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

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
Structure of MUPIROCIN CALCIUM

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

HIDE SMILES / InChI

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

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

Description
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

Curator's Comment: Beecham Group plc. is a predecessor of GlaxoSmithKline plc.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
7.0 nM [Kd]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
BACTROBAN

Approved Use

Mupirocin Ointment USP, 2% is indicated for the topical treatment of impetigo due to: S. aureus and S. pyogenes.

Launch Date

1987
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
634.22 μg/mL
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

AUC

ValueDoseCo-administeredAnalytePopulation
183.59 μg × h/mL
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

T1/2

ValueDoseCo-administeredAnalytePopulation
0.1 h
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

Funbound

ValueDoseCo-administeredAnalytePopulation
3%
single, intravenous
MUPIROCIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse 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%)
Rash (1.1%)
Nausea (1.1%)
Abdominal pain (< 1%)
Application site burning (< 1%)
Cellulitis (< 1%)
Dermatitis (< 1%)
Dizziness (< 1%)
Pruritus (< 1%)
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 = 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%)
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)
Sources:
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

AEs

AESignificanceDosePopulation
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:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer






Drug as perpetrator​
PubMed

PubMed

TitleDatePubMed
On the mode of action of pseudomonic acid: inhibition of protein synthesis in Staphylococcus aureus.
1978 Apr
Antibacterial activity of mupirocin (pseudomonic acid), a new antibiotic for topical use.
1985 Apr
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
Resistance to and synthesis of the antibiotic mupirocin.
2010 Apr
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
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 Fri Dec 15 15:51:19 GMT 2023
Edited
by admin
on Fri Dec 15 15:51:19 GMT 2023
Record UNII
RG38I2P540
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
MUPIROCIN CALCIUM
EP   MART.   ORANGE BOOK   USAN   USP   USP-RS   VANDF  
USAN  
Official Name English
MUPIROCIN CALCIUM [EP MONOGRAPH]
Common Name English
MUPIROCIN CALCIUM HYDRATE [JAN]
Common Name English
(αE,2S,3R,4R,5S)-5-[(2S,3S,4S,5S)-2,3-Epoxy-5-hydroxy-4-methylhexyl]tetrahydro-3,4-dihydroxy-β-methyl-2H-pyran-2-crotonic acid, ester with 9-hydroxynonanoic acid, calcium salt (2:1), dihydrate
Common Name English
BRL-4910F
Code English
NONANOIC ACID, 9-((3-METHYL-1-OXO-4-(TETRAHYDRO-3,4-DIHYDROXY-5-((3-(2-HYDROXY-1-METHYLPROPYL)OXIRANYL)METHYL)-2H-PYRAN-2-YL)-2-BUTENYL)OXY)-, CALCIUM SALT (2:1), DIHYDRATE, (2S-(2.ALPHA.(E),3.BETA.,4.BETA.,5.ALPHA.(2R*,3R*(1R*,2R*))))-
Common Name English
MUPIROCIN CALCIUM DIHYDRATE
Common Name English
MUPIROCIN CALCIUM [USP MONOGRAPH]
Common Name English
BRL 4910F
Code English
MUPIROCIN CALCIUM [MART.]
Common Name English
MUPIROCIN CALCIUM [USP-RS]
Common Name English
BACTROBAN
Brand Name English
MUPIROCIN CALCIUM [USAN]
Common Name English
MUPIROCIN CALCIUM [ORANGE BOOK]
Common Name English
CALCIUM MUPIROCIN DIHYDRATE
Common Name English
Mupirocin calcium hydrate [WHO-DD]
Common Name English
MUPIROCIN CALCIUM [VANDF]
Common Name English
MUPIROCIN CALCIUM HYDRATE
JAN  
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C28394
Created by admin on Fri Dec 15 15:51:20 GMT 2023 , Edited by admin on Fri Dec 15 15:51:20 GMT 2023
Code System Code Type Description
EVMPD
SUB21790
Created by admin on Fri Dec 15 15:51:20 GMT 2023 , Edited by admin on Fri Dec 15 15:51:20 GMT 2023
PRIMARY
DAILYMED
RG38I2P540
Created by admin on Fri Dec 15 15:51:20 GMT 2023 , Edited by admin on Fri Dec 15 15:51:20 GMT 2023
PRIMARY
CAS
115074-43-6
Created by admin on Fri Dec 15 15:51:19 GMT 2023 , Edited by admin on Fri Dec 15 15:51:19 GMT 2023
PRIMARY
USAN
GG-71
Created by admin on Fri Dec 15 15:51:20 GMT 2023 , Edited by admin on Fri Dec 15 15:51:20 GMT 2023
PRIMARY
RXCUI
221128
Created by admin on Fri Dec 15 15:51:20 GMT 2023 , Edited by admin on Fri Dec 15 15:51:20 GMT 2023
PRIMARY RxNorm
ChEMBL
CHEMBL719
Created by admin on Fri Dec 15 15:51:20 GMT 2023 , Edited by admin on Fri Dec 15 15:51:20 GMT 2023
PRIMARY
DRUG BANK
DBSALT001049
Created by admin on Fri Dec 15 15:51:20 GMT 2023 , Edited by admin on Fri Dec 15 15:51:20 GMT 2023
PRIMARY
CHEBI
145818
Created by admin on Fri Dec 15 15:51:20 GMT 2023 , Edited by admin on Fri Dec 15 15:51:20 GMT 2023
PRIMARY
SMS_ID
100000076263
Created by admin on Fri Dec 15 15:51:20 GMT 2023 , Edited by admin on Fri Dec 15 15:51:20 GMT 2023
PRIMARY
CHEBI
34858
Created by admin on Fri Dec 15 15:51:20 GMT 2023 , Edited by admin on Fri Dec 15 15:51:20 GMT 2023
PRIMARY
CHEBI
7025
Created by admin on Fri Dec 15 15:51:20 GMT 2023 , Edited by admin on Fri Dec 15 15:51:20 GMT 2023
PRIMARY
NCI_THESAURUS
C61851
Created by admin on Fri Dec 15 15:51:20 GMT 2023 , Edited by admin on Fri Dec 15 15:51:20 GMT 2023
PRIMARY
PUBCHEM
5282317
Created by admin on Fri Dec 15 15:51:20 GMT 2023 , Edited by admin on Fri Dec 15 15:51:20 GMT 2023
PRIMARY
EVMPD
SUB14612MIG
Created by admin on Fri Dec 15 15:51:20 GMT 2023 , Edited by admin on Fri Dec 15 15:51:20 GMT 2023
PRIMARY
FDA UNII
RG38I2P540
Created by admin on Fri Dec 15 15:51:20 GMT 2023 , Edited by admin on Fri Dec 15 15:51:20 GMT 2023
PRIMARY
RS_ITEM_NUM
1448912
Created by admin on Fri Dec 15 15:51:20 GMT 2023 , Edited by admin on Fri Dec 15 15:51:20 GMT 2023
PRIMARY
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