U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C35H61NO12.H3O4P
Molecular Weight 785.8535
Optical Activity UNSPECIFIED
Defined Stereocenters 18 / 18
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of OLEANDOMYCIN PHOSPHATE

SMILES

OP(O)(O)=O.[H][C@@]1(C[C@H](OC)[C@@H](O)[C@H](C)O1)O[C@H]2[C@H](C)[C@@H](O[C@]3([H])O[C@H](C)C[C@@H]([C@H]3O)N(C)C)[C@@H](C)C[C@@]4(CO4)C(=O)[C@H](C)[C@@H](O)[C@@H](C)[C@@H](C)OC(=O)[C@@H]2C

InChI

InChIKey=RLPCJGKQKFMBEI-UOBLTHIJSA-N
InChI=1S/C35H61NO12.H3O4P/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;1-5(2,3)4/h16-31,34,37-39H,12-15H2,1-11H3;(H3,1,2,3,4)/t16-,17+,18-,19+,20+,21+,22+,23-,24-,25-,26-,27-,28-,29+,30-,31-,34-,35+;/m0./s1

HIDE SMILES / InChI

Description
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

Curator's Comment: Through the intact blood-brain barrier does not pass.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: 50S ribosomal subunit formation in Staphylococcus aureus cells
Target ID: Streptococcus pneumoniae growth
339.6 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Unknown

Approved Use

Unknown
Curative
MATROMYCIN

Approved Use

Unknown
Curative
Unknown

Approved Use

Unknown
Curative
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
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

T1/2

ValueDoseCo-administeredAnalytePopulation
63 min
unknown, unknown
OLEANDOMYCIN serum
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer





Drug as perpetrator​

Drug as perpetrator​

Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
PubMed

PubMed

TitleDatePubMed
[First clinical experience with oleandomycin and double spectrum antibiotic sigmamycin].
1957 Apr 6
[Severe enterosepsis treated with sigmamycin].
1957 May
Oleoandomycin.
1958 Jul
Synergy of four macrolide antibiotics with chloroquine against chloroquine-resistant Plasmodium falciparum in vitro.
1986
Patents

Sample Use Guides

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.
Name Type Language
OLEANDOMYCIN PHOSPHATE
JAN   MART.   MI   WHO-DD  
Common Name English
OLEANDOMYCIN PHOSPHATE [MART.]
Common Name English
Oleandomycin phosphate [WHO-DD]
Common Name English
OLEANDOMYCIN PHOSPHATE (1:1)
Common Name English
OLEANDOMYCIN PHOSPHATE [JAN]
Common Name English
MATROMYCIN
Brand Name English
OLEANDOMYCIN PHOSPHATE [MI]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C261
Created by admin on Fri Dec 15 15:48:56 GMT 2023 , Edited by admin on Fri Dec 15 15:48:56 GMT 2023
Code System Code Type Description
ECHA (EC/EINECS)
230-351-7
Created by admin on Fri Dec 15 15:48:56 GMT 2023 , Edited by admin on Fri Dec 15 15:48:56 GMT 2023
PRIMARY
EPA CompTox
DTXSID9045398
Created by admin on Fri Dec 15 15:48:56 GMT 2023 , Edited by admin on Fri Dec 15 15:48:56 GMT 2023
PRIMARY
CAS
7060-74-4
Created by admin on Fri Dec 15 15:48:56 GMT 2023 , Edited by admin on Fri Dec 15 15:48:56 GMT 2023
PRIMARY
ChEMBL
CHEMBL606258
Created by admin on Fri Dec 15 15:48:56 GMT 2023 , Edited by admin on Fri Dec 15 15:48:56 GMT 2023
PRIMARY
PUBCHEM
72492
Created by admin on Fri Dec 15 15:48:56 GMT 2023 , Edited by admin on Fri Dec 15 15:48:56 GMT 2023
PRIMARY
DRUG BANK
DBSALT002277
Created by admin on Fri Dec 15 15:48:56 GMT 2023 , Edited by admin on Fri Dec 15 15:48:56 GMT 2023
PRIMARY
CHEBI
16869
Created by admin on Fri Dec 15 15:48:56 GMT 2023 , Edited by admin on Fri Dec 15 15:48:56 GMT 2023
PRIMARY
EVMPD
SUB03497MIG
Created by admin on Fri Dec 15 15:48:56 GMT 2023 , Edited by admin on Fri Dec 15 15:48:56 GMT 2023
PRIMARY
SMS_ID
100000085917
Created by admin on Fri Dec 15 15:48:56 GMT 2023 , Edited by admin on Fri Dec 15 15:48:56 GMT 2023
PRIMARY
MERCK INDEX
m8188
Created by admin on Fri Dec 15 15:48:56 GMT 2023 , Edited by admin on Fri Dec 15 15:48:56 GMT 2023
PRIMARY Merck Index
NCI_THESAURUS
C61865
Created by admin on Fri Dec 15 15:48:56 GMT 2023 , Edited by admin on Fri Dec 15 15:48:56 GMT 2023
PRIMARY
FDA UNII
8681H0C27P
Created by admin on Fri Dec 15 15:48:56 GMT 2023 , Edited by admin on Fri Dec 15 15:48:56 GMT 2023
PRIMARY