Compound

D0009 | Antimycin A

Molecular Formula C28H40N2O9
Molecular Weight 548.6
Structure
Trade names Fintrol (chemical piscicide)
Description a secondary metabolites produced by Streptomyces bacteria; Classical respiratory inhibitors; Inhibits cytochrome b-c1; complex III inhibitor

Toxicity Dose Time Species Model Method Action Positive criterion Reference
OXYGEN CONSUMPTION RATE (OCR) 4±0.2 nM 2 minutes human HepG2 Measurement of OCR decrease EC50 7
ELECTRON TRANSPORT CHAIN decrease 26
ELECTRON TRANSPORT CHAIN decrease 35
ELECTRON TRANSPORT CHAIN bovine isolated heart mitochondria cytochrome bc1 complex affect 166
ECAR 100±20 nM 2 minutes human HepG2 Measurement of ECAR increase EC50 7
GLUCOSE GALACTOSE IC50 RATIO 5.9 (42.1nM/7.1nM) 24hr L6 ATP levels in high-glucose (25 mM) or galactose (10 mM) medium glucose/galactose IC50 ratio 325
GLUCOSE GALACTOSE IC50 RATIO 10.7 (176.5nM/16.5nM) 24hr H9c2 ATP levels in high-glucose (25 mM) or galactose (10 mM) medium glucose/galactose IC50 ratio 325
GLUCOSE GALACTOSE IC50 RATIO 17.7(58.1nM/3.3nM) 24hr HepG2 ATP levels in high-glucose (25 mM) or galactose (10 mM) medium glucose/galactose IC50 ratio 325
GLUCOSE GALACTOSE IC50 RATIO 12000 LUHMES (Lund human mesencephalic) cells Glc–Gal–NeuriTox assay EC25(NA) [Glc/Gal] 326
MITOCHONDRIAL MOTILITY 100 μM decrease 217

Target Dose Time Species Model Method Action Positive criterion Reference
Quinol--cytochrome-c reductase inhibitor 26
Quinol--cytochrome-c reductase inhibitor 35
Quinol--cytochrome-c reductase 12000 LUHMES (Lund human mesencephalic) cells Glc–Gal–NeuriTox assay EC25(NA) [Glc/Gal] 326
Cytochrome b 185
Qi site (Qn site or quinone reduction site) bovine isolated heart mitochondria cytochrome bc1 complex inhibitor 166

Pictogram Signal Statements Precautionary Statement Codes
Danger

Aggregated GHS information provided by 192 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.


H300 (100%): Fatal if swallowed [Danger Acute toxicity, oral]


H400 (100%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]


H410 (80.21%): Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard]


Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.


P264, P270, P273, P301+P310, P321, P330, P391, P405, and P501; (The corresponding statement to each P-code can be found at the GHS Classification page.)

Organism Test type Route Dose (normalized dose) Effect Source
mouse LD50 intraperitoneal 7600ug/kg (7.6mg/kg) "Index of Antibiotics from Actinomycetes," Umezawa, H. et al., eds., Tokyo, Univ. of Tokyo Press, 1967Vol. -, Pg. 144, 1967.
bird - wild LD50 oral 5mg/kg (5mg/kg) Antimicrobial Agents and Chemotherapy Vol. -, Pg. 757, 1966.
rat LD50 oral 1469mg/kg (1469mg/kg) Journal of Drug Research. Vol. 7(2), Pg. 1, 1975.
duck LD50 oral 2900ug/kg (2.9mg/kg) Antimicrobial Agents and Chemotherapy Vol. -, Pg. 757, 1966.
rat LD50 intraperitoneal 810ug/kg (0.81mg/kg) lungs, thorax, or respiration: other changes Cancer Research. Vol. 13, Pg. 49, 1953.
mouse LD50 intramuscular 1gm/kg (1000mg/kg) Journal of Drug Research. Vol. 7(2), Pg. 1, 1975.
quail LD50 oral 39mg/kg (39mg/kg) Antimicrobial Agents and Chemotherapy Vol. -, Pg. 757, 1966.
domestic animals - goat/sheep LD50 oral > 1mg/kg (1mg/kg) Antimicrobial Agents and Chemotherapy Vol. -, Pg. 757, 1966.
mouse LD50 intravenous 900ug/kg (0.9mg/kg) "Index of Antibiotics from Actinomycetes," Umezawa, H. et al., eds., Tokyo, Univ. of Tokyo Press, 1967Vol. -, Pg. 144, 1967.
mouse LD50 intraperitoneal 820ug/kg (0.82mg/kg) Journal of Antibiotics, Series A. Vol. 11, Pg. A26, 1958.
mouse LD50 subcutaneous 1600ug/kg (1.6mg/kg) "Antibiotics: Origin, Nature, and Properties," Korzyoski, T., et al., eds., Washington, DC, American Soc. for Microbiology, 1978Vol. 2, Pg. 1078, 1978.
rat LD50 oral 28mg/kg (28mg/kg) Antimicrobial Agents and Chemotherapy Vol. -, Pg. 757, 1966.
mouse LD50 intravenous 893ug/kg (0.893mg/kg) Journal of Antibiotics, Series A. Vol. 9, Pg. 63, 1956.
pigeon LD50 oral 2mg/kg (2mg/kg) Antimicrobial Agents and Chemotherapy Vol. -, Pg. 757, 1966.
rabbit LD50 oral 10mg/kg (10mg/kg) Antimicrobial Agents and Chemotherapy Vol. -, Pg. 757, 1966.
chicken LD50 oral > 160mg/kg (160mg/kg) Antimicrobial Agents and Chemotherapy Vol. -, Pg. 757, 1966.
dog LD50 oral > 5mg/kg (5mg/kg) Antimicrobial Agents and Chemotherapy Vol. -, Pg. 757, 1966.
guinea pig LD50 oral 1800ug/kg (1.8mg/kg) Antimicrobial Agents and Chemotherapy Vol. -, Pg. 757, 1966.
rat LD50 subcutaneous 25mg/kg (25mg/kg) "Antibiotics: Origin, Nature, and Properties," Korzyoski, T., et al., eds., Washington, DC, American Soc. for Microbiology, 1978Vol. 2, Pg. 1078, 1978.
mouse LD50 oral 55mg/kg (55mg/kg) Antimicrobial Agents and Chemotherapy Vol. -, Pg. 757, 1966.
mouse LD50 subcutaneous 25mg/kg (25mg/kg) "Index of Antibiotics from Actinomycetes," Umezawa, H. et al., eds., Tokyo, Univ. of Tokyo Press, 1967Vol. -, Pg. 144, 1967.


