# Fosmidomycin

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Chemical compound

Not to be confused with [Fosfomycin](/source/Fosfomycin).

Pharmaceutical compound

Fosmidomycin Clinical data ATC code none Identifiers IUPAC name 3-[Formyl(hydroxy)amino]propylphosphonic acid CAS Number 66508-53-0 N PubChem CID 572 DrugBank DB02948 Y ChemSpider 555 Y UNII 5829E3D9I9 ChEBI CHEBI:443725 Y ChEMBL ChEMBL203125 Y CompTox Dashboard (EPA) DTXSID70216712 Chemical and physical data Formula C4H10NO5P Molar mass 183.100 g·mol−1 3D model (JSmol) Interactive image SMILES O=P(O)(O)CCCN(O)C=O InChI InChI=1S/C4H10NO5P/c6-4-5(7)2-1-3-11(8,9)10/h4,7H,1-3H2,(H2,8,9,10) Y Key:GJXWDTUCERCKIX-UHFFFAOYSA-N Y NY (what is this?) (verify)

**Fosmidomycin** is an [antibiotic](/source/Antibiotic) that was originally isolated from culture broths of bacteria of the genus *[Streptomyces](/source/Streptomyces)*.[1] It specifically inhibits [DXP reductoisomerase](/source/DXP_reductoisomerase), a key enzyme in the [non-mevalonate pathway](/source/Non-mevalonate_pathway) of [isoprenoid](/source/Isoprenoid) biosynthesis. It is a structural analogue of [2-C-methyl-D-erythrose 4-phosphate](/source/2-C-methyl-D-erythrose_4-phosphate). It inhibits the *[E. coli](/source/E._coli)* enzyme with a KI value of 38 nM (4), [MTB](/source/Magnetotactic_bacteria) at 80 nM, and the *[Francisella](/source/Francisella)* enzyme at 99 nM.[2] Several mutations in the *E. coli* [DXP reductoisomerase](/source/DXP_reductoisomerase) were found to confer resistance to fosmidomycin.[3][4]

## Use in malaria

The discovery of the [non-mevalonate pathway](/source/Non-mevalonate_pathway) in [malaria parasites](/source/Malaria_parasites) has indicated the use of fosmidomycin and other such inhibitors as [antimalarial](/source/Antimalarial_drug) drugs.[5] Indeed, fosmidomycin has been tested in combination treatment with [clindamycin](/source/Clindamycin) for treatment of [malaria](/source/Malaria) with favorable results.[6][7][8] It has been shown that an increase in copy number of the target enzyme ([DXP reductoisomerase](/source/DXP_reductoisomerase)) correlates with *[in vitro](/source/In_vitro)* fosmidomycin resistance in the lethal [malaria](/source/Malaria) parasite, *[Plasmodium falciparum](/source/Plasmodium_falciparum)*.[9]

## References

1. **[^](#cite_ref-1)** Iguchi E, Okuhara M, Kohsaka M, Aoki H, Imanaka H (January 1980). ["Studies on new phosphonic acid antibiotics. II. Taxonomic studies on producing organisms of the phosphonic acid and related compounds"](https://doi.org/10.7164%2Fantibiotics.33.18). *The Journal of Antibiotics*. **33** (1): 19–23. [doi](/source/Doi_(identifier)):[10.7164/antibiotics.33.18](https://doi.org/10.7164%2Fantibiotics.33.18). [PMID](/source/PMID_(identifier)) [7372546](https://pubmed.ncbi.nlm.nih.gov/7372546).

1. **[^](#cite_ref-pmid20011597_2-0)** Jawaid S, Seidle H, Zhou W, Abdirahman H, Abadeer M, Hix JH, van Hoek ML, Couch RD (December 2009). ["Kinetic characterization and phosphoregulation of the Francisella tularensis 1-deoxy-D-xylulose 5-phosphate reductoisomerase (MEP synthase)"](https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2788227). *PLOS ONE*. **4** (12) e8288. [Bibcode](/source/Bibcode_(identifier)):[2009PLoSO...4.8288J](https://ui.adsabs.harvard.edu/abs/2009PLoSO...4.8288J). [doi](/source/Doi_(identifier)):[10.1371/journal.pone.0008288](https://doi.org/10.1371%2Fjournal.pone.0008288). [PMC](/source/PMC_(identifier)) [2788227](https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2788227). [PMID](/source/PMID_(identifier)) [20011597](https://pubmed.ncbi.nlm.nih.gov/20011597).

1. **[^](#cite_ref-3)** Armstrong CM, Meyers DJ, Imlay LS, Freel Meyers C, Odom AR (September 2015). ["Resistance to the antimicrobial agent fosmidomycin and an FR900098 prodrug through mutations in the deoxyxylulose phosphate reductoisomerase gene (dxr)"](https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4538460). *Antimicrobial Agents and Chemotherapy*. **59** (9): 5511–9. [doi](/source/Doi_(identifier)):[10.1128/AAC.00602-15](https://doi.org/10.1128%2FAAC.00602-15). [PMC](/source/PMC_(identifier)) [4538460](https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4538460). [PMID](/source/PMID_(identifier)) [26124156](https://pubmed.ncbi.nlm.nih.gov/26124156).

