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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 of MUPIROCIN

SMILES

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

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 500.6222
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 8 / 8
E/Z Centers 1
Optical Activity UNSPECIFIED

Description

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 TargetPharmacologyConditionPotency
7.0 nM [Kd]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
BACTROBAN

T1/2

ValueDoseCo-administeredAnalytePopulation
30 min
single, intravenous
MUPIROCIN plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
3%
single, intravenous
MUPIROCIN plasma
Homo sapiens

Doses

AEs

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer






Drug as perpetrator​

PubMed

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
Record UNII
D0GX863OA5
Record Status Validated (UNII)
Record Version