Details of the Drug

General Information of Drug (ID: DMWX683)

Drug Name

Mupirocin

Synonyms

Bactoderm; Bactroban; Centany; MRC; Mupirocina; Mupirocine; Mupirocinum; Plasimine; Bactroban Nasal; Mupirocina [Spanish]; Mupirocine [French]; Mupirocinum [Latin]; Pseudomonic acid; Pseudomonic acid A; BRL 4910A; BRL-4910A; Bactroban (TN); Centany (TN); Mupirocin (USP/INN); Mupirocin, 14C-Labeled; 5,9-Anhydro-2,3,4,8-tetradeoxy-8-[[3-(2-hydroxy-1-methylpropyl)oxiranyl]methyl]-3-methyl-[2E,8[2S,3S(1S,2S); 8-Carboxyoctyl (E)-4-(2S,3R,4R,5S)-5-((2S,3S,4S,5S)-2,3-epoxy-5-hydroxy-4-methylhexyl)-3,4-dihydroxytetrahydro-2H-pyran-2-yl)-3-methylcrotonat; 9-[(E)-4-[(2S,3R,4R,5S)-3,4-dihydroxy-5-[[(2S,3S)-3-[(2S,3S)-3-hydroxybutan-2-yl]oxiran-2-yl]methyl]oxan-2-yl]-3-methylbut-2-enoyl]oxynonanoic acid

Indication

Disease Entry	ICD 11	Status	REF
Bacterial infection	1A00-1C4Z	Approved	[1]

Therapeutic Class

Antibiotics

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 2

Molecular Weight (mw)

500.6

Topological Polar Surface Area (xlogp)

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

ADMET Property

Elimination: Following the application of Centany (mupirocin ointment),2% to a 400 cm2 area on the back of 23 healthy volunteers once daily for 7 days, the mean (range) cumulative urinary excretion of monic acid over 24 hrs following the last administration was 1.25% (0.2% to 3.0%) of the administered dose of mupirocin [2]
Half-life: The concentration or amount of drug in body reduced by one-half in 20 - 40 minutes [3]
Metabolism: The drug is metabolized via the hepatic [2]

Chemical Identifiers

Formula: C26H44O9
IUPAC Name: 9-[(E)-4-[(2S,3R,4R,5S)-3,4-dihydroxy-5-[[(2S,3S)-3-[(2S,3S)-3-hydroxybutan-2-yl]oxiran-2-yl]methyl]oxan-2-yl]-3-methylbut-2-enoyl]oxynonanoic acid
Canonical SMILES: C[C@H]([C@H]1[C@@H](O1)C[C@H]2CO[C@H]([C@@H]([C@@H]2O)O)C/C(=C/C(=O)OCCCCCCCCC(=O)O)/C)[C@H](C)O
InChI: 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
InChIKey: MINDHVHHQZYEEK-HBBNESRFSA-N

Cross-matching ID

PubChem CID: 446596
ChEBI ID: CHEBI:7025
CAS Number: 12650-69-0
DrugBank ID: DB00410
TTD ID: D03JSJ
ACDINA ID: D01263

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Bacterial Isoleucyl-tRNA synthetase (Bact ileS)	TT6KYJ5	SYI_ECOLI	Modulator	[4]

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Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction Atlas of This Drug

Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG

DIG Name	DIG ID	PubChem CID	Functional Classification
Benzyl alcohol	E00010	244	Antimicrobial preservative; Solvent
Cetyl alcohol	E00061	2682	Coating agent; Emollient; Emulsifying agent; Stiffening agent
Polyethylene glycol 3350	E00652	Not Available	Coating agent; Diluent; Ointment base; Plasticizing agent; Solvent; Suppository base; lubricant
Polyethylene glycol 400	E00653	Not Available	Coating agent; Diluent; Ointment base; Plasticizing agent; Solvent; Suppository base; lubricant
Stearyl alcohol	E00172	8221	Emollient; Emulsifying agent; Stiffening agent; Viscosity-controlling agent
Water	E00035	962	Solvent
Phenoxyethanol	E00329	31236	Antimicrobial preservative
Polyoxyl 20 cetyl ether	E00452	2724259	Emulsifying agent; Ointment base; Solubilizing agent; Surfactant
Xanthan gum	E00694	Not Available	Bioadhesive material; Emulsifying agent; Gelling agent; Modified-release agent; Suspending agent; Viscosity-controlling agent
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⏷ Show the Full List of 9 Pharmaceutical Excipients of This Drug

Pharmaceutical Formulation

Formulation Name	Drug Dosage	Dosage Form	Route
Mupirocin eq 2% base cream	eq 2% base	Cream	Topical
Mupirocin 2% ointment	2%	Ointment	Topical

Jump to Detail Pharmaceutical Formulation Page of This Drug

References

1	Has nature already identified all useful antibacterial targets Curr Opin Microbiol. 2008 Oct;11(5):387-92.
2	MUPIROCIN OINTMENT - FDA Label
3	MUPIROCIN OINTMENT USP, 2% - DailyMed
4	Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services.
5	Chemical modification of reveromycin A and its biological activities. Bioorg Med Chem Lett. 2002 Dec 2;12(23):3363-6.