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Details

Stereochemistry ABSOLUTE
Molecular Formula C35H61NO12
Molecular Weight 687.8583
Optical Activity UNSPECIFIED
Defined Stereocenters 18 / 18
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of OLEANDOMYCIN

SMILES

[H][C@]2(O[C@@H]1O[C@H](C)C[C@@H]([C@H]1O)N(C)C)[C@@H](C)C[C@@]3(CO3)C(=O)[C@H](C)[C@@H](O)[C@@H](C)[C@@H](C)OC(=O)[C@H](C)[C@@]([H])(O[C@H]4C[C@H](OC)[C@@H](O)[C@H](C)O4)[C@@H]2C

InChI

InChIKey=RZPAKFUAFGMUPI-QESOVKLGSA-N
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

HIDE SMILES / InChI

Description

Oleandomycin is a macrolide antibiotic, which was first described under the designation P.A.105 by Sobin, English, and Celmer (1954-5). Later it appeared on the market under three names and in two forms: as pure oleandomycin ("matromycin," Pfizer; "romicil," Hoffmann-La Roche) and as a mixture with twice its weight of tetracycline ("sigmamycin," Pfizer). Oleandomycin can be employed to inhibit the activities of bacteria responsible for causing infections in the upper respiratory tract much like Erythromycin can. Both can affect staphylococcus and enterococcus genera. Oleoandomycin is reported to inhibit most gram-positive bacteria, but has only a slight inhibiting effect on gram-negative bacteria, rickettsiae, and larger viruses. The spectrum of activity on micro-organisms is therefore wider than that of penicillin and streptomycin, but narrower than that of chloramphenicol and the tetracyclines. Oleandomycin is approved as a veterinary antibiotic in some countries. It has been approved as a swine and poultry antibiotic in the United States. However, it is currently only approved in the United States for production uses. Oleandomycin is a bacteriostatic agent. Like erythromycin, oleandomycin binds to the 50s subunit of bacterial ribosomes, inhibiting the completion of proteins vital to survival and replication. It interferes with translational activity but also with 50s subunit formation. However, unlike erythromycin and its effective synthetic derivatives, it lacks a 12-hydroxyl group and a 3-methoxy group. This change in structure may adversely affect its interactions with 50S structures and explain why it is a less powerful antibiotic.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
339.6 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Unknown
Curative
MATROMYCIN
Curative
Unknown
Curative
Unknown

Cmax

ValueDoseCo-administeredAnalytePopulation
0.8 mg/L
500 mg single, oral
OLEANDOMYCIN serum
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
63 min
unknown, unknown
OLEANDOMYCIN serum
Homo sapiens

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer





Drug as perpetrator​

Tox targets

PubMed

Sample Use Guides

In Vivo Use Guide
Sigmamycin in dosage of 500 or 250 mg. 6-hrly, for 5 days appears to be a very effective method of treating non-specific urethritis
Route of Administration: Oral
In Vitro Use Guide
Of 58 strains of Staph. pyogenes initially tested for sensitivity to oleandomycin, 54 were inhibited by a concentration of 0.5 ug/ml.