Page last updated: 2024-12-11

cefatrizine

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Description

Cefatrizine: Orally active semisynthetic cephalosporin antibiotic with broad-spectrum activity. [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

cefatrizine : A cephalosporin compound having (1H-1,2,3-triazol-4-ylsulfanyl)methyl and [(2R)-2-amino-2-(4-hydroxyphenyl)]acetamido side-groups. An antibacterial drug first prepared in the 1970s, it has more recently been found to be an inhibitor of eukaryotic elongation factor-2 kinase (eEF2K), which is known to regulate apoptosis, autophagy and ER stress in many types of human cancers. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID6410758
CHEMBL ID1095284
CHEBI ID131730
SCHEMBL ID49503
MeSH IDM0003717

Synonyms (65)

Synonym
(6r,7r)-7-{[(2r)-2-amino-2-(4-hydroxyphenyl)acetyl]amino}-8-oxo-3-[(1h-1,2,3-triazol-4-ylthio)methyl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
cefatrizine
51627-14-6
cefatrizine (usan)
D02406
(6r,7r)-7-((r)-2-amino-2-(p-hydroxyphenyl)acetamido)-8-oxo-3-((v-triazol-4-ylthio)methyl)-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid
cetrazil
cefatrizino [inn-spanish]
bls 640
s 640p
trizina
cepticol
cefatrix
skf 60771
einecs 257-324-2
bl-s 640
5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 7-((amino(4-hydroxyphenyl)acetyl)amino)-8-oxo-3-((1h-1,2,3-triazol-4-ylthio)methyl)-, (6r-(6alpha,7beta(r*)))-
cefatrizinum [inn-latin]
latocef
bricef
antibiotic bl-s 640
cefatrizine [usan:inn:ban]
cephatriazine
orosporina
s-640p
j01db07
CHEMBL1095284
bl-s640
(7r)-7-(alpha-d-4-hydroxyphenylglycylamino)-3-(1h-1,2,3-triazol-4-ylthiomethyl)-3-cephem-4-carboxylic acid
cefatrizina
cefatrizinum
CHEBI:131730
(6r,7r)-7-{[(2r)-2-amino-2-(4-hydroxyphenyl)acetyl]amino}-8-oxo-3-[(1h-1,2,3-triazol-4-ylsulfanyl)methyl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
NCGC00185755-01
(6r,7r)-7-[[(2r)-2-amino-2-(4-hydroxyphenyl)acetyl]amino]-8-oxo-3-(2h-triazol-4-ylsulfanylmethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
dtxsid7022752 ,
dtxcid902752
cas-51627-14-6
tox21_113376
A828691
(6r,7r)-7-[[(2r)-2-amino-2-(4-hydroxyphenyl)-1-oxoethyl]amino]-8-oxo-3-[(2h-triazol-4-ylthio)methyl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
(6r,7r)-7-[[(2r)-2-azanyl-2-(4-hydroxyphenyl)ethanoyl]amino]-8-oxidanylidene-3-(2h-1,2,3-triazol-4-ylsulfanylmethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
cefatrizino
unii-8p4w949t8k
8p4w949t8k ,
cefatrizine [usan]
cefatrizine [mi]
cefatrizine [jan]
cefatrizine [inn]
cefatrizine [who-dd]
cefatrizine propylene glycolate [jan]
cefatrizine [mart.]
5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 7-((amino(4-hydroxyphenyl)acetyl)amino)-8-oxo-3-((1h-1,2,3-triazol-4-ylthio)methyl)-, (6r-(6.alpha.,7.beta.(r*)))-
SCHEMBL49503
UOCJDOLVGGIYIQ-PBFPGSCMSA-N
AKOS030530887
t-amyl
Q3009981
DB13266
cefathiamidine,(s)
(6r,7r)-3-(acetoxymethyl)-7-(2-((e)-n,n'-diisopropylcarbamimidoylthio)acetamido)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
(6r,7r)-3-(((1h-1,2,3-triazol-5-yl)thio)methyl)-7-((r)-2-amino-2-(4-hydroxyphenyl)acetamido)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
gtpl12204
CS-0079891
HY-123024

