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Details

Stereochemistry ABSOLUTE
Molecular Formula C26H44O9
Molecular Weight 500.6232
Optical Activity UNSPECIFIED
Defined Stereocenters 8 / 8
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of MUPIROCIN

SMILES

C/C(=C(/[H])\C(=O)OCCCCCCCCC(=O)O)/C[C@@]1([H])[C@@]([H])([C@@]([H])([C@@]([H])(C[C@@]2([H])[C@]([H])([C@@]([H])(C)[C@]([H])(C)O)O2)CO1)O)O

InChI

InChIKey=MINDHVHHQZYEEK-HBBNESRFSA-N
InChI=1S/C26H44O9/c1-16(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/h13,17-21,24-27,31-32H,4-12,14-15H2,1-3H3,(H,28,29)/b16-13+/t17-,18-,19-,20-,21-,24+,25-,26-/m0/s1

HIDE SMILES / InChI

Molecular Formula C26H44O9
Molecular Weight 500.6232
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

5.6790719E11
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
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 Jun 25 21:05:01 UTC 2021
Edited
by admin
on Fri Jun 25 21:05:01 UTC 2021
Record UNII
D0GX863OA5
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
MUPIROCIN
EP   GREEN BOOK   INN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
INN   USAN  
Official Name English
MUPIROCIN [USP MONOGRAPH]
Common Name English
CENTANY
Brand Name English
NSC-759182
Code English
MUPIROCIN [MART.]
Common Name English
MUPIROCIN [GREEN BOOK]
Common Name English
MUPIROCIN [USAN]
Common Name English
MUPIROCIN [EP MONOGRAPH]
Common Name English
MUPIROCIN [USP-RS]
Common Name English
(2E)-5,9-ANHYDRO-2,3,4,8-TETRADEOXY-8-(((2S,3S)-3-((1S,2S)-2-HYDROXY-1-METHYLPROPYL)OXIRANYL)METHYL)-3-METHYL-L-TALO-NON-2-ENONIC ACID, 8-CARBOXYOCTYL ESTER
Common Name English
MUPIROCIN [ORANGE BOOK]
Common Name English
(E)-(2S,3R,4R,5S)-5-((2S,3S,4S,5S)-2,3-EPOXY-5-HYDROXY-4-METHYLHEXYL)TETRAHYDRO-3,4-DIHYDROXY-.BETA.-METHYL-2H-PYRAN-2-CROTONIC ACID, ESTER WITH 9-HYDROXYNONANOIC ACID
Common Name English
TURIXIN
Brand Name English
BRL-4910A
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)-, (2S-(2.ALPHA.(E),3.BETA.,4.BETA.,5.ALPHA.(2R*,3R*(1R*,2R*))))-
Common Name English
BACTODERM
Brand Name English
TRANS-PSEUDOMONIC ACID
Common Name English
MUPIROCIN [WHO-DD]
Common Name English
BRL 4910A
Code English
MUPIROCIN [MI]
Common Name English
MUPIROCIN [INN]
Common Name English
PSEUDOMONIC ACID
Common Name English
MUPIROCIN [USP]
Common Name English
MUPIROCIN [VANDF]
Common Name English
Classification Tree Code System Code
WHO-ESSENTIAL MEDICINES LIST 13.2
Created by admin on Fri Jun 25 21:05:01 UTC 2021 , Edited by admin on Fri Jun 25 21:05:01 UTC 2021
WHO-ATC D06AX09
Created by admin on Fri Jun 25 21:05:01 UTC 2021 , Edited by admin on Fri Jun 25 21:05:01 UTC 2021
WHO-ATC R01AX06
Created by admin on Fri Jun 25 21:05:01 UTC 2021 , Edited by admin on Fri Jun 25 21:05:01 UTC 2021
CFR 21 CFR 524.1465
Created by admin on Fri Jun 25 21:05:01 UTC 2021 , Edited by admin on Fri Jun 25 21:05:01 UTC 2021
