CEFOTIAM

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 Search

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
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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Penicillin-binding protein 1A 45 Target ID: CHEMBL1813 Sources: https://www.ncbi.nlm.nih.gov/pubmed/371539	Binding Agent 996
Penicillin-binding protein 1B 21 Target ID: CHEMBL1814 Sources: https://www.ncbi.nlm.nih.gov/pubmed/371539	Binding Agent 996
Penicillin-binding protein 2 24 Target ID: CHEMBL1840 Sources: https://www.ncbi.nlm.nih.gov/pubmed/371539	Binding Agent 996
Bacterial penicillin-binding protein 226 Target ID: CHEMBL2354204 Sources: https://www.ncbi.nlm.nih.gov/pubmed/379387	Inhibitor 7728
Escherichia coli 78 Target ID: CHEMBL354 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15535040	Inhibitor 7728

Conditions

Condition	Modality	Targets	Highest Phase	Product
Cystitis 26 Sources: http://www.mims.com/india/drug/info/cefotiam?type=full&mtype=generic#Indications	Curative		Approved 8043	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
Respiratory tract infections 84 Sources: http://www.mims.com/india/drug/info/cefotiam?type=full&mtype=generic#Indications	Curative		Approved 8043	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

C_max

Value	Dose	Co-administered	Analyte	Population
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
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

T_1/2

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
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: https://pubmed.ncbi.nlm.nih.gov/6287388	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: https://pubmed.ncbi.nlm.nih.gov/6287388	Sources: https://pubmed.ncbi.nlm.nih.gov/6287388
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: https://pubmed.ncbi.nlm.nih.gov/6325736	unhealthy, adult n = 26 Health Status: unhealthy Condition: chronic sinusitis \| otitis media Age Group: adult Population Size: 26 Sources: https://pubmed.ncbi.nlm.nih.gov/6325736	Sources: https://pubmed.ncbi.nlm.nih.gov/6325736
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: https://pubmed.ncbi.nlm.nih.gov/6270413	unhealthy, children n = 26 Health Status: unhealthy Age Group: children Population Size: 26 Sources: https://pubmed.ncbi.nlm.nih.gov/6270413	Sources: https://pubmed.ncbi.nlm.nih.gov/6270413

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
OAT1 554 OAT3 588

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
OAT3 590	inhibitor 3045 Sources: https://pubmed.ncbi.nlm.nih.gov/16098483/	yes [IC50 212.6 uM]
OAT1 558	inhibitor 3045 Sources: https://pubmed.ncbi.nlm.nih.gov/16098483/	yes [IC50 639.7 uM]

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:355510	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:355510
ChemicalBook	CB7367629	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB7367629
ZINC	ZINC000003830445	http://zinc15.docking.org/substances/ZINC000003830445
eMolecules	31229753	https://www.emolecules.com/cgi-bin/more?vid=31229753