Research Excerpts

Pharmacokinetics

ExcerptReferenceRelevance
" Although the pharmacokinetic characteristics of the drugs after intravenous injection were similar to other beta-lactam antibiotics, significant differences between the cephalosporins examined were found in respect of certain kinetic parameters."( Clinical pharmacokinetics of five oral cephalosporins in calves.
Kurtz, B; Paz, R; Soback, S; Ziv, G, 1987
)
0.27
" Oral renal clearance and half-life values corresponded well to the intravenous values."( Human intravenous pharmacokinetics and absolute oral bioavailability of cefatrizine.
Gaver, RC; Pfeffer, M; Ximenez, J, 1983
)
0.5
" pharmacokinetic data on 670 drugs representing, to our knowledge, the largest publicly available set of human clinical pharmacokinetic data."( Trend analysis of a database of intravenous pharmacokinetic parameters in humans for 670 drug compounds.
Lombardo, F; Obach, RS; Waters, NJ, 2008
)
0.35

Bioavailability

The oral bioavailability of cefatrizine was studied in four groups, each of ten healthy young male volunteers. The plots of the percentage of drug unabsorbed showed an almost constant rate of absorption with a tendency to move toward first-order kinetics at the end of the process.

ExcerptReferenceRelevance
"A pharmacokinetic model incorporating saturable rate of absorption of the Michaelis-Menten type was recently developed to fit cefatrizine (CFZ) plasma concentrations with time following oral administration of 500-mg capsules to humans."( Theoretical model for both saturable rate and extent of absorption: simulations of cefatrizine data.
Couet, WR; Guedes, JP; Reigner, BG; Tozer, TN, 1991
)
0.71
" The plots of the percentage of drug unabsorbed and the apparent rate of cefatrizine absorption as a function of time showed, first, a delay and, then, an almost constant rate of absorption with a tendency to move toward first-order kinetics at the end of the process."( Saturable rate of cefatrizine absorption after oral administration to humans.
Couet, W; Fourtillan, JB; Guedes, JP; Reigner, BG; Tozer, TN, 1990
)
0.84
" The bioavailability of the drugs was about 35 per cent of the administered dose."( Clinical pharmacokinetics of five oral cephalosporins in calves.
Kurtz, B; Paz, R; Soback, S; Ziv, G, 1987
)
0.27
"The oral bioavailability of cefatrizine was studied in four groups, each of ten healthy young male volunteers."( Pharmacokinetics of cefatrizine after oral administration in human volunteers.
Ghezzi, A; La Rosa, F; Mastrandrea, V; Ripa, S, 1985
)
0.89
" Relative absorption at the high dose would be sufficiently slow that an absorption "window" would be passed before maximum bioavailability could be attained."( Human intravenous pharmacokinetics and absolute oral bioavailability of cefatrizine.
Gaver, RC; Pfeffer, M; Ximenez, J, 1983
)
0.5
"Gestation was found to decrease substantially both cefatrizine oral bioavailability and maximum serum plasma concentration (42."( Pharmacokinetics of oral cefatrizine in pregnant and non-pregnant women with reference to fetal distribution.
Antsaklis, A; Daskalakis, G; Ismailos, G; Karabinas, C; Mesogitis, S; Papantoniou, N; Papapanagiotou, A, 2007
)
0.89
"Our results indicate that gestation decreases the oral bioavailability of cefatrizine."( Pharmacokinetics of oral cefatrizine in pregnant and non-pregnant women with reference to fetal distribution.
Antsaklis, A; Daskalakis, G; Ismailos, G; Karabinas, C; Mesogitis, S; Papantoniou, N; Papapanagiotou, A, 2007
)
0.87
"Oral bioavailability (F) is a product of fraction absorbed (Fa), fraction escaping gut-wall elimination (Fg), and fraction escaping hepatic elimination (Fh)."( Physicochemical space for optimum oral bioavailability: contribution of human intestinal absorption and first-pass elimination.
Chang, G; El-Kattan, A; Miller, HR; Obach, RS; Rotter, C; Steyn, SJ; Troutman, MD; Varma, MV, 2010
)
0.36
"The ATP-binding cassette transporter P-glycoprotein (P-gp) is known to limit both brain penetration and oral bioavailability of many chemotherapy drugs."( A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
Ambudkar, SV; Brimacombe, KR; Chen, L; Gottesman, MM; Guha, R; Hall, MD; Klumpp-Thomas, C; Lee, OW; Lee, TD; Lusvarghi, S; Robey, RW; Shen, M; Tebase, BG, 2019
)
0.51

