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Mupirocin

CHEBI:CHEBI_7025

Definition

An alpha,beta-unsaturated ester resulting from the formal condensation of the alcoholic hydroxy group of 9-hydroxynonanoic acid with the carboxy group of (2E)-4-[(2S)-tetrahydro-2H-pyran-2-yl]-3-methylbut-2-enoic acid in which the tetrahydropyranyl ring is substituted at positions 3 and 4 by hydroxy groups and at position 5 by a {(2S,3S)-3-[(2S,3S)-3-hydroxybutan-2-yl]oxiran-2-yl}methyl group. Originally isolated from the Gram-negative bacterium Pseudomonas fluorescens, it is used as a topical antibiotic for the treatment of Gram-positive bacterial infections.

Chemical Information

Molecular Formula
C26H44O9
Molecular Mass
500.62220
Charge
0
SMILES
C[C@H](O)[C@H](C)[C@@H]1O[C@H]1C[C@H]1CO[C@@H](C\C(C)=C\C(=O)OCCCCCCCCC(O)=O)[C@H](O)[C@@H]1O
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

Alternative Names

  • 9-({(2E)-4-[(2S,3R,4R,5S)-3,4-dihydroxy-5-({(2S,3S)-3-[(2S,3S)-3-hydroxybutan-2-yl]oxiran-2-yl}methyl)tetrahydro-2H-pyran-2-yl]-3-methylbut-2-enoyl}oxy)nonanoic acid
  • Bactroban
  • Centany
  • mupirocin
  • mupirocina
  • mupirocine
  • mupirocinum
  • Pseudomonic acid A

Drug Classification

Important Medical Information

⚕️ This information is sourced from ChEBI (Chemical Entities of Biological Interest) database and is intended for educational purposes only.

  • Always consult with a healthcare professional before starting, stopping, or modifying any medication.
  • Side effects may vary and this list may not be comprehensive.
  • Drug interactions may occur with other medications.

Additional Identifiers

DRON_00010000
42372
oboInOwl#hasDbXref
Wikipedia:Mupirocin
core#notation
CHEBI:7025

Additional References

Wikipedia:Mupirocin

🔍 Click on any linked disease name to learn more about the conditions this medication is used to treat, or explore related drug classifications for more information about similar medications.

Additional Attributes

oboInOwl#hasOBONamespace
chebi_ontology
DRON_00010000
42372
oboInOwl#hasDbXref
Wikipedia:Mupirocin
oboInOwl#hasAlternativeId
CHEBI:44038
oboInOwl#id
CHEBI:7025
brand_name
Pirnuo
brand_name_base
Pirnuo
generic_name
mupirocin calcium
product_ndc
51927-0296
RO_0000087
http://purl.obolibrary.org/obo/CHEBI_48001
oboInOwl#inSubset
http://purl.obolibrary.org/obo/chebi#3_STAR
chebi#is_conjugate_acid_of
http://purl.obolibrary.org/obo/CHEBI_145790
route
TOPICAL
package_ndc
51927-0296-0
spl_id
f7eafae0-c9cc-e6d5-e053-6394a90a1859
rxcui
2286614
manufacturer_name
REMEDYREPACK INC.
active_ingredient_strength
5 kg/5kg
active_ingredient_name
MUPIROCIN CALCIUM
unii
RG38I2P540
spl_set_id
f1a01044-8f2e-4e91-e053-2995a90af722
nui
N0000175516
package_marketing_start_date
20190121
upc
0368071432121
product_type
BULK INGREDIENT
listing_expiration_date
20241231
marketing_category
BULK INGREDIENT FOR HUMAN PRESCRIPTION COMPOUNDING
labeler_name
REMEDYREPACK INC.
dosage_form
OINTMENT
marketing_start_date
20120701
application_number
ANDA214811
package_description
1 kg in 1 BOTTLE (51927-0296-0)
core#notation
CHEBI:7025
pharm_class_epc
RNA Synthetase Inhibitor Antibacterial [EPC]
pharm_class
RNA Synthetase Inhibitors [MoA]
pharm_class_moa
RNA Synthetase Inhibitors [MoA]
22-rdf-syntax-ns#type
http://www.w3.org/2002/07/owl#Class
has_treatment
http://purl.obolibrary.org/obo/DOID_3261
rdf-schema#domain
https://w3id.org/def/predibionto#has_side_effect6556
chebi#is_conjugate_base_of
http://purl.obolibrary.org/obo/CHEBI_145790
owl#someValuesFrom
t549087
owl#annotatedSource
t276651