1. **[^](#cite_ref-4)** Pines G, Oh EJ, Bassalo MC, Choudhury A, Garst AD, Fankhauser RG, Eckert CA, Gill RT (November 2018). ["Genomic Deoxyxylulose Phosphate Reductoisomerase (DXR) Mutations Conferring Resistance to the Antimalarial Drug Fosmidomycin in E. coli"](https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6928208). *ACS Synthetic Biology*. **7** (12): 2824–2832. [doi](/source/Doi_(identifier)):[10.1021/acssynbio.8b00219](https://doi.org/10.1021%2Facssynbio.8b00219). [PMC](/source/PMC_(identifier)) [6928208](https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6928208). [PMID](/source/PMID_(identifier)) [30462485](https://pubmed.ncbi.nlm.nih.gov/30462485).

1. **[^](#cite_ref-Jomaa1999_5-0)** Jomaa H, Wiesner J, Sanderbrand S, Altincicek B, Weidemeyer C, Hintz M, Türbachova I, Eberl M, Zeidler J, Lichtenthaler HK, Soldati D, Beck E (September 1999). "Inhibitors of the nonmevalonate pathway of isoprenoid biosynthesis as antimalarial drugs". *Science*. **285** (5433): 1573–6. [doi](/source/Doi_(identifier)):[10.1126/science.285.5433.1573](https://doi.org/10.1126%2Fscience.285.5433.1573). [PMID](/source/PMID_(identifier)) [10477522](https://pubmed.ncbi.nlm.nih.gov/10477522).

1. **[^](#cite_ref-Borrmann2004_6-0)** Borrmann S, Adegnika AA, Matsiegui PB, Issifou S, Schindler A, Mawili-Mboumba DP, Baranek T, Wiesner J, Jomaa H, Kremsner PG (March 2004). ["Fosmidomycin-clindamycin for Plasmodium falciparum Infections in African children"](https://doi.org/10.1086%2F381785). *The Journal of Infectious Diseases*. **189** (5): 901–8. [doi](/source/Doi_(identifier)):[10.1086/381785](https://doi.org/10.1086%2F381785). [PMID](/source/PMID_(identifier)) [14976608](https://pubmed.ncbi.nlm.nih.gov/14976608).

1. **[^](#cite_ref-Borrmann2006_7-0)** Borrmann S, Lundgren I, Oyakhirome S, Impouma B, Matsiegui PB, Adegnika AA, Issifou S, Kun JF, Hutchinson D, Wiesner J, Jomaa H, Kremsner PG (August 2006). ["Fosmidomycin plus clindamycin for treatment of pediatric patients aged 1 to 14 years with Plasmodium falciparum malaria"](https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1538678). *Antimicrobial Agents and Chemotherapy*. **50** (8): 2713–8. [doi](/source/Doi_(identifier)):[10.1128/AAC.00392-06](https://doi.org/10.1128%2FAAC.00392-06). [PMC](/source/PMC_(identifier)) [1538678](https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1538678). [PMID](/source/PMID_(identifier)) [16870763](https://pubmed.ncbi.nlm.nih.gov/16870763).

1. **[^](#cite_ref-Ruangweerayut2008_8-0)** Ruangweerayut R, Looareesuwan S, Hutchinson D, Chauemung A, Banmairuroi V, Na-Bangchang K (October 2008). ["Assessment of the pharmacokinetics and dynamics of two combination regimens of fosmidomycin-clindamycin in patients with acute uncomplicated falciparum malaria"](https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2600645). *Malaria Journal*. **7** (1) 225. [doi](/source/Doi_(identifier)):[10.1186/1475-2875-7-225](https://doi.org/10.1186%2F1475-2875-7-225). [PMC](/source/PMC_(identifier)) [2600645](https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2600645). [PMID](/source/PMID_(identifier)) [18973702](https://pubmed.ncbi.nlm.nih.gov/18973702).

1. **[^](#cite_ref-Dharia2009_9-0)** Dharia NV, Sidhu AB, Cassera MB, Westenberger SJ, Bopp SE, Eastman RT, Plouffe D, Batalov S, Park DJ, Volkman SK, Wirth DF, Zhou Y, [Fidock DA](/source/David_A._Fidock), Winzeler EA (February 2009). ["Use of high-density tiling microarrays to identify mutations globally and elucidate mechanisms of drug resistance in Plasmodium falciparum"](https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2688282). *Genome Biology*. **10** (2): R21. [doi](/source/Doi_(identifier)):[10.1186/gb-2009-10-2-r21](https://doi.org/10.1186%2Fgb-2009-10-2-r21). [PMC](/source/PMC_(identifier)) [2688282](https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2688282). [PMID](/source/PMID_(identifier)) [19216790](https://pubmed.ncbi.nlm.nih.gov/19216790).

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Adapted from the Wikipedia article [Fosmidomycin](https://en.wikipedia.org/wiki/Fosmidomycin) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Fosmidomycin?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.