Fosfomycin
Identification
- Name
- Fosfomycin
- Accession Number
- DB00828
- Description
An antibiotic produced by Streptomyces fradiae.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Fosfomycin (DB00828)
- Weight
- Average: 138.059
Monoisotopic: 138.008195224 - Chemical Formula
- C3H7O4P
- Synonyms
- (-)-(1R,2S)-(1,2-Epoxypropyl)phosphonic acid
- (1R,2S)-epoxypropylphosphonic acid
- (2R-cis)-(3-Methyloxiranyl)phosphonic acid
- 1R-cis-(1,2-epoxypropyl)phosphonic acid
- cis-(1R,2S)-epoxypropylphosphonic acid
- FCM
- Fosfocina
- Fosfomicina
- Fosfomycin
- Fosfomycine
- Fosfomycinum
- L-cis-1,2-epoxypropylphosphonic acid
- Phosphomycin
- Phosphonemycin
- Phosphonomycin
- External IDs
- J01XX01
Pharmacology
- Indication
For the treatment of uncomplicated urinary tract infections (acute cystitis) in women due to susceptible strains of Escherichia coli and Enterococcus faecalis.
- Associated Conditions
- Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
Learn More- Pharmacodynamics
Fosfomycin is a broad spectrum antibiotic that concentrates in kidney and bladder and is used to treat uncomplicated urinary tract infections. Fosfomycin also reduces nephrotoxicity and ototoxicity of platinum-containing anti-tumor agents.
- Mechanism of action
Fosfomycin is a phosphoenolpyruvate analogue produced by Streptomyces that irreversibly inhibits enolpyruvate transferase (MurA), which prevents the formation of N-acetylmuramic acid, an essential element of the peptidoglycan cell wall.
Target Actions Organism AUDP-N-acetylglucosamine 1-carboxyvinyltransferase inhibitorEscherichia coli (strain K12) - Absorption
Fosfomycin tromethamine is rapidly absorbed following oral administration and converted to fosfomycin. Oral bioavailability under fasting conditions is 37%. When given with food, oral bioavailability is reduced to 30%
- Volume of distribution
- 136.1 ±44.1 L
- Protein binding
0% (not bound to plasma proteins)
- Metabolism
No transformation, excreted unchanged
- Route of elimination
Fosfomycin is excreted unchanged in both urine and feces.
- Half-life
5.7 (± 2.8) hours. The elimination half-life is 40 hours in anuric patients undergoing hemodialysis.
- Clearance
- 16.9 +/- 3.5 L/hr
- Adverse Effects
Learn about our commercial Adverse Effects data.
Learn More- Toxicity
LD50>5 g/kg (rats). Side effects may include diarrhea
- Affected organisms
- Enteric bacteria and other eubacteria
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Unlock Additional DataAbacavir Fosfomycin may decrease the excretion rate of Abacavir which could result in a higher serum level. Acarbose Acarbose may decrease the excretion rate of Fosfomycin which could result in a higher serum level. Aceclofenac Aceclofenac may decrease the excretion rate of Fosfomycin which could result in a higher serum level. Acemetacin Acemetacin may decrease the excretion rate of Fosfomycin which could result in a higher serum level. Acenocoumarol The risk or severity of bleeding can be increased when Fosfomycin is combined with Acenocoumarol. Acetaminophen Acetaminophen may decrease the excretion rate of Fosfomycin which could result in a higher serum level. Acetazolamide Acetazolamide may increase the excretion rate of Fosfomycin which could result in a lower serum level and potentially a reduction in efficacy. Acetylsalicylic acid Acetylsalicylic acid may decrease the excretion rate of Fosfomycin which could result in a higher serum level. Aclidinium Fosfomycin may decrease the excretion rate of Aclidinium which could result in a higher serum level. Acrivastine Fosfomycin may decrease the excretion rate of Acrivastine which could result in a higher serum level. Additional Data Available- Extended DescriptionExtended DescriptionAvailable for Purchase
Extended description of the mechanism of action and particular properties of each drug interaction.
Learn more - SeveritySeverityAvailable for Purchase
A severity rating for each drug interaction, from minor to major.
Learn more - Evidence LevelEvidence LevelAvailable for Purchase
A rating for the strength of the evidence supporting each drug interaction.
Learn more - ActionActionAvailable for Purchase
An effect category for each drug interaction. Know how this interaction affects the subject drug.
Learn more
- Food Interactions
- Take with or without food. The absorption is unaffected by food.
