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

Details

Stereochemistry ABSOLUTE
Molecular Formula 2C26H43O9.Ca
Molecular Weight 1039.306
Optical Activity UNSPECIFIED
Defined Stereocenters 16 / 16
E/Z Centers 2
Charge 0

SHOW SMILES / InChI
Structure of MUPIROCIN CALCIUM ANHYDROUS

SMILES

[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=HAXVBVDETFUQGV-LNQHITRNSA-L
InChI=1S/2C26H44O9.Ca/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);/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 C26H43O9
Molecular Weight 499.6142
Charge -1
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

Beecham Group
47
Curator's Comment: Beecham Group plc. is a predecessor of GlaxoSmithKline plc.

Approval Year

1987
121
Targets

Targets

Primary TargetPharmacologyConditionPotency
Binding Agent
1076
 7.0 nM [Kd]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Approved
8583
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
30 min
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/050591s034lbl.pdf
single, intravenous
 MUPIROCIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
3%
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/050591s034lbl.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/050746s013lbl.pdf
healthy, adult
Health Status: healthy
Age Group: adult
Sex: unknown
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/050746s013lbl.pdf
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/050746s013lbl.pdf
500 mg single, oral
Overdose
Dose: 500 mg
Route: oral
Route: single
Dose: 500 mg
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/050746s013lbl.pdf
healthy, adult
Health Status: healthy
Age Group: adult
Sex: unknown
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/050746s013lbl.pdf
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/050746s013lbl.pdf
2 % 3 times / day steady, topical
Recommended
Dose: 2 %, 3 times / day
Route: topical
Route: steady
Dose: 2 %, 3 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/050746s013lbl.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/050746s013lbl.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/050746s013lbl.pdf
2 % 3 times / day steady, topical
Recommended
Dose: 2 %, 3 times / day
Route: topical
Route: steady
Dose: 2 %, 3 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/050746s013lbl.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/050746s013lbl.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/050746s013lbl.pdf
2 % 1 times / day steady, topical
Recommended
Dose: 2 %, 1 times / day
Route: topical
Route: steady
Dose: 2 %, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/29728181/
unhealthy, children
Health Status: unhealthy
Age Group: children
Sex: unknown
Sources:
https://pubmed.ncbi.nlm.nih.gov/29728181/
Sources:
https://pubmed.ncbi.nlm.nih.gov/29728181/
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/050746s013lbl.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/050746s013lbl.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/050746s013lbl.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/050746s013lbl.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/050746s013lbl.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/050746s013lbl.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/050746s013lbl.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/050746s013lbl.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/050746s013lbl.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/050746s013lbl.pdf
Cellulitis < 1%
2 % 3 times / day steady, topical
Recommended
Dose: 2 %, 3 times / day
Route: topical
Route: steady
Dose: 2 %, 3 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/050746s013lbl.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/050746s013lbl.pdf
Dermatitis < 1%
2 % 3 times / day steady, topical
Recommended
Dose: 2 %, 3 times / day
Route: topical
Route: steady
Dose: 2 %, 3 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/050746s013lbl.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/050746s013lbl.pdf
Dizziness < 1%
2 % 3 times / day steady, topical
Recommended
Dose: 2 %, 3 times / day
Route: topical
Route: steady
Dose: 2 %, 3 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/050746s013lbl.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/050746s013lbl.pdf
Pruritus < 1%
2 % 3 times / day steady, topical
Recommended
Dose: 2 %, 3 times / day
Route: topical
Route: steady
Dose: 2 %, 3 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/050746s013lbl.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/050746s013lbl.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/050746s013lbl.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/050746s013lbl.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/050746s013lbl.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/050746s013lbl.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/050746s013lbl.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/050746s013lbl.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/050746s013lbl.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/050746s013lbl.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/050746s013lbl.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/050746s013lbl.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/050746s013lbl.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/050746s013lbl.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/050746s013lbl.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/050746s013lbl.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/050746s013lbl.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/050746s013lbl.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/050746s013lbl.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/050746s013lbl.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/050746s013lbl.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/050746s013lbl.pdf
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer
CYP2C8
1057

CYP2B6
926

BSEP
550

MRP2
499

MRP3
246

MRP4
290
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
BSEP
554
 no [IC50 >133 uM]
MRP2
625
 no [IC50 >133 uM]
MRP3
326
 no [IC50 >133 uM]
MRP4
345
 no [IC50 >133 uM]
CYP2B6
1160
 no
CYP2C8
1117
 no
Sourcing

