Fosmidomycin sodium salt
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| Category | Antibiotics |
| Catalog number | BBF-04360 |
| CAS | 66508-37-0 |
| Molecular Weight | 205.08 |
| Molecular Formula | C4H9NO5P.Na |
| Purity | ≥95% |
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Description
Fosmidomycin is an antimalarial and antibiotic originally isolated from culture broths of bacteria of the genus Streptomyces and has been used as an inhibitor of DOXP reductoisomerase, a key enzyme in the non-mevalonate pathway of isoprenoid biosynthesis.
Specification
| Related CAS | 66508-53-0 (free acid) |
| Synonyms | Antibiotic FR31564; FR31564; P-[3-(formylhydroxyamino)propyl]-phosphonic acid, monosodium salt; (3-(N-Hydroxyformamido)propyl)phosphonic acid sodium salt; Phosphonic acid, (3-(formylhydroxyamino)propyl)-, monosodium salt |
| Storage | Store at -20°C under inert atmosphere |
| IUPAC Name | sodium;3-[formyl(hydroxy)amino]propyl-hydroxyphosphinate |
| Canonical SMILES | C(CN(C=O)O)CP(=O)(O)[O-].[Na+] |
| InChI | 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 |
Properties
| Appearance | White to Beige Solid |
| Boiling Point | 463.7°C at 760 mmHg |
| Melting Point | 78-81°C |
| Solubility | Slightly soluble in Methanol (Heated), Water |
Reference Reading
1. Fosmidomycin for the treatment of malaria
Steffen Borrmann, Hassan Jomaa, Jochen Wiesner Parasitol Res . 2003 Jun;90 Suppl 2:S71-6. doi: 10.1007/s00436-002-0770-9.
In malaria parasites, isoprenoids are synthesised by the mevalonate independent 1-deoxy- D-xylulose 5-phosphate (DOXP) pathway. Fosmidomycin, a natural antibiotic originally developed for the treatment of bacterial infections, represents an inhibitor of DOXP reductoisomerase, an essential enzyme of this pathway. In recent clinical studies it was shown that fosmidomycin is effective in curing uncomplicated Plasmodium falciparum malaria in humans. The treatment was well tolerated and resulted in a fast parasite and fever clearance. However, the high rate of recrudescence precludes the use of fosmidomycin as a monotherapy. In drug combination studies, synergy of fosmidomycin with clindamycin was observed. Clinical studies with a fosmidomycin-clindamycin combination are currently ongoing.
2. Mechanism and inhibition of 1-deoxy-D-xylulose-5-phosphate reductoisomerase
Andrew S Murkin, Svetlana A Kholodar, Kathryn A Manning Bioorg Chem . 2014 Dec;57:171-185. doi: 10.1016/j.bioorg.2014.06.001.
The non-mevalonate or 2-C-methyl-d-erythritol-4-phosphate (MEP) pathway is responsible for generating isoprenoid precursors in plants, protozoa, and bacteria. Because this pathway is absent in humans, its enzymes represent potential targets for the development of herbicides and antibiotics. 1-Deoxy-d-xylulose (DXP) reductoisomerase (DXR) is a particularly attractive target that catalyzes the pathway's first committed step: the sequential isomerization and NADPH-dependent reduction of DXP to MEP. This article provides a comprehensive review of the mechanistic and structural investigations on DXR, including its discovery and validation as a drug target, elucidation of its chemical and kinetic mechanisms, characterization of inhibition by the natural antibiotic fosmidomycin, and identification of structural features that provide the molecular basis for inhibition of and catalysis.
3. Apicoplast Metabolism: Parasite's Achilles' Heel
Harsh Vardhan Singh, Prakasha Kempaiah, Manmeet Rawat, Kavita Kadian, Yash Gupta Curr Top Med Chem . 2018;18(22):1987-1997. doi: 10.2174/1568026619666181130134742.
Malaria continues to impinge heavily on mankind, with five continents still under its clasp. Widespread and rapid emergence of drug resistance in the Plasmodium parasite to current therapies accentuate the quest for novel drug targets and antimalarial compounds. Plasmodium parasites, maintain a non-photosynthetic relict organelle known as Apicoplast. Among the four major pathways of Apicoplast, biosynthesis of isoprenoids via Methylerythritol phosphate (MEP) pathway is the only indispensable function of Apicoplast that occurs during different stages of the malaria parasite. Moreover, the human host lacks MEP pathway. MEP pathway is a validated repertoire of novel antimalarial and antibacterial drug targets. Fosmidomycin, an efficacious antimalarial compound against IspC enzyme of MEP pathway is already in clinical trials as a combination drugs. Exploitation of other enzymes of MEP pathway would provide a much-needed impetus to the antimalarial drug discovery programs for the elimination of malaria. We outline the cardinal features of the MEP pathway enzymes and progress made towards the characterization of new inhibitors.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
