Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C18H23N9O4S3 |
Molecular Weight | 525.6321 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CN(C)CCn1c(nnn1)SCC2=C(C(=O)O)N3C(=O)[C@]([H])([C@@]3([H])SC2)N=C(Cc4csc(=N)[nH]4)O
InChI
InChIKey=QYQDKDWGWDOFFU-IUODEOHRSA-N
InChI=1S/C18H23N9O4S3/c1-25(2)3-4-26-18(22-23-24-26)34-7-9-6-32-15-12(14(29)27(15)13(9)16(30)31)21-11(28)5-10-8-33-17(19)20-10/h8,12,15H,3-7H2,1-2H3,(H2,19,20)(H,21,28)(H,30,31)/t12-,15-/m1/s1
DescriptionSources: http://www.drugbank.ca/drugs/DB00229Curator's Comment:: Description was created based on several sources, including
Sources: http://www.drugbank.ca/drugs/DB00229
Curator's Comment:: Description was created based on several sources, including
Cefotiam is a third generation beta-lactam cephalosporin antibiotic. It has broad spectrum activity against Gram positive and Gram negative bacteria. It does not have activity against Pseudomonas aeruginosa. The bactericidal activity of cefotiam results from the inhibition of cell wall synthesis via affinity for penicillin-binding proteins (PBPs).
CNS Activity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL1813 Sources: https://www.ncbi.nlm.nih.gov/pubmed/371539 |
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Target ID: CHEMBL1814 Sources: https://www.ncbi.nlm.nih.gov/pubmed/371539 |
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Target ID: CHEMBL1840 Sources: https://www.ncbi.nlm.nih.gov/pubmed/371539 |
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Target ID: CHEMBL2354204 Sources: https://www.ncbi.nlm.nih.gov/pubmed/379387 |
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Target ID: CHEMBL354 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15535040 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Curative | CEFOTIAM Approved UseParenteral Prophylaxis for surgical infection, Postoperative infections, Bacterial septicaemia, Bone and joint infections, Cholangitis, Cholecystitis, Peritonitis, Prostatitis, Pyelonephritis, Respiratory tract infections, Skin and soft tissue infections, Infections caused by susceptible organisms, Cystitis, Urethritis Launch Date5.6790719E11 |
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Curative | CEFOTIAM Approved UseParenteral Prophylaxis for surgical infection, Postoperative infections, Bacterial septicaemia, Bone and joint infections, Cholangitis, Cholecystitis, Peritonitis, Prostatitis, Pyelonephritis, Respiratory tract infections, Skin and soft tissue infections, Infections caused by susceptible organisms, Cystitis, Urethritis Launch Date5.6790719E11 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
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124.6 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9266270 |
2 g single, intravenous dose: 2 g route of administration: Intravenous experiment type: SINGLE co-administered: |
CEFOTIAM serum | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
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18.8 mg/kg EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9266270 |
2 g single, intravenous dose: 2 g route of administration: Intravenous experiment type: SINGLE co-administered: |
CEFOTIAM unknown | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
171.7 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9266270 |
2 g single, intravenous dose: 2 g route of administration: Intravenous experiment type: SINGLE co-administered: |
CEFOTIAM serum | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1.5 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9266270 |
2 g single, intravenous dose: 2 g route of administration: Intravenous experiment type: SINGLE co-administered: |
CEFOTIAM serum | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
2.2 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9266270 |
2 g single, intravenous dose: 2 g route of administration: Intravenous experiment type: SINGLE co-administered: |
CEFOTIAM unknown | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
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2 g 1 times / day multiple, intramuscular Studied dose Dose: 2 g, 1 times / day Route: intramuscular Route: multiple Dose: 2 g, 1 times / day Sources: |
unhealthy, 23 - 76 years n = 30 Health Status: unhealthy Condition: urinary tract infections Age Group: 23 - 76 years Sex: M+F Population Size: 30 Sources: |
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7 g 1 times / day multiple, intravenous Studied dose Dose: 7 g, 1 times / day Route: intravenous Route: multiple Dose: 7 g, 1 times / day Sources: |
unhealthy, adult n = 26 Health Status: unhealthy Condition: chronic sinusitis | otitis media Age Group: adult Population Size: 26 Sources: |
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200 mg/kg 1 times / day multiple, intravenous Studied dose Dose: 200 mg/kg, 1 times / day Route: intravenous Route: multiple Dose: 200 mg/kg, 1 times / day Sources: |
unhealthy, children n = 26 Health Status: unhealthy Age Group: children Population Size: 26 Sources: |
PubMed
Title | Date | PubMed |
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Rat renal organic anion transporter rOAT1 mediates transport of urinary-excreted cephalosporins, but not of biliary-excreted cefoperazone. | 2002 |
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Renal function in surgical patients after administration of low-flow sevoflurane and amikacin. | 2002 |
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[Comparative studies on activities of antimicrobial agents against causative organisms isolated from patients with urinary tract infections (2000). I. Susceptibility distribution]. | 2002 Aug |
