fosfomycin ๐Ÿถ Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
antibiotics, produced by Streptomyces strains 1243 23155-02-4

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • fosfomycin trometamol
  • fosfomycin
  • fosfomycin tromethamine
An antibiotic produced by Streptomyces fradiae.
  • Molecular weight: 138.06
  • Formula: C3H7O4P
  • CLOGP: -0.03
  • LIPINSKI: 0
  • HAC: 4
  • HDO: 2
  • TPSA: 70.06
  • ALOGS: -0.47
  • ROTB: 1

  • Status: OFP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
3 g O
8 g P

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 3 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 50 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 82 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 192.90 ยตM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 31 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 0.32 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 2 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 1 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 1.90 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
Dec. 19, 1996 FDA ZAMBON SPA

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Drug reaction with eosinophilia and systemic symptoms 45.23 21.63 26 3191 28398 50573509
Respiratory alkalosis 35.70 21.63 11 3206 2508 50599399
Mechanical urticaria 32.41 21.63 7 3210 390 50601517
Enterococcal infection 31.52 21.63 13 3204 6885 50595022
Umbilical cord around neck 31.02 21.63 6 3211 192 50601715
Gastroenteritis clostridial 29.99 21.63 7 3210 555 50601352
Urosepsis 29.65 21.63 16 3201 15449 50586458
Pathogen resistance 26.94 21.63 11 3206 5678 50596229
Foetal heart rate decreased 26.43 21.63 5 3212 142 50601765
Wrist deformity 26.06 21.63 8 3209 1801 50600106
Hyponatraemia 25.55 21.63 31 3186 96108 50505799
Serotonin syndrome 25.09 21.63 17 3200 24696 50577211
Drug interaction 24.82 21.63 45 3172 199576 50402331
Epstein-Barr virus test positive 24.79 21.63 6 3211 555 50601352
Stevens-Johnson syndrome 24.59 21.63 16 3201 21736 50580171
Hepatocellular injury 24.34 21.63 17 3200 25930 50575977
Purpura 24.01 21.63 12 3205 9899 50592008
Skin test positive 23.87 21.63 6 3211 649 50601258
Meconium in amniotic fluid 23.78 21.63 5 3212 245 50601662
Maternal exposure before pregnancy 23.73 21.63 10 3207 5587 50596320
Atrial septal defect 22.53 21.63 10 3207 6331 50595576
Enterocolitis 22.19 21.63 10 3207 6557 50595350
Leukocoria 22.09 21.63 3 3214 8 50601899
Brain abscess 21.95 21.63 7 3210 1784 50600123

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Pathogen resistance 132.24 35.41 36 1219 8080 29565192
Drug resistance 58.87 35.41 25 1230 21515 29551757
Klebsiella infection 39.65 35.41 14 1241 7335 29565937

FDA Adverse Event Reporting System (Geriatric)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Pathogen resistance 127.47 21.53 42 3868 12501 64482321
Drug resistance 70.95 21.53 37 3873 35065 64459757
Klebsiella infection 38.77 21.53 18 3892 13263 64481559
Enterococcal infection 38.03 21.53 18 3892 13848 64480974
Acute kidney injury 36.01 21.53 82 3828 449158 64045664
Drug reaction with eosinophilia and systemic symptoms 35.35 21.53 28 3882 54189 64440633
Drug level increased 29.75 21.53 21 3889 34175 64460647
Abortion spontaneous 28.00 21.53 18 3892 25125 64469697
Streptococcal infection 27.78 21.53 12 3898 7467 64487355
Mechanical urticaria 27.76 21.53 6 3904 352 64494470
Respiratory alkalosis 27.70 21.53 10 3900 3887 64490935
Hyponatraemia 27.33 21.53 39 3871 148300 64346522
Urinary tract infection 25.20 21.53 48 3862 231548 64263274
Maternal exposure before pregnancy 24.99 21.53 9 3901 3474 64491348
Purpura non-thrombocytopenic 24.74 21.53 5 3905 211 64494611
Gastroenteritis clostridial 23.10 21.53 6 3904 776 64494046
Urosepsis 22.60 21.53 15 3895 22079 64472743
Leukocoria 22.24 21.53 3 3907 8 64494814
Epstein-Barr virus test positive 21.65 21.53 6 3904 992 64493830
Epileptic encephalopathy 21.55 21.53 5 3905 405 64494417

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

SourceCodeDescription
ATC J01XX01 ANTIINFECTIVES FOR SYSTEMIC USE
ANTIBACTERIALS FOR SYSTEMIC USE
OTHER ANTIBACTERIALS
Other antibacterials
MeSH PA D000900 Anti-Bacterial Agents
MeSH PA D000890 Anti-Infective Agents
CHEBI has role CHEBI:33281 antibiotics
CHEBI has role CHEBI:78379 EC 2.5.1.7 inhibitors

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Urinary tract infectious disease indication 68566005
Escherichia coli urinary tract infection indication 301011002
Enterococcus Urinary Tract Infection indication
Kidney disease contraindication 90708001 DOID:557
Pseudomembranous enterocolitis contraindication 397683000




๐Ÿถ Veterinary Drug Use

None

๐Ÿถ Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 0.54 acidic
pKa2 5.59 acidic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
UDP-N-acetylglucosamine 1-carboxyvinyltransferase Enzyme INHIBITOR IC50 7 CHEMBL CHEMBL
UDP-N-acetylglucosamine 1-carboxyvinyltransferase 1 Enzyme WOMBAT-PK
UDP-N-acetylglucosamine 1-carboxyvinyltransferase 2 Enzyme WOMBAT-PK
UDP-N-acetylglucosamine 1-carboxyvinyltransferase Enzyme IC50 4.98 CHEMBL

External reference:

IDSource
4024047 VUID
N0000022052 NUI
D00925 KEGG_DRUG
78964-85-9 SECONDARY_CAS_RN
4021007 VANDF
4024047 VANDF
C0016610 UMLSCUI
CHEBI:62419 CHEBI
FCN PDB_CHEM_ID
CHEMBL1757 ChEMBL_ID
DB00828 DRUGBANK_ID
CHEMBL1200331 ChEMBL_ID
D005578 MESH_DESCRIPTOR_UI
446987 PUBCHEM_CID
3014 INN_ID
10813 IUPHAR_LIGAND_ID
2N81MY12TE UNII
142135 RXNORM
29490 MMSL
340066 MMSL
4765 MMSL
d04106 MMSL
004467 NDDF
004468 NDDF
108720006 SNOMEDCT_US
108721005 SNOMEDCT_US
372534005 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Monurol HUMAN PRESCRIPTION DRUG LABEL 1 0456-4300 POWDER 3 g ORAL NDA 22 sections
FOSFOMYCIN TROMETHAMINE HUMAN PRESCRIPTION DRUG LABEL 1 50090-5826 POWDER 3 g ORAL ANDA 20 sections
Fosfomycin Tromethamine Human Prescription Drug Label 1 67877-749 GRANULE, FOR SOLUTION 3 g ORAL ANDA 21 sections
FOSFOMYCIN TROMETHAMINE HUMAN PRESCRIPTION DRUG LABEL 1 69097-579 GRANULE, FOR SOLUTION 3 g ORAL ANDA 18 sections
FOSFOMYCIN TROMETHAMINE HUMAN PRESCRIPTION DRUG LABEL 1 70700-268 POWDER 3 g ORAL ANDA 20 sections
Fosfomycin Tromethamine HUMAN PRESCRIPTION DRUG LABEL 1 82036-4274 POWDER 3 g ORAL NDA authorized generic 22 sections