Products
- Product Ingredients
Ingredient UNII CAS InChI Key Fosfomycin calcium monohydrate T330QG2NYS 26469-67-0 MSHCINMVQZDXTG-JSTPYPERSA-N Fosfomycin disodium 97MMO19FNO 26016-99-9 QZIQJIKUVJMTDG-UHFFFAOYSA-L Fosfomycin tromethamine 7FXW6U30GY 78964-85-9 QZJIMDIBFFHQDW-LMLSDSMGSA-N - International/Other Brands
- Veramina (Roux-Ocefa)
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Unlock Additional DataFosfomycin Powder for Oral Solution Powder, for solution Oral Endo Ventures Ltd Not applicable Not applicable Canada 
Ivozfo Powder, for solution Intravenous Verity Pharmaceuticals Inc. Not applicable Not applicable Canada Ivozfo Powder, for solution Intravenous Verity Pharmaceuticals Inc. Not applicable Not applicable Canada Ivozfo Powder, for solution Intravenous Verity Pharmaceuticals Inc. 2020-02-12 Not applicable Canada Monurol Powder 3 g/1 Oral Allergan, Inc. 1996-12-19 Not applicable US 
Monurol Powder, for solution 3 g Oral Paladin Labs Inc 1999-09-15 Not applicable Canada Additional Data Available- Application NumberApplication NumberAvailable for Purchase
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct CodeAvailable for Purchase
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
Learn more
- Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Unlock Additional DataFosfomycin Tromethamine Powder 3 g/1 Oral Xiromed Llc 2020-10-06 Not applicable US Jamp-fosfomycin Powder, for solution Oral Jamp Pharma Corporation 2018-08-02 Not applicable Canada Additional Data Available- Application NumberApplication NumberAvailable for Purchase
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct CodeAvailable for Purchase
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
Learn more
Categories
- ATC Codes
- J01XX01 — Fosfomycin
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as organic phosphonic acids. These are organic compounds containing phosphonic acid.
- Kingdom
- Organic compounds
- Super Class
- Organic acids and derivatives
- Class
- Organic phosphonic acids and derivatives
- Sub Class
- Organic phosphonic acids
- Direct Parent
- Organic phosphonic acids
- Alternative Parents
- Oxacyclic compounds / Epoxides / Organopnictogen compounds / Organophosphorus compounds / Organooxygen compounds / Organic oxides / Hydrocarbon derivatives
- Substituents
- Aliphatic heteromonocyclic compound / Hydrocarbon derivative / Organic oxide / Organic oxygen compound / Organoheterocyclic compound / Organooxygen compound / Organophosphonic acid / Organophosphorus compound / Organopnictogen compound / Oxacycle
- Molecular Framework
- Aliphatic heteromonocyclic compounds
- External Descriptors
- epoxide, phosphonic acids (CHEBI:28915) / Aliphatic compounds (C06454)
Chemical Identifiers
- UNII
- 2N81MY12TE
- CAS number
- 23155-02-4
- InChI Key
- YMDXZJFXQJVXBF-STHAYSLISA-N
- InChI
- InChI=1S/C3H7O4P/c1-2-3(7-2)8(4,5)6/h2-3H,1H3,(H2,4,5,6)/t2-,3+/m0/s1
- IUPAC Name
- [(2R,3S)-3-methyloxiran-2-yl]phosphonic acid
- SMILES
- C[C@@H]1O[C@@H]1P(O)(O)=O
References
- Synthesis Reference
Graziano Castaldi, Claudio Giordano, "Process for the preparation of intermediates for the synthesis of fosfomycin." U.S. Patent US4937367, issued March, 1972.
US4937367- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0014966
- KEGG Drug
- D04253
- KEGG Compound
- C06454
- PubChem Compound
- 446987
- PubChem Substance
- 46506665
- ChemSpider
- 394204
- BindingDB
- 50024894
- 4550
- ChEBI
- 28915
- ChEMBL
- CHEMBL1757
- ZINC
- ZINC000001530427
- Therapeutic Targets Database
- DAP000767
- PharmGKB
- PA164748039
- PDBe Ligand
- FCN
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- PDRhealth
- PDRhealth Drug Page
- Wikipedia
- Fosfomycin
- AHFS Codes
- 08:36.00 — Urinary Anti-infectives
- PDB Entries
- 1lqp / 2bnn / 3d41 / 3quo / 4ir0 / 4jd1 / 4jh3 / 4jh4 / 4jh5 / 4jh6 … show 2 more
- FDA label
- Download (267 KB)
- MSDS
- Download (61.1 KB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Completed Prevention Allograft Rejection / Asymptomatic Bacteriuria / Hospitalizations / Microbiologic Resistance / Urinary Tract Infection 1 4 Completed Prevention Asymptomatic Bacteriuria / Urinary Tract Infection 1 4 Completed Prevention Urinary Tract Infection 1 4 Completed Treatment Infective Endocarditis 1 4 Completed Treatment Urinary Tract Infection 2 4 Recruiting Prevention Complications / Infection / Prostate Cancer 1 4 Recruiting Treatment Prosthetic Joint Infection 1 4 Terminated Treatment Urinary Tract Infection 1 4 Unknown Status Treatment Cystitis / Urinary Tract Infection 1 3 Completed Treatment Gonorrhea 1
Pharmacoeconomics
- Manufacturers
- Zambon spa italy
- Packagers
- Forest Pharmaceuticals
- Zambon Ltd.
