Cas no 66508-37-0 (Fosmidomycin sodium salt)

Fosmidomycin sodium salt is a potent and selective inhibitor of 1-deoxy-D-xylulose-5-phosphate reductoisomerase (DXR), a key enzyme in the non-mevalonate pathway of isoprenoid biosynthesis. This compound is particularly valuable in research applications targeting bacterial and apicomplexan pathogens, including Plasmodium falciparum, due to its ability to disrupt essential metabolic pathways. Its high solubility in aqueous solutions enhances its utility in in vitro and in vivo studies. Fosmidomycin sodium salt is widely used in biochemical and pharmacological research to investigate isoprenoid biosynthesis inhibition, antimicrobial mechanisms, and potential therapeutic applications. The sodium salt form ensures improved stability and handling compared to the free acid.
Fosmidomycin sodium salt structure
Fosmidomycin sodium salt structure
Product Name:Fosmidomycin sodium salt
CAS No:66508-37-0
MF:C4H9NNaO5P
MW:205.081493139267
CID:826487
PubChem ID:5141362
Update Time:2025-05-26

Fosmidomycin sodium salt Chemical and Physical Properties

Names and Identifiers

    • FOSMIDOMYCIN, SODIUM SALT
    • Fosmidomycin (sodium salt)
    • sodium,3-[formyl(hydroxy)amino]propyl-hydroxyphosphinate
    • Fosmidomycin sodium salt
    • Fosmidomycin
    • FR 31564
    • Antibiotic FR 31564
    • FR-31564
    • 66508-37-0 (sodium)
    • DTXSID10216711
    • SCHEMBL4432387
    • AKOS030254266
    • sodium;3-[formyl(hydroxy)amino]propyl-hydroxyphosphinate
    • FT-0613838
    • 66508-37-0
    • Fosmidomycin Sodium
    • CS-0067087
    • Phosphonic acid, (3-(formylhydroxyamino)propyl)-, monosodium salt
    • FOSMIDOMYCIN MONOSODIUM SALT [MI]
    • Q27280957
    • CHEMBL2164257
    • sodium hydrogen [3-(N-hydroxyformamido)propyl]phosphonate
    • HY-112853
    • IYI1EW66CX
    • FOSMIDOMYCIN MONOSODIUM SALT
    • (3-(Formylhydroxyamino)propyl)phosphonic acid monosodium salt
    • UNII-IYI1EW66CX
    • FOSMIDOMYCIN SODIUM [JAN]
    • sodium;3-[ormyl(hydroxy)amino]propyl-hydroxyphosphinate
    • CHEBI:201600
    • Fosmidomycin sodium salt?
    • G14344
    • DTXCID40139202
    • Inchi: 1S/C4H10NO5P.Na/c6-4-5(7)2-1-3-11(8,9)10;/h4,7H,1-3H2,(H2,8,9,10);/q;+1/p-1
    • InChI Key: ZZPUYRHMTGOTEU-UHFFFAOYSA-M
    • SMILES: P(CCCN(C=O)O)(=O)(O)[O-].[Na+]

Computed Properties

  • Exact Mass: 159.99000
  • Monoisotopic Mass: 183.029659
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 12
  • Rotatable Bond Count: 5
  • Complexity: 166
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Topological Polar Surface Area: 98.1
  • XLogP3: -2.239

Experimental Properties

  • Melting Point: 189-191°C
  • Boiling Point: 463.7°C at 760 mmHg
  • Flash Point: 234.3°C
  • Stability/Shelf Life: Hygroscopic
  • PSA: 82.70000
  • LogP: 0.34710

Fosmidomycin sodium salt Security Information

  • Hazard Category Code: 34
  • Safety Instruction: 26-27-36/37/39-45
  • Hazardous Material Identification: C
  • Storage Condition:Please store the product under the recommended conditions in the Certificate of Analysis.

Fosmidomycin sodium salt Customs Data

  • HS CODE:2931900090
  • Customs Data:

    China Customs Code:

    2931900090

    Overview:

    2931900090. Other organic-Inorganic compound. VAT:17.0%. Tax refund rate:13.0%. Regulatory conditions:AB(Customs clearance form for Inbound Goods,Customs clearance form for outbound goods). MFN tariff:6.5%. general tariff:30.0%

    Summary:

    2931900090. other organo-inorganic compounds. VAT:17.0%. Tax rebate rate:13.0%. Supervision conditions:AB(certificate of inspection for goods inward,certificate of inspection for goods outward). MFN tariff:6.5%. General tariff:30.0%

