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
-
monocarboxylic acidView Class →
CHEBI:25384
-
secondary alcoholView Class →
CHEBI:35681
-
epoxideView Class →
CHEBI:32955
-
oxanesView Class →
CHEBI:46942
-
triolView Class →
CHEBI:27136
-
alpha,beta-unsaturated carboxylic esterView Class →
CHEBI:51737
-
t275517
-
t276151
-
t276342
-
t276388
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
- core#notation
- CHEBI:7025
- DRON_00010000
- 42372
- oboInOwl#hasDbXref
- Wikipedia:Mupirocin
Additional References
🔍 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
- 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
- spl_id
- f8fe5a7f-8967-4c08-e053-6394a90ae607
- product_ndc
- 51927-0010
- route
- TOPICAL
- package_ndc
- 51927-0296-0
- package_marketing_start_date
- 27-APR-13
- package_description
- 1 kg in 1 BOTTLE (51927-0296-0)
- 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
- upc
- 0368071432121
- 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
- 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
- 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
- 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