Details
Stereochemistry | ABSOLUTE |
Molecular Formula | 2C26H43O9.Ca.2H2O |
Molecular Weight | 1075.337 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 16 / 16 |
E/Z Centers | 2 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
O.O.[Ca++].C[C@H](O)[C@H](C)[C@@H]1O[C@H]1C[C@H]2CO[C@@H](C\C(C)=C\C(=O)OCCCCCCCCC([O-])=O)[C@H](O)[C@@H]2O.C[C@H](O)[C@H](C)[C@@H]3O[C@H]3C[C@H]4CO[C@@H](C\C(C)=C\C(=O)OCCCCCCCCC([O-])=O)[C@H](O)[C@@H]4O
InChI
InChIKey=DDHVILIIHBIMQU-YJGQQKNPSA-L
InChI=1S/2C26H44O9.Ca.2H2O/c2*1-16(13-23(30)33-11-9-7-5-4-6-8-10-22(28)29)12-20-25(32)24(31)19(15-34-20)14-21-26(35-21)17(2)18(3)27;;;/h2*13,17-21,24-27,31-32H,4-12,14-15H2,1-3H3,(H,28,29);;2*1H2/q;;+2;;/p-2/b2*16-13+;;;/t2*17-,18-,19-,20-,21-,24+,25-,26-;;;/m00.../s1
Molecular Formula | C26H44O9 |
Molecular Weight | 500.6222 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 8 / 8 |
E/Z Centers | 1 |
Optical Activity | UNSPECIFIED |
Molecular Formula | Ca |
Molecular Weight | 40.078 |
Charge | 2 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Molecular Formula | HO |
Molecular Weight | 17.0073 |
Charge | -1 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
DescriptionCurator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/mesh/68016712 |
https://www.ncbi.nlm.nih.gov/pubmed/659331
Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/mesh/68016712 |
https://www.ncbi.nlm.nih.gov/pubmed/659331
Mupirocin (BACTROBAN®) is an antibiotic from a strain of Pseudomonas fluorescens. It has shown excellent activity against gram-positive staphylococci and streptococci. The antibiotic is used primarily for the treatment of primary and secondary skin disorders, nasal infections, and wound healing. Mupirocin inhibits bacterial protein synthesis by reversibly and specifically binding to bacterial isoleucyltransfer RNA (tRNA) synthetase. It also severely inhibits RNA synthesis. DNA and cell wall peptidoglycan synthesis are inhibited to a lesser extent and interference with these processes is considered to be a secondary effect. Mupirocin is bactericidal at concentrations achieved by topical administration.
Originator
Sources: https://www.ncbi.nlm.nih.gov/pubmed/3923922
Curator's Comment: Beecham Group plc. is a predecessor of GlaxoSmithKline plc.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL1982 |
7.0 nM [Kd] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Curative | BACTROBAN Approved UseMupirocin Ointment USP, 2% is indicated for the topical treatment of impetigo due to: S. aureus and S. pyogenes. Launch Date1987 |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
30 min |
single, intravenous |
MUPIROCIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
3% |
single, intravenous |
MUPIROCIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
252 mg single, intravenous Overdose Dose: 252 mg Route: intravenous Route: single Dose: 252 mg Sources: |
healthy, adult Health Status: healthy Age Group: adult Sex: unknown Sources: |
|
500 mg single, oral Overdose Dose: 500 mg Route: oral Route: single Dose: 500 mg Sources: |
healthy, adult Health Status: healthy Age Group: adult Sex: unknown Sources: |
|
2 % 3 times / day steady, topical Recommended Dose: 2 %, 3 times / day Route: topical Route: steady Dose: 2 %, 3 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: |
Other AEs: Headache, Rash... Other AEs: Headache (1.7%) Sources: Rash (1.1%) Nausea (1.1%) Abdominal pain (< 1%) Application site burning (< 1%) Cellulitis (< 1%) Dermatitis (< 1%) Dizziness (< 1%) Pruritus (< 1%) |
2 % 3 times / day steady, topical Recommended Dose: 2 %, 3 times / day Route: topical Route: steady Dose: 2 %, 3 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: |
Other AEs: Nausea, Headache... Other AEs: Nausea (4.9%) Sources: Headache (3.6%) Application site burning (3.6%) Pruritus (2.4%) Abdominal pain (1 patient) Bleeding (1 patient) Pain (1 patient) Hives (1 patient) Dry skin (1 patient) Rash (1 patient) |
2 % 1 times / day steady, topical Recommended Dose: 2 %, 1 times / day Route: topical Route: steady Dose: 2 %, 1 times / day Sources: |
unhealthy, children Health Status: unhealthy Age Group: children Sex: unknown Sources: |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Nausea | 1.1% | 2 % 3 times / day steady, topical Recommended Dose: 2 %, 3 times / day Route: topical Route: steady Dose: 2 %, 3 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: |
Rash | 1.1% | 2 % 3 times / day steady, topical Recommended Dose: 2 %, 3 times / day Route: topical Route: steady Dose: 2 %, 3 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: |
Headache | 1.7% | 2 % 3 times / day steady, topical Recommended Dose: 2 %, 3 times / day Route: topical Route: steady Dose: 2 %, 3 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: |
Abdominal pain | < 1% | 2 % 3 times / day steady, topical Recommended Dose: 2 %, 3 times / day Route: topical Route: steady Dose: 2 %, 3 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: |
Application site burning | < 1% | 2 % 3 times / day steady, topical Recommended Dose: 2 %, 3 times / day Route: topical Route: steady Dose: 2 %, 3 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: |
Cellulitis | < 1% | 2 % 3 times / day steady, topical Recommended Dose: 2 %, 3 times / day Route: topical Route: steady Dose: 2 %, 3 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: |
