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oleandomycin
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oleandomycin

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Oleandomycin is a macrolide antibiotic. It is synthesized from strains of Streptomyces antibioticus. It is weaker than erythromycin.

Key facts

Drug.Verifiedfields
changed
Drug.verifiedrevid
447815338
Drug.IUPAC_name
(3R,5R,6S,7R,8R,11R,12S,13R,14S,15S)-14-((2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yloxy)-6-hydroxy-12-((2R,4S,5S,6S)-5-hydroxy-4-methoxy-6-methyltetrahydro-2H-pyran-2-yloxy)-5,7,8,11,13,15-hexamethyl-1,9-dioxaspiro[2.13]hexadecane-4,10-dione
Drug.image
Oleandomycin.svg
Drug.image_class
skin-invert-image
Drug.CAS_number
3922-90-5
Drug.ATC_prefix
J01
Drug.ATC_suffix
FA05
Drug.PubChem
5284598
Drug.ChEMBL
606258
Drug.ChemSpiderID
4447646
Drug.UNII
P8ZQ646136
Drug.C
35
Drug.H
61
Drug.N
1
Drug.O
12
Drug.smiles
O=C4[C@H](C)[C@@H](O)[C@@H](C)[C@H](OC(=O)[C@@H]([C@@H](O[C@@H]1O[C@H]([C@H](O)[C@@H](OC)C1)C)[C@H](C)[C@@H](O[C@@H]2O[C@H](C)C[C@H](N(C)C)[C@H]2O)[C@@H](C)C[C@@]43OC3)C)C
Drug.StdInChI
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

via Wikipedia infobox

Research

1,803 papers

via PubMed

Wikidata facts

Mass
687.419376
Show 4 more facts
chemical formula
C₃₅H₆₁NO₁₂
canonical SMILES
CC1CC(C(C(O1)OC2C(CC3(CO3)C(=O)C(C(C(C(OC(=O)C(C(C2C)OC4CC(C(C(O4)C)O)OC)C)C)C)O)C)C)O)N(C)C
defined daily dose
1
isomeric SMILES
C[C@@H]1C[C@@H]([C@H]([C@@H](O1)O[C@H]2[C@H](C[C@@]3(CO3)C(=O)[C@@H]([C@H]([C@H]([C@H](OC(=O)[C@@H]([C@H]([C@@H]2C)O[C@H]4C[C@@H]([C@H]([C@@H](O4)C)O)OC)C)C)C)O)C)C)O)N(C)C
Sources (5)

via Wikidata · CC0

~5 min read

Article

12 sections
Contents
  • Medical uses
  • Pharmacology
  • Mechanism of action
  • Relative strength
  • Chemistry
  • Polyketide biosynthesis
  • Post-PKS modifications
  • History
  • Sigmamycine combination drug
  • Society and culture
  • Brand names
  • References

Oleandomycin is a macrolide antibiotic. It is synthesized from strains of Streptomyces antibioticus. It is weaker than erythromycin.

It used to be sold under the brand name Sigmamycine, combined with tetracycline, and made by the company Rosa-Phytopharma in France.

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