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Details

Stereochemistry ABSOLUTE
Molecular Formula C18H23N9O4S3.2ClH
Molecular Weight 598.55
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CEFOTIAM HYDROCHLORIDE

SMILES

Cl.Cl.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=BWRRTAXZCKVRON-DGPOFWGLSA-N
InChI=1S/C18H23N9O4S3.2ClH/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);2*1H/t12-,15-;;/m1../s1

HIDE SMILES / InChI
Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE
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
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

Takeda Pharmaceutical
69
Curator's Comment: Cefotiam was launched as Pansporin in February 1981 by Takeda Pharmaceutical # Takeda Pharmaceutical, Japan

Approval Year

1988
90
Targets

Targets

Primary TargetPharmacologyConditionPotency
Binding Agent
1076
Binding Agent
1076
Binding Agent
1076
Inhibitor
8504
Inhibitor
8504
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
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
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
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
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

AUC

ValueDoseCo-administeredAnalytePopulation
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

T1/2

ValueDoseCo-administeredAnalytePopulation
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

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:
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

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer
OAT1
725

OAT3
747
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
OAT3
749
 yes [IC50 212.6 uM]
OAT1
730
 yes [IC50 639.7 uM]
Sourcing

Sourcing

Vendor/AggregatorIDURL
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

PubMed

TitleDatePubMed
Rhabdomyolysis developing after transcatheter arterial chemoembolization for hepatocellular carcinoma.
2009-11
[Successful treatment of Legionella pneumonia with moxifloxacin in a hemodialysis patient].
2009-07
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
Role of pathogenic oral flora in postoperative pneumonia following brain surgery.
2009-06-29
Emphysematous pyelonephritis successfully treated by early intervention using a renoureteral catheter.
2009-06
[Two cases of emphysematous pyelonephritis successfully treated by transurethral catheterization].
2009-05
Review of the occurrence of anti-infectives in contaminated wastewaters and natural and drinking waters.
2009-05
Effect of iron-chelator deferiprone on the in vitro growth of staphylococci.
2009-04
Systemic use of antibiotics does not prevent postoperative infection in elective colorectal surgery: a randomized controlled trial.
2009-02
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
Effects of treatment with antimicrobial agents on the human colonic microflora.
2008-12
Tardive seizure and antibiotics: case reports and review of the literature.
2008-12
Adaptive responses of renal organic anion transporter 3 (OAT3) during cholestasis.
2008-07
Penetration and exposure of cefotiam into the peritoneal fluid of abdominal surgery patients after intravenous administration.
2008-06
Involvement of multidrug resistance-associated protein 2 (Abcc2) in molecular weight-dependent biliary excretion of beta-lactam antibiotics.
2008-06
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
Comparison of remifentanil and fentanyl for postoperative pain control after abdominal hysterectomy.
2008-04-30
Quantitative prediction of oral absorption of PEPT1 substrates based on in vitro uptake into Caco-2 cells.
2008-04-16
Development of breakpoints of cephems for intraabdominal infections based on pharmacokinetics and pharmacodynamics in the peritoneal fluid of patients.
2008-04
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
Acute syphilitic chorioretinitis after a missed primary diagnosis: a case report.
2008-02-01
Spermatic cord abscess with concurrent prostatic abscess involving the seminal vesicle.
2008-02
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
Malakoplakia of the kidney.
2008-02
Randomized prospective comparison of fosfomycin and cefotiam for prevention of postoperative infection following urological surgery.
2007-10
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
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
[Fundamental study on the selection of antimicrobial prophylactic agents in abdominal surgery].
2007-08
Cl- -dependent upregulation of human organic anion transporters: different effects on transport kinetics between hOAT1 and hOAT3.
2007-07
In vitro activity of cefotiam against oxacillin-resistant Staphylococcus epidermidis strains--reevaluation of beta-lactam antibiotics efficiency on MRSE.
2007-06
Success of countermeasures against respiratory infection after digestive surgery by strict blood and fluid resuscitation.
2007-06
Protection against cephalosporin-induced lipid peroxidation and nephrotoxicity by (+)-cyanidanol-3 and vitamin E.
2007-06
Risk factors for mediastinitis after cardiac surgery - a retrospective analysis of 1700 patients.
2007-05-20
Antibiotic prophylaxis in cerebrospinal fluid shunting: reassessment of Cefotiam penetration into human CSF.
2007-02
Antimicrobial therapy for acute cholecystitis: Tokyo Guidelines.
2007
Antimicrobial therapy for acute cholangitis: Tokyo Guidelines.
2007
Antibiotic prophylaxis in radical prostatectomy: 1-day versus 4-day treatments.
2006-12
[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
[Sensitivity surveillance of Streptococcus pneumoniae isolates for several antibiotics in Gifu prefecture (2004)].
2006-06
High frequency oscillatory ventilation and prone positioning in a porcine model of lavage-induced acute lung injury.
2006-04-03
Placental transfer of antibiotics administered to the mother: a review.
2006-02
Genetic analyses of beta-lactamase negative ampicillin-resistant strains of Haemophilus influenzae isolated in Okinawa, Japan.
2006-02
Endotoxin shock due to Vibrio vulnificus infection.
2006-01-19
[Role of Ph-SA in enhancing bactericidal activity of beta-lactam antibiotics].
2006-01
Children undergoing cardiac surgery for complex cardiac defects show imbalance between pro- and anti-thrombotic activity.
2006
[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
[Soft tissue infections in oral, maxillofacial, and plastic surgery. Bacterial spectra and antibiotics].
2005-11
Does cardiac surgery in newborn infants compromise blood cell reactivity to endotoxin?
2005-10-05
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
[A case of anaphylactic shock due to an antibiotic used preoperatively].
2005-10
Patents

