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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
Structure of CEFOTIAM

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

HIDE SMILES / InChI

Description
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).

Originator

Curator's Comment:: Cefotiam was launched as Pansporin in February 1981 by Takeda Pharmaceutical # Takeda Pharmaceutical, Japan

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
CEFOTIAM

Approved Use

Parenteral 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 Date

5.6790719E11
Curative
CEFOTIAM

Approved Use

Parenteral 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 Date

5.6790719E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
124.6 mg/L
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
18.8 mg/kg
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

AUC

ValueDoseCo-administeredAnalytePopulation
171.7 mg × h/L
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

T1/2

ValueDoseCo-administeredAnalytePopulation
1.5 h
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
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

Doses

DosePopulationAdverse events​
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:
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:
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:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer


Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
yes [IC50 212.6 uM]
yes [IC50 639.7 uM]
PubMed

PubMed

TitleDatePubMed
Rat renal organic anion transporter rOAT1 mediates transport of urinary-excreted cephalosporins, but not of biliary-excreted cefoperazone.
2002
Renal function in surgical patients after administration of low-flow sevoflurane and amikacin.
2002
[Comparative studies on activities of antimicrobial agents against causative organisms isolated from patients with urinary tract infections (2000). I. Susceptibility distribution].
2002 Aug
[A questionnaire survey on antimicrobial chemotherapy for acute peritonitis].
2002 Dec
[Antibacterial activities of fosfomycin against several fresh clinical isolates--comparison of the test methods for antibacterial activity].
2002 Dec
Trends in antimicrobial susceptibility of the Streptococcus milleri group.
2002 Jun
[A case of bacteremic group A streptococcus infection with organ dysfunction following a minor skin abrasion].
2002 Nov
[Susceptibilities of bacteria isolated from patients with lower respiratory infectious diseases to antibiotics (2000)].
2002 Oct
[A questionnaire survey on the theory of postoperative infection prophylaxis in urology].
2002 Oct
[beta-lactamase-producing activity and antimicrobial susceptibility of major pathogenic bacteria isolated from clinical samples. Japan beta-lactamase Research Group].
2002 Sep
Suitability of cefotiam and cefuroxime axetil for the perioperative short-term prophylaxis in tonsillectomy patients.
2003
[Prophylactic antibiotics in lumbar disc surgery: analysis of 1,030 procedures].
2003
[Antimicrobial activity of fosfomycin against beta-lactamase-producing methicillin-sensitive Staphylococcus aureus and methicillin-sensitive coagulase-negative staphylococci].
2003 Apr
Oral antibiotic prophylaxis can influence the inflammatory response in aortic aneurysm repair: results of a randomized clinical study.
2003 Apr
Enhancement of antimicrobial effects of various antibiotics against methicillin-resistant Staphylococcus aureus (MRSA) by combination with fosfomycin.
2003 Dec
[A questionnaire survey on the theory of postoperative infection prophylaxis in otorhinolaryngology].
2003 Feb
Successful treatment of a Salmonella aortic arch aneurysm.
2003 Feb
Natural antibiotic susceptibility of Proteus spp., with special reference to P. mirabilis and P. penneri strains.
2003 Feb
Protection with antibody to tumor necrosis factor differs with similarly lethal Escherichia coli versus Staphylococcus aureus pneumonia in rats.
2003 Jul
Inhibitory effect of zinc on PEPT1-mediated transport of glycylsarcosine and beta-lactam antibiotics in human intestinal cell line Caco-2.
2003 Sep
Beta-lactamase stability of faropenem.
2003 Sep
Recovery of the susceptibility of isolated bacterium achieved by giving long-established antibiotics as prophylaxis against postoperative infections.
2004
[Comparative studies on activities of antimicrobial agents against causative organisms isolated from patients with urinary tract infections (2002). I. Susceptibility distribution].
2004 Jun
[Susceptibilities of bacteria isolated from patients with lower respiratory infectious diseases to antibiotics (2002)].
2004 Jun
Flupenthixol and cefotiam: effects on vitamin A metabolism in rats.
2004 Oct
Activity of nadifloxacin (OPC-7251) and seven other antimicrobial agents against aerobic and anaerobic Gram-positive bacteria isolated from bacterial skin infections.
2004 Oct
[Molecular epidemiology of Haemophilus influenzae strains isolated from patients with meningitis during 1999 to 2003].
2004 Sep
The significance of the intraoperative repeated dosing of antimicrobials for preventing surgical wound infection in colorectal surgery.
2005
[Antimicrobial activity of fosfomycin under various conditions against standard strains, beta-lactam resistant strains, and multidrug efflux system mutants].
2005 Apr
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
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
High frequency oscillatory ventilation and prone positioning in a porcine model of lavage-induced acute lung injury.
2006 Apr 3
Antibiotic prophylaxis in radical prostatectomy: 1-day versus 4-day treatments.
2006 Dec
Placental transfer of antibiotics administered to the mother: a review.
2006 Feb
Antimicrobial therapy for acute cholecystitis: Tokyo Guidelines.
2007
Protection against cephalosporin-induced lipid peroxidation and nephrotoxicity by (+)-cyanidanol-3 and vitamin E.
2007 Jun
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
Comparison of remifentanil and fentanyl for postoperative pain control after abdominal hysterectomy.
2008 Apr 30
Tardive seizure and antibiotics: case reports and review of the literature.
2008 Dec
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
Acute syphilitic chorioretinitis after a missed primary diagnosis: a case report.
2008 Feb 1
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
Adaptive responses of renal organic anion transporter 3 (OAT3) during cholestasis.
2008 Jul
Penetration and exposure of cefotiam into the peritoneal fluid of abdominal surgery patients after intravenous administration.
2008 Jun
Involvement of multidrug resistance-associated protein 2 (Abcc2) in molecular weight-dependent biliary excretion of beta-lactam antibiotics.
2008 Jun
Effect of iron-chelator deferiprone on the in vitro growth of staphylococci.
2009 Apr
[Successful treatment of Legionella pneumonia with moxifloxacin in a hemodialysis patient].
2009 Jul
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
Role of pathogenic oral flora in postoperative pneumonia following brain surgery.
2009 Jun 29
Rhabdomyolysis developing after transcatheter arterial chemoembolization for hepatocellular carcinoma.
2009 Nov
Patents

