Page last updated: 2024-12-06

cefminox

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Description

cefminox : A second-generation cephamycin antibiotic having [(1-methyl-1H-tetrazol-5-yl)sulfanyl]methyl and 2-{[(2S)-2-amino-2-carboxyethyl]sulfanyl}acetamido side-groups located respectively at positions 3 and 7beta of the cephem nucleus. A broad-spectrum bactericide, it is especially effective against Gram-negative and anaerobic bacteria. [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 CID71141
CHEMBL ID1276342
CHEBI ID135817
SCHEMBL ID49565
MeSH IDM0133680

Synonyms (34)

Synonym
NCGC00181749-01
D07642
cefminox (inn)
75481-73-1
cmnx
5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 7-((((2-amino-2-carboxyethyl)thio)acetyl)amino)-7-methoxy-3-(((1-methyl-1h-tetrazol-5-yl)thio)methyl)-8-oxo-, (6r-(6alpha,7alpha,7(s*)))-
ccris 5270
5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 7-(((((2s)-2-amino-2-carboxyethyl)thio)acetyl)amino)-7-methoxy-3-(((1-methyl-1h-tetrazol-5-yl)thio)methyl)-8-oxo-, (6r,7s)-
cefminox
(6r,7s)-7-(2-{[(2s)-2-amino-2-carboxyethyl]sulfanyl}acetamido)-7-methoxy-3-{[(1-methyl-1h-tetrazol-5-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
(7s)-7-(2-{[(2s)-2-amino-2-carboxyethyl]sulfanyl}acetamido)-7-methoxy-3-{[(1-methyl-1h-tetrazol-5-yl)sulfanyl]methyl}-3,4-didehydrocepham-4-carboxylic acid
cefminoxum
CHEBI:135817
84305-41-9
(6r,7s)-7-[[2-[(2s)-2-amino-3-hydroxy-3-oxopropyl]sulfanylacetyl]amino]-7-methoxy-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
CHEMBL1276342
pw08y13465 ,
unii-pw08y13465
cefminoxum [latin]
mt 141
cefminox [inn]
AKOS015895987
SCHEMBL49565
cefminox [mi]
5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 7-((2-(((2s)-2-amino-2-carboxyethyl)thio)acetyl)amino)-7-methoxy-3-(((1-methyl-1h-tetrazol-5-yl)thio)methyl)-8-oxo-, (6r,7s)-
mt-141 free acid
cefminox [who-dd]
(6r,7s)-7-(2-(((s)-2-amino-2-carboxyethyl)thio)acetamido)-7-methoxy-3-(((1-methyl-1h-tetrazol-5-yl)thio)methyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid
5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 7-((((2-amino-2-carboxyethyl)thio)acetyl)amino)-7-methoxy-3-(((1-methyl-1h-tetrazol-5-yl)thio)methyl)-8-oxo-, (6r-(6.alpha.,7.alpha.,7(s*)))-
Q5057239
DB09062
DTXSID301016174
gtpl12255
(6r,7s)-7-[[2-[(2s)-2-amino-2-carboxyethyl]sulfanylacetyl]amino]-7-methoxy-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Research Excerpts

Overview

Cefminox is a new cephamycin antibiotic. D-amino acid moiety derived from D-cysteine at the C-7B side chain.

ExcerptReferenceRelevance
"Cefminox is a new cephamycin antibiotic possessing a D-amino acid moiety derived from D-cysteine at the C-7B side chain. "( Pharmacology of cefminox, a new bactericidal cephamycin.
Omoto, S; Watanabe, S, 1990
)
2.07

Effects

ExcerptReferenceRelevance
"Cefminox has proved to be 4-16 times more active than cefoxitin against enteric Gram-negative bacilli commonly involved in cholecystitis, secondary peritonitis, intraabdominal abscesses and gynecological infections."( [Should cefminox substitute cefoxitin in infections caused by bacteria susceptible to both drugs?].
Burillo, A; Dámaso, D; Losada, I; Rogero, G, 1999
)
1.46

Toxicity

ExcerptReferenceRelevance
" The toxic effects of MT-141 were as follows."( [Toxicological studies on a new cephamycin, MT-141. VI. Its chronic toxicity in beagle dogs].
Kawaoto, H; Kumagai, K; Kurebe, M; Niizato, T; Sasaki, H; Seki, M; Suzuki, H; Yokota, M, 1984
)
0.27