Patents

JP2003515526A
470
JP4792032B2
112
JPH07215875A
4

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 Mon Mar 31 18:20:33 GMT 2025
Edited
by admin
on Mon Mar 31 18:20:33 GMT 2025
Record UNII
H7V12WDZ93
Record Status Validated (UNII)
Record Version
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Name Type Language
CEFOTIAM DIHYDROCHLORIDE
MI  
Preferred Name English
CEFOTIAM HYDROCHLORIDE
MART.   ORANGE BOOK   USAN   USP   USP-RS   WHO-DD  
USAN  
Official Name English
Cefotiam hydrochloride [WHO-DD]
Common Name English
CGP-14221/E
Code English
CEFOTIAM HCL
Common Name English
CEFOTIAM HYDROCHLORIDE [MART.]
Common Name English
CEFOTIAM DIHYDROCHLORIDE [MI]
Common Name English
5-THIA-1-AZABICYCLO(4.2.0)OCT-2-ENE-2-CARBOXYLIC ACID, 7-((2-(2-AMINO-4-THIAZOLYL)ACETYL)AMINO)-3-(((1-(2-(DIMETHYLAMINO)ETHYL)-1H-TETRAZOL-5-YL)THIO)METHYL)-8-OXO-, HYDROCHLORIDE (1:2), (6R,7R)-
Systematic Name English
CEFOTIAM HYDROCHLORIDE [USAN]
Common Name English
ABBOTT-48999
Code English
5-THIA-1-AZABICYCLO(4.2.0)OCT-2-ENE-2-CARBOXYLIC ACID, 7-(((2-AMINO-4-THIAZOLYL)ACETYL)-AMINO)-3-(((1-(2-(DIMETHYLAMINO)ETHYL)-1H-TETRAZOL-5-YL)-THIO)METHYL)-8-OXO-, HYDROCHLORIDE, (6R-TRANS)-
Common Name English
CEFOTIAM HYDROCHLORIDE [USP IMPURITY]
Common Name English
SCE 963
Code English
CEFOTIAM HYDROCHLORIDE [ORANGE BOOK]
Common Name English
NSC-758164
Code English
CERADON
Brand Name English
CEFOTIAM HYDROCHLORIDE [USP-RS]
Common Name English
7(R)-(2-(2-AMINO-4-THIAZOLYL)ACETAMIDO)-3-(((1-(2-(DIMETHYLAMINO)ETHYL)-1H-TETRAZOL-5-YL)THIO)METHYL)-3-CEPHEM-4-CARBOXYLIC ACID DIHYDROCHLORIDE
Common Name English
(6R,7R)-7-[2-(2-Amino-4-thiazolyl)acetamido]-3-[[[1-[2-(dimethylamino)ethyl]-1H-tetrazol-5-yl]thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid dihydrochloride
Systematic Name English
CEFOTIAM HYDROCHLORIDE [JAN]
Common Name English
SCE-963
Code English
Classification Tree Code System Code
NCI_THESAURUS C357
Created by admin on Mon Mar 31 18:20:33 GMT 2025 , Edited by admin on Mon Mar 31 18:20:33 GMT 2025
Code System Code Type Description
MERCK INDEX
m3206
Created by admin on Mon Mar 31 18:20:33 GMT 2025 , Edited by admin on Mon Mar 31 18:20:33 GMT 2025
PRIMARY Merck Index
EPA CompTox
DTXSID1045538
Created by admin on Mon Mar 31 18:20:33 GMT 2025 , Edited by admin on Mon Mar 31 18:20:33 GMT 2025
PRIMARY
DRUG BANK
DBSALT000796
Created by admin on Mon Mar 31 18:20:33 GMT 2025 , Edited by admin on Mon Mar 31 18:20:33 GMT 2025
PRIMARY
NSC
758164
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PRIMARY
PUBCHEM
47896
Created by admin on Mon Mar 31 18:20:33 GMT 2025 , Edited by admin on Mon Mar 31 18:20:33 GMT 2025
PRIMARY
SMS_ID
100000085999
Created by admin on Mon Mar 31 18:20:33 GMT 2025 , Edited by admin on Mon Mar 31 18:20:33 GMT 2025
PRIMARY
ECHA (EC/EINECS)
266-312-6
Created by admin on Mon Mar 31 18:20:33 GMT 2025 , Edited by admin on Mon Mar 31 18:20:33 GMT 2025
PRIMARY
CAS
66309-69-1
Created by admin on Mon Mar 31 18:20:33 GMT 2025 , Edited by admin on Mon Mar 31 18:20:33 GMT 2025
PRIMARY
CHEBI
31374
Created by admin on Mon Mar 31 18:20:33 GMT 2025 , Edited by admin on Mon Mar 31 18:20:33 GMT 2025
PRIMARY
ChEMBL
CHEMBL1296
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PRIMARY
RS_ITEM_NUM
1098005
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PRIMARY
RXCUI
236202
Created by admin on Mon Mar 31 18:20:33 GMT 2025 , Edited by admin on Mon Mar 31 18:20:33 GMT 2025
PRIMARY RxNorm
FDA UNII
H7V12WDZ93
Created by admin on Mon Mar 31 18:20:33 GMT 2025 , Edited by admin on Mon Mar 31 18:20:33 GMT 2025
PRIMARY
EVMPD
SUB01126MIG
Created by admin on Mon Mar 31 18:20:33 GMT 2025 , Edited by admin on Mon Mar 31 18:20:33 GMT 2025
PRIMARY
NCI_THESAURUS
C65302
Created by admin on Mon Mar 31 18:20:33 GMT 2025 , Edited by admin on Mon Mar 31 18:20:33 GMT 2025
PRIMARY
Related Record Type Details
Structure of CEFOTIAM
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of CEFOTIAM
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