cefluprenam

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth

Description

cefluprenam: has broad antibacterial spectrum; structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

cefluprenam : A fourth-generation cephalosporin antibiotic having (1E)-3-[(2-amino-2-oxoethyl)(ethyl)methylazaniumyl]prop-1-en-1-yl and {(2Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-[(fluoromethoxy)imino]acetyl}amino side groups located at positions 3 and 7 respectively. [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 Source	ID
PubMed CID	6536774
CHEMBL ID	2074822
CHEBI ID	3488
SCHEMBL ID	75058
MeSH ID	M0203138

Synonyms (26)

Synonym
cefprenam
cefluprenam
e-1077 ,
cefluprenam [inn]
2-propen-1-aminium, n-(2-amino-2-oxoethyl)-3-(7-(((5-amino-1,2,4-thiadiazol-3-yl)((fluoromethoxy)imino)acetyl)amino)-2-carboxy-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-en-3-yl)-n-ethyl-n-methyl-, inner salt, (6r-(3(e),6-alpha,7-beta(z)))-
(-)-((e)-3-((6r,7r)-7-(2-(5-amino-1,2,4-thiadiazol-3-yl)glyoxylamido)-2-carboxy-8-oxo-5-thia-1-azabicyclo (4.2.0)oct-2-en-3-yl)allyl)(carbamoylmethyl)ethylmethylammonium hydroxide, inner salt, 7(sup 2)-(z)-(o-(fluoromethyl)oxime)
antibiotic e 1077
e 1077
116853-25-9
cefluprenam (jan/inn)
D01054
(6r,7r)-3-[(e)-3-[(2-amino-2-oxoethyl)-ethyl-methylazaniumyl]prop-1-enyl]-7-[[(2e)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(fluoromethoxyimino)acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
(6r,7r)-3-[(e)-3-[(2-amino-2-oxoethyl)-ethyl-methylazaniumyl]prop-1-enyl]-7-[[(2z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(fluoromethoxyimino)acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
CHEMBL2074822
unii-098633q42p
098633q42p ,
SCHEMBL75058
cefluprenam [mart.]
cefluprenam [jan]
7-({(2z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-[(fluoromethoxy)imino]acetyl}amino)-3-[(1e)-3-[(2-amino-2-oxoethyl)(ethyl)methylazaniumyl]prop-1-en-1-yl]-3,4-didehydrocepham-4-carboxylate
(6r,7r)-3-{(1e)-3-[(2-amino-2-oxoethyl)(ethyl)methylazaniumyl]prop-1-en-1-yl}-7-({(2z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-[(fluoromethoxy)imino]acetyl}amino)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
cefluprenamum
CHEBI:3488
(6r,7r)-7-((e)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-((fluoromethoxy)imino)acetamido)-3-((e)-3-((2-amino-2-oxoethyl)(ethyl)(methyl)ammonio)prop-1-en-1-yl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
DTXSID001029568
AKOS040748101

[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

Role	Description
antimicrobial agent	A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
[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 (2)

Class	Description
cephalosporin	A 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.
thiadiazoles
[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 (23)

Assay ID	Title	Year	Journal	Article
AID1079937	Severe hepatitis, defined as possibly life-threatening liver failure or through clinical observations. Value is number of references indexed. [column 'MASS' in source]
AID1079945	Animal toxicity known. [column 'TOXIC' in source]
AID678867	TP_TRANSPORTER: inhibition of Gly-Sar uptake (Gly-Sar: 25 uM, Cefluprenam: 2500uM) in PEPT2-expressing HeLa cells	2000	The Journal of biological chemistry, Jan-21, Volume: 275, Issue:3	beta-lactam antibiotics as substrates for OCTN2, an organic cation/carnitine transporter.
AID682282	TP_TRANSPORTER: inhibition of Carnitine uptake (Carnitine: 0.02 uM, Cefluprenam: 2500 uM) in OCTN2-expressing HeLa cells	2000	The Journal of biological chemistry, Jan-21, Volume: 275, Issue:3	beta-lactam antibiotics as substrates for OCTN2, an organic cation/carnitine transporter.
AID1079941	Liver damage due to vascular disease: peliosis hepatitis, hepatic veno-occlusive disease, Budd-Chiari syndrome. Value is number of references indexed. [column 'VASC' in source]
AID1079949	Proposed mechanism(s) of liver damage. [column 'MEC' in source]
AID1079947	Comments (NB not yet translated). [column 'COMMENTAIRES' in source]
AID1079942	Steatosis, proven histopathologically. Value is number of references indexed. [column 'STEAT' in source]
AID1079938	Chronic 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]
AID680846	TP_TRANSPORTER: inhibition of Gly-Sar uptake (Gly-Sar: 50 uM, Cefluprenam: 2500uM) in PEPT1-expressing HeLa cells	2000	The Journal of biological chemistry, Jan-21, Volume: 275, Issue:3	beta-lactam antibiotics as substrates for OCTN2, an organic cation/carnitine transporter.
AID1079943	Malignant tumor, proven histopathologically. Value is number of references indexed. [column 'T.MAL' in source]
AID1079933	Acute 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
AID1079946	Presence of at least one case with successful reintroduction. [column 'REINT' in source]
AID1079936	Choleostatic 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]
AID1079934	Highest frequency of acute liver toxicity observed during clinical trials, expressed as a percentage. [column '% AIGUE' in source]
AID1079944	Benign tumor, proven histopathologically. Value is number of references indexed. [column 'T.BEN' in source]
AID1079940	Granulomatous liver disease, proven histopathologically. Value is number of references indexed. [column 'GRAN' in source]
AID681717	TP_TRANSPORTER: inhibition of Carnitine uptake (Carnitine: 0.02 uM, Cefluprenam: 2500 uM) in OCTN2-expressing HeLa cells	2000	The Journal of biological chemistry, Jan-21, Volume: 275, Issue:3	beta-lactam antibiotics as substrates for OCTN2, an organic cation/carnitine transporter.
AID1079948	Times to onset, minimal and maximal, observed in the indexed observations. [column 'DELAI' in source]
AID1079931	Moderate 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]
AID1079935	Cytolytic 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]
AID1079932	Highest frequency of moderate liver toxicity observed during clinical trials, expressed as a percentage. [column '% BIOL' in source]
AID1079939	Cirrhosis, proven histopathologically. Value is number of references indexed. [column 'CIRRH' in source]
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (10)

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	0 (0.00)	18.7374
1990's	9 (90.00)	18.2507
2000's	1 (10.00)	29.6817
2010's	0 (0.00)	24.3611
2020's	0 (0.00)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication Type	This drug (%)	All Drugs (%)
Trials	3 (25.00%)	5.53%
Reviews	0 (0.00%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	9 (75.00%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Trials	Classes	Roles
acetaldehyde Acetaldehyde: A colorless, flammable liquid used in the manufacture of acetic acid, perfumes, and flavors. It is also an intermediate in the metabolism of alcohol. It has a general narcotic action and also causes irritation of mucous membranes. Large doses may cause death from respiratory paralysis.. acetaldehyde : The aldehyde formed from acetic acid by reduction of the carboxy group. It is the most abundant carcinogen in tobacco smoke.. aldehyde : A compound RC(=O)H, in which a carbonyl group is bonded to one hydrogen atom and to one R group.. acetyl group : A group, formally derived from acetic acid by dehydroxylation, which is fundamental to the biochemistry of all forms of life. When bound to coenzyme A, it is central to the metabolism of carbohydrates and fats.	1.98	1	0	aldehyde	carcinogenic agent; EC 3.5.1.4 (amidase) inhibitor; electron acceptor; Escherichia coli metabolite; human metabolite; mouse metabolite; mutagen; oxidising agent; Saccharomyces cerevisiae metabolite; teratogenic agent
cephaloridine Cephaloridine: A cephalosporin antibiotic.. cefaloridine : A cephalosporin compound having pyridinium-1-ylmethyl and 2-thienylacetamido side-groups. A first-generation semisynthetic derivative of cephalosporin C.	2	1	0	beta-lactam antibiotic allergen; cephalosporin; semisynthetic derivative	antibacterial drug
penicillin g Penicillin G: A penicillin derivative commonly used in the form of its sodium or potassium salts in the treatment of a variety of infections. It is effective against most gram-positive bacteria and against gram-negative cocci. It has also been used as an experimental convulsant because of its actions on GAMMA-AMINOBUTYRIC ACID mediated synaptic transmission.. benzylpenicillin : A penicillin in which the substituent at position 6 of the penam ring is a phenylacetamido group.	2	1	0	penicillin allergen; penicillin	antibacterial drug; drug allergen; epitope
ampicillin Ampicillin: Semi-synthetic derivative of penicillin that functions as an orally active broad-spectrum antibiotic.. ampicillin : A penicillin in which the substituent at position 6 of the penam ring is a 2-amino-2-phenylacetamido group.	2	1	0	beta-lactam antibiotic; penicillin allergen; penicillin	antibacterial drug
cyclacillin Cyclacillin: A cyclohexylamido analog of PENICILLANIC ACID.	2	1	0	penicillin	antibacterial drug
cephalexin Cephalexin: A semisynthetic cephalosporin antibiotic with antimicrobial activity similar to that of CEPHALORIDINE or CEPHALOTHIN, but somewhat less potent. It is effective against both gram-positive and gram-negative organisms.. cephalexin : A semisynthetic first-generation cephalosporin antibiotic having methyl and beta-(2R)-2-amino-2-phenylacetamido groups at the 3- and 7- of the cephem skeleton, respectively. It is effective against both Gram-negative and Gram-positive organisms, and is used for treatment of infections of the skin, respiratory tract and urinary tract.	2	1	0	beta-lactam antibiotic allergen; cephalosporin; semisynthetic derivative	antibacterial drug
cephradine Cephradine: A semi-synthetic cephalosporin antibiotic.. cephradine : A first-generation cephalosporin antibiotic with a methyl substituent at position 3, and a (2R)-2-amino-2-cyclohexa-1,4-dien-1-ylacetamido substituent at position 7, of the cephem skeleton.	2	1	0	beta-lactam antibiotic allergen; cephalosporin	antibacterial drug
cefadroxil anhydrous Cefadroxil: Long-acting, broad-spectrum, water-soluble, CEPHALEXIN derivative.. cefadroxil : A cephalosporin bearing methyl and (2R)-2-amino-2-(4-hydroxyphenyl)acetamido groups at positions 3 and 7, respectively, of the cephem skeleton.	2	1	0	cephalosporin	antibacterial drug
cephalosporin c cephalosporin C: RN given refers to parent cpd; structure in Merck, 9th ed, #1937. cephalosporin C : A cephalosporin antibiotic carrying a 3-acetoxymethyl substituent and a 6-oxo-N(6)-L-lysino group at position 7.	5.89	9	3	cephalosporin	fungal metabolite
glycidyl nitrate glycidyl nitrate: a nitric oxide donor; structure in first source. peptidoglycan : A peptidoglycosaminoglycan formed by alternating residues of beta-(1->4)-linked N-acetylglucosamine and N-acetylmuramic acid {2-amino-3-O-[(S)-1-carboxyethyl]-2-deoxy-D-glucose} residues. Attached to the carboxy group of the muramic acid is a peptide chain of three to five amino acids.	1.98	1	0
cefoxitin Cefoxitin: A semisynthetic cephamycin antibiotic resistant to beta-lactamase.. cefoxitin : A semisynthetic cephamycin antibiotic which, in addition to the methoxy group at the 7alpha position, has 2-thienylacetamido and carbamoyloxymethyl side-groups. It is resistant to beta-lactamase.	1.98	1	0	beta-lactam antibiotic allergen; cephalosporin; cephamycin; semisynthetic derivative	antibacterial drug
cefixime [no description available]	2	1	0	cephalosporin	antibacterial drug; drug allergen
cefepime Cefepime: A fourth-generation cephalosporin antibacterial agent that is used in the treatment of infections, including those of the abdomen, urinary tract, respiratory tract, and skin. It is effective against PSEUDOMONAS AERUGINOSA and may also be used in the empiric treatment of FEBRILE NEUTROPENIA.. cefepime : A cephalosporin bearing (1-methylpyrrolidinium-1-yl)methyl and (2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetamido groups at positions 3 and 7, respectively, of the cephem skeleton.	2	1	0	cephalosporin; oxime O-ether	antibacterial drug
ceftazidime [no description available]	2	1	0	cephalosporin; oxime O-ether	antibacterial drug; drug allergen; EC 2.4.1.129 (peptidoglycan glycosyltransferase) inhibitor
cefclidin cefclidin: structure given in first source. cefclidin : A fourth-generation cephalosporin antibiotic having (4-carbamoyl-1-azoniabicyclo[2.2.2]octan-1-yl)methyl and [(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]amino side groups located at positions 3 and 7 respectively.	1.98	1	0	cephalosporin; thiadiazoles
cefdinir [no description available]	2	1	0	cephalosporin; ketoxime	antibacterial drug