Dermatitis | < 1% | 2 % 3 times / day steady, topical Recommended Dose: 2 %, 3 times / day Route: topical Route: steady Dose: 2 %, 3 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: |
Dizziness | < 1% | 2 % 3 times / day steady, topical Recommended Dose: 2 %, 3 times / day Route: topical Route: steady Dose: 2 %, 3 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: |
Pruritus | < 1% | 2 % 3 times / day steady, topical Recommended Dose: 2 %, 3 times / day Route: topical Route: steady Dose: 2 %, 3 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: |
Abdominal pain | 1 patient | 2 % 3 times / day steady, topical Recommended Dose: 2 %, 3 times / day Route: topical Route: steady Dose: 2 %, 3 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: |
Bleeding | 1 patient | 2 % 3 times / day steady, topical Recommended Dose: 2 %, 3 times / day Route: topical Route: steady Dose: 2 %, 3 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: |
Dry skin | 1 patient | 2 % 3 times / day steady, topical Recommended Dose: 2 %, 3 times / day Route: topical Route: steady Dose: 2 %, 3 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: |
Hives | 1 patient | 2 % 3 times / day steady, topical Recommended Dose: 2 %, 3 times / day Route: topical Route: steady Dose: 2 %, 3 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: |
Pain | 1 patient | 2 % 3 times / day steady, topical Recommended Dose: 2 %, 3 times / day Route: topical Route: steady Dose: 2 %, 3 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: |
Rash | 1 patient | 2 % 3 times / day steady, topical Recommended Dose: 2 %, 3 times / day Route: topical Route: steady Dose: 2 %, 3 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: |
Pruritus | 2.4% | 2 % 3 times / day steady, topical Recommended Dose: 2 %, 3 times / day Route: topical Route: steady Dose: 2 %, 3 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: |
Application site burning | 3.6% | 2 % 3 times / day steady, topical Recommended Dose: 2 %, 3 times / day Route: topical Route: steady Dose: 2 %, 3 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: |
Headache | 3.6% | 2 % 3 times / day steady, topical Recommended Dose: 2 %, 3 times / day Route: topical Route: steady Dose: 2 %, 3 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: |
Nausea | 4.9% | 2 % 3 times / day steady, topical Recommended Dose: 2 %, 3 times / day Route: topical Route: steady Dose: 2 %, 3 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: |
Sample Use Guides
Apply a small amount of mupirocin (BACTROBAN®) cream, with a cotton swab or gauze pad, to the affected area 3 times daily for 10 days.
Route of Administration:
Topical
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/3923922
The MIC values for mupirocin were: 0.12 ug/ml (Staphylococcus aureus NCTC 6571), 0.12 ug/ml (Streptococcus pyogenes (A) 5936), 0.12 ug/ml (Streptococcus pneumoniae 1760).
Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 18:11:04 GMT 2025
by
admin
on
Mon Mar 31 18:11:04 GMT 2025
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Record UNII |
RG38I2P540
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Record Status |
Validated (UNII)
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Record Version |
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-
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NCI_THESAURUS |
C28394
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SUB21790
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RG38I2P540
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115074-43-6
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GG-71
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221128
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CHEMBL719
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DBSALT001049
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145818
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34858
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7025
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C61851
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5282317
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SUB14612MIG
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RG38I2P540
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1448912
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ANHYDROUS->SOLVATE | |||
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (HPLC)
USP
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PARENT -> SALT/SOLVATE | |||
|
BASIS OF STRENGTH->SUBSTANCE |
ASSAY (HPLC)
EP
|
Related Record | Type | Details | ||
---|---|---|---|---|
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IMPURITY -> PARENT |
UNSPECIFIED
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
|
||
|
IMPURITY -> PARENT |
UNSPECIFIED
EP
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IMPURITY -> PARENT |
UNSPECIFIED
EP
|
||
|
IMPURITY -> PARENT |
UNSPECIFIED
EP
|
||
|
IMPURITY -> PARENT |
UNSPECIFIED
EP
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
IMPURITY -> PARENT |
UNSPECIFIED
EP
|
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IMPURITY -> PARENT |
UNSPECIFIED
EP
|
||
|
IMPURITY -> PARENT |
UNSPECIFIED
EP
|
Related Record | Type | Details | ||
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ACTIVE MOIETY |