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[A questionnaire survey on antimicrobial chemotherapy for acute peritonitis]. | 2002 Dec |
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[Antibacterial activities of fosfomycin against several fresh clinical isolates--comparison of the test methods for antibacterial activity]. | 2002 Dec |
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Trends in antimicrobial susceptibility of the Streptococcus milleri group. | 2002 Jun |
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[A case of bacteremic group A streptococcus infection with organ dysfunction following a minor skin abrasion]. | 2002 Nov |
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[Susceptibilities of bacteria isolated from patients with lower respiratory infectious diseases to antibiotics (2000)]. | 2002 Oct |
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[A questionnaire survey on the theory of postoperative infection prophylaxis in urology]. | 2002 Oct |
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[beta-lactamase-producing activity and antimicrobial susceptibility of major pathogenic bacteria isolated from clinical samples. Japan beta-lactamase Research Group]. | 2002 Sep |
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Suitability of cefotiam and cefuroxime axetil for the perioperative short-term prophylaxis in tonsillectomy patients. | 2003 |
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[Prophylactic antibiotics in lumbar disc surgery: analysis of 1,030 procedures]. | 2003 |
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[Antimicrobial activity of fosfomycin against beta-lactamase-producing methicillin-sensitive Staphylococcus aureus and methicillin-sensitive coagulase-negative staphylococci]. | 2003 Apr |
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Oral antibiotic prophylaxis can influence the inflammatory response in aortic aneurysm repair: results of a randomized clinical study. | 2003 Apr |
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Enhancement of antimicrobial effects of various antibiotics against methicillin-resistant Staphylococcus aureus (MRSA) by combination with fosfomycin. | 2003 Dec |
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[A questionnaire survey on the theory of postoperative infection prophylaxis in otorhinolaryngology]. | 2003 Feb |
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Successful treatment of a Salmonella aortic arch aneurysm. | 2003 Feb |
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Natural antibiotic susceptibility of Proteus spp., with special reference to P. mirabilis and P. penneri strains. | 2003 Feb |
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Protection with antibody to tumor necrosis factor differs with similarly lethal Escherichia coli versus Staphylococcus aureus pneumonia in rats. | 2003 Jul |
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Inhibitory effect of zinc on PEPT1-mediated transport of glycylsarcosine and beta-lactam antibiotics in human intestinal cell line Caco-2. | 2003 Sep |
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Beta-lactamase stability of faropenem. | 2003 Sep |
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Recovery of the susceptibility of isolated bacterium achieved by giving long-established antibiotics as prophylaxis against postoperative infections. | 2004 |
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[Comparative studies on activities of antimicrobial agents against causative organisms isolated from patients with urinary tract infections (2002). I. Susceptibility distribution]. | 2004 Jun |
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[Susceptibilities of bacteria isolated from patients with lower respiratory infectious diseases to antibiotics (2002)]. | 2004 Jun |
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Flupenthixol and cefotiam: effects on vitamin A metabolism in rats. | 2004 Oct |
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Activity of nadifloxacin (OPC-7251) and seven other antimicrobial agents against aerobic and anaerobic Gram-positive bacteria isolated from bacterial skin infections. | 2004 Oct |
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[Molecular epidemiology of Haemophilus influenzae strains isolated from patients with meningitis during 1999 to 2003]. | 2004 Sep |
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The significance of the intraoperative repeated dosing of antimicrobials for preventing surgical wound infection in colorectal surgery. | 2005 |
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[Antimicrobial activity of fosfomycin under various conditions against standard strains, beta-lactam resistant strains, and multidrug efflux system mutants]. | 2005 Apr |
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Resorbable screws versus pins for optimal transplant fixation (SPOT) in anterior cruciate ligament replacement with autologous hamstring grafts: rationale and design of a randomized, controlled, patient and investigator blinded trial [ISRCTN17384369]. | 2005 Feb 21 |
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In vitro activity of beta-lactams, macrolides, telithromycin, and fluoroquinolones against clinical isolates of Streptococcus pneumoniae: correlation between drug resistance and genetic characteristics. | 2005 Oct |
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High frequency oscillatory ventilation and prone positioning in a porcine model of lavage-induced acute lung injury. | 2006 Apr 3 |
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Antibiotic prophylaxis in radical prostatectomy: 1-day versus 4-day treatments. | 2006 Dec |