- Dosage Forms
Form Route Strength Powder Oral 2 g Granule Oral 3 g Injection, powder, for solution Parenteral 40 mg/ml Tablet, effervescent 3 g Capsule 500 MG Tablet 1 G Injection, powder, for solution 2 g Injection, powder, for solution Intravenous 8 g Injection, powder, for solution Intravenous 1 g Injection, powder, for solution Intravenous 4 g Injection, powder, for solution Parenteral 4 g Injection, powder, for solution Parenteral 8 g Granule, for solution Oral 3 g Injection, powder, lyophilized, for solution Intravenous 1 g Injection, powder, lyophilized, for solution Intravenous 4 g Injection, powder, for solution 1 g Injection, powder, for solution 4 g Tablet 500 mg Powder, for suspension Oral 3 g Powder, for solution Parenteral 40 MG/ML Powder, for solution Intravenous Powder, for solution Oral Granule, for solution Oral 2 G Powder Oral 3 g/1 Powder, for solution Oral 3 g Capsule, coated Oral 500 mg Powder Oral 3 g - Prices
Unit description Cost Unit Monurol 3 gm Packets 50.87USD packet Monurol 3 gm sachet 47.07USD each Viramune 200 mg tablet 9.48USD tablet DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 94 °C PhysProp water solubility 50 mg/mL (Sodium salt) Not Available logP -1.6 Not Available - Predicted Properties
Property Value Source Water Solubility 46.9 mg/mL ALOGPS logP -0.86 ALOGPS logP -0.74 ChemAxon logS -0.47 ALOGPS pKa (Strongest Acidic) 1.25 ChemAxon pKa (Strongest Basic) -4.3 ChemAxon Physiological Charge -1 ChemAxon Hydrogen Acceptor Count 4 ChemAxon Hydrogen Donor Count 2 ChemAxon Polar Surface Area 70.06 Å2 ChemAxon Rotatable Bond Count 1 ChemAxon Refractivity 25.87 m3·mol-1 ChemAxon Polarizability 10.8 Å3 ChemAxon Number of Rings 1 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter No ChemAxon Veber's Rule No ChemAxon MDDR-like Rule No ChemAxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption - 0.5 Blood Brain Barrier + 0.9382 Caco-2 permeable - 0.6652 P-glycoprotein substrate Non-substrate 0.7234 P-glycoprotein inhibitor I Non-inhibitor 0.8938 P-glycoprotein inhibitor II Non-inhibitor 0.9878 Renal organic cation transporter Non-inhibitor 0.9505 CYP450 2C9 substrate Non-substrate 0.7514 CYP450 2D6 substrate Non-substrate 0.8332 CYP450 3A4 substrate Non-substrate 0.6513 CYP450 1A2 substrate Non-inhibitor 0.8492 CYP450 2C9 inhibitor Non-inhibitor 0.8551 CYP450 2D6 inhibitor Non-inhibitor 0.9202 CYP450 2C19 inhibitor Non-inhibitor 0.8016 CYP450 3A4 inhibitor Non-inhibitor 0.9624 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.944 Ames test Non AMES toxic 0.6575 Carcinogenicity Non-carcinogens 0.6059 Biodegradation Not ready biodegradable 0.894 Rat acute toxicity 2.5802 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9456 hERG inhibition (predictor II) Non-inhibitor 0.9491
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key GC-MS Spectrum - GC-MS (2 TMS) GC-MS splash10-03di-2980000000-005d5b96a1e9219362d0 Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available GC-MS Spectrum - GC-MS GC-MS splash10-03di-2980000000-005d5b96a1e9219362d0 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
- Kind
- Protein
- Organism
- Escherichia coli (strain K12)
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Udp-n-acetylglucosamine 1-carboxyvinyltransferase activity
- Specific Function
- Cell wall formation. Adds enolpyruvyl to UDP-N-acetylglucosamine. Target for the antibiotic fosfomycin.
- Gene Name
- murA
- Uniprot ID
- P0A749
- Uniprot Name
- UDP-N-acetylglucosamine 1-carboxyvinyltransferase
- Molecular Weight
- 44817.24 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
- Kim DH, Lees WJ, Kempsell KE, Lane WS, Duncan K, Walsh CT: Characterization of a Cys115 to Asp substitution in the Escherichia coli cell wall biosynthetic enzyme UDP-GlcNAc enolpyruvyl transferase (MurA) that confers resistance to inactivation by the antibiotic fosfomycin. Biochemistry. 1996 Apr 16;35(15):4923-8. [PubMed:8664284]
- Eschenburg S, Priestman M, Schonbrunn E: 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. Epub 2004 Nov 5. [PubMed:15531591]
- McCoy AJ, Sandlin RC, Maurelli AT: 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. [PubMed:12562791]
- Brown ED, Vivas EI, Walsh CT, Kolter R: MurA (MurZ), the enzyme that catalyzes the first committed step in peptidoglycan biosynthesis, is essential in Escherichia coli. J Bacteriol. 1995 Jul;177(14):4194-7. [PubMed:7608103]
- Samland AK, Amrhein N, Macheroux P: 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. [PubMed:10529188]
Drug created on June 13, 2005 07:24 / Updated on January 18, 2021 16:18