CEFOTIAM

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C18H23N9O4S3
Molecular Weight	525.628
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CN(C)CCN1N=NN=C1SCC2=C(N3[C@H](SC2)[C@H](NC(=O)CC4=CSC(N)=N4)C3=O)C(O)=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

Molecular Formula	C18H23N9O4S3
Molecular Weight	525.628
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

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 1076
Penicillin-binding protein 1B 22 Target ID: CHEMBL1814 Sources: https://www.ncbi.nlm.nih.gov/pubmed/371539	Binding Agent 1076
Penicillin-binding protein 2 24 Target ID: CHEMBL1840 Sources: https://www.ncbi.nlm.nih.gov/pubmed/371539	Binding Agent 1076
Bacterial penicillin-binding protein 234 Target ID: CHEMBL2354204 Sources: https://www.ncbi.nlm.nih.gov/pubmed/379387	Inhibitor 8504
Escherichia coli 82 Target ID: CHEMBL354 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15535040	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Cystitis 27 Sources: http://www.mims.com/india/drug/info/cefotiam?type=full&mtype=generic#Indications	Curative		Approved 8583	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 1987
Respiratory tract infections 85 Sources: http://www.mims.com/india/drug/info/cefotiam?type=full&mtype=generic#Indications	Curative		Approved 8583	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 1987

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 muscle	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 muscle	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 Health Status: unhealthy Age Group: 23 - 76 years Sex: M+F 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 Health Status: unhealthy Age Group: adult 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 Health Status: unhealthy Age Group: children 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 725 OAT3 747

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
OAT3 749	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/16098483/	yes [IC50 212.6 uM]
OAT1 730	inhibitor 4027 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
eMolecules	31229753	https://www.emolecules.com/cgi-bin/more?vid=31229753
ZINC	ZINC000003830445	http://zinc15.docking.org/substances/ZINC000003830445