PubMed

Title	Date	PubMed
Rat renal organic anion transporter rOAT1 mediates transport of urinary-excreted cephalosporins, but not of biliary-excreted cefoperazone.	2002	15618660
Renal function in surgical patients after administration of low-flow sevoflurane and amikacin.	2002	14566491
[Comparative studies on activities of antimicrobial agents against causative organisms isolated from patients with urinary tract infections (2000). I. Susceptibility distribution].	2002 Aug	12378869
[A questionnaire survey on antimicrobial chemotherapy for acute peritonitis].	2002 Dec	12621738
[Antibacterial activities of fosfomycin against several fresh clinical isolates--comparison of the test methods for antibacterial activity].	2002 Dec	12621737
Trends in antimicrobial susceptibility of the Streptococcus milleri group.	2002 Jun	12111565
[A case of bacteremic group A streptococcus infection with organ dysfunction following a minor skin abrasion].	2002 Nov	12508480
[Susceptibilities of bacteria isolated from patients with lower respiratory infectious diseases to antibiotics (2000)].	2002 Oct	12532637
[A questionnaire survey on the theory of postoperative infection prophylaxis in urology].	2002 Oct	12532634
[beta-lactamase-producing activity and antimicrobial susceptibility of major pathogenic bacteria isolated from clinical samples. Japan beta-lactamase Research Group].	2002 Sep	12599526
Suitability of cefotiam and cefuroxime axetil for the perioperative short-term prophylaxis in tonsillectomy patients.	2003	12642969
[Prophylactic antibiotics in lumbar disc surgery: analysis of 1,030 procedures].	2003	12582943
[Antimicrobial activity of fosfomycin against beta-lactamase-producing methicillin-sensitive Staphylococcus aureus and methicillin-sensitive coagulase-negative staphylococci].	2003 Apr	12825415
Oral antibiotic prophylaxis can influence the inflammatory response in aortic aneurysm repair: results of a randomized clinical study.	2003 Apr	12797394
Enhancement of antimicrobial effects of various antibiotics against methicillin-resistant Staphylococcus aureus (MRSA) by combination with fosfomycin.	2003 Dec	14691650
[A questionnaire survey on the theory of postoperative infection prophylaxis in otorhinolaryngology].	2003 Feb	12723395
Successful treatment of a Salmonella aortic arch aneurysm.	2003 Feb	12692933
Natural antibiotic susceptibility of Proteus spp., with special reference to P. mirabilis and P. penneri strains.	2003 Feb	12678409
Protection with antibody to tumor necrosis factor differs with similarly lethal Escherichia coli versus Staphylococcus aureus pneumonia in rats.	2003 Jul	12826846
Inhibitory effect of zinc on PEPT1-mediated transport of glycylsarcosine and beta-lactam antibiotics in human intestinal cell line Caco-2.	2003 Sep	14567632
Beta-lactamase stability of faropenem.	2003 Sep	14504433
Recovery of the susceptibility of isolated bacterium achieved by giving long-established antibiotics as prophylaxis against postoperative infections.	2004	15338342
[Comparative studies on activities of antimicrobial agents against causative organisms isolated from patients with urinary tract infections (2002). I. Susceptibility distribution].	2004 Jun	15376785
[Susceptibilities of bacteria isolated from patients with lower respiratory infectious diseases to antibiotics (2002)].	2004 Jun	15376784
Flupenthixol and cefotiam: effects on vitamin A metabolism in rats.	2004 Oct	15522128
Activity of nadifloxacin (OPC-7251) and seven other antimicrobial agents against aerobic and anaerobic Gram-positive bacteria isolated from bacterial skin infections.	2004 Oct	15452398
[Molecular epidemiology of Haemophilus influenzae strains isolated from patients with meningitis during 1999 to 2003].	2004 Sep	15508718
The significance of the intraoperative repeated dosing of antimicrobials for preventing surgical wound infection in colorectal surgery.	2005	16133667
[Antimicrobial activity of fosfomycin under various conditions against standard strains, beta-lactam resistant strains, and multidrug efflux system mutants].	2005 Apr	15997654
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	15723704
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	16258826
High frequency oscillatory ventilation and prone positioning in a porcine model of lavage-induced acute lung injury.	2006 Apr 3	16584548
Antibiotic prophylaxis in radical prostatectomy: 1-day versus 4-day treatments.	2006 Dec	17118023
Placental transfer of antibiotics administered to the mother: a review.	2006 Feb	16502764
Antimicrobial therapy for acute cholecystitis: Tokyo Guidelines.	2007	17252301
Protection against cephalosporin-induced lipid peroxidation and nephrotoxicity by (+)-cyanidanol-3 and vitamin E.	2007 Jun	17581687
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	17982717
Comparison of remifentanil and fentanyl for postoperative pain control after abdominal hysterectomy.	2008 Apr 30	18452255
Tardive seizure and antibiotics: case reports and review of the literature.	2008 Dec	18580694
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	19092628
Acute syphilitic chorioretinitis after a missed primary diagnosis: a case report.	2008 Feb 1	18241329
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	18306469
Adaptive responses of renal organic anion transporter 3 (OAT3) during cholestasis.	2008 Jul	18480179
Penetration and exposure of cefotiam into the peritoneal fluid of abdominal surgery patients after intravenous administration.	2008 Jun	18606586
Involvement of multidrug resistance-associated protein 2 (Abcc2) in molecular weight-dependent biliary excretion of beta-lactam antibiotics.	2008 Jun	18339814
Effect of iron-chelator deferiprone on the in vitro growth of staphylococci.	2009 Apr	19399272
[Successful treatment of Legionella pneumonia with moxifloxacin in a hemodialysis patient].	2009 Jul	19637806
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	19212757
Role of pathogenic oral flora in postoperative pneumonia following brain surgery.	2009 Jun 29	19563632
Rhabdomyolysis developing after transcatheter arterial chemoembolization for hepatocellular carcinoma.	2009 Nov	19680719

Patents

Sample Use Guides

In Vivo Use Guide

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

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

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