NDF-RT N0000175516
Created by admin on Fri Jun 25 21:05:01 UTC 2021 , Edited by admin on Fri Jun 25 21:05:01 UTC 2021
NDF-RT N0000175515
Created by admin on Fri Jun 25 21:05:01 UTC 2021 , Edited by admin on Fri Jun 25 21:05:01 UTC 2021
NCI_THESAURUS C28394
Created by admin on Fri Jun 25 21:05:01 UTC 2021 , Edited by admin on Fri Jun 25 21:05:01 UTC 2021
WHO-VATC QD06AX09
Created by admin on Fri Jun 25 21:05:01 UTC 2021 , Edited by admin on Fri Jun 25 21:05:01 UTC 2021
WHO-VATC QR01AX06
Created by admin on Fri Jun 25 21:05:01 UTC 2021 , Edited by admin on Fri Jun 25 21:05:01 UTC 2021
Code System Code Type Description
PUBCHEM
446596
Created by admin on Fri Jun 25 21:05:01 UTC 2021 , Edited by admin on Fri Jun 25 21:05:01 UTC 2021
PRIMARY
MESH
D016712
Created by admin on Fri Jun 25 21:05:01 UTC 2021 , Edited by admin on Fri Jun 25 21:05:01 UTC 2021
PRIMARY
DRUG BANK
DB00410
Created by admin on Fri Jun 25 21:05:01 UTC 2021 , Edited by admin on Fri Jun 25 21:05:01 UTC 2021
PRIMARY
LACTMED
Mupirocin
Created by admin on Fri Jun 25 21:05:01 UTC 2021 , Edited by admin on Fri Jun 25 21:05:01 UTC 2021
PRIMARY
CAS
12650-69-0
Created by admin on Fri Jun 25 21:05:01 UTC 2021 , Edited by admin on Fri Jun 25 21:05:01 UTC 2021
PRIMARY
NCI_THESAURUS
C29271
Created by admin on Fri Jun 25 21:05:01 UTC 2021 , Edited by admin on Fri Jun 25 21:05:01 UTC 2021
PRIMARY
INN
5276
Created by admin on Fri Jun 25 21:05:01 UTC 2021 , Edited by admin on Fri Jun 25 21:05:01 UTC 2021
PRIMARY
RXCUI
42372
Created by admin on Fri Jun 25 21:05:01 UTC 2021 , Edited by admin on Fri Jun 25 21:05:01 UTC 2021
PRIMARY RxNorm
MERCK INDEX
M7658
Created by admin on Fri Jun 25 21:05:01 UTC 2021 , Edited by admin on Fri Jun 25 21:05:01 UTC 2021
PRIMARY Merck Index
USP_CATALOG
1448901
Created by admin on Fri Jun 25 21:05:01 UTC 2021 , Edited by admin on Fri Jun 25 21:05:01 UTC 2021
PRIMARY USP-RS
ChEMBL
CHEMBL719
Created by admin on Fri Jun 25 21:05:01 UTC 2021 , Edited by admin on Fri Jun 25 21:05:01 UTC 2021
PRIMARY
WIKIPEDIA
MUPIROCIN
Created by admin on Fri Jun 25 21:05:01 UTC 2021 , Edited by admin on Fri Jun 25 21:05:01 UTC 2021
PRIMARY
FDA UNII
D0GX863OA5
Created by admin on Fri Jun 25 21:05:01 UTC 2021 , Edited by admin on Fri Jun 25 21:05:01 UTC 2021
PRIMARY
DRUG CENTRAL
1857
Created by admin on Fri Jun 25 21:05:01 UTC 2021 , Edited by admin on Fri Jun 25 21:05:01 UTC 2021
PRIMARY
EPA CompTox
12650-69-0
Created by admin on Fri Jun 25 21:05:01 UTC 2021 , Edited by admin on Fri Jun 25 21:05:01 UTC 2021
PRIMARY
EVMPD
SUB09093MIG
Created by admin on Fri Jun 25 21:05:01 UTC 2021 , Edited by admin on Fri Jun 25 21:05:01 UTC 2021
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
SUBSTANCE->BASIS OF STRENGTH
SALT/SOLVATE -> PARENT
BINDER->LIGAND
BINDING
Related Record Type Details
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC