Structure via PubChem · Public domain (PubChem)
oleandomycin
Sign in to saveOleandomycin 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
Chemical data
- Formula
- C35H61NO12
- Molecular weight
- 687.9 g/mol
- IUPAC name
- (3R,5S,6S,7R,8S,9R,12R,13R,14S,15R)-6-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-14-hydroxy-8-[(2R,4S,5S,6S)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy-5,7,9,12,13,15-hexamethyl-1,11-dioxaspiro[2.13]hexadecane-10,16-dione
- 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
- InChIKey
- RZPAKFUAFGMUPI-QESOVKLGSA-N
- XLogP
- 2.6
- Polar surface area
- 166 Ų
- H-bond donors
- 3
- H-bond acceptors
- 13
- Formal charge
- 0
via PubChem
Research
1,803 papers- OLEANDOMYCIN phosphate.Journal of the American Medical Association · 1958
- [Oleandomycin].Vie medicale (Paris, France : 1920) · 1958
- [SENSITIVITY TO OLEANDOMYCIN].Alergia · 1964
- Oleandomycin and triacetyloleandomycin.Pediatric clinics of North America · 1961
- [Tetracyn-oleandomycin in urology].La Semaine des hopitaux: therapeutique · 1960
via PubMed
Wikidata facts
- Subclass of
- macrolides
- Mass
- 687.419376
Show 6 more facts
- chemical formula
- C₃₅H₆₁NO₁₂
- route of administration
- oral administration
- 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
- subject has role
- antibiotic
- 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
via Wikidata · CC0
~5 min read
Encyclopedic overview
12 sectionsContents
- 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.
Excerpted from Wikipedia’s “oleandomycin” article, available under the CC BY-SA 4.0 licence.