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Placental transfer of antibiotics administered to the mother: a review. | 2006 Feb |
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Antimicrobial therapy for acute cholecystitis: Tokyo Guidelines. | 2007 |
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Protection against cephalosporin-induced lipid peroxidation and nephrotoxicity by (+)-cyanidanol-3 and vitamin E. | 2007 Jun |
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Antibacterial activity and PK/PD of ceftriaxone against penicillin-resistant Streptococcus pneumoniae and beta-lactamase-negative ampicillin-resistant Haemophilus influenzae isolates from patients with community-acquired pneumonia. | 2007 Oct |
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Comparison of remifentanil and fentanyl for postoperative pain control after abdominal hysterectomy. | 2008 Apr 30 |
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Tardive seizure and antibiotics: case reports and review of the literature. | 2008 Dec |
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Long-term intravenous administration of antibiotics for lumbar spinal surgery prolongs the duration of hospital stay and time to normalize body temperature after surgery. | 2008 Dec 15 |
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Acute syphilitic chorioretinitis after a missed primary diagnosis: a case report. | 2008 Feb 1 |
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First outbreak of multidrug-resistant Klebsiella pneumoniae producing both SHV-12-type extended-spectrum beta-lactamase and DHA-1-type AmpC beta-lactamase at a Korean hospital. | 2008 Feb 29 |
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Adaptive responses of renal organic anion transporter 3 (OAT3) during cholestasis. | 2008 Jul |
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Penetration and exposure of cefotiam into the peritoneal fluid of abdominal surgery patients after intravenous administration. | 2008 Jun |
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Involvement of multidrug resistance-associated protein 2 (Abcc2) in molecular weight-dependent biliary excretion of beta-lactam antibiotics. | 2008 Jun |
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Effect of iron-chelator deferiprone on the in vitro growth of staphylococci. | 2009 Apr |
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[Successful treatment of Legionella pneumonia with moxifloxacin in a hemodialysis patient]. | 2009 Jul |
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Investigation of the sensitising and cross-sensitising potential of textile dyes and beta-lactam antibiotics using a biphasic mice local lymph node assay. | 2009 Jul |
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Role of pathogenic oral flora in postoperative pneumonia following brain surgery. | 2009 Jun 29 |
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Rhabdomyolysis developing after transcatheter arterial chemoembolization for hepatocellular carcinoma. | 2009 Nov |
Sample Use Guides
Oral
Prophylaxis of surgical infections; Susceptible infections
Adult: 200-400 mg bid.
Parenteral
Prophylaxis of surgical infections; Susceptible infections
Adult: As hydrochloride: Up to 6 g daily IV/IM in divided doses according to severity of infection. As hexetil hydrochloride: 200-400 mg bid.
Route of Administration:
Other
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/17867489
In time-kill studies, Cefotiam had high bactericidal activity against Staphylococcus epidermidis strains with low Cefotiam MIC (< or = 2.0 microg/ml), regardless of whether they were mecA positive.
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Classification Tree | Code System | Code | ||
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WHO-ATC |
J01DC07
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NCI_THESAURUS |
C357
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WHO-VATC |
QJ01DC07
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Code System | Code | Type | Description | ||
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43708
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PRIMARY | |||
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91W6Z2N718
Created by
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PRIMARY | |||
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DB00229
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PRIMARY | |||
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SUB07407MIG
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CEFOTIAM
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61622-34-2
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PRIMARY | |||
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548
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PRIMARY | |||
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4565
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PRIMARY | |||
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D015310
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C65301
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PRIMARY | |||
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2188
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PRIMARY | RxNorm | ||
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61622-34-2
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CHEMBL1296
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M3206
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PRIMARY | Merck Index |
ACTIVE MOIETY
SALT/SOLVATE (PARENT)