mag-fura 2 in Salmonella enterica.	2004-08-01	15268937
A novel mechanism of regulation of cardiac contractility by mitochondrial functional state.	2004-08	15284222
Control of oxidative phosphorylation during insect metamorphosis.	2004-08	15072964
Rotenone-sensitive mitochondrial potential in Phytomonas serpens: electrophoretic Ca(2+) accumulation.	2004-06-07	15178471
[Development of monoclonal-based enzyme-linked immunosorbent assay and immunochromatographic assay for lasalocid and semduramicin].	2004-06	15468928
Dynamics of polymorphism of acidocalcisomes in Leishmania parasites.	2004-05	15138840
Mechanisms of caspase-1 activation by P2X7 receptor-mediated K+ release.	2004-05	15075209
Regulation of mesangial cell Na+/Ca2+ exchanger isoforms.	2004-05	15040000
Glu496 to Ala polymorphism in the P2X7 receptor impairs ATP-induced IL-1 beta release from human monocytes.	2004-03-15	15004138
Inorganic polyphosphate in mitochondria of Saccharomyces cerevisiae at phosphate limitation and phosphate excess.	2004-03	15040953
Isolation and selection of ionophore-tolerant Eimeria precocious lines: E. tenella, E. maxima and E. acervulina.	2004-02-06	15154593
Regulation of connexin43 protein complexes by intracellular acidification.	2004-02-06	14699011
Correction of defective early tyrosinase processing by bafilomycin A1 and monensin in pink-eyed dilution melanocytes.	2004-02	14717843
Possible mechanism of polycation liposome (PCL)-mediated gene transfer.	2004-01-28	14757217
Cytochrome c, an ideal antioxidant.	2003-12	14641051
Analysis of phenomena involved in the apical growth of Phycomyces blakesleeanus.	2003-12	14610640
Tellurite uptake by cells of the facultative phototroph Rhodobacter capsulatus is a Delta pH-dependent process.	2003-11-20	14623086
A new method for in vitro detection of microbially produced mitochondrial toxins.	2003-11-06	14599472
Dietary microbial toxins and type 1 diabetes.	2003-11	14679104
Critical role for cathepsin B in mediating caspase-1-dependent interleukin-18 maturation and caspase-1-independent necrosis triggered by the microbial toxin nigericin.	2003-09	12934070
[3H]-DA release evoked by low pH medium and internal H+ accumulation in rat hypothalamic synaptosomes: involvement of calcium ions.	2003-07	12605878
EPR study of light-induced regulation of photosynthetic electron transport in Synechocystis sp. strain PCC 6803.	2003-06-05	12782283
Stimulation of potassium cycling in mitochondria by long-chain fatty acids.	2003-06-05	12765769
Cyclosporin A-sensitive decrease in the transmembrane potential across the inner membrane of liver mitochondria induced by low concentrations of fatty acids and Ca2+.	2003-04	12765520
Cyclic electron flow within PSII protects PSII from its photoinhibition in thylakoid membranes from spinach chloroplasts.	2003-04	12721388
Thylakoid targeting of Tat passenger proteins shows no delta pH dependence in vivo.	2003-02-17	12574117
A novel neutral amino acid transporter from the hyperthermophilic archaeon Thermococcus sp. KS-1.	2003-02	12761179
Physiological and morphological evidences for the presence acidocalcisomes in Trypanosoma evansi: single cell fluorescence and 31P NMR studies.	2002-12-07	12467971
S-Nitrosoglutathione induces functional DeltaF508-CFTR in airway epithelial cells.	2002-09-27	12270130
Vesicle transmembrane potential is required for translocation to the cytosol of externally added FGF-1.	2002-09-02	12198150
Cyclic electron flow within PSII functions in intact chloroplasts from spinach leaves.	2002-08	12198198

Patents

Sample Use Guides

In Vivo Use Guide

Mice: 4 mg/kg/day every 2 days

Route of Administration: Intraperitoneal

In Vitro Use Guide

Nigericin inhibits gram-positive bacteria at levels below 0.5 ug/ml, but levels above 60 ug/ml are required to inhibit gram-negative bacteria such as Escherichia coli. Mycobacterium smegmatis and Candida albicans are inhibited at 2 ug/ml, and fungi are inhibited at somewhat higher concentrations. The antibiotic is not active against bacteriophages at 500 ug/ml.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 19:35:21 GMT 2025` Edited by `admin` on `Mon Mar 31 19:35:21 GMT 2025`
Record UNII	RRU6GY95IS
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NIGERICIN

Common Name

English

ANTIBIOTIC K 178

Preferred Name

English

ANTIBIOTIC X-464

Code

English

HELIXIN C

Common Name

English

AZALOMYCIN M

Common Name

English

NIGERICIN [MI]

Common Name

English

POLYETHERIN A

Common Name

English

Code System Code Type Description

WIKIPEDIA

NIGERICIN