Mupirocin
Also known as Pseudomonic acid, Mupirocine, Pseudomonic acid A
Key facts
What buyers check first
- CAS number
- 12650-69-0
- Formula
- C26H44O9
- Molar mass
- 500.63 g/mol
- EC number
- 603-145-3
- HS code
- 294190
- Category
- Antibiotics and anti-infectives
What is Mupirocin?
Plain description, key identifiers and synonyms
Mupirocin is 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. It has a role as an antibacterial drug, a protein synthesis inhibitor and a bacterial metabolite. It is a monocarboxylic acid, a triol, an epoxide, a secondary alcohol, a member of oxanes and an alpha,beta-unsaturated carboxylic ester. It is a conjugate acid of a mupirocin(1-).
Identifiers
Registry numbers, names and line notations, tap to copy
- 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
- CAS number
- 12650-69-0 CAS number cross-checkedOther or deprecated CAS: 80558-54-9
- EC number
- 603-145-3
- Molecular formula
- C26H44O9
- UNII
- D0GX863OA5
- MDL number
- MFCD01711620, MFCD11977847
- InChIKey
- MINDHVHHQZYEEK-HBBNESRFSA-N
- 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
- Canonical SMILES
- CC(=CC(=O)OCCCCCCCCC(=O)O)CC1OCC(CC2OC2C(C)C(C)O)C(O)C1O
- Isomeric 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
Synonyms
- Pseudomonic acid
- Mupirocine
- Pseudomonic acid A
- Centany
- Bactoderm
- Mupirocina
- Mupirocinum
- Turixin
- trans-Pseudomonic acid
- BRL 4910A
- 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
- 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)-
- 9-{[(2E)-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]oxy}nonanoic acid
- 14C-Labeled Mupirocin
- Bactoderm Ointment
- Mupirocin 2%
- 9-(((2E)-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)oxy)nonanoic acid
- 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
- 9-({(2E)-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}oxy)nonanoic acid
- 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)-
- Muricin
- Sx Pre-Op Prep Pouch
- Mupirocin, 14C Labeled
- Mupirocin Ointment USP, 2%
- Bactroban
Show all 35 synonymsShow fewer synonyms
- Bactroban (TN)
- MRC
- Plasimine
- 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
- Bactroban Ointment
- Centany (TN)
- Mupirocin Neo-Sensitabs
- Mupirocin (USP/INN)
- Bactroban,
- Mupirocin,
Physical and chemical properties
Measured values and descriptors computed from the structure
Physical and chemical properties
Measured values, check the supplier specification for your grade
No measured properties are recorded for this substance yet. Ask suppliers for a technical data sheet.
Values vary by grade. Ask suppliers for the COA or TDS of the batch you buy.
Computed descriptors
Calculated from the structure, useful for screening and formulation
| Molecular weight | 500.63 g/molcalc.Computed value |
|---|---|
| Exact mass | 500.2985 Dacalc.Computed value |
| LogP (octanol/water) | 2.59calc.Computed value |
| Topological polar surface area | 146.1 Ųcalc.Computed value |
| Hydrogen bond donors | 4calc.Computed value |
| Hydrogen bond acceptors | 8calc.Computed value |
| Rotatable bonds | 16calc.Computed value |
| Heavy atoms | 35calc.Computed value |
| Rings | 2calc.Computed value |
| Aromatic rings | 0calc.Computed value |
| Fraction sp3 carbons | 0.85calc.Computed value |
| Formal charge | 0calc.Computed value |
| Stereocentres | 8calc.Computed value |
| Lipinski rule of five | Passes (1 violation)calc.Computed value |
Calculated for screening. Confirm critical figures with the supplier.
Murcko scaffold
The ring system that remains when every side chain is removed
C1COCC(CC2CO2)C1
2 rings, 10 atoms, the 3-[(Oxiran-2-yl)methyl]oxane ring system.
24 other chemicals share this scaffoldSafety and hazards
GHS classification summary, not a safety data sheet
Hazard statements
- H302Harmful if swallowed.
- H315Causes skin irritation.
- H317May cause an allergic skin reaction.
- H319Causes serious eye irritation.
Precautionary statements (16)
- P261Avoid breathing dust, fume, gas, mist, vapours or spray.
- P264Wash skin thoroughly after handling.
- P264 + P265Wash skin thoroughly after handling. Do not touch eyes.
- P270Do not eat, drink or smoke when using this product.
- P272Contaminated work clothing should not be allowed out of the workplace.
