CAS 3922-90-5

Oleandomycin

Description:

Oleandomycin is a macrolide antibiotic that is structurally related to erythromycin. It is produced by the fermentation of certain strains of Streptomyces, specifically Streptomyces antibioticus. Oleandomycin exhibits antibacterial activity primarily against Gram-positive bacteria and some Gram-negative organisms, making it effective in treating various bacterial infections. The compound functions by inhibiting bacterial protein synthesis, binding to the 50S ribosomal subunit, which prevents the elongation of the polypeptide chain during translation. Oleandomycin is typically administered orally and is known for its relatively low toxicity. However, it can cause side effects such as gastrointestinal disturbances and allergic reactions in some individuals. Its use has declined with the advent of newer antibiotics, but it remains of interest in certain clinical scenarios. The chemical structure of oleandomycin includes a large lactone ring, which is characteristic of macrolide antibiotics, contributing to its mechanism of action and pharmacological properties.

Formula:C₃₅H₆₁NO₁₂

InChI:InChI=1S/C35H61NO12/c1-16-14-35(15-43-35)32(40)19(4)27(37)18(3)22(7)46-33(41)21(6)31(47-26-13-25(42-11)28(38)23(8)45-26)20(5)30(16)48-34-29(39)24(36(9)10)12-17(2)44-34/h16-31,34,37-39H,12-15H2,1-11H3/t16-,17+,18-,19+,20+,21+,22+,23-,24-,25-,26-,27-,28-,29+,30-,31-,34-,35+/m0/s1

InChI key:InChIKey=RZPAKFUAFGMUPI-QESOVKLGSA-N

SMILES:O=C1[C@]2(CO2)C[C@H](C)[C@H](O[C@H]3[C@H](O)[C@@H](N(C)C)C[C@@H](C)O3)[C@@H](C)[C@H](O[C@H]4C[C@H](OC)[C@@H](O)[C@H](C)O4)[C@@H](C)C(=O)O[C@H](C)[C@H](C)[C@H](O)[C@H]1C

Synonyms:

1,9-Dioxaspiro[2.13]hexadecane, oleandomycin deriv.
1,9-Dioxaspiro[2.13]hexadecane-4,10-dione, 12-[(2,6-dideoxy-3-O-methyl-α-L</smallcap>-arabino-hexopyranosyl)oxy]-6-hydroxy-5,7,8,11,13,15-hexamethyl-14-[[3,4,6-trideoxy-3-(dimethylamino)-β-<smallcap>D-xylo-hexopyranosyl]oxy]-, [3R-(3R*,5R*,6S*,7R*,8R*,11R*,12S*,13R*,14S*,15S*)]-
1,9-Dioxaspiro[2.13]hexadecane-4,10-dione, 12-[(2,6-dideoxy-3-O-methyl-α-L-arabino-hexopyranosyl)oxy]-6-hydroxy-5,7,8,11,13,15-hexamethyl-14-[[3,4,6-trideoxy-3-(dimethylamino)-β-D-xylo-hexopyranosyl]oxy]-, [3R-(3R*,5R*,6S*,7R*,8R*,11R*,12S*,13R*,14S*,15S*)]-
Amimycin
Antibiotic PA 105
Landomycin
Nonanoic acid, 8-(3,5-dihydroxy-2,4-dimethylhexanoyl)-5-(4-dimethylaminotetrahydro-3-hydroxy-6-methylpyran-2-yloxy)-8,9-epoxy-2,4,6-trimethyl-3-(tetrahydro-5-hydroxy-4-methoxy-6-methylpyran-2-yloxy)-, μ-lactone
Oleandomicina
Oleandomycin A
Oleandomycine
Pa 105
Pa 775
Romicil
[3R-(3R*,5R*,6S*,7R*,8R*,11R*,12S*,13R*,14S*,15S*)]-12-[(2,6-Dideoxy-3-O-methyl-α-L</smallcap>-arabino-hexopyranosyl)oxy]-6-hydroxy-5,7,8,11,13,15-hexamethyl-14-[[3,4,6-trideoxy-3-(dimethylamino)-β-<smallcap>D-xylo-hexopyranosyl]oxy]-1,9-dioxaspiro[2.13]hexadecane-4,10-dione
[3R-(3R*,5R*,6S*,7R*,8R*,11R*,12S*,13R*,14S*,15S*)]-12-[(2,6-Dideoxy-3-O-methyl-α-L-arabino-hexopyranosyl)oxy]-6-hydroxy-5,7,8,11,13,15-hexamethyl-14-[[3,4,6-trideoxy-3-(dimethylamino)-β-D-xylo-hexopyranosyl]oxy]-1,9-dioxaspiro[2.13]hexadecane-4,10-dione
(3S,5R,6S,7R,8R,11R,12S,13R,14S,15S)-12-[(2,6-dideoxy-3-O-methylhexopyranosyl)oxy]-6-hydroxy-5,7,8,11,13,15-hexamethyl-4,10-dioxo-1,9-dioxaspiro[2.13]hexadec-14-yl 3,4,6-trideoxy-3-(dimethylamino)hexopyranoside
Oleandomycin
12-((2,6-Didesoxy-3-O-methyl-alpha-K-arabino-hexopyranosyl)oxy)-8-hydroxy-5,7,8,11,13,15-hexamethyl-14-((3,4,6-tridesoxy-3-dimethylamino-beta-D-xylo-hexopyranosyl)oxy)-1,9-dioxaspiro(2.13)hexadecan-4,10-dion
Oleandomycinum [INN-Latin]
(3R,5R,6S,7R,8R,11S,12S,13R,14S,15S)-6-hydroxy-5,7,8,11,13,15-hexamethyl-4,10-dioxo-14-{[3,4,6-trideoxy-3-(dimethylamino)-beta-D-xylo-hexopyranosyl]oxy}-1,9-dioxaspiro[2.13]hexadec-12-yl 2,6-dideoxy-3-O-methyl-alpha-L-arabino-hexopyranoside
AI3-50163
HSDB 7442
(3R,5R,6S,7R,8R,11R,12S,13R,14S,15S)-6-hydroxy-5,7,8,11,13,15-hexamethyl-4,10-dioxo-14-{[3,4,6-trideoxy-3-(dimethylamino)-beta-D-xylo-hexopyranosyl]oxy}-1,9-dioxaspiro[2.13]hexadec-12-yl 2,6-dideoxy-3-O-methyl-alpha-L-arabino-hexopyranoside
Oleandomycin (chloroform solvate)
Oleandomycine [INN-French]
(3S,5R,6S,7R,8R,11R,12S,13R,14S,15S)-6-hydroxy-5,7,8,11,13,15-hexamethyl-4,10-dioxo-14-{[3,4,6-trideoxy-3-(dimethylamino)-D-xylo-hexopyranosyl]oxy}-1,9-dioxaspiro[2.13]hexadec-12-yl 2,6-dideoxy-3-O-methyl-alpha-L-arabino-hexopyranoside phosphate (salt)
(3S,5R,6S,7R,8R,11R,12S,13R,14S,15S)-6-hydroxy-5,7,8,11,13,15-hexamethyl-4,10-dioxo-14-{[3,4,6-trideoxy-3-(dimethylamino)-beta-D-xylo-hexopyranosyl]oxy}-1,9-dioxaspiro[2.13]hexadec-12-yl 2,6-dideoxy-3-O-methyl-alpha-L-arabino-hexopyranoside
Oleandomycine [French]
UNII-P8ZQ646136
Oleandomicina [INN-Spanish]
Matromycin
See more synonyms

