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

Stem definitionDrug idCAS RN
antibiotics, cefalosporanic acid derivatives 550 35607-66-0

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • cefoxitin
  • cefoxitin sodium
  • cephoxitin
  • cefoxitin sodium salt
A semisynthetic cephamycin antibiotic resistant to beta-lactamase.
  • Molecular weight: 427.45
  • Formula: C16H17N3O7S2
  • CLOGP: -0.32
  • LIPINSKI: 0
  • HAC: 10
  • HDO: 3
  • TPSA: 148.26
  • ALOGS: -3.34
  • ROTB: 8

  • Status: OFP

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

Drug dosage:

DoseUnitRoute
6 g P

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 3 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 1000 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 85 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 401.04 ยตM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 0 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 0.17 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 3.60 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.73 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 0.81 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
Oct. 18, 1978 FDA

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
Systemic mastocytosis 112.32 30.01 15 970 145 50603994
Drug reaction with eosinophilia and systemic symptoms 82.82 30.01 28 957 28396 50575743
Catatonia 49.42 30.01 12 973 3724 50600415
Drug resistance 48.60 30.01 17 968 18972 50585167
Pathogen resistance 39.76 30.01 11 974 5678 50598461
Anaphylactic reaction 34.31 30.01 18 967 54037 50550102
Cardiac arrest 31.97 30.01 20 965 83631 50520508

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
Drug reaction with eosinophilia and systemic symptoms 61.23 39.38 24 737 27968 29545798

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
Drug reaction with eosinophilia and systemic symptoms 131.25 28.67 51 1726 54166 64442789
Systemic mastocytosis 98.56 28.67 15 1762 267 64496688
Ototoxicity 54.14 28.67 13 1764 2710 64494245
Anaphylactic shock 50.92 28.67 22 1755 30306 64466649
Rash maculo-papular 50.45 28.67 25 1752 47001 64449954
Pathogen resistance 49.65 28.67 17 1760 12526 64484429
Drug resistance 44.72 28.67 21 1756 35081 64461874
Catatonia 36.80 28.67 12 1765 7608 64489347
Anaphylactic reaction 36.47 28.67 23 1754 68641 64428314
Thrombocytopenia 33.94 28.67 36 1741 223765 64273190
Treatment failure 33.81 28.67 27 1750 116789 64380166
Nephropathy toxic 33.68 28.67 14 1763 17500 64479455
Mycobacterium chelonae infection 31.37 28.67 8 1769 2129 64494826

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

SourceCodeDescription
ATC J01DC01 ANTIINFECTIVES FOR SYSTEMIC USE
ANTIBACTERIALS FOR SYSTEMIC USE
OTHER BETA-LACTAM ANTIBACTERIALS
Second-generation cephalosporins
FDA CS M0003827 Cephalosporins
FDA EPC N0000175488 Cephalosporin Antibacterial
MeSH PA D000900 Anti-Bacterial Agents
MeSH PA D000890 Anti-Infective Agents
CHEBI has role CHEBI:36047 antibacterial drugs

