Record Information |
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Version | 4.0 |
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Status | Expected but not Quantified |
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Creation Date | 2012-09-06 15:16:52 UTC |
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Update Date | 2020-02-26 21:41:35 UTC |
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HMDB ID | HMDB0015421 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Cefamandole |
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Description | Cefamandole is only found in individuals that have used or taken this drug. It is a broad-spectrum cephalosporin antibiotic. The clinically used form of cefamandole is the formate ester cefamandole nafate, a prodrug which is administered parenterally. Cefamandole is no longer available in the United States.Like all beta-lactam antibiotics, cefamandole binds to specific penicillin-binding proteins (PBPs) located inside the bacterial cell wall, causing the inhibition of the third and last stage of bacterial cell wall synthesis. Cell lysis is then mediated by bacterial cell wall autolytic enzymes such as autolysins; it is possible that cefamandole interferes with an autolysin inhibitor. |
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Structure | |
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Synonyms | Value | Source |
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(6R,7R)-7-(R)-Mandelamido-3-(((1-methyl-1H-tetrazol-5-yl)thio)methyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-carboxylic acid | ChEBI | (6R,7R)-7-{[(2R)-2-hydroxy-2-phenylacetyl]amino}-3-{[(1-methyl-1H-tetrazol-5-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid | ChEBI | Cefadole | ChEBI | Cefamandol | ChEBI | Cefamandolum | ChEBI | Cephadole | ChEBI | Cephamandole | ChEBI | L-Cefamandole | ChEBI | CMD | Kegg | (6R,7R)-7-(R)-Mandelamido-3-(((1-methyl-1H-tetrazol-5-yl)thio)methyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-carboxylate | Generator | (6R,7R)-7-{[(2R)-2-hydroxy-2-phenylacetyl]amino}-3-{[(1-methyl-1H-tetrazol-5-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate | Generator | (6R,7R)-7-{[(2R)-2-hydroxy-2-phenylacetyl]amino}-3-{[(1-methyl-1H-tetrazol-5-yl)sulphanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate | Generator | (6R,7R)-7-{[(2R)-2-hydroxy-2-phenylacetyl]amino}-3-{[(1-methyl-1H-tetrazol-5-yl)sulphanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid | Generator | Cefamandole nafate | HMDB | Compound 83405 | HMDB |
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Chemical Formula | C18H18N6O5S2 |
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Average Molecular Weight | 462.503 |
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Monoisotopic Molecular Weight | 462.078009096 |
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IUPAC Name | (6R,7R)-7-[(2R)-2-hydroxy-2-phenylacetamido]-3-{[(1-methyl-1H-1,2,3,4-tetrazol-5-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid |
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Traditional Name | cefamandole |
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CAS Registry Number | 34444-01-4 |
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SMILES | [H][C@]12SCC(CSC3=NN=NN3C)=C(N1C(=O)[C@H]2NC(=O)[C@H](O)C1=CC=CC=C1)C(O)=O |
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InChI Identifier | InChI=1S/C18H18N6O5S2/c1-23-18(20-21-22-23)31-8-10-7-30-16-11(15(27)24(16)12(10)17(28)29)19-14(26)13(25)9-5-3-2-4-6-9/h2-6,11,13,16,25H,7-8H2,1H3,(H,19,26)(H,28,29)/t11-,13-,16-/m1/s1 |
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InChI Key | OLVCFLKTBJRLHI-AXAPSJFSSA-N |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as cephalosporins. Cephalosporins are compounds containing a 1,2-thiazine fused to a 2-azetidinone to for a oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid moiety or a derivative thereof. |
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Kingdom | Organic compounds |
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Super Class | Organoheterocyclic compounds |
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Class | Lactams |
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Sub Class | Beta lactams |
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Direct Parent | Cephalosporins |
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Alternative Parents | |
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Substituents | - Cephalosporin
- N-acyl-alpha amino acid or derivatives
- Alpha-amino acid or derivatives
- Phenylacetamide
- Aryl thioether
- Alkylarylthioether
- Benzenoid
- Meta-thiazine
- Monocyclic benzene moiety
- Heteroaromatic compound
- Tetrazole
- Azole
- Tertiary carboxylic acid amide
- Carboxamide group
- Azetidine
- Secondary alcohol
- Secondary carboxylic acid amide
- Azacycle
- Carboxylic acid derivative
- Carboxylic acid
- Dialkylthioether
- Monocarboxylic acid or derivatives
- Sulfenyl compound
- Hemithioaminal
- Thioether
- Organic oxygen compound
- Alcohol
- Organic nitrogen compound
- Organopnictogen compound
- Organic oxide
- Organonitrogen compound
- Organooxygen compound
- Organosulfur compound
- Aromatic alcohol
- Hydrocarbon derivative
- Carbonyl group
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic heteropolycyclic compounds |
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External Descriptors | |
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Ontology |
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Disposition | Biological location: |
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Role | Industrial application: |
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Physical Properties |
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State | Solid |
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Experimental Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 0.58 g/L | Not Available | LogP | 0.50 | SANGSTER (1994) |
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Predicted Properties | |
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| Spectrum Type | Description | Splash Key | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0a4i-1900000000-171ae249ec803b8d5abd | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive | splash10-004i-0900000000-fb3cc081c83b0d53a10c | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-05dl-4698600000-8b8ba1529bcdbe274bfa | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0ab9-4956100000-2107c26a4908fb9913eb | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-05fr-3390000000-2cd8861a785705076af0 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-014l-1910200000-8214388978bd4c2b1ca7 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0aor-9710000000-6d5c2f7837d35a1fb4fe | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0ar3-9530000000-32e2979223057f6e2cf1 | Spectrum |
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