MUPIROCIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C26H44O9
Molecular Weight	500.6222
Optical Activity	UNSPECIFIED
Defined Stereocenters	8 / 8
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[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

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

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/050746s020lbl.pdf
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

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Isoleucyl-tRNA synthetase 3 Target ID: CHEMBL1982 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/050746s020lbl.pdf	Binding Agent 1064		7.0 nM [Kd]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Secondarily infected traumatic skin lesions 3 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/050746s020lbl.pdf	Curative		Approved 8429	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

C_max

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 EXPERIMENT https://www.degruyter.com/view/journals/ejnm/8/3/article-p139.xml	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 EXPERIMENT https://www.degruyter.com/view/journals/ejnm/8/3/article-p139.xml	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

T_1/2

Value	Dose	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 EXPERIMENT https://www.degruyter.com/view/journals/ejnm/8/3/article-p139.xml	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 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

F_unbound

Value	Dose	Co-administered	Analyte	Population
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

Dose	Population	Adverse 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 n = 339 Health Status: unhealthy Condition: various skin lesions Age Group: adult Sex: unknown Population Size: 339 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 n = 82 Health Status: unhealthy Condition: secondarily infected eczema Age Group: adult Sex: unknown Population Size: 82 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 n = 8 Health Status: unhealthy Condition: tympanostomy tube otorrhea caused by methicillin-resistant Staphylococcus aureus Age Group: children Sex: unknown Population Size: 8 Sources: https://pubmed.ncbi.nlm.nih.gov/29728181/	Sources: https://pubmed.ncbi.nlm.nih.gov/29728181/

AEs

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP2C8 911 CYP2B6 810 BSEP 402 MRP2 383 MRP3 157 MRP4 204

Drug as perpetrator

Target	Modality	Activity
BSEP 403	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/23956101/	no [IC50 >133 uM]
MRP2 475	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/23956101/	no [IC50 >133 uM]
MRP3 207	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/23956101/	no [IC50 >133 uM]
MRP4 238	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/23956101/	no [IC50 >133 uM]
CYP2B6 1001	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/17101742/	no
CYP2C8 965	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/15601807/	no

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:7025	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:7025
ChemicalBook	CB0689829	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB0689829
MolPort	MolPort-003-666-882	https://www.molport.com/shop/molecule-link/MolPort-003-666-882
ZINC	ZINC000004102194	http://zinc15.docking.org/substances/ZINC000004102194
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

PubMed

Title	Date	PubMed
On the mode of action of pseudomonic acid: inhibition of protein synthesis in Staphylococcus aureus.	1978 Apr	659331
Antibacterial activity of mupirocin (pseudomonic acid), a new antibiotic for topical use.	1985 Apr	3923922
Mupirocin resistance in staphylococci: development and transfer of isoleucyl-tRNA synthetase-mediated resistance in vitro.	1999 Apr	10212417
Mutations affecting the Rossman fold of isoleucyl-tRNA synthetase are correlated with low-level mupirocin resistance in Staphylococcus aureus.	2002 Feb	11796355
Prediction of genotoxicity of chemical compounds by statistical learning methods.	2005 Jun	15962942
Resistance to and synthesis of the antibiotic mupirocin.	2010 Apr	20190824

Patents

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).

Name

Type

Language

MUPIROCIN

Official Name

English

MUPIROCIN [USP MONOGRAPH]

Common Name

English

CENTANY

Brand Name

English

NSC-759182

Code

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]oxiranyl]methyl]-3-methyl-, 8-carboxyoctyl ester, (2E)-

Systematic Name

English

9-[[(2E)-4-[(2S,3R,4R,5S)-3,4-Dihydroxy-5-[[(2S,3S)-3-[(1S,2S)-2-hydroxy-1-methylpropyl]oxiranyl]methyl]tetrahydro-2H-pyran-2-yl]-3-methylbut-2-enoyl]oxy]nonanoic acid

Common Name

English

MUPIROCIN [MART.]

Common Name

English

MUPIROCIN [USP IMPURITY]

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-β-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

BRL 4910A

Code

English

Mupirocin [WHO-DD]

Common Name

English

MUPIROCIN [MI]

Common Name

English

mupirocin [INN]

Common Name

English

PSEUDOMONIC ACID

Common Name

English

MUPIROCIN [VANDF]

Common Name

English

Classification Tree Code System Code

WHO-ESSENTIAL MEDICINES LIST

13.2