Condition	Relationship Strength	Studies	Trials
Autolysis The spontaneous disintegration of tissues or cells by the action of their own autogenous enzymes.	1.98	1	0
Bacterial Disease [description not available]	3.78	2	1
Necrotizing Pyelonephritis [description not available]	1.98	1	0
Bacterial Infections Infections by bacteria, general or unspecified.	3.78	2	1
Pyelonephritis Inflammation of the KIDNEY involving the renal parenchyma (the NEPHRONS); KIDNEY PELVIS; and KIDNEY CALICES. It is characterized by ABDOMINAL PAIN; FEVER; NAUSEA; VOMITING; and occasionally DIARRHEA.	1.98	1	0
Urinary Tract Infections Inflammatory responses of the epithelium of the URINARY TRACT to microbial invasions. They are often bacterial infections with associated BACTERIURIA and PYURIA.	2.39	2	0
Bacteremia The presence of viable bacteria circulating in the blood. Fever, chills, tachycardia, and tachypnea are common acute manifestations of bacteremia. The majority of cases are seen in already hospitalized patients, most of whom have underlying diseases or procedures which render their bloodstreams susceptible to invasion.	1.98	1	0
Infections, Respiratory [description not available]	3.38	1	1
Respiratory Tract Infections Invasion of the host RESPIRATORY SYSTEM by microorganisms, usually leading to pathological processes or diseases.	8.38	1	1
Disease Models, Animal Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.	1.99	1	0
Infections, Pseudomonas [description not available]	1.99	1	0
Urinary Calculi Low-density crystals or stones in any part of the URINARY TRACT. Their chemical compositions often include CALCIUM OXALATE, magnesium ammonium phosphate (struvite), CYSTINE, or URIC ACID.	1.99	1	0
Bacterial Infections, Gram-Positive [description not available]	1.99	1	0
Infections, Proteus [description not available]	1.99	1	0
Pseudomonas Infections Infections with bacteria of the genus PSEUDOMONAS.	1.99	1	0
Gram-Positive Bacterial Infections Infections caused by bacteria that retain the crystal violet stain (positive) when treated by the gram-staining method.	1.99	1	0
Infections, Klebsiella [description not available]	1.98	1	0
Group A Strep Infection [description not available]	1.98	1	0
Klebsiella Infections Infections with bacteria of the genus KLEBSIELLA.	1.98	1	0
Streptococcal Infections Infections with bacteria of the genus STREPTOCOCCUS.	1.98	1	0

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