Details of the Drug

General Information of Drug (ID: DMVGPMX)

Drug Name
Fosfomycin
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
Indication
Disease Entry ICD 11 Status REF
Bacterial infection 1A00-1C4Z Approved [1]
Urinary tract infection GC08 Approved [2]
Therapeutic Class
Antibiotics
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 138.06
Logarithm of the Partition Coefficient (xlogp) -1.4
Rotatable Bond Count (rotbonds) 1
Hydrogen Bond Donor Count (hbonddonor) 2
Hydrogen Bond Acceptor Count (hbondacc) 4
ADMET Property
Absorption Tmax
The time to maximum plasma concentration (Tmax) is 1.5 h [3]
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 3: high solubility and low permeability [4]
Bioavailability
The bioavailability of drug is 55% [3]
Clearance
The clearance of drug is 17 +/- 4.7 L/h [5]
Elimination
82% of drug is excreted from urine in the unchanged form [4]
Half-life
The concentration or amount of drug in body reduced by one-half in 5.7 (?2.8) hours [6]
Metabolism
The drug is not metabolised [7]
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 192.901 micromolar/kg/day [8]
Unbound Fraction
The unbound fraction of drug in plasma is 1% [9]
Vd
The volume of distribution (Vd) of drug is 0.3 L/kg [7]
Water Solubility
The ability of drug to dissolve in water is measured as 50 mg/mL [4]
Chemical Identifiers
Formula
C3H7O4P
IUPAC Name
[(2R,3S)-3-methyloxiran-2-yl]phosphonic acid
Canonical SMILES
C[C@H]1[C@H](O1)P(=O)(O)O
InChI
InChI=1S/C3H7O4P/c1-2-3(7-2)8(4,5)6/h2-3H,1H3,(H2,4,5,6)/t2-,3+/m0/s1
InChIKey
YMDXZJFXQJVXBF-STHAYSLISA-N
Cross-matching ID
PubChem CID
446987
ChEBI ID
CHEBI:28915
CAS Number
23155-02-4
DrugBank ID
DB00828
TTD ID
D01GYT
INTEDE ID
DR0749
Combinatorial Drugs (CBD) Click to Jump to the Detailed CBD Information of This Drug
Repurposed Drugs (RPD) Click to Jump to the Detailed RPD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Bacterial UDP-N-acetylglucosamine carboxyvinyltransferase (Bact murA) TTICX3S MURA_ECOLI Inhibitor [10]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Glutathione S-transferase alpha-1 (GSTA1)
Main DME 		DE4ZHS1 GSTA1_HUMAN Substrate [11]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
C-reactive protein (CRP) OT0RFT8F CRP_HUMAN Gene/Protein Processing [12]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 Has nature already identified all useful antibacterial targets Curr Opin Microbiol. 2008 Oct;11(5):387-92.
2 Fosfomycin FDA Label
3 Wen YG, Shang DW, Xie HZ, Wang XP, Ni XJ, Zhang M, Lu W, Qiu C, Liu X, Li FF, Li X, Luo FT: Population pharmacokinetics of blonanserin in Chinese healthy volunteers and the effect of the food intake. Hum Psychopharmacol. 2013 Mar;28(2):134-41. doi: 10.1002/hup.2290. Epub 2013 Feb 18.
4 BDDCS applied to over 900 drugs
5 Wenzler E, Ellis-Grosse EJ, Rodvold KA: Pharmacokinetics, Safety, and Tolerability of Single-Dose Intravenous (ZTI-01) and Oral Fosfomycin in Healthy Volunteers. Antimicrob Agents Chemother. 2017 Aug 24;61(9). pii: AAC.00775-17. doi: 10.1128/AAC.00775-17. Print 2017 Sep.
6 FDA Approved Drug Products: Monurol (fosfomycin tromethamine)
7 Elroby SA, Makki MS, Sobahi TR, Hilal RH: Toward the understanding of the metabolism of levodopa I. DFT investigation of the equilibrium geometries, acid-base properties and levodopa-water complexes. Int J Mol Sci. 2012;13(4):4321-39. doi: 10.3390/ijms13044321. Epub 2012 Apr 2.
8 Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
9 Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
10 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.
11 Formation of an adduct between fosfomycin and glutathione: a new mechanism of antibiotic resistance in bacteria. Antimicrob Agents Chemother. 1988 Oct;32(10):1552-6.
12 [Successful treatment of MRSA-associated glomerulonephritis with antibiotic therapy]. Nihon Jinzo Gakkai Shi. 2003;45(1):37-41.