Oleandomycin

Oleandomycin
Systematic (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
Clinical data
AHFS/Drugs.com	International Drug Names
Identifiers
CAS Number	3922-90-5^Y
ATC code	J01FA05
PubChem	CID 5284598
ChemSpider	4447646^Y
UNII	P8ZQ646136^Y
ChEMBL	CHEMBL606258^N
Chemical data
Formula	C₃₅H₆₁NO₁₂
Molar mass	687.858 g/mol
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
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^Y Key:RZPAKFUAFGMUPI-KGIGTXTPSA-N^Y
^NY (what is this?) (verify)

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.

Antibacterials: protein synthesis inhibitors (J01A, J01B, J01F, J01G, QJ01XQ)

30S

Aminoglycosides
(initiation inhibitors)

-mycin (Streptomyces)	Streptomycin^# Dihydrostreptomycin Neomycin^# Framycetin Paromomycin Ribostamycin Kanamycin^# Amikacin Arbekacin Bekanamycin Dibekacin Tobramycin Spectinomycin^# Hygromycin B Paromomycin

-micin (Micromonospora)	Gentamicin^# Netilmicin Sisomicin Isepamicin Verdamicin Astromicin

Tetracycline antibiotics
(tRNA binding)

Tetracyclines	Doxycycline^# Chlortetracycline Clomocycline Demeclocycline Lymecycline Meclocycline Metacycline Minocycline Oxytetracycline Penimepicycline Rolitetracycline Tetracycline

Glycylcyclines	Tigecycline

50S

Oxazolidinone
(initiation inhibitors)

Peptidyl transferase

Amphenicols	Chloramphenicol^# Azidamfenicol Thiamphenicol Florfenicol

Pleuromutilins	Retapamulin Tiamulin Valnemulin

MLS (transpeptidation/translocation)

Macrolides	Azithromycin^# Clarithromycin Dirithromycin Erythromycin^# Flurithromycin Josamycin Midecamycin Miocamycin Oleandomycin Rokitamycin Roxithromycin Spiramycin Troleandomycin Tylosin Ketolides Telithromycin Cethromycin Solithromycin^†

Lincosamides	Clindamycin^# Lincomycin Pirlimycin

Streptogramins	Pristinamycin Quinupristin/dalfopristin Virginiamycin

EF-G

Steroid antibacterials	Fusidic acid

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

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