  • (2R,3S,6S,7R,8R)-3-[(3-formamido-2-hydroxybenzoyl)amino]-8-hexyl-2,6-dimethyl-4,9-dioxo-1,5-dioxonan-7-yl 3-methylbutanoate (3S,6S,2R,7R,8R)-3-[(3-carbonylamino-2-hydroxyphenyl)carbonylamino]-8-hexyl-2, 6-dimethyl-4,9-dioxo-1,5-dioxonan-7-yl 3-methylbutanoate 116095-18-2
    1397-94-0 3-Methylbutanoic acid 3-[[3-(formylamino)-2-hydroxybenzoyl]amino]-8-hexyl-2,6-dimethyl-4,9-dioxo-1,5-dioxonan-7-yl ester 642-15-9
    75G3NMU1TS 8S75R39Y6J AIDS032154
    AKOS015889205 AWB Antimycin A
    Antimycin A1b Antimycin-A Antipiricullin
    BCP9000305 BDBM50191588 Butanoic acid, 2(or3)-methyl-,(2R,3S,6S,7R,8R)-3-[[3-(formylamino)-2-hydroxybenzoyl]amino]-8-hexyl-2,6-dimethyl-4,9-dioxo-1,5-dioxonan-7-ylester (9CI)
    Butanoic acid, 3-methyl-, 3-((3-(formylamino)-2-hydroxybenzoyl)amino)-8-hexyl-2,6-dimethyl-4,9-dioxo-1,5-dioxonan-7-yl ester, (2R-(2R*,3S*,6S*,7R*,8R*))- CCG-208457 CCRIS 924
    CHEBI:22584 CHEBI:2762 CHEMBL211501
    Caswell No. 052B DTXSID3058668 EPA Pesticide Chemical Code 006314
    Fintrol HSDB 6417 LS-21350
    NCGC00017338-02 NCGC00017338-03 NCGC00017338-04
    NCGC00017338-05 NCGC00142516-01 NCGC00142516-02
    NCGC00142516-03 SCHEMBL218354 SR-05000002233
    SR-05000002233-2 SR-05000002233-3 ST057184
    UNII-75G3NMU1TS UNII-8771CCP8LT component UIFFUZWRFRDZJC-SBOOETFBSA-N UNII-8S75R39Y6J
    UNII-8S75R39Y6J component UIFFUZWRFRDZJC-SBOOETFBSA-N VA10306 Virosin
    ZINC5224254 [(2R,3S,6S,7R,8R)-3-[(3-formamido-2-hydroxy-benzoyl)amino]-8-hexyl-2,6-dimethyl-4,9-dioxo-1,5-dioxonan-7-yl] 3-methylbutanoate [(2r,3s,6s,7r,8r)-3-[(3-Formamido-2-Oxidanyl-Phenyl)carbonylamino]-8-Hexyl-2,6-Dimethyl-4,9-Bis(Oxidanylidene)-1,5-Dioxonan-7-Yl] 3-Methylbutanoate
    antimycin A1 isovaleric acid 8-ester with 3-formamido-N-(7-hexyl-8-hydroxy-4,9-dimethyl-2,6-dioxo-1,5-dioxonan-3-yl)salicylamide

    CAS Number 116095-18-2, 1397-94-0, 27220-56-0, 642-15-9
    PubChem Compound 14957
    KEGG Compound ID C11339
    ChEBI 22584
    ChemSpider 14246
    Wikipedia Antimycin A

    1. Zarazuela Zolkipli-Cunningham & Marni J.Falk. (2017)
    2. Wallace, 2008
    3. Chan et al. (2005)
    4. Meyer et al. (2013)