Sourcing

Vendor/AggregatorIDURL
ChEBI
CHEBI:7025
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:7025
ChemicalBook
CB0689829
https://www.chemicalbook.com/ChemicalProductProperty_EN_CB0689829
eMolecules
27678882
https://www.emolecules.com/cgi-bin/more?vid=27678882
eMolecules
31267427
https://www.emolecules.com/cgi-bin/more?vid=31267427
eMolecules
592210
https://www.emolecules.com/cgi-bin/more?vid=592210
MolPort
MolPort-003-666-882
https://www.molport.com/shop/molecule-link/MolPort-003-666-882
ZINC
ZINC000004102194
http://zinc15.docking.org/substances/ZINC000004102194
PubMed

PubMed

TitleDatePubMed
Resistance to and synthesis of the antibiotic mupirocin.
2010-04
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005-06
The isoleucyl-tRNA synthetase mutation V588F conferring mupirocin resistance in glycopeptide-intermediate Staphylococcus aureus is not associated with a significant fitness burden.
2004-01
Mutations affecting the Rossman fold of isoleucyl-tRNA synthetase are correlated with low-level mupirocin resistance in Staphylococcus aureus.
2002-02
Mupirocin resistance in staphylococci: development and transfer of isoleucyl-tRNA synthetase-mediated resistance in vitro.
1999-04
Antibacterial activity of mupirocin (pseudomonic acid), a new antibiotic for topical use.
1985-04
On the mode of action of pseudomonic acid: inhibition of protein synthesis in Staphylococcus aureus.
1978-04
Patents

Patents

07737177
3
20010003007
3
JP2001500477A
122
JP2001521945A
47
JP2002511777A
420
JP2002541233A
406
JP2003515526A
470
JP2004059585A
3
JP2005162728A
3
JP2009501065A
33
JP2009526755A
475
JP2009541210A
80
JP2011526302A
67
JP2011528275A
456
JP2013543518A
3
JP3553083B2
51
JP4718445B2
36
JP4849764B2
75
JPH08269067A
3
JPH09157269A
3
JPH09510976A
15
JPS05432473A
3
JPS05490179A
3
JPS05815973A
3
JPS5270083A
3
JPS54103871A
3
JPS54103872A
3
JPS54106474A
3
JPS5412375A
3
JPS5412376A
3
JPS54125672A
3
JPS54125673A
3
JPS54148790A
3
JPS5432473A
3
JPS5459281A
3
JPS5490179A
3
JPS5815973A
3
US3977943
3
US4071536
3
US4289703
3

Sample Use Guides

In Vivo Use Guide
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 Mon Mar 31 18:59:42 GMT 2025
Edited
by admin
on Mon Mar 31 18:59:42 GMT 2025
Record UNII
870F25Y7EK
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
BACTROBAN NASAL
Preferred Name English
MUPIROCIN CALCIUM ANHYDROUS
Common Name English
CALCIUM PSEUDOMONATE
Common Name English
L-TALO-NON-2-ENONIC ACID, 5,9-ANHYDRO-2,3,4,8-TETRADEOXY-8-(((2S,3S)-3-((1S,2S)-2-HYDROXY-1-METHYLPROPYL)-2-OXIRANYL)METHYL)-3-METHYL-, 8-CARBOXYOCTYL ESTER, CALCIUM SALT (2:1), (2E)-
Common Name English
CALCIUM MUPIROCIN
Common Name English
Mupirocin calcium [WHO-DD]
Common Name English
Code System Code Type Description
FDA UNII
870F25Y7EK
Created by admin on Mon Mar 31 18:59:42 GMT 2025 , Edited by admin on Mon Mar 31 18:59:42 GMT 2025
PRIMARY
CAS
104486-81-9
Created by admin on Mon Mar 31 18:59:42 GMT 2025 , Edited by admin on Mon Mar 31 18:59:42 GMT 2025
PRIMARY
PUBCHEM
6435927
Created by admin on Mon Mar 31 18:59:42 GMT 2025 , Edited by admin on Mon Mar 31 18:59:42 GMT 2025
PRIMARY
CHEBI
145818
Created by admin on Mon Mar 31 18:59:42 GMT 2025 , Edited by admin on Mon Mar 31 18:59:42 GMT 2025
PRIMARY
EPA CompTox
DTXSID90883142
Created by admin on Mon Mar 31 18:59:42 GMT 2025 , Edited by admin on Mon Mar 31 18:59:42 GMT 2025
PRIMARY
Related Record Type Details
Structure of MUPIROCIN
PARENT -> SALT/SOLVATE
Structure of MUPIROCIN CALCIUM
SOLVATE->ANHYDROUS
Related Record Type Details
Structure of MUPIROCIN
ACTIVE MOIETY
NIH
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