PubMed

Title	Date	PubMed
Rhabdomyolysis developing after transcatheter arterial chemoembolization for hepatocellular carcinoma.	2009-11	19680719
[Successful treatment of Legionella pneumonia with moxifloxacin in a hemodialysis patient].	2009-07	19637806
Investigation of the sensitising and cross-sensitising potential of textile dyes and beta-lactam antibiotics using a biphasic mice local lymph node assay.	2009-07	19212757
Role of pathogenic oral flora in postoperative pneumonia following brain surgery.	2009-06-29	19563632
Emphysematous pyelonephritis successfully treated by early intervention using a renoureteral catheter.	2009-06	19554406
[Two cases of emphysematous pyelonephritis successfully treated by transurethral catheterization].	2009-05	19507543
Review of the occurrence of anti-infectives in contaminated wastewaters and natural and drinking waters.	2009-05	19479007
Effect of iron-chelator deferiprone on the in vitro growth of staphylococci.	2009-04	19399272
Systemic use of antibiotics does not prevent postoperative infection in elective colorectal surgery: a randomized controlled trial.	2009-02	19280298
Long-term intravenous administration of antibiotics for lumbar spinal surgery prolongs the duration of hospital stay and time to normalize body temperature after surgery.	2008-12-15	19092628
Effects of treatment with antimicrobial agents on the human colonic microflora.	2008-12	19337440
Tardive seizure and antibiotics: case reports and review of the literature.	2008-12	18580694
Adaptive responses of renal organic anion transporter 3 (OAT3) during cholestasis.	2008-07	18480179
Penetration and exposure of cefotiam into the peritoneal fluid of abdominal surgery patients after intravenous administration.	2008-06	18606586
Involvement of multidrug resistance-associated protein 2 (Abcc2) in molecular weight-dependent biliary excretion of beta-lactam antibiotics.	2008-06	18339814
Postmortem diagnosis of fatal anaphylaxis during intravenous administration of therapeutic and diagnostic agents: evaluation of clinical laboratory parameters and immunohistochemistry in three cases.	2008-05	18035583
Comparison of remifentanil and fentanyl for postoperative pain control after abdominal hysterectomy.	2008-04-30	18452255
Quantitative prediction of oral absorption of PEPT1 substrates based on in vitro uptake into Caco-2 cells.	2008-04-16	18276092
Development of breakpoints of cephems for intraabdominal infections based on pharmacokinetics and pharmacodynamics in the peritoneal fluid of patients.	2008-04	18622678
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.	2008-02-29	18306469
Acute syphilitic chorioretinitis after a missed primary diagnosis: a case report.	2008-02-01	18241329
Spermatic cord abscess with concurrent prostatic abscess involving the seminal vesicle.	2008-02	18301983
Prophylactic antibiotics given within 24 hours of surgery, compared with antibiotics given for 72 hours perioperatively, increased the rate of methicillin-resistant Staphylococcus aureus isolated from surgical site infections.	2008-02	18297449
Malakoplakia of the kidney.	2008-02	18215711
Randomized prospective comparison of fosfomycin and cefotiam for prevention of postoperative infection following urological surgery.	2007-10	17982722
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.	2007-10	17982717
Bacterial eradication rates with shortened courses of 2nd- and 3rd-generation cephalosporins versus 10 days of penicillin for treatment of group A streptococcal tonsillopharyngitis in adults.	2007-10	17908614
[Fundamental study on the selection of antimicrobial prophylactic agents in abdominal surgery].	2007-08	18018416
Cl- -dependent upregulation of human organic anion transporters: different effects on transport kinetics between hOAT1 and hOAT3.	2007-07	17429031
In vitro activity of cefotiam against oxacillin-resistant Staphylococcus epidermidis strains--reevaluation of beta-lactam antibiotics efficiency on MRSE.	2007-06	17867489
Success of countermeasures against respiratory infection after digestive surgery by strict blood and fluid resuscitation.	2007-06	17593504
Protection against cephalosporin-induced lipid peroxidation and nephrotoxicity by (+)-cyanidanol-3 and vitamin E.	2007-06	17581687
Risk factors for mediastinitis after cardiac surgery - a retrospective analysis of 1700 patients.	2007-05-20	17511885
Antibiotic prophylaxis in cerebrospinal fluid shunting: reassessment of Cefotiam penetration into human CSF.	2007-02	17487803
Antimicrobial therapy for acute cholecystitis: Tokyo Guidelines.	2007	17252301
Antimicrobial therapy for acute cholangitis: Tokyo Guidelines.	2007	17252298
Antibiotic prophylaxis in radical prostatectomy: 1-day versus 4-day treatments.	2006-12	17118023
[Comparative studies on activities of antimicrobial agents against causative organisms isolated from patients with urinary tract infections (2004). III. Secular changes in susceptibility].	2006-08	17111595
[Sensitivity surveillance of Streptococcus pneumoniae isolates for several antibiotics in Gifu prefecture (2004)].	2006-06	16913401
High frequency oscillatory ventilation and prone positioning in a porcine model of lavage-induced acute lung injury.	2006-04-03	16584548
Placental transfer of antibiotics administered to the mother: a review.	2006-02	16502764
Genetic analyses of beta-lactamase negative ampicillin-resistant strains of Haemophilus influenzae isolated in Okinawa, Japan.	2006-02	16495632
Endotoxin shock due to Vibrio vulnificus infection.	2006-01-19	16935803
[Role of Ph-SA in enhancing bactericidal activity of beta-lactam antibiotics].	2006-01	16468640
Children undergoing cardiac surgery for complex cardiac defects show imbalance between pro- and anti-thrombotic activity.	2006	17125503
[Comparative studies on activities of antimicrobial agents against causative organisms isolated from patients with urinary tract infections (2003). III. Secular changes in susceptibility].	2005-12	16521346
[Soft tissue infections in oral, maxillofacial, and plastic surgery. Bacterial spectra and antibiotics].	2005-11	16228187
Does cardiac surgery in newborn infants compromise blood cell reactivity to endotoxin?	2005-10-05	16277717
In vitro activity of beta-lactams, macrolides, telithromycin, and fluoroquinolones against clinical isolates of Streptococcus pneumoniae: correlation between drug resistance and genetic characteristics.	2005-10	16258826
[A case of anaphylactic shock due to an antibiotic used preoperatively].	2005-10	16231774

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.

Substance Class	Chemical Created by `admin` on `Wed Apr 02 08:57:00 GMT 2025` Edited by `admin` on `Wed Apr 02 08:57:00 GMT 2025`
Record UNII	91W6Z2N718
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ASPIL

Preferred Name

English

CEFOTIAM

Official Name

English

J01DC07

Code

English

CEFOTIAM [JAN]

Common Name

English

cefotiam [INN]

Common Name

English

CEFOTIAM [MI]

Common Name

English

Cefotiam [WHO-DD]

Common Name

English

Classification Tree Code System Code

WHO-ATC

J01DC07