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 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.
Name Type Language
CEFOTIAM
INN   MI   WHO-DD  
INN  
Official Name English
ASPIL
Brand Name English
CEFOTIAM [WHO-DD]
Common Name English
J01DC07
Code English
CEFOTIAM [JAN]
Common Name English
CEFOTIAM [INN]
Common Name English
CEFOTIAM [MI]
Common Name English
Classification Tree Code System Code
WHO-ATC J01DC07
Created by admin on Sat Jun 26 04:31:20 UTC 2021 , Edited by admin on Sat Jun 26 04:31:20 UTC 2021
NCI_THESAURUS C357
Created by admin on Sat Jun 26 04:31:20 UTC 2021 , Edited by admin on Sat Jun 26 04:31:20 UTC 2021
WHO-VATC QJ01DC07
Created by admin on Sat Jun 26 04:31:20 UTC 2021 , Edited by admin on Sat Jun 26 04:31:20 UTC 2021
Code System Code Type Description
PUBCHEM
43708
Created by admin on Sat Jun 26 04:31:20 UTC 2021 , Edited by admin on Sat Jun 26 04:31:20 UTC 2021
PRIMARY
FDA UNII
91W6Z2N718
Created by admin on Sat Jun 26 04:31:20 UTC 2021 , Edited by admin on Sat Jun 26 04:31:20 UTC 2021
PRIMARY
DRUG BANK
DB00229
Created by admin on Sat Jun 26 04:31:20 UTC 2021 , Edited by admin on Sat Jun 26 04:31:20 UTC 2021
PRIMARY
EVMPD
SUB07407MIG
Created by admin on Sat Jun 26 04:31:20 UTC 2021 , Edited by admin on Sat Jun 26 04:31:20 UTC 2021
PRIMARY
WIKIPEDIA
CEFOTIAM
Created by admin on Sat Jun 26 04:31:20 UTC 2021 , Edited by admin on Sat Jun 26 04:31:20 UTC 2021
PRIMARY
CAS
61622-34-2
Created by admin on Sat Jun 26 04:31:20 UTC 2021 , Edited by admin on Sat Jun 26 04:31:20 UTC 2021
PRIMARY
DRUG CENTRAL
548
Created by admin on Sat Jun 26 04:31:20 UTC 2021 , Edited by admin on Sat Jun 26 04:31:20 UTC 2021
PRIMARY
INN
4565
Created by admin on Sat Jun 26 04:31:20 UTC 2021 , Edited by admin on Sat Jun 26 04:31:20 UTC 2021
PRIMARY
MESH
D015310
Created by admin on Sat Jun 26 04:31:20 UTC 2021 , Edited by admin on Sat Jun 26 04:31:20 UTC 2021
PRIMARY
NCI_THESAURUS
C65301
Created by admin on Sat Jun 26 04:31:20 UTC 2021 , Edited by admin on Sat Jun 26 04:31:20 UTC 2021
PRIMARY
RXCUI
2188
Created by admin on Sat Jun 26 04:31:20 UTC 2021 , Edited by admin on Sat Jun 26 04:31:20 UTC 2021
PRIMARY RxNorm
EPA CompTox
61622-34-2
Created by admin on Sat Jun 26 04:31:20 UTC 2021 , Edited by admin on Sat Jun 26 04:31:20 UTC 2021
PRIMARY
ChEMBL
CHEMBL1296
Created by admin on Sat Jun 26 04:31:20 UTC 2021 , Edited by admin on Sat Jun 26 04:31:20 UTC 2021
PRIMARY
MERCK INDEX
M3206
Created by admin on Sat Jun 26 04:31:20 UTC 2021 , Edited by admin on Sat Jun 26 04:31:20 UTC 2021
PRIMARY Merck Index