cefotetan Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
antibiotics, cefalosporanic acid derivatives 547 69712-56-7

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • cefotetan
  • cefotetan disodium
  • apacef
A semisynthetic cephamycin antibiotic that is administered intravenously or intramuscularly. The drug is highly resistant to a broad spectrum of beta-lactamases and is active against a wide range of both aerobic and anaerobic gram-positive and gram-negative microorganisms.
  • Molecular weight: 575.60
  • Formula: C17H17N7O8S4
  • CLOGP: -1.54
  • LIPINSKI: 2
  • HAC: 15
  • HDO: 4
  • TPSA: 219.93
  • ALOGS: -3.04
  • ROTB: 9

  • Status: OFP

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

Drug dosage:

DoseUnitRoute
4 g P

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 3 Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 67 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 148.91 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
Vd (Volume of distribution) 0.13 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 0.42 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.15 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 4.50 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
Dec. 27, 1985 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
Haemolytic anaemia 53.87 51.41 10 75 9832 46676145

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

Pharmacologic Action:

SourceCodeDescription
ATC J01DC05 ANTIINFECTIVES FOR SYSTEMIC USE
ANTIBACTERIALS FOR SYSTEMIC USE
OTHER BETA-LACTAM ANTIBACTERIALS
Second-generation cephalosporins
FDA CS M0003827 Cephalosporins
FDA EPC N0000175488 Cephalosporin Antibacterial
CHEBI has role CHEBI:36047 antibacterial drugs
MeSH PA D000900 Anti-Bacterial Agents
MeSH PA D000890 Anti-Infective Agents

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Bacterial septicemia indication 10001005 DOID:0040085
Infection of skin AND/OR subcutaneous tissue indication 19824006
Staphylococcal pneumonia indication 22754005
Pneumonia due to Streptococcus indication 34020007
Lower respiratory tract infection indication 50417007
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
Endometritis indication 78623009 DOID:1002
Female genital tract infection indication 125585007
Infectious disease of abdomen indication 128070006
Bacterial infection due to Klebsiella pneumoniae indication 186435004
Proteus pneumonia indication 195888009
Escherichia coli urinary tract infection indication 301011002
Proteus urinary tract infection indication 301012009
Streptococcus pyogenes infection indication 302809008
Bacterial urinary infection indication 312124009
Infection due to Staphylococcus aureus indication 406602003
Osteomyelitis due to Staphylococcus aureus indication 428783003
Peptostreptococcus infection indication 135341000119101
Inflammatory Disease of Female Pelvic Organs indication
Fusobacterium Endometritis indication
Streptococcal Endometritis indication
E. Coli Peritonitis indication
Proteus Pelvic Inflammatory Disease indication
Fusobacterium Pelvic Inflammatory Disease indication
Staphylococcus Aureus Joint Infection indication
Peptostreptococcus Pelvic Inflammatory Disease indication
Proteus Endometritis indication
Skin and Skin Structure Bacteroides Fragilis Infection indication
Peptococcus Pelvic Inflammatory Disease indication
E. Coli Endometritis indication
Bacteroides Peritonitis indication
Bacteroides Endometritis indication
Staphylococcus Endometritis indication
Streptococcal Peritonitis indication
E. Coli Pelvic Inflammatory Disease indication
Skin and Skin Structure Fusobacterium Infection indication
Skin and Skin Structure Peptococcus Infection indication
Staphylococcus Epidermidis Skin and Skin Structure Infection indication
Pelvic Inflammatory Disease with Neisseria Gonorrhea indication
Peptococcus Endometritis indication
Bacteroides Pelvic Inflammatory Disease indication
Clostridium Peritonitis indication
Skin and Skin Structure Proteus Infection indication
Peptococcus Peritonitis indication
Streptococcal Pelvic Inflammatory Disease indication
Peptostreptococcus Endometritis indication
Skin and Skin Structure Streptococcus Agalactiae Infection indication
Staphylococcus Pelvic Inflammatory Disease indication
Prevention of Perioperative Infection indication
Klebsiella Pneumoniae Peritonitis indication
Infection of bone off-label use 111253001
Infectious disorder of joint off-label use 363162000
Vitamin K deficiency contraindication 52675005 DOID:11249
Disorder of digestive system contraindication 53619000 DOID:77
Hemolytic anemia contraindication 61261009 DOID:583
Factor II deficiency contraindication 73975000
Kidney disease contraindication 90708001 DOID:557
Disease of liver contraindication 235856003 DOID:409
Pseudomembranous enterocolitis contraindication 397683000

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 2.85 acidic
pKa2 3.37 acidic
pKa3 12.14 acidic
pKa4 13.27 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
Interstitial collagenase Enzyme IC50 4.89 WOMBAT-PK
72 kDa type IV collagenase Enzyme IC50 4.49 WOMBAT-PK
Catechol O-methyltransferase Enzyme IC50 4.85 WOMBAT-PK
Prostaglandin G/H synthase 2 Enzyme IC50 5.05 WOMBAT-PK
Matrix metalloproteinase-9 Enzyme IC50 4.72 WOMBAT-PK
Bacterial penicillin-binding protein Enzyme INHIBITOR CHEMBL CHEMBL
Penicillin-binding protein 1A Enzyme WOMBAT-PK

External reference:

IDSource
4019664 VUID
N0000147756 NUI
D00260 KEGG_DRUG
74356-00-6 SECONDARY_CAS_RN
4018461 VANDF
4019664 VANDF
C1564559 UMLSCUI
CHEBI:3499 CHEBI
CHEMBL474579 ChEMBL_ID
CHEMBL1201098 ChEMBL_ID
DB01330 DRUGBANK_ID
D015313 MESH_DESCRIPTOR_UI
53025 PUBCHEM_CID
10936 IUPHAR_LIGAND_ID
4931 INN_ID
48SPP0PA9Q UNII
203141 RXNORM
118717 MMSL
4379 MMSL
d00055 MMSL
002736 NDDF
004850 NDDF
13585009 SNOMEDCT_US
370355004 SNOMEDCT_US
46146008 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Cefotetan HUMAN PRESCRIPTION DRUG LABEL 1 0143-9670 INJECTION, POWDER, FOR SOLUTION 1 g INTRAMUSCULAR ANDA 18 sections
Cefotetan HUMAN PRESCRIPTION DRUG LABEL 1 0143-9671 INJECTION, POWDER, FOR SOLUTION 2 g INTRAMUSCULAR ANDA 18 sections
Cefotetan and Dextrose HUMAN PRESCRIPTION DRUG LABEL 1 0264-3173 INJECTION, SOLUTION 1 g INTRAVENOUS NDA 27 sections
Cefotetan and Dextrose HUMAN PRESCRIPTION DRUG LABEL 1 0264-3175 INJECTION, SOLUTION 2 g INTRAVENOUS NDA 27 sections
Cefotan HUMAN PRESCRIPTION DRUG LABEL 1 52565-052 INJECTION, POWDER, FOR SOLUTION 1 g INTRAVENOUS NDA 11 sections
CEFOTAN HUMAN PRESCRIPTION DRUG LABEL 1 52565-053 INJECTION, POWDER, FOR SOLUTION 2 g INTRAVENOUS NDA 11 sections
Cefotetan Human Prescription Drug Label 1 63323-385 INJECTION, POWDER, FOR SOLUTION 1 g INTRAVENOUS ANDA 12 sections
Cefotetan Human Prescription Drug Label 1 63323-386 INJECTION, POWDER, FOR SOLUTION 2 g INTRAVENOUS ANDA 12 sections