Purity (%)

100

Found 8 products.

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Oleandomycin
CAS:
- 3922-90-5
Formula:C₃₅H₆₁NO₁₂
Purity:99.0%
Color and Shape:Solid
Molecular weight:687.8583
Ref: IN-DA00CJ6G
5mg
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Oleandomycin
CAS:
- 3922-90-5
Formula:C₃₅H₆₁NO₁₂
Purity:≥ 95.0%
Color and Shape:White powder
Molecular weight:687.90
Ref: 7W-GA0872
ne
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Oleandomycin 1000 µg/mL in Acetonitrile
Controlled ProductPlease note that this is a controlled product in some countries, and needs to be treated in accordance with the relevant regulations. Be aware this might entail additional expenses and documentation.
CAS:
- 3922-90-5
Formula:C₃₅H₆₁NO₁₂
Color and Shape:Colourless
Molecular weight:687.86
Ref: 04-A15725990AL-1000
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Oleandomycin
CAS:
- 3922-90-5
Formula:C₃₅H₆₁NO₁₂
Molecular weight:687.87
Ref: 4Z-O-101001
5mg
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10mg
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Oleandomycin
CAS:
- 3922-90-5
Applications Antibiotic substance produced by Streptomyces antibioticus no. ATCC 11891. Antibacterial. References Sous, H., et al.: Arzneim.-Forsch., 8, 386 (1958), Hahn, et al.: Antibiotics, 1, 378 (1967), 
Formula:C₃₅H₆₁NO₁₂
Color and Shape:Neat
Molecular weight:687.86
Ref: TR-O517500
1mg
249.00€
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10mg
1,596.00€
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2500µg
521.00€
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Oleandomycin
CAS:
- 3922-90-5
Purity:98%
Molecular weight:687.867981
Ref: 10-F951503
5mg
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Oleandomycin
CAS:
- 3922-90-5
Oleandomycin is a macrolide antibiotic, which is derived from the bacterium *Streptomyces antibioticus*. This antibiotic functions by binding to the 50S subunit of the bacterial ribosome, thereby inhibiting protein synthesis. The interruption of this essential process ultimately leads to the cessation of bacterial growth and replication.
Formula:C₃₅H₆₁NO₁₂
Purity:Min. 95%
Color and Shape:White Powder
Molecular weight:687.86 g/mol
Ref: 3D-AO16827
50mg
2,113.00€
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100mg
3,168.00€
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250mg
5,281.00€
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Oleandomycin
CAS:
- 3922-90-5
Oleandomycin, a macrolide antibiotic structurally similar to Erythromycin, exhibits antimicrobial activity.
Formula:C₃₅H₆₁NO₁₂
Purity:98%
Color and Shape:White Amorphous Powder Solid
Molecular weight:687.86
Ref: TM-T16382
50mg
Discontinued
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