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]
| ID Source | ID |
|---|---|
| PubMed CID | 6536774 |
| CHEMBL ID | 2074822 |
| CHEBI ID | 3488 |
| SCHEMBL ID | 75058 |
| MeSH ID | M0203138 |
| 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 |
| 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] | |
| 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] | |
| 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] | ||||
| 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] | ||
| 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] | ||