Fosmidomycin sodium
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MedKoo CAT#: 328004

CAS#: 66508-37-0 (sodium)

Description: Fosmidomycin, also known as FR-31564, is a protein synthesis inhibitor potentially for the treatment of plasmodium falciparum malaria. Fosmidomycin is an antibiotic that was originally isolated from culture broths of bacteria of the genus Streptomyces. It specifically inhibits DXP reductoisomerase, a key enzyme in the non-mevalonate pathway of isoprenoid biosynthesis. It is a structural analogue of 2-C-methyl-D-erythrose 4-phosphate. It inhibits the E. coli enzyme with a KI value of 38 nM, MTB at 80 nM, and the Francisella enzyme at 99 nM.

Chemical Structure

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Fosmidomycin sodium
CAS# 66508-37-0 (sodium)
Instruction

Theoretical Analysis

MedKoo Cat#: 328004
Name: Fosmidomycin sodium
CAS#: 66508-37-0 (sodium)
Chemical Formula: C4H9NNaO5P
Exact Mass: 0.00
Molecular Weight: 205.082
Elemental Analysis: C, 23.43; H, 4.42; N, 6.83; Na, 11.21; O, 39.01; P, 15.10

Price and Availability

Size Price Availability Quantity
5mg USD 350 2 weeks
10mg USD 650 2 weeks
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Related CAS #: 66508-37-0 (sodium); 66508-53-0 (free)  

Synonym: Fosmidomycin sodium; FR-31564; FR 31564; FR31564.

IUPAC/Chemical Name: (3-(Formylhydroxyamino)propyl)phosphonic acid monosodium salt

InChi Key: ZZPUYRHMTGOTEU-UHFFFAOYSA-M

InChi Code: 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

SMILES Code: ON(CCCP([O-])(O)=O)C=O.[Na+]

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info: Related CAS# CAS#66508-37-0 (Fosmidomycin sodium) CAS#66508-53-0 (Fosmidomycin)

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 205.08 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Sooriyaarachchi S, Chofor R, Risseeuw MD, Bergfors T, Pouyez J, Dowd CS, Maes L, Wouters J, Jones TA, Van Calenbergh S, Mowbray SL. Targeting an Aromatic Hotspot in Plasmodium falciparum 1-Deoxy-d-xylulose-5-phosphate Reductoisomerase with β-Arylpropyl Analogues of Fosmidomycin. ChemMedChem. 2016 Sep 20;11(18):2024-36. doi: 10.1002/cmdc.201600249. Epub 2016 Aug 3. PubMed PMID: 27487410.

2: Guggisberg AM, Sundararaman SA, Lanaspa M, Moraleda C, González R, Mayor A, Cisteró P, Hutchinson D, Kremsner PG, Hahn BH, Bassat Q, Odom AR. Whole-Genome Sequencing to Evaluate the Resistance Landscape Following Antimalarial Treatment Failure With Fosmidomycin-Clindamycin. J Infect Dis. 2016 Oct 1;214(7):1085-91. doi: 10.1093/infdis/jiw304. Epub 2016 Jul 20. PubMed PMID: 27443612; PubMed Central PMCID: PMC5021231.

3: Fernandes JF, Lell B, Agnandji ST, Obiang RM, Bassat Q, Kremsner PG, Mordmüller B, Grobusch MP. Fosmidomycin as an antimalarial drug: a meta-analysis of clinical trials. Future Microbiol. 2015;10(8):1375-90. doi: 10.2217/FMB.15.60. Epub 2015 Jul 31. PubMed PMID: 26228767.

4: Armstrong CM, Meyers DJ, Imlay LS, Freel Meyers C, Odom AR. Resistance to the antimicrobial agent fosmidomycin and an FR900098 prodrug through mutations in the deoxyxylulose phosphate reductoisomerase gene (dxr). Antimicrob Agents Chemother. 2015 Sep;59(9):5511-9. doi: 10.1128/AAC.00602-15. Epub 2015 Jun 29. PubMed PMID: 26124156; PubMed Central PMCID: PMC4538460.

5: Faísca Phillips AM, Nogueira F, Murtinheira F, Barros MT. Synthesis and antimalarial evaluation of prodrugs of novel fosmidomycin analogues. Bioorg Med Chem Lett. 2015;25(10):2112-6. doi: 10.1016/j.bmcl.2015.03.077. Epub 2015 Mar 31. PubMed PMID: 25881827.

6: Chofor R, Sooriyaarachchi S, Risseeuw MD, Bergfors T, Pouyez J, Johny C, Haymond A, Everaert A, Dowd CS, Maes L, Coenye T, Alex A, Couch RD, Jones TA, Wouters J, Mowbray SL, Van Calenbergh S. Synthesis and bioactivity of β-substituted fosmidomycin analogues targeting 1-deoxy-D-xylulose-5-phosphate reductoisomerase. J Med Chem. 2015 Apr 9;58(7):2988-3001. doi: 10.1021/jm5014264. Epub 2015 Mar 31. PubMed PMID: 25781377.

7: Gadakh B, Pouyez J, Wouters J, Venkatesham A, Cos P, Van Aerschot A. N-acylated sulfonamide congeners of fosmidomycin lack any inhibitory activity against DXR. Bioorg Med Chem Lett. 2015 Apr 1;25(7):1577-9. doi: 10.1016/j.bmcl.2015.02.006. Epub 2015 Feb 12. PubMed PMID: 25726328.

8: Brücher K, Gräwert T, Konzuch S, Held J, Lienau C, Behrendt C, Illarionov B, Maes L, Bacher A, Wittlin S, Mordmüller B, Fischer M, Kurz T. Prodrugs of reverse fosmidomycin analogues. J Med Chem. 2015 Feb 26;58(4):2025-35. doi: 10.1021/jm5019719. Epub 2015 Feb 12. PubMed PMID: 25633870.

