Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C35H61NO12.ClH |
Molecular Weight | 724.319 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 18 / 18 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.[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=CWYHZGJSHPPEHY-UOBLTHIJSA-N
InChI=1S/C35H61NO12.ClH/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;1H/t16-,17+,18-,19+,20+,21+,22+,23-,24-,25-,26-,27-,28-,29+,30-,31-,34-,35+;/m0./s1
Molecular Formula | ClH |
Molecular Weight | 36.461 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Molecular Formula | C35H61NO12 |
Molecular Weight | 687.8583 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 18 / 18 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionSources: http://www.ncbi.nlm.nih.gov/pubmed/13436854Curator's Comment: Description was created based on several sources, including http://www.biovet.com/products/A%20P%20I%20s/Oleandomycin%20Phosphate.pdf and http://www.ncbi.nlm.nih.gov/pubmed/13545323
Sources: http://www.ncbi.nlm.nih.gov/pubmed/13436854
Curator's Comment: Description was created based on several sources, including http://www.biovet.com/products/A%20P%20I%20s/Oleandomycin%20Phosphate.pdf and http://www.ncbi.nlm.nih.gov/pubmed/13545323
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
Sources: http://en.medicine-cure.com/ovr4_1202.htm
Curator's Comment: Through the intact blood-brain barrier does not pass.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: 50S ribosomal subunit formation in Staphylococcus aureus cells Sources: http://www.ncbi.nlm.nih.gov/pubmed/9806980 |
|||
Target ID: GO:0016049 Sources: http://www.ncbi.nlm.nih.gov/pubmed/9806980 |
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Target ID: Streptococcus pneumoniae growth Sources: http://www.ncbi.nlm.nih.gov/pubmed/2708138 |
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Target ID: CHEMBL240 Sources: http://www.ncbi.nlm.nih.gov/pubmed/12065733 |
339.6 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Curative | Unknown Approved UseUnknown |
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Curative | MATROMYCIN Approved UseUnknown |
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Curative | Unknown Approved UseUnknown |
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Curative | Unknown Approved UseUnknown |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
0.8 mg/L |
500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered: |
OLEANDOMYCIN serum | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
63 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/4067847 |
unknown, unknown |
OLEANDOMYCIN serum | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Sample Use Guides
In Vivo Use Guide
Sources: http://www.ncbi.nlm.nih.gov/pubmed/13523198
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
Sources: http://www.ncbi.nlm.nih.gov/pubmed/13436854
Of 58 strains of Staph. pyogenes initially tested for sensitivity to oleandomycin, 54 were inhibited by a concentration of 0.5 ug/ml.
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 08:58:04 GMT 2023
by
admin
on
Sat Dec 16 08:58:04 GMT 2023
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Record UNII |
0SEZ96A40Y
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Record Status |
Validated (UNII)
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Record Version |
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