Record Information |
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Version | 1.0 |
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Creation Date | 2016-05-22 03:43:44 UTC |
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Update Date | 2016-11-09 01:15:28 UTC |
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Accession Number | CHEM016789 |
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Identification |
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Common Name | Mezlocillin |
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Class | Small Molecule |
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Description | A penicillin in which the substituent at position 6 of the penam ring is a (2R)-2-[3-(methanesulfonyl)-2-oxoimidazolidine-1-carboxamido]-2-phenylacetamido group. |
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Contaminant Sources | - HMDB Contaminants - Urine
- STOFF IDENT Compounds
- ToxCast & Tox21 Chemicals
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Contaminant Type | Not Available |
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Chemical Structure | |
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Synonyms | Value | Source |
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(2S,5R,6R)-3,3-Dimethyl-6-{[(2R)-2-({[3-(methylsulfonyl)-2-oxoimidazolidin-1-yl]carbonyl}amino)-2-phenylacetyl]amino}-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid | ChEBI | 6beta-{(2R)-2-[3-(methanesulfonyl)-2-oxoimidazolidine-1-carboxamido]-2-phenylacetamido}penicillanic acid | ChEBI | Mezlin | ChEBI | Mezlocilina | ChEBI | Mezlocilline | ChEBI | Mezlocillinum | ChEBI | (2S,5R,6R)-3,3-Dimethyl-6-{[(2R)-2-({[3-(methylsulfonyl)-2-oxoimidazolidin-1-yl]carbonyl}amino)-2-phenylacetyl]amino}-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate | Generator | (2S,5R,6R)-3,3-Dimethyl-6-{[(2R)-2-({[3-(methylsulphonyl)-2-oxoimidazolidin-1-yl]carbonyl}amino)-2-phenylacetyl]amino}-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate | Generator | (2S,5R,6R)-3,3-Dimethyl-6-{[(2R)-2-({[3-(methylsulphonyl)-2-oxoimidazolidin-1-yl]carbonyl}amino)-2-phenylacetyl]amino}-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid | Generator | 6b-{(2R)-2-[3-(methanesulfonyl)-2-oxoimidazolidine-1-carboxamido]-2-phenylacetamido}penicillanate | Generator | 6b-{(2R)-2-[3-(methanesulfonyl)-2-oxoimidazolidine-1-carboxamido]-2-phenylacetamido}penicillanic acid | Generator | 6b-{(2R)-2-[3-(methanesulphonyl)-2-oxoimidazolidine-1-carboxamido]-2-phenylacetamido}penicillanate | Generator | 6b-{(2R)-2-[3-(methanesulphonyl)-2-oxoimidazolidine-1-carboxamido]-2-phenylacetamido}penicillanic acid | Generator | 6beta-{(2R)-2-[3-(methanesulfonyl)-2-oxoimidazolidine-1-carboxamido]-2-phenylacetamido}penicillanate | Generator | 6beta-{(2R)-2-[3-(methanesulphonyl)-2-oxoimidazolidine-1-carboxamido]-2-phenylacetamido}penicillanate | Generator | 6beta-{(2R)-2-[3-(methanesulphonyl)-2-oxoimidazolidine-1-carboxamido]-2-phenylacetamido}penicillanic acid | Generator | 6Β-{(2R)-2-[3-(methanesulfonyl)-2-oxoimidazolidine-1-carboxamido]-2-phenylacetamido}penicillanate | Generator | 6Β-{(2R)-2-[3-(methanesulfonyl)-2-oxoimidazolidine-1-carboxamido]-2-phenylacetamido}penicillanic acid | Generator | 6Β-{(2R)-2-[3-(methanesulphonyl)-2-oxoimidazolidine-1-carboxamido]-2-phenylacetamido}penicillanate | Generator | 6Β-{(2R)-2-[3-(methanesulphonyl)-2-oxoimidazolidine-1-carboxamido]-2-phenylacetamido}penicillanic acid | Generator | Bayf 1353 | HMDB | Curasan brand OF mezlocillin sodium (sterile) | HMDB | Baypen | HMDB | Melocin | HMDB | Sodium, mezlocillin | HMDB | Mezlocillin sodium | HMDB | Bay F 1353 | HMDB | Bay-F 1353 | HMDB | Bayer brand OF mezlocillin sodium (sterile) | HMDB | Meslocillin | HMDB |
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Chemical Formula | C21H25N5O8S2 |
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Average Molecular Mass | 539.582 g/mol |
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Monoisotopic Mass | 539.114 g/mol |
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CAS Registry Number | 51481-65-3 |
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IUPAC Name | (2S,5R,6R)-6-[(2R)-2-[(3-methanesulfonyl-2-oxoimidazolidine-1-carbonyl)amino]-2-phenylacetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid |
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Traditional Name | mezlocillin |
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SMILES | [H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)[C@H](NC(=O)N1CCN(C1=O)S(C)(=O)=O)C1=CC=CC=C1)C(O)=O |
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InChI Identifier | InChI=1S/C21H25N5O8S2/c1-21(2)14(18(29)30)26-16(28)13(17(26)35-21)22-15(27)12(11-7-5-4-6-8-11)23-19(31)24-9-10-25(20(24)32)36(3,33)34/h4-8,12-14,17H,9-10H2,1-3H3,(H,22,27)(H,23,31)(H,29,30)/t12-,13-,14+,17-/m1/s1 |
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InChI Key | YPBATNHYBCGSSN-VWPFQQQWSA-N |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as peptides. Peptides are compounds containing an amide derived from two or more amino carboxylic acid molecules (the same or different) by formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another. |
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Kingdom | Organic compounds |
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Super Class | Organic acids and derivatives |
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Class | Carboxylic acids and derivatives |
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Sub Class | Amino acids, peptides, and analogues |
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Direct Parent | Peptides |
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Alternative Parents | |
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Substituents | - Alpha peptide
- Penicillin
- N-acyl-alpha amino acid or derivatives
- N-carbamoyl-alpha-amino acid or derivatives
- Alpha-amino acid amide
- N