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++].[H][C@@]2(C[C@H]1CO[C@@H](C\C(C)=C\C(=O)OCCCCCCCCC([O-])=O)[C@H](O)[C@@H]1O)O[C@@]2([H])[C@@H](C)[C@H](C)O.[H][C@@]4(C[C@H]3CO[C@@H](C\C(C)=C\C(=O)OCCCCCCCCC([O-])=O)[C@H](O)[C@@H]3O)O[C@@]4([H])[C@@H](C)[C@H](C)O
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
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 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
634.22 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/31536765 |
40 mg/kg single, intravenous dose: 40 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered: |
MUPIROCIN plasma | Oryctolagus cuniculus population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
273 μg/mL |
40 mg/kg single, intravenous dose: 40 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered: |
MUPIROCIN plasma | Mus musculus population: UNHEALTHY age: ADULT sex: FEMALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
183.59 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/31536765 |
40 mg/kg single, intravenous dose: 40 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered: |
MUPIROCIN plasma | Oryctolagus cuniculus population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
1100 μg × min/mL |
40 mg/kg single, intravenous dose: 40 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered: |
MUPIROCIN plasma | Mus musculus population: UNHEALTHY age: ADULT sex: FEMALE food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
0.1 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/31536765 |
40 mg/kg single, intravenous dose: 40 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered: |
MUPIROCIN plasma | Oryctolagus cuniculus population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
5.28 min |
40 mg/kg single, intravenous dose: 40 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered: |
MUPIROCIN plasma | Mus musculus population: UNHEALTHY age: ADULT sex: FEMALE food status: UNKNOWN |
|
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 n = 339 Health Status: unhealthy Condition: various skin lesions Age Group: adult Sex: unknown Population Size: 339 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 n = 82 Health Status: unhealthy Condition: secondarily infected eczema Age Group: adult Sex: unknown Population Size: 82 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 n = 8 Health Status: unhealthy Condition: tympanostomy tube otorrhea caused by methicillin-resistant Staphylococcus aureus Age Group: children Sex: unknown Population Size: 8 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 n = 339 Health Status: unhealthy Condition: various skin lesions Age Group: adult Sex: unknown Population Size: 339 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 n = 339 Health Status: unhealthy Condition: various skin lesions Age Group: adult Sex: unknown Population Size: 339 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 n = 339 Health Status: unhealthy Condition: various skin lesions Age Group: adult Sex: unknown Population Size: 339 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 n = 339 Health Status: unhealthy Condition: various skin lesions Age Group: adult Sex: unknown Population Size: 339 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 n = 339 Health Status: unhealthy Condition: various skin lesions Age Group: adult Sex: unknown Population Size: 339 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 n = 339 Health Status: unhealthy Condition: various skin lesions Age Group: adult Sex: unknown Population Size: 339 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 n = 339 Health Status: unhealthy Condition: various skin lesions Age Group: adult Sex: unknown Population Size: 339 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 n = 339 Health Status: unhealthy Condition: various skin lesions Age Group: adult Sex: unknown Population Size: 339 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 n = 339 Health Status: unhealthy Condition: various skin lesions Age Group: adult Sex: unknown Population Size: 339 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 n = 82 Health Status: unhealthy Condition: secondarily infected eczema Age Group: adult Sex: unknown Population Size: 82 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 n = 82 Health Status: unhealthy Condition: secondarily infected eczema Age Group: adult Sex: unknown Population Size: 82 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 n = 82 Health Status: unhealthy Condition: secondarily infected eczema Age Group: adult Sex: unknown Population Size: 82 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 n = 82 Health Status: unhealthy Condition: secondarily infected eczema Age Group: adult Sex: unknown Population Size: 82 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 n = 82 Health Status: unhealthy Condition: secondarily infected eczema Age Group: adult Sex: unknown Population Size: 82 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 n = 82 Health Status: unhealthy Condition: secondarily infected eczema Age Group: adult Sex: unknown Population Size: 82 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 n = 82 Health Status: unhealthy Condition: secondarily infected eczema Age Group: adult Sex: unknown Population Size: 82 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 n = 82 Health Status: unhealthy Condition: secondarily infected eczema Age Group: adult Sex: unknown Population Size: 82 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 n = 82 Health Status: unhealthy Condition: secondarily infected eczema Age Group: adult Sex: unknown Population Size: 82 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 n = 82 Health Status: unhealthy Condition: secondarily infected eczema Age Group: adult Sex: unknown Population Size: 82 Sources: |
PubMed
Title | Date | PubMed |
---|---|---|
Mupirocin resistance in staphylococci: development and transfer of isoleucyl-tRNA synthetase-mediated resistance in vitro. | 1999 Apr |
|
Mutations affecting the Rossman fold of isoleucyl-tRNA synthetase are correlated with low-level mupirocin resistance in Staphylococcus aureus. | 2002 Feb |
|
The isoleucyl-tRNA synthetase mutation V588F conferring mupirocin resistance in glycopeptide-intermediate Staphylococcus aureus is not associated with a significant fitness burden. | 2004 Jan |
|
Prediction of genotoxicity of chemical compounds by statistical learning methods. | 2005 Jun |
Patents
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).
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C28394
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ACTIVE MOIETY
SUBSTANCE RECORD