Dosage Studied

ExcerptRelevanceReference
"8% of the drug dosed were excreted at active form in urine."( [Study on a new cephamycin preparation cefminox in the field of pediatrics].
Chikaoka, H; Hirama, Y; Matsumoto, K; Nakazawa, S; Narita, A; Sato, H; Suzuki, H; Tazoe, K, 1985
)
0.54
" The drug was administered intravenously as one shot injection at a mean daily dosage of 76."( [Fundamental and clinical studies of cefminox in children].
Fujimoto, T; Ishimoto, K; Koga, T; Motohiro, T; Nishiyama, T; Sakata, Y; Shimada, Y; Tanaka, K; Tominaga, K; Tomita, N, 1985
)
0.54
"4% of the drug dosed recovered from the urine within the first 8 hours on an average."( [Fundamental and clinical studies on cefminox in the field of pediatrics].
Iwai, N; Katayama, M; Mizoguchi, F; Shibata, M; Taneda, Y, 1985
)
0.54
" The dosage of the drug was 21."( [Therapeutic effects of cefminox in the treatment of various infections of infants and children].
Hamawaki, M; Kitamura, I; Kubonishi, S; Kuramitsu, M; Kurashige, T; Morita, H; Ogura, H; Ozaki, H; Tone, Y; Wakiguchi, H, 1985
)
0.58
" The dosage was 2 to 4 g/day in 2 divided doses and the treatment was continued for a period 2 to 17 days."( [Clinical study of cefminox in respiratory tract infections].
Ikeda, H; Kaneko, T; Murohashi, K; Odagiri, S; Suzuki, K, 1985
)
0.6
" As a rule, CMNX was administered intravenously at a dosage of 1 g each twice a day by drip infusion route."( [Use of cefminox in infections in the field of obstetrics and gynecology].
Furukawa, K; Igarashi, A; Koga, S; Nakagawa, K; Nakakuki, M; Okamura, K; Yamada, K, 1985
)
0.7
" Clinically, in 7 cases of female genital infections (4 cases of parametritis, 1 case of intrauterine infection, 1 case of pyometra and 1 case of pelveoperitonitis), CMNX was administered at a daily dosage of 2 g in 2 divided doses as intravenous drip infusions taking 90 minutes each."( [Basic and clinical studies on cefminox in the field of obstetrics and gynecology].
Hirabayashi, K; Okada, E, 1985
)
0.56
" MT-141 at all dosage levels caused no lethal effect on rats."( [Toxicological studies of a new cephamycin, MT-141. III. Its chronic toxicity in rats].
Hayasaka, H; Kawaoto, H; Kurebe, M; Niizato, T; Watanabe, H; Yokota, M, 1984
)
0.27
"MT-141 was dosed to male and female Beagle dogs through intravenous (i."( [Toxicological studies on a new cephamycin, MT-141. VI. Its chronic toxicity in beagle dogs].
Kawaoto, H; Kumagai, K; Kurebe, M; Niizato, T; Sasaki, H; Seki, M; Suzuki, H; Yokota, M, 1984
)
0.27
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (2)

ClassDescription
cephamycinAny member of the cephamycin sub-group of cephem antibiotics, differing from cephalosporins in possessing a methoxy group at the 7alpha-position of the cephem nucleus, and in being resistant to beta-lactamase.
tetrazolesAn azole in which the five-membered heterocyclic aromatic skeleton contains four N atoms and one C atom.
[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]

Bioassays (24)

