GRADE & PURITY Moligand™, ≥98%(HPLC)

Synonyms

DISODIUM (2R,3S)-3-METHYLOXIRAN-2-YLPHOSPHONATE | Phosphomycin disodium salt, antibacterial MurA inhibitor | Q27272022 | (1R,2S)(-)-(1,2-Epoxypropyl)phosphonic acid disodium salt | Disodium (1R,2S)-(1,2-epoxypropyl)phosphonate | MFCD00130143 | EN300-12210

Storage

Store at 2-8°C,Protected from light

Shipped In

Wet ice

Overview

Phosphomycin, also known as Fosfomycin, is an antibiotic produced by Streptomyces fradiae. It is used to treat uncomplicated urinary tract infections and to reduce nephrotoxicity and ototoxicity of platinum-containing anti-tumor agents. It is used for susceptibility studies of Klebsiella pneumoniae and to study in vitro susceptibility testing procedures for fosfomycin tromethamine

Specifications

Synonyms

DISODIUM (2R, 3S)-3-METHYLOXIRAN-2-YLPHOSPHONATE | Phosphomycin disodium salt, antibacterial MurA inhibitor | Q27272022 | (1R, 2S)(-)-(1, 2-Epoxypropyl)phosphonic acid disodium salt | Disodium (1R, 2S)-(1, 2-epoxypropyl)phosphonate | MFCD00130143 | EN300-12210

Specifications & Purity

Moligand™, ≥98%(HPLC)

Biochemical and Physiological Mechanisms

Antibiotic that concentrates in kidney and bladder; reduces nephrotoxicity and ototoxicity of platinum-containing anti-tumor agents. Fosfomycin is a phosphoenolpyruvate analog that irreversibly inhibits UDP-GlcNAc enolpyruvyl tranferase (MurA), an enzyme

Storage

Store at 2-8°C, Protected from light

Shipped In

Wet ice

This product requires cold chain shipping. Ground and other economy services are not available.

Grade

Moligand™

Note

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Purity

≥98%(HPLC)

Names and Identifiers

• Pubchem Sid: 504754709
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504754709
• Canonical Smiles: CC1C(O1)P(=O)([O-])[O-].[Na+].[Na+]
• IUPAC Name: disodium;[(2R,3S)-3-methyloxiran-2-yl]-dioxido-oxo-λ5-phosphane
• InChIKey: QZIQJIKUVJMTDG-JSTPYPERSA-L
• INCHI: 1S/C3H7O4P.2Na/c1-2-3(7-2)8(4,5)6;;/h2-3H,1H3,(H2,4,5,6);;/q;2*+1/p-2/t2-,3+;;/m0../s1
• Isomeric SMILES: C[C@H]1[C@H](O1)P(=O)([O-])[O-].[Na+].[Na+]
• Alternate CAS: 23155-02-4
• Molecular Weight: 182.02
• Beilstein: 4604425
• Reaxy-Rn: 9154748
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=9154748&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic acids and derivatives
    • Class Organic phosphonic acids and derivatives
      • Subclass Organic phosphonic acids

• Kingdom: Organic compounds
• Superclass: Organic acids and derivatives
• Class: Organic phosphonic acids and derivatives
• Subclass: Organic phosphonic acids
• Intermediate Tree Nodes: Not available
• Direct Parent: Organic phosphonic acids
• Alternative Parents: Oxacyclic compounds Epoxides Organopnictogen compounds Organophosphorus compounds Organooxygen compounds Organic sodium salts Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aliphatic heteromonocyclic compounds
• Substituents: Organophosphonic acid - Oxacycle - Organic alkali metal salt - Organoheterocyclic compound - Oxirane - Organic oxygen compound - Organopnictogen compound - Organic oxide - Hydrocarbon derivative - Organic sodium salt - Organic salt - Organophosphorus compound - Organooxygen compound - Aliphatic heteromonocyclic compound
• Description: This compound belongs to the class of organic compounds known as organic phosphonic acids. These are organic compounds containing phosphonic acid.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

KDM4A Tchem Lysine-specific demethylase 4A (52245 Activities)

Discover Target: KDM4A

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Associated Targets(non-human)

ampC Beta-lactamase AmpC (62480 Activities)

Discover Target: ampC

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Ralstonia solanacearum (520 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Staphylococcus aureus (210822 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Escherichia coli (133304 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Bacillus subtilis (32866 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Bacillus cereus (7522 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mechanisms of Action

Chemical and Physical Properties

• Solubility: Freely soluble in water or aqueous solution；Slightly soluble in methanol
• Sensitivity: Heat sensitive；Light sensitive
• Specific Rotation[α]: -5° (C=5,H2O)
• Molecular Weight: 182.020 g/mol
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 181.972 Da
• Monoisotopic Mass: 181.972 Da
• Topological Polar Surface Area: 75.700 Ų
• Heavy Atom Count: 10
• Formal Charge: 0
• Complexity: 127.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 2
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 3

XLogP3

References

1. Lin Li-Bin, Jian Xiao, Qiang Zhang, Rui Han, Biao Xu, Sheng-Xiang Yang, Wen-Bo Han, Jiang-Jiang Tang, Jin-Ming Gao.  (2021)  Eremophilane Sesquiterpenoids with Antibacterial and Anti-inflammatory Activities from the Endophytic Fungus Septoria rudbeckiae.  JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY,      [PMID:34605647] [10.1021/acs.jafc.1c04131]

2. Wen Jiang, Wenhao Lao, Zhe Xu, Yiping Feng, Jiuli Ruan.  (2025)  Degradation of antibiotic fosfomycin by peroxymonosulfate/ferrate and simultaneous phosphate removal with in situ formed ferric nanoparticles.  Environmental Science-Nano,      [PMID:] [10.1039/D5EN00701A]