Drug Use | Suggest Off label Use Form| |View source of the data|

DiseaseRelationSNOMED_IDDOID
Septicemia due to Escherichia coli indication 9323009
Bacterial septicemia indication 10001005 DOID:0040085
Gonorrhea indication 15628003 DOID:7551
Infection of skin AND/OR subcutaneous tissue indication 19824006
Acute gonococcal cervicitis indication 20943002 DOID:10615
Staphylococcal pneumonia indication 22754005
Streptococcal septicemia indication 29577008
Postoperative infection indication 33910007
Pneumonia due to Streptococcus indication 34020007
Peritonitis indication 48661000
Pneumonia due to Escherichia coli indication 51530003
Bacterial pneumonia indication 53084003 DOID:874
Klebsiella cystitis indication 60867007
Acute gonococcal endometritis indication 65295003 DOID:7527
Haemophilus influenzae pneumonia indication 70036007
Infection due to Escherichia coli indication 71057007
Rhinoscleroma indication 72409005 DOID:11336
Abscess of lung indication 73452002 DOID:0060317
Abdominal abscess indication 75100008
Endometritis indication 78623009 DOID:1002
Septicemia due to Bacteroides indication 79587009
Infection of bone indication 111253001
Female genital tract infection indication 125585007
Infectious disease of abdomen indication 128070006
Bacterial infection due to Klebsiella pneumoniae indication 186435004
Female pelvic cellulitis indication 280486004
Escherichia coli urinary tract infection indication 301011002
Proteus urinary tract infection indication 301012009
Streptococcus pyogenes infection indication 302809008
Bacterial urinary infection indication 312124009
Infectious disorder of joint indication 363162000
Infection due to Staphylococcus aureus indication 406602003
Osteomyelitis due to Staphylococcus aureus indication 428783003
Sepsis due to Staphylococcus aureus indication 448417001
Peptostreptococcus infection indication 135341000119101
Skin and Skin Structure Clostridium Infection indication
Staphylococcus Lung Abscess indication
Klebsiella Pneumoniae Peritonitis indication
Prevention of Perioperative Infection indication
Bacteroides Pelvic Inflammatory Disease indication
Vaginal Hysterectomy Infection Prevention indication
Peptococcus Pelvic Inflammatory Disease indication
Transurethral Prostatectomy Infection Prevention indication
Skin and Skin Structure Peptococcus Infection indication
Peptococcus Pelvic Cellulitis indication
Clostridium Pelvic Inflammatory Disease indication
Intra-Abdominal Klebsiella Abscess indication
Klebsiella Lung Abscess indication
Skin and Skin Structure Proteus Infection indication
Clostridium Endometritis indication
Clostridium Peritonitis indication
E. Coli Peritonitis indication
Haemophilus Influenzae Lung Abscess indication
Peptococcus Endometritis indication
Morganella Morganii Urinary Tract Infection indication
Staphylococcus Epidermidis Skin and Skin Structure Infection indication
Bacteroides Lung Abscess indication
Peptostreptococcus Endometritis indication
Streptococcus Lung Abscess indication
Inflammatory Disease of Female Pelvic Organs indication
Intra-Abdominal E. Coli Abscess indication
Pelvic Inflammatory Disease with Neisseria Gonorrhea indication
Clostridium Pelvic Cellulitis indication
Peptostreptococcus Pelvic Inflammatory Disease indication
Peptostreptococcus Pelvic Cellulitis indication
Bacteroides Pelvic Cellulitis indication
Staphylococcus Aureus Joint Infection indication
E. Coli Pelvic Cellulitis indication
E. Coli Endometritis indication
E. Coli Pelvic Inflammatory Disease indication
Bacteroides Pneumonia indication
Bacteroides Endometritis indication
Infection Prevention for GI Surgery indication
Intra-Abdominal Clostridium Abscess indication
Intra-Abdominal Bacteroides Abscess indication
Group B Streptococcus Pelvic Inflammatory Disease indication
Neisseria Gonorrhea Pelvic Cellulitis indication
Skin and Skin Structure Bacteroides Fragilis Infection indication
Cesarean Section Infection Prevention indication
Bacteroides Peritonitis indication
Providencia Urinary Tract Infection indication
E. Coli Lung Abscess indication
Acute gonococcal urethritis off-label use 29864006
Gonorrhea of rectum off-label use 42746002
Colitis contraindication 64226004 DOID:0060180
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 2.54 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
Bacterial penicillin-binding protein Enzyme INHIBITOR CHEMBL CHEMBL
Beta-lactamase Enzyme WOMBAT-PK
Beta-lactamase Enzyme Ki 6.85 CHEMBL
Penicillin-binding protein 1A Enzyme WOMBAT-PK
Beta-lactamase Enzyme Ki 6.30 CHEMBL
Streptokinase A Enzyme EC50 5.48 WOMBAT-PK
Beta-lactamase Enzyme Ki 7 CHEMBL

External reference:

IDSource
4019665 VUID
N0000147757 NUI
D00913 KEGG_DRUG
33564-30-6 SECONDARY_CAS_RN
203118 RXNORM
4017965 VANDF
4019665 VANDF
C0007557 UMLSCUI
CHEBI:209807 CHEBI
CFX PDB_CHEM_ID
CHEMBL1200530 ChEMBL_ID
CHEMBL996 ChEMBL_ID
D002440 MESH_DESCRIPTOR_UI
DB01331 DRUGBANK_ID
441199 PUBCHEM_CID
10937 IUPHAR_LIGAND_ID
3397 INN_ID
6OEV9DX57Y UNII
33155 MMSL
37872 MMSL
4380 MMSL
82774 MMSL
d00094 MMSL
002722 NDDF
004843 NDDF
372780005 SNOMEDCT_US
57670008 SNOMEDCT_US
84165004 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Cefoxitin HUMAN PRESCRIPTION DRUG LABEL 1 0143-9876 INJECTION, POWDER, FOR SOLUTION 10 g INTRAVENOUS ANDA 27 sections
Cefoxitin HUMAN PRESCRIPTION DRUG LABEL 1 0143-9877 INJECTION, POWDER, FOR SOLUTION 2 g INTRAVENOUS ANDA 26 sections
Cefoxitin HUMAN PRESCRIPTION DRUG LABEL 1 0143-9878 INJECTION, POWDER, FOR SOLUTION 1 g INTRAVENOUS ANDA 26 sections
Cefoxitin and Dextrose HUMAN PRESCRIPTION DRUG LABEL 1 0264-3123 INJECTION, SOLUTION 1 g INTRAVENOUS NDA 24 sections
Cefoxitin and Dextrose HUMAN PRESCRIPTION DRUG LABEL 1 0264-3125 INJECTION, SOLUTION 2 g INTRAVENOUS NDA 24 sections
Cefoxitin HUMAN PRESCRIPTION DRUG LABEL 1 25021-109 INJECTION, POWDER, FOR SOLUTION 1 g INTRAVENOUS ANDA 25 sections
Cefoxitin HUMAN PRESCRIPTION DRUG LABEL 1 25021-110 INJECTION, POWDER, FOR SOLUTION 2 g INTRAVENOUS ANDA 25 sections
Cefoxitin HUMAN PRESCRIPTION DRUG LABEL 1 25021-111 INJECTION, POWDER, FOR SOLUTION 10 g INTRAVENOUS ANDA 27 sections
Cefoxitin HUMAN PRESCRIPTION DRUG LABEL 1 44567-245 INJECTION, POWDER, FOR SOLUTION 1 g INTRAVENOUS ANDA 23 sections
Cefoxitin HUMAN PRESCRIPTION DRUG LABEL 1 44567-245 INJECTION, POWDER, FOR SOLUTION 1 g INTRAVENOUS ANDA 23 sections
Cefoxitin HUMAN PRESCRIPTION DRUG LABEL 1 44567-246 INJECTION, POWDER, FOR SOLUTION 2 g INTRAVENOUS ANDA 23 sections
Cefoxitin HUMAN PRESCRIPTION DRUG LABEL 1 44567-246 INJECTION, POWDER, FOR SOLUTION 2 g INTRAVENOUS ANDA 23 sections
Cefoxitin HUMAN PRESCRIPTION DRUG LABEL 1 44567-247 INJECTION, POWDER, FOR SOLUTION 10 g INTRAVENOUS ANDA 24 sections
Cefoxitin Human Prescription Drug Label 1 63323-341 POWDER, FOR SOLUTION 1 g INTRAVENOUS ANDA 23 sections
Cefoxitin Human Prescription Drug Label 1 63323-341 POWDER, FOR SOLUTION 1 g INTRAVENOUS ANDA 23 sections
Cefoxitin Human Prescription Drug Label 1 63323-342 POWDER, FOR SOLUTION 2 g INTRAVENOUS ANDA 23 sections
Cefoxitin Human Prescription Drug Label 1 63323-342 POWDER, FOR SOLUTION 2 g INTRAVENOUS ANDA 23 sections
Cefoxitin HUMAN PRESCRIPTION DRUG LABEL 1 66288-4100 INJECTION, POWDER, FOR SOLUTION 100 g INTRAVENOUS ANDA 27 sections