Fosmidomycin sodium salt Pricemore >>

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Fosmidomycin sodium salt Production Method

Fosmidomycin sodium salt Related Literature

Additional information on Fosmidomycin sodium salt

Introduction to Fosmidomycin Sodium Salt (CAS No: 66508-37-0) in Modern Pharmaceutical Research

Fosmidomycin sodium salt, identified by the Chemical Abstracts Service Number (CAS No) 66508-37-0, is a notable compound with significant applications in the field of pharmaceutical chemistry and biochemistry. This compound, derived from the fermentation of *Actinosynnema pretiosum*, has garnered considerable attention due to its unique mechanism of action and potential in addressing critical therapeutic challenges. The sodium salt form enhances its solubility and bioavailability, making it a valuable candidate for further development in drug formulations.

The primary pharmacological interest in Fosmidomycin sodium salt lies in its potent inhibitory effects against bacterial glycyltransferases, which are essential enzymes in the bacterial folate biosynthesis pathway. By specifically targeting and inhibiting these enzymes, fosmidomycin disrupts the synthesis of dihydropteroate, a crucial intermediate in folate production. This mechanism distinguishes it from traditional antibiotics that often target different pathways or bacterial structures, offering a novel approach to combat resistant bacterial strains.

Recent advancements in the study of Fosmidomycin sodium salt have highlighted its potential in treating infections caused by Gram-positive and some Gram-negative bacteria. Notably, research has demonstrated its efficacy against methicillin-resistant *Staphylococcus aureus* (MRSA) and other multidrug-resistant organisms. The compound's ability to inhibit bacterial growth without significant toxicity to human cells makes it an attractive option for developing new antibiotics. Furthermore, its mode of action does not overlap with existing antibiotics, reducing the risk of cross-resistance development.

In clinical trials, Fosmidomycin sodium salt has shown promising results in treating skin and soft tissue infections, as well as urinary tract infections. The sodium salt formulation has improved patient compliance due to better oral bioavailability and reduced gastrointestinal side effects compared to earlier versions of the compound. These findings have prompted further investigation into its use as a monotherapy or in combination with other antibiotics to enhance therapeutic outcomes.

The chemical structure of Fosmidomycin sodium salt (CAS No: 66508-37-0) features a unique bicyclic lactone ring system combined with an N-glycosidic linkage. This structure contributes to its high affinity for bacterial glycyltransferases while minimizing interactions with human enzymes. Structural biology studies have provided detailed insights into how fosmidomycin binds to its target enzyme, offering valuable information for rational drug design and the development of derivatives with improved properties.

One of the most compelling aspects of Fosmidomycin sodium salt is its potential role in addressing antibiotic resistance. As bacterial resistance to conventional antibiotics continues to rise, there is an urgent need for novel therapeutic agents that can overcome these challenges. Fosmidomycin's unique mechanism of action provides a promising alternative for treating infections caused by resistant bacteria. Additionally, its natural origin as a fermentation product aligns with the growing trend toward biopharmaceuticals derived from microbial sources.

Research is also exploring the use of Fosmidomycin sodium salt in combination therapies to enhance efficacy and reduce the likelihood of resistance development. For instance, studies have investigated its synergistic effects when used alongside quinolones or beta-lactam antibiotics. These combination approaches could provide clinicians with more effective treatment options for complex infections while minimizing the reliance on single-agent therapies.

The synthesis and optimization of Fosmidomycin sodium salt remain active areas of research. Advances in synthetic chemistry have enabled more efficient production methods, reducing costs and improving scalability for pharmaceutical applications. Additionally, efforts are underway to develop semi-synthetic derivatives that retain the desirable pharmacological properties of fosmidomycin while enhancing stability, solubility, or target specificity.

The safety profile of Fosmidomycin sodium salt has been extensively evaluated through preclinical and clinical studies. While generally well-tolerated, some side effects such as gastrointestinal discomfort have been reported at higher doses. However, these effects are often mild and transient, making fosmidomycin a favorable candidate for broad therapeutic use. Ongoing research aims to further refine dosing regimens and formulations to maximize efficacy while minimizing adverse effects.

In conclusion, Fosmidomycin sodium salt (CAS No: 66508-37-0) represents a significant advancement in antibiotic development due to its unique mechanism of action against bacterial glycyltransferases and its potential to address antibiotic resistance challenges. Its natural origin, combined with recent breakthroughs in synthetic chemistry and clinical applications, positions it as a cornerstone in modern pharmaceutical research. As further studies continue to uncover its full therapeutic potential, fosmidomycin-based therapies are poised to play a crucial role in combating infectious diseases worldwide.

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