Antimycin A

Names

[ CAS No. ]:
642-15-9

[ Name ]:
Antimycin A

[Synonym ]:
dihydrosamidin
Antimycin A1
(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
Isovaleric Acid 8-Ester with 3-Formamide-N-(7-hexyl-8-hydroxy-4,9-dimethyl-2,6-dioxo-1,5-dioxonan-3-yl)salicylamide
Antimycin A

Biological Activity

[Description]:

Antimycin A1 is a specific electron transfer inhibitor of ubiquinol-cytochrome c oxidoreductase. Antimycin A1 inhibits angiogenesis through decrease in VEGF production caused by inhibition of HIF-1α activation[1][2].

[Related Catalog]:

Research Areas >> Cancer

[In Vitro]

Antimycin A, a mixture of Antimycins A1, A2, A3, and A4, is an antibiotic produced by Streptomyces species and displays antifungal, insecticidal, nematocidal, and piscicidal properties[3]. Antimycin A inhibits Bcl-2 and Bcl-xL proteins, inducing apoptosis[4].

[References]

[1]. Hoeon Kim, et al. Structure of Antimycin A1, a Specific Electron Transfer Inhibitor of Ubiquinol-Cytochrome c Oxidoreductase. J. Am. Chem. Soc. 1999, 121, 20, 4902-4903.

[2]. Maeda M, et al. Inhibition of angiogenesis and HIF-1alpha activity by antimycin A1. Biol Pharm Bull. 2006;29(7):1344-1348.

[3]. Liu J, et al, Biosynthesis of antimycins with a reconstituted 3-formamidosalicylate pharmacophore in Escherichia coli. ACS Synth Biol. 2015;4(5):559-565.

[4]. Tzung SP, et al. Antimycin A mimics a cell-death-inducing Bcl-2 homology domain 3. Nat Cell Biol. 2001;3(2):183-191.

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
757.9±60.0 °C at 760 mmHg

[ Melting Point ]:
139-140ºC

[ Molecular Formula ]:
C₂₈H₄₀N₂O₉

[ Molecular Weight ]:
548.625

[ Flash Point ]:
412.1±32.9 °C

[ Exact Mass ]:
548.273376

[ PSA ]:
157.33000

[ LogP ]:
4.68

[ Vapour Pressure ]:
0.0±2.6 mmHg at 25°C

[ Index of Refraction ]:
1.545

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: NY1503500

CHEMICAL NAME :: Isovaleric acid, 8-ester with 3-formamido-N-(7-hexyl-8-hydroxy-4,9-dimethyl-2,6-dio xo-1,5- dioxonan-3-yl)salicylamide

CAS REGISTRY NUMBER :: 642-15-9

LAST UPDATED :: 199309

DATA ITEMS CITED :: 5

MOLECULAR FORMULA :: C28-H40-N2-O9

MOLECULAR WEIGHT :: 548.70

WISWESSER LINE NOTATION :: T B666 COV KO&&TJ L1 L1 MOV1Y1&1 NOV1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 1469 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JDGRAX Journal of Drug Research. (National Organization for Drug Research and Control, POB 29, Cairo, Egypt) V.2- 1969- Volume(issue)/page/year: 7(2),1,1975

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 7600 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: 85FZAT "Index of Antibiotics from Actinomycetes," Umezawa, H. et al., eds., Tokyo, Univ. of Tokyo Press, 1967 Volume(issue)/page/year: -,144,1967

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 25 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: 85FZAT "Index of Antibiotics from Actinomycetes," Umezawa, H. et al., eds., Tokyo, Univ. of Tokyo Press, 1967 Volume(issue)/page/year: -,144,1967

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 900 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: 85FZAT "Index of Antibiotics from Actinomycetes," Umezawa, H. et al., eds., Tokyo, Univ. of Tokyo Press, 1967 Volume(issue)/page/year: -,144,1967

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intramuscular

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JDGRAX Journal of Drug Research. (National Organization for Drug Research and Control, POB 29, Cairo, Egypt) V.2- 1969- Volume(issue)/page/year: 7(2),1,1975

Safety Information

[ Hazard Codes ]:
Xi

[ Risk Phrases ]:
23/24/25

[ RIDADR ]:
UN 3172

[ Packaging Group ]:
II

[ Hazard Class ]:
6.1(a)