Drug Information
Drug General Information | Top | |||
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Drug ID |
D01GYT
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Former ID |
DAP000767
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Drug Name |
Fosfomycin
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Synonyms |
FCM; Phosphomycin; Phosphonemycin; Phosphonomycin; Priomicina; Veramina; Disodium fosfomycin; Disodium phosphonomycin; Fosfocina disodium salt; Fosfomycin disodium; Fosfomycin disodium salt; Fosfomycin sodium; Fosfomycin sodium salt; Fosmicin S; Phosphomycin disodium salt; Phosphonomycin disodium salt; Phosphonomycin sodium; Sodium fosfomycin; MK 955; FOM-Na; Fosfomycin sodium (JP15); Fosmicin S (TN); Fosfomycin (USAN/INN); L-cis-1,2-epoxypropylphosphonic acid; Disodium (1R,2S)-(1,2-epoxypropyl)phosphonate; Disodium[(2r,3s)-3-methyloxiran-2-yl]phosphonate; [(2R,3S)-3-methyloxiran-2-yl]phosphonic acid; Phosphonic acid, (3-methyloxiranyl)-, disodium salt, (2R-cis)-(9CI); (-)-(1R,2S)-(1,2-Epoxypropyl)phosphonicacid; (1R,2S)(-)-(1,2-Epoxypropyl)phosphonic acid disodium salt; (1R,2S)-(1,2-Epoxypropyl)phosphonic acid; (1R,2S)-epoxypropylphosphonate; (1R,2S)-epoxypropylphosphonic acid; (2R-cis)-(3-Methyloxiranyl)phosphonic acid disodium salt
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Drug Type |
Small molecular drug
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Indication | Bacterial infection [ICD-11: 1A00-1C4Z; ICD-10: A00-B99] | Approved | [1] | |
Therapeutic Class |
Antibiotics
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Structure |
Download2D MOL |
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Formula |
C3H7O4P
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Canonical SMILES |
CC1C(O1)P(=O)(O)O
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InChI |
1S/C3H7O4P/c1-2-3(7-2)8(4,5)6/h2-3H,1H3,(H2,4,5,6)/t2-,3+/m0/s1
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InChIKey |
YMDXZJFXQJVXBF-STHAYSLISA-N
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CAS Number |
CAS 23155-02-4
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PubChem Compound ID | ||||
PubChem Substance ID |
8687, 606108, 7887444, 8013956, 8027671, 10299988, 14747737, 15297304, 36889264, 46506665, 47206194, 50126493, 50767051, 57404778, 92298260, 93166606, 96099807, 103707732, 103934869, 104637332, 116933583, 124349057, 124385179, 129815629, 134338052, 134994616, 137006369, 140608615, 142971088, 160658318, 160964170, 162008097, 162496683, 164187510, 164187514, 164187516, 164187519, 164187529, 174551524, 175266349, 179150196, 226434285, 241044746, 250133924
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ChEBI ID |
CHEBI:28915
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ADReCS Drug ID | BADD_D00965 ; BADD_D00966 | |||
SuperDrug ATC ID |
J01XX01
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SuperDrug CAS ID |
cas=023155024
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Interaction between the Drug and Microbe | Top | |||
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The Abundace of Studied Microbe(s) Regulated by Drug | ||||
The Order in the Taxonomic Hierarchy of the following Microbe(s): Bacillales | ||||
Studied Microbe: Staphylococcus
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[2] | |||
Hierarchy | ||||
Abundance Change | No significant change | |||
Experimental Species | Human | Experimental Sample | Faeces | |
Disease or Condition | Healthy | |||
Description | The abundance of Staphylococcus was not significantly changed by Fosfomycin. | |||
The Order in the Taxonomic Hierarchy of the following Microbe(s): Bacteroidales | ||||
Studied Microbe: Bacteroides
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[3] | |||
Hierarchy | ||||
Abundance Change | No significant change | |||
Experimental Species | Human | Experimental Sample | Faeces | |
Disease or Condition | Healthy | |||
Description | The abundance of Bacteroides was not significantly changed by Fosfomycin. | |||
The Order in the Taxonomic Hierarchy of the following Microbe(s): Enterobacterales | ||||
Studied Microbe: Enterobacter
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[2] | |||