Dosage Studied

ExcerptRelevanceReference
" The observed increase in Cmax and the lengthening of t1/2 could suggest a reduction of dosing frequency in patients with severe renal impairment."( Pharmacokinetics of oral cefatrizine in patients with impaired renal function.
Couet, W; Fauvel, JP; Fourtillan, JB; Laville, M; Pozet, N, 1991
)
0.58
"A comparison was made of cefatrizine in dosages of 75 mg/kg/day administered once daily or twice daily and erythromycin in a mean daily dosage of 50 mg/kg given in three divided doses for the treatment of acute infections of the ear, nose, and throat in children."( Comparison of cefatrizine and erythromycin for pediatric ear, nose, and throat infections.
Ciampini, M; Cremonesi, G; Stura, M; Tarantino, V, 1987
)
0.94
" Provisional oral dosage regimens were computed for each cephalosporin on the basis of the MIC data and the kinetic parameters derived from intravenous and oral drug administration."( Clinical pharmacokinetics of five oral cephalosporins in calves.
Kurtz, B; Paz, R; Soback, S; Ziv, G, 1987
)
0.27
" It is not expected that the observed bioavailability decrease at doses exceeding 500 mg will have any therapeutic significance, since clinical studies are establishing efficacy for a recommended unit dosage regimen of 500 mg."( Human intravenous pharmacokinetics and absolute oral bioavailability of cefatrizine.
Gaver, RC; Pfeffer, M; Ximenez, J, 1983
)
0.5
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (2)

RoleDescription
antibacterial drugA drug used to treat or prevent bacterial infections.
EC 2.7.11.20 (elongation factor 2 kinase) inhibitorAny EC 2.7.11.* (protein-serine/threonine kinase) inhibitor that interferes with the action of elongation factor 2 kinase (EC 2.7.11.20).
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (6)

ClassDescription
cephalosporinA class of beta-lactam antibiotics differing from the penicillins in having a 6-membered, rather than a 5-membered, side ring. Although cephalosporins are among the most commonly used antibiotics in the treatment of routine infections, and their use is increasing over time, they can cause a range of hypersensitivity reactions, from mild, delayed-onset cutaneous reactions to life-threatening anaphylaxis in patients with immunoglobulin E (IgE)-mediated allergy.
semisynthetic derivativeAny organic molecular entity derived from a natural product by partial chemical synthesis.
carboxylic acidA carbon oxoacid acid carrying at least one -C(=O)OH group and having the structure RC(=O)OH, where R is any any monovalent functional group. Carboxylic acids are the most common type of organic acid.
triazolesAn azole in which the five-membered heterocyclic aromatic skeleton contains three N atoms and two C atoms.
phenolsOrganic aromatic compounds having one or more hydroxy groups attached to a benzene or other arene ring.
amino acid amideAn amide of an amino acid formed formally by conversion of the carboxy group to a carboxamido group.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (4)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
LuciferasePhotinus pyralis (common eastern firefly)Potency25.57480.007215.758889.3584AID624030
GLS proteinHomo sapiens (human)Potency6.30960.35487.935539.8107AID624170
hypothetical protein, conservedTrypanosoma bruceiPotency31.62280.223911.245135.4813AID624173
estrogen nuclear receptor alphaHomo sapiens (human)Potency21.31380.000229.305416,493.5996AID743069
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (24)