- P280Wear protective gloves, protective clothing, eye protection and face protection.
- P301 + P317If swallowed: Get medical help.
- P302 + P352If on skin: Wash with plenty of water.
- P305 + P351 + P338If in eyes: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
- P321Specific treatment (see supplemental first aid instructions on the label).
- P330Rinse mouth.
- P332 + P317If skin irritation occurs: Get medical help.
- P333 + P317If skin irritation or rash occurs: Get medical help.
- P337 + P317If eye irritation persists: Get medical help.
- P362 + P364Take off contaminated clothing. And wash it before reuse.
- P501Dispose of contents and container in accordance with local regulations.
GHS classification summary, not a safety data sheet (SDS). Classifications can differ by supplier, grade and concentration. Always check the supplier's SDS.
Full safety data and first aidMupirocin suppliers
Sponsored listings first, then the documented ranking: membership, verification, replies, completeness, freshness and ratings
- China, HangzhouUnclaimed profileMupirocinGrade, purity and minimum order on requestPrice on request
- India, SuratUnclaimed profileMupirocinGrade, purity and minimum order on requestPrice on request
- ChinaUnclaimed profileMupirocinGrade, purity and minimum order on requestPrice on request
- ChinaUnclaimed profileMupirocinGrade, purity and minimum order on requestPrice on request
- India ManufacturerUnclaimed profileMupirocinGrade, purity and minimum order on requestPrice on request
- China, Hangzhou ManufacturerUnclaimed profileMupirocinGrade, purity and minimum order on requestPrice on request
- China, HangzhouUnclaimed profileMupirocinGrade, purity and minimum order on requestPrice on request
- Hong Kong ManufacturerUnclaimed profileMupirocinGrade, purity and minimum order on requestPrice on request
- China, Taizhou ManufacturerUnclaimed profileMupirocinGrade, purity and minimum order on requestPrice on request
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Where suppliers are based
140 suppliers in 24 countries
- China35
- United States31
- India23
- Bangladesh8
- Germany5
- Spain3
- and 18 more countries
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Mupirocin price
Indicative price range per kg from live supplier offers
Suppliers quote this chemical on request. Send one free request and compare quotes side by side.
Uses and applications
What the substance is used for, by industry and function
Use classes: Animal Drugs.
Industries and functions
Pharmacological actions
- Anti-Bacterial Agents
- Protein Synthesis Inhibitors
Roles
- antibacterial agent
- antibacterial drug
- antiinfective agent
- antimicrobial agent
- antimicrobial drug
- bacterial metabolite
- enzyme inhibitor
- metabolite
- pathway inhibitor
- pharmaceutical
- prokaryotic metabolite
- protein synthesis inhibitor
Pharmacology
Mupirocin is a RNA Synthetase Inhibitor Antibacterial. The mechanism of action of mupirocin is as a RNA Synthetase Inhibitor.
Regulatory status
Inventories, regulations and trade controls that list this substance
Health and food
- Active ingredient in FDA approved drug labels
HS code and trade data
Customs classification and reported world trade statistics
Global trade
World import and export statistics for the HS code Mupirocin is traded under.
Antibiotics, other
- China39.7%
- United States11.3%
- Switzerland * partner reported10.9%
* Partner reported figures, a lower bound.
The HS code shown for Mupirocin is indicative (it was assigned by structure rules). Confirm the classification with your customs broker before shipping.
Frequently asked questions
Quick answers about Mupirocin, based on the data on this page
What is Mupirocin?
What is the CAS number of Mupirocin?
What is the molecular formula and weight of Mupirocin?
What is Mupirocin used for?
Is Mupirocin hazardous?
What is the HS code of Mupirocin?
Where can I buy Mupirocin?
Where can I buy Mupirocin in India?
What is the price of Mupirocin?
Guides for buyers
Practical guides that help when you source, ship or handle Mupirocin
- Article, QualityPharma grades explained: IP vs BP vs USP vs EPWhat the Indian, British, US and European pharmacopoeias are, how their monographs differ, what multi grade claims mean and why a grade alone does not make a product fit for medicines.Read
- Guide, SafetyHow to read a safety data sheet in 10 minutesA section by section method to pull the essentials out of any 16 section SDS: identity, hazards, composition, storage, PPE, properties, transport and emergency measures.Read
- Guide, SafetyGHS pictograms, signal words and hazard statements explainedA practical guide to the nine GHS pictograms, the signal words Danger and Warning, H and P statements, and how to read a chemical label in seconds.Read
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