Assay IDTitleYearJournalArticle
AID1079939Cirrhosis, proven histopathologically. Value is number of references indexed. [column 'CIRRH' in source]
AID534382Antibacterial activity against Escherichia coli K-12 W1895 transconjugant harboring pCF243 by microdilution method2008Antimicrobial agents and chemotherapy, Nov, Volume: 52, Issue:11
KHM-1, a novel plasmid-mediated metallo-beta-lactamase from a Citrobacter freundii clinical isolate.
AID1079949Proposed mechanism(s) of liver damage. [column 'MEC' in source]
AID1079945Animal toxicity known. [column 'TOXIC' in source]
AID1079942Steatosis, proven histopathologically. Value is number of references indexed. [column 'STEAT' in source]
AID1079934Highest frequency of acute liver toxicity observed during clinical trials, expressed as a percentage. [column '% AIGUE' in source]
AID1079933Acute liver toxicity defined via clinical observations and clear clinical-chemistry results: serum ALT or AST activity > 6 N or serum alkaline phosphatases activity > 1.7 N. This category includes cytolytic, choleostatic and mixed liver toxicity. Value is
AID1079938Chronic liver disease either proven histopathologically, or through a chonic elevation of serum amino-transferase activity after 6 months. Value is number of references indexed. [column 'CHRON' in source]
AID534379Antibacterial activity against Citrobacter freundii KHM243 clinical isolate by microdilution method2008Antimicrobial agents and chemotherapy, Nov, Volume: 52, Issue:11
KHM-1, a novel plasmid-mediated metallo-beta-lactamase from a Citrobacter freundii clinical isolate.
AID1079941Liver damage due to vascular disease: peliosis hepatitis, hepatic veno-occlusive disease, Budd-Chiari syndrome. Value is number of references indexed. [column 'VASC' in source]
AID1079932Highest frequency of moderate liver toxicity observed during clinical trials, expressed as a percentage. [column '% BIOL' in source]
AID1079936Choleostatic liver toxicity, either proven histopathologically or where the ratio of maximal ALT or AST activity above normal to that of Alkaline Phosphatase is < 2 (see ACUTE). Value is number of references indexed. [column 'CHOLE' in source]
AID534391Antibacterial activity against Escherichia coli JM109 by microdilution method2008Antimicrobial agents and chemotherapy, Nov, Volume: 52, Issue:11
KHM-1, a novel plasmid-mediated metallo-beta-lactamase from a Citrobacter freundii clinical isolate.
AID1079944Benign tumor, proven histopathologically. Value is number of references indexed. [column 'T.BEN' in source]
AID534388Antibacterial activity against Escherichia coli JM109 harboring recombinant pKHM-1 by microdilution method2008Antimicrobial agents and chemotherapy, Nov, Volume: 52, Issue:11
KHM-1, a novel plasmid-mediated metallo-beta-lactamase from a Citrobacter freundii clinical isolate.
AID1079948Times to onset, minimal and maximal, observed in the indexed observations. [column 'DELAI' in source]
AID1079937Severe hepatitis, defined as possibly life-threatening liver failure or through clinical observations. Value is number of references indexed. [column 'MASS' in source]
AID1079935Cytolytic liver toxicity, either proven histopathologically or where the ratio of maximal ALT or AST activity above normal to that of Alkaline Phosphatase is > 5 (see ACUTE). Value is number of references indexed. [column 'CYTOL' in source]
AID534385Antibacterial activity against Escherichia coli K-12 W1895 by microdilution method2008Antimicrobial agents and chemotherapy, Nov, Volume: 52, Issue:11
KHM-1, a novel plasmid-mediated metallo-beta-lactamase from a Citrobacter freundii clinical isolate.
AID1079931Moderate liver toxicity, defined via clinical-chemistry results: ALT or AST serum activity 6 times the normal upper limit (N) or alkaline phosphatase serum activity of 1.7 N. Value is number of references indexed. [column 'BIOL' in source]
AID1079940Granulomatous liver disease, proven histopathologically. Value is number of references indexed. [column 'GRAN' in source]
AID1079947Comments (NB not yet translated). [column 'COMMENTAIRES' in source]
AID1079946Presence of at least one case with successful reintroduction. [column 'REINT' in source]
AID1079943Malignant tumor, proven histopathologically. Value is number of references indexed. [column 'T.MAL' in source]
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (110)

TimeframeStudies, This Drug (%)All Drugs %
pre-199078 (70.91)18.7374
1990's23 (20.91)18.2507
2000's5 (4.55)29.6817
2010's4 (3.64)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 33.92

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 moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index33.92 (24.57)
Research Supply Index4.80 (2.92)
Research Growth Index4.12 (4.65)
Search Engine Demand Index45.89 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (33.92)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials10 (9.01%)5.53%
Reviews1 (0.90%)6.00%
Case Studies9 (8.11%)4.05%
Observational0 (0.00%)0.25%
Other91 (81.98%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]