Hierarchy | ||||
Abundance Change | Increase | |||
Experimental Species | Human | Experimental Sample | Faeces | |
Disease or Condition | Healthy | |||
Description | The abundance of Klebsiella-Enterobacter was increased by Fosfomycin. | |||
Studied Microbe: Escherichia
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[2] | |||
Hierarchy | ||||
Abundance Change | Decrease | |||
Experimental Species | Human | Experimental Sample | Faeces | |
Disease or Condition | Healthy | |||
Description | The abundance of Escherichia was decreased by Fosfomycin. | |||
Studied Microbe: Klebsiella
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[2] | |||
Hierarchy | ||||
Abundance Change | Increase | |||
Experimental Species | Human | Experimental Sample | Faeces | |
Disease or Condition | Healthy | |||
Description | The abundance of Klebsiella-Enterobacter was increased by Fosfomycin. | |||
The Order in the Taxonomic Hierarchy of the following Microbe(s): Eubacteriales | ||||
Studied Microbe: Clostridium difficile
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[3] | |||
Hierarchy | ||||
Abundance Change | No significant change | |||
Experimental Species | Human | Experimental Sample | Faeces | |
Disease or Condition | Healthy | |||
Description | The abundance of Clostridium difficile was not significantly changed by Fosfomycin. | |||
The Order in the Taxonomic Hierarchy of the following Microbe(s): Lactobacillales | ||||
Studied Microbe: Enterococcus
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[3] | |||
Hierarchy | ||||
Abundance Change | Decrease | |||
Experimental Species | Human | Experimental Sample | Faeces | |
Disease or Condition | Healthy | |||
Description | The abundance of Enterococcus was decreased by Fosfomycin. | |||
Studied Microbe: Lactobacillus
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[3] | |||
Hierarchy | ||||
Abundance Change | No significant change | |||
Experimental Species | Human | Experimental Sample | Faeces | |
Disease or Condition | Healthy | |||
Description | The abundance of Lactobacillus was not significantly changed by Fosfomycin. | |||
The Order in the Taxonomic Hierarchy of the following Microbe(s): Saccharomycetales | ||||
Studied Microbe: Candida
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[2] | |||
Hierarchy | ||||
Abundance Change | No significant change | |||
Experimental Species | Human | Experimental Sample | Faeces | |
Disease or Condition | Healthy | |||
Description | The abundance of Candida was not significantly changed by Fosfomycin. |
Drug Resistance Mutation (DRM) | Top | |||
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DRM | DRM Info |
Target and Pathway | Top | |||
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Target(s) | Bacterial UDP-N-acetylglucosamine carboxyvinyltransferase (Bact murA) | Target Info | Inhibitor | [4], [5], [6], [7] |
References | Top | |||
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REF 1 | Has nature already identified all useful antibacterial targets Curr Opin Microbiol. 2008 Oct;11(5):387-92. | |||
REF 2 | Effect of fosfomycin on the fecal microflora of man. Chemotherapy. 1977;23 Suppl 1:117-26. | |||
REF 3 | Influence of fosfomycin on the intestinal and pharyngeal flora of man. Infection. 1991 Jan-Feb;19(1):18-20. | |||
REF 4 | Evidence that the fosfomycin target Cys115 in UDP-N-acetylglucosamine enolpyruvyl transferase (MurA) is essential for product release. J Biol Chem. 2005 Feb 4;280(5):3757-63. | |||
REF 5 | Conditional lethal amber mutations in essential Escherichia coli genes. J Bacteriol. 2004 May;186(9):2673-81. | |||
REF 6 | In vitro and in vivo functional activity of Chlamydia MurA, a UDP-N-acetylglucosamine enolpyruvyl transferase involved in peptidoglycan synthesis and fosfomycin resistance. J Bacteriol. 2003 Feb;185(4):1218-28. | |||
REF 7 | Lysine 22 in UDP-N-acetylglucosamine enolpyruvyl transferase from Enterobacter cloacae is crucial for enzymatic activity and the formation of covalent adducts with the substrate phosphoenolpyruvate and the antibiotic fosfomycin. Biochemistry. 1999 Oct 5;38(40):13162-9. |
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