9: Konzuch S, Umeda T, Held J, Hähn S, Brücher K, Lienau C, Behrendt CT, Gräwert T, Bacher A, Illarionov B, Fischer M, Mordmüller B, Tanaka N, Kurz T. Binding modes of reverse fosmidomycin analogs toward the antimalarial target IspC. J Med Chem. 2014 Nov 13;57(21):8827-38. doi: 10.1021/jm500850y. Epub 2014 Oct 20. PubMed PMID: 25254502.

10: Malott RJ, Wu CH, Lee TD, Hird TJ, Dalleska NF, Zlosnik JE, Newman DK, Speert DP. Fosmidomycin decreases membrane hopanoids and potentiates the effects of colistin on Burkholderia multivorans clinical isolates. Antimicrob Agents Chemother. 2014 Sep;58(9):5211-9. doi: 10.1128/AAC.02705-14. Epub 2014 Jun 23. PubMed PMID: 24957830; PubMed Central PMCID: PMC4135860.

11: Kholodar SA, Tombline G, Liu J, Tan Z, Allen CL, Gulick AM, Murkin AS. Alteration of the flexible loop in 1-deoxy-D-xylulose-5-phosphate reductoisomerase boosts enthalpy-driven inhibition by fosmidomycin. Biochemistry. 2014 Jun 3;53(21):3423-31. doi: 10.1021/bi5004074. Epub 2014 May 22. PubMed PMID: 24825256; PubMed Central PMCID: PMC4045324.

12: Zhang XN, Wang ZS, Gao W, Huang LQ. [Effects on Salvia miltiorrhiza hairy roots of tanshinones content accumulation after treated with fosmidomycin]. Zhongguo Zhong Yao Za Zhi. 2013 Dec;38(24):4263-6. Chinese. PubMed PMID: 24791527.

13: Fox DT, Schmidt EN, Tian H, Dhungana S, Valentine MC, Warrington NV, Phillips PD, Finney KB, Cope EK, Leid JG, Testa CA, Koppisch AT. Sub-inhibitory fosmidomycin exposures elicits oxidative stress in Salmonella enterica serovar Typhimurium LT2. PLoS One. 2014 Apr 21;9(4):e95271. doi: 10.1371/journal.pone.0095271. eCollection 2014. PubMed PMID: 24751777; PubMed Central PMCID: PMC3994034.

14: Chofor R, Risseeuw MD, Pouyez J, Johny C, Wouters J, Dowd CS, Couch RD, Van Calenbergh S. Synthetic Fosmidomycin analogues with altered chelating moieties do not inhibit 1-deoxy-d-xylulose 5-phosphate Reductoisomerase or Plasmodium falciparum growth in vitro. Molecules. 2014 Feb 24;19(2):2571-87. doi: 10.3390/molecules19022571. PubMed PMID: 24566322.

15: Hemmerlin A, Tritsch D, Hammann P, Rohmer M, Bach TJ. Profiling of defense responses in Escherichia coli treated with fosmidomycin. Biochimie. 2014 Apr;99:54-62. doi: 10.1016/j.biochi.2013.11.008. Epub 2013 Nov 18. PubMed PMID: 24262605.

16: Kunfermann A, Lienau C, Illarionov B, Held J, Gräwert T, Behrendt CT, Werner P, Hähn S, Eisenreich W, Riederer U, Mordmüller B, Bacher A, Fischer M, Groll M, Kurz T. IspC as target for antiinfective drug discovery: synthesis, enantiomeric separation, and structural biology of fosmidomycin thia isosters. J Med Chem. 2013 Oct 24;56(20):8151-62. doi: 10.1021/jm4012559. Epub 2013 Oct 7. PubMed PMID: 24032981.

17: Sparr C, Purkayastha N, Kolesinska B, Gengenbacher M, Amulic B, Matuschewski K, Seebach D, Kamena F. Improved efficacy of fosmidomycin against Plasmodium and Mycobacterium species by combination with the cell-penetrating peptide octaarginine. Antimicrob Agents Chemother. 2013 Oct;57(10):4689-98. doi: 10.1128/AAC.00427-13. Epub 2013 Jul 15. PubMed PMID: 23856773; PubMed Central PMCID: PMC3811453.

18: Jansson AM, Więckowska A, Björkelid C, Yahiaoui S, Sooriyaarachchi S, Lindh M, Bergfors T, Dharavath S, Desroses M, Suresh S, Andaloussi M, Nikhil R, Sreevalli S, Srinivasa BR, Larhed M, Jones TA, Karlén A, Mowbray SL. DXR inhibition by potent mono- and disubstituted fosmidomycin analogues. J Med Chem. 2013 Aug 8;56(15):6190-9. doi: 10.1021/jm4006498. Epub 2013 Jul 17. PubMed PMID: 23819803.

19: Zinglé C, Kuntz L, Tritsch D, Grosdemange-Billiard C, Rohmer M. Modifications around the hydroxamic acid chelating group of fosmidomycin, an inhibitor of the metalloenzyme 1-deoxyxylulose 5-phosphate reductoisomerase (DXR). Bioorg Med Chem Lett. 2012 Nov 1;22(21):6563-7. doi: 10.1016/j.bmcl.2012.09.021. Epub 2012 Sep 15. PubMed PMID: 23025997.

20: Mackie RS, McKenney ES, van Hoek ML. Resistance of Francisella novicida to fosmidomycin associated with mutations in the glycerol-3-phosphate transporter. Front Microbiol. 2012 Aug 9;3:226. doi: 10.3389/fmicb.2012.00226. eCollection 2012. PubMed PMID: 22905031; PubMed Central PMCID: PMC3417576.