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

[H][C@]12SCC(CSC3=NN=NN3CCN(C)C)=C(N1C(=O)[C@H]2NC(=O)CC4=CSC(N)=N4)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

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 1064
Penicillin-binding protein 1B 22 Target ID: CHEMBL1814 Sources: https://www.ncbi.nlm.nih.gov/pubmed/371539	Binding Agent 1064
Penicillin-binding protein 2 24 Target ID: CHEMBL1840 Sources: https://www.ncbi.nlm.nih.gov/pubmed/371539	Binding Agent 1064
Bacterial penicillin-binding protein 233 Target ID: CHEMBL2354204 Sources: https://www.ncbi.nlm.nih.gov/pubmed/379387	Inhibitor 8297
Escherichia coli 82 Target ID: CHEMBL354 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15535040	Inhibitor 8297

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 8429	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 8429	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 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 599 OAT3 642

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
OAT3 644	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/16098483/	yes [IC50 212.6 uM]
OAT1 603	inhibitor 3277 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
Campylobacter, Salmonella, Shigella and Escherichia coli in live and dressed poultry from metropolitan accra.	2001 Dec 4	11764888
Rat renal organic anion transporter rOAT1 mediates transport of urinary-excreted cephalosporins, but not of biliary-excreted cefoperazone.	2002	15618660
[A questionnaire survey on the theory of postoperative infection prophylaxis in urology].	2002 Oct	12532634
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
[Post-marketing surveillance of antibacterial activities of cefozopran against various clinical isolates--I. Gram-positive bacteria].	2003 Oct	14692380
Beta-lactamase stability of faropenem.	2003 Sep	14504433
[Susceptibilities of bacteria isolated from patients with lower respiratory infectious diseases to antibiotics (2002)].	2004 Jun	15376784
[A case of pulmonary nocardiosis with a polypoid lesion in a bronchus].	2004 Oct	15566003
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
Human organic anion transporter hOAT3 is a potent transporter of cephalosporin antibiotics, in comparison with hOAT1.	2005 Oct 1	16098483
Does cardiac surgery in newborn infants compromise blood cell reactivity to endotoxin?	2005 Oct 5	16277717
[Comparative studies on activities of antimicrobial agents against causative organisms isolated from patients with urinary tract infections (2004). III. Secular changes in susceptibility].	2006 Aug	17111595
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
[Role of Ph-SA in enhancing bactericidal activity of beta-lactam antibiotics].	2006 Jan	16468640
Antimicrobial therapy for acute cholecystitis: Tokyo Guidelines.	2007	17252301
Antimicrobial therapy for acute cholangitis: Tokyo Guidelines.	2007	17252298
[Fundamental study on the selection of antimicrobial prophylactic agents in abdominal surgery].	2007 Aug	18018416
Antibiotic prophylaxis in cerebrospinal fluid shunting: reassessment of Cefotiam penetration into human CSF.	2007 Feb	17487803
Protection against cephalosporin-induced lipid peroxidation and nephrotoxicity by (+)-cyanidanol-3 and vitamin E.	2007 Jun	17581687
Development of breakpoints of cephems for intraabdominal infections based on pharmacokinetics and pharmacodynamics in the peritoneal fluid of patients.	2008 Apr	18622678
Effects of treatment with antimicrobial agents on the human colonic microflora.	2008 Dec	19337440
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
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 Feb	18297449
[Two cases of emphysematous pyelonephritis successfully treated by transurethral catheterization].	2009 May	19507543

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

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