CEFOTIAM HEXETIL

Details

Stereochemistry	EPIMERIC
Molecular Formula	C27H37N9O7S3
Molecular Weight	695.834
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 3
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)OC(C)OC(=O)OC5CCCCC5

InChI

InChIKey=VVFDMWZLBPUKTD-ZKRNHDOASA-N

InChI=1S/C27H37N9O7S3/c1-15(42-27(40)43-18-7-5-4-6-8-18)41-24(39)21-16(13-46-26-31-32-33-35(26)10-9-34(2)3)12-44-23-20(22(38)36(21)23)30-19(37)11-17-14-45-25(28)29-17/h14-15,18,20,23H,4-13H2,1-3H3,(H2,28,29)(H,30,37)/t15?,20-,23-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C27H37N9O7S3
Molecular Weight	695.834
Charge	0
Count

Stereochemistry	EPIMERIC
Additional Stereochemistry	No
Defined Stereocenters	2 / 3
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 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
[Comparative studies on activities of antimicrobial agents against causative organisms isolated from patients with urinary tract infections (2003). III. Secular changes in susceptibility].	2005 Dec	16521346
[Soft tissue infections in oral, maxillofacial, and plastic surgery. Bacterial spectra and antibiotics].	2005 Nov	16228187
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
[A case of anaphylactic shock due to an antibiotic used preoperatively].	2005 Oct	16231774
Does cardiac surgery in newborn infants compromise blood cell reactivity to endotoxin?	2005 Oct 5	16277717
Children undergoing cardiac surgery for complex cardiac defects show imbalance between pro- and anti-thrombotic activity.	2006	17125503
High frequency oscillatory ventilation and prone positioning in a porcine model of lavage-induced acute lung injury.	2006 Apr 3	16584548
[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
Genetic analyses of beta-lactamase negative ampicillin-resistant strains of Haemophilus influenzae isolated in Okinawa, Japan.	2006 Feb	16495632
[Role of Ph-SA in enhancing bactericidal activity of beta-lactam antibiotics].	2006 Jan	16468640
Endotoxin shock due to Vibrio vulnificus infection.	2006 Jul-Aug	16935803
[Sensitivity surveillance of Streptococcus pneumoniae isolates for several antibiotics in Gifu prefecture (2004)].	2006 Jun	16913401
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
Cl- -dependent upregulation of human organic anion transporters: different effects on transport kinetics between hOAT1 and hOAT3.	2007 Jul	17429031
In vitro activity of cefotiam against oxacillin-resistant Staphylococcus epidermidis strains--reevaluation of beta-lactam antibiotics efficiency on MRSE.	2007 Jun	17867489
Success of countermeasures against respiratory infection after digestive surgery by strict blood and fluid resuscitation.	2007 Jun	17593504
Protection against cephalosporin-induced lipid peroxidation and nephrotoxicity by (+)-cyanidanol-3 and vitamin E.	2007 Jun	17581687
Risk factors for mediastinitis after cardiac surgery - a retrospective analysis of 1700 patients.	2007 May 20	17511885
Randomized prospective comparison of fosfomycin and cefotiam for prevention of postoperative infection following urological surgery.	2007 Oct	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 Oct	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 Oct	17908614
Development of breakpoints of cephems for intraabdominal infections based on pharmacokinetics and pharmacodynamics in the peritoneal fluid of patients.	2008 Apr	18622678
Quantitative prediction of oral absorption of PEPT1 substrates based on in vitro uptake into Caco-2 cells.	2008 Apr 16	18276092
Comparison of remifentanil and fentanyl for postoperative pain control after abdominal hysterectomy.	2008 Apr 30	18452255
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
Spermatic cord abscess with concurrent prostatic abscess involving the seminal vesicle.	2008 Feb	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 Feb	18297449
Malakoplakia of the kidney.	2008 Feb	18215711
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
Postmortem diagnosis of fatal anaphylaxis during intravenous administration of therapeutic and diagnostic agents: evaluation of clinical laboratory parameters and immunohistochemistry in three cases.	2008 May	18035583
Effect of iron-chelator deferiprone on the in vitro growth of staphylococci.	2009 Apr	19399272
Systemic use of antibiotics does not prevent postoperative infection in elective colorectal surgery: a randomized controlled trial.	2009 Feb	19280298
[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
Emphysematous pyelonephritis successfully treated by early intervention using a renoureteral catheter.	2009 Jun	19554406
Role of pathogenic oral flora in postoperative pneumonia following brain surgery.	2009 Jun 29	19563632
[Two cases of emphysematous pyelonephritis successfully treated by transurethral catheterization].	2009 May	19507543
Review of the occurrence of anti-infectives in contaminated wastewaters and natural and drinking waters.	2009 May	19479007
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.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 09:49:47 GMT 2023` Edited by `admin` on `Sat Dec 16 09:49:47 GMT 2023`
Record UNII	J92A81Y99T
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CEFOTIAM HEXETIL

Common Name

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-, 1-(((CYCLOHEXYLOXY)CARBONYL)OXY)ETHYL ESTER, (6R,7R)-

Systematic Name

English

CEFOTIAM HEXETIL ESTER

Common Name

English

CTM-HE

Common Name

English

Code System Code Type Description

EPA CompTox

DTXSID20914817