Assay IDTitleYearJournalArticle
AID1296008Cytotoxic Profiling of Annotated Libraries Using Quantitative High-Throughput Screening2020SLAS discovery : advancing life sciences R & D, 01, Volume: 25, Issue:1
Cytotoxic Profiling of Annotated and Diverse Chemical Libraries Using Quantitative High-Throughput Screening.
AID1346986P-glycoprotein substrates identified in KB-3-1 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID651635Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
AID1346987P-glycoprotein substrates identified in KB-8-5-11 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID425653Renal clearance in human2009Journal of medicinal chemistry, Aug-13, Volume: 52, Issue:15
Physicochemical determinants of human renal clearance.
AID567091Drug absorption in human assessed as human intestinal absorption rate2011European journal of medicinal chemistry, Jan, Volume: 46, Issue:1
Prediction of drug intestinal absorption by new linear and non-linear QSPR.
AID444050Fraction unbound in human plasma2010Journal of medicinal chemistry, Feb-11, Volume: 53, Issue:3
Physicochemical space for optimum oral bioavailability: contribution of human intestinal absorption and first-pass elimination.
AID540209Volume of distribution at steady state in human after iv administration2008Drug metabolism and disposition: the biological fate of chemicals, Jul, Volume: 36, Issue:7
Trend analysis of a database of intravenous pharmacokinetic parameters in humans for 670 drug compounds.
AID540213Half life in human after iv administration2008Drug metabolism and disposition: the biological fate of chemicals, Jul, Volume: 36, Issue:7
Trend analysis of a database of intravenous pharmacokinetic parameters in humans for 670 drug compounds.
AID444057Fraction escaping hepatic elimination in human2010Journal of medicinal chemistry, Feb-11, Volume: 53, Issue:3
Physicochemical space for optimum oral bioavailability: contribution of human intestinal absorption and first-pass elimination.
AID444053Renal clearance in human2010Journal of medicinal chemistry, Feb-11, Volume: 53, Issue:3
Physicochemical space for optimum oral bioavailability: contribution of human intestinal absorption and first-pass elimination.
AID444051Total clearance in human2010Journal of medicinal chemistry, Feb-11, Volume: 53, Issue:3
Physicochemical space for optimum oral bioavailability: contribution of human intestinal absorption and first-pass elimination.
AID540212Mean residence time in human after iv administration2008Drug metabolism and disposition: the biological fate of chemicals, Jul, Volume: 36, Issue:7
Trend analysis of a database of intravenous pharmacokinetic parameters in humans for 670 drug compounds.
AID444058Volume of distribution at steady state in human2010Journal of medicinal chemistry, Feb-11, Volume: 53, Issue:3
Physicochemical space for optimum oral bioavailability: contribution of human intestinal absorption and first-pass elimination.
AID540211Fraction unbound in human after iv administration2008Drug metabolism and disposition: the biological fate of chemicals, Jul, Volume: 36, Issue:7
Trend analysis of a database of intravenous pharmacokinetic parameters in humans for 670 drug compounds.
AID592681Apparent permeability across human Caco2 cell membrane after 2 hrs by LC-MS/MS analysis2011Bioorganic & medicinal chemistry, Apr-15, Volume: 19, Issue:8
QSAR-based permeability model for drug-like compounds.
AID540210Clearance in human after iv administration2008Drug metabolism and disposition: the biological fate of chemicals, Jul, Volume: 36, Issue:7
Trend analysis of a database of intravenous pharmacokinetic parameters in humans for 670 drug compounds.
AID444052Hepatic clearance in human2010Journal of medicinal chemistry, Feb-11, Volume: 53, Issue:3
Physicochemical space for optimum oral bioavailability: contribution of human intestinal absorption and first-pass elimination.
AID444055Fraction absorbed in human2010Journal of medicinal chemistry, Feb-11, Volume: 53, Issue:3
Physicochemical space for optimum oral bioavailability: contribution of human intestinal absorption and first-pass elimination.
AID476929Human intestinal absorption in po dosed human2010European journal of medicinal chemistry, Mar, Volume: 45, Issue:3
Neural computational prediction of oral drug absorption based on CODES 2D descriptors.
AID425652Total body clearance in human2009Journal of medicinal chemistry, Aug-13, Volume: 52, Issue:15
Physicochemical determinants of human renal clearance.
AID444056Fraction escaping gut-wall elimination in human2010Journal of medicinal chemistry, Feb-11, Volume: 53, Issue:3
Physicochemical space for optimum oral bioavailability: contribution of human intestinal absorption and first-pass elimination.
AID444054Oral bioavailability in human2010Journal of medicinal chemistry, Feb-11, Volume: 53, Issue:3
Physicochemical space for optimum oral bioavailability: contribution of human intestinal absorption and first-pass elimination.
AID1159607Screen for inhibitors of RMI FANCM (MM2) intereaction2016Journal of biomolecular screening, Jul, Volume: 21, Issue:6
A High-Throughput Screening Strategy to Identify Protein-Protein Interaction Inhibitors That Block the Fanconi Anemia DNA Repair Pathway.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (70)

TimeframeStudies, This Drug (%)All Drugs %
pre-199040 (57.14)18.7374
1990's13 (18.57)18.2507
2000's6 (8.57)29.6817
2010's8 (11.43)24.3611
2020's3 (4.29)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 109.06

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be very strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index109.06 (24.57)
Research Supply Index4.45 (2.92)
Research Growth Index4.33 (4.65)
Search Engine Demand Index195.48 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (109.06)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials11 (14.86%)5.53%
Reviews3 (4.05%)6.00%
Case Studies2 (2.70%)4.05%
Observational0 (0.00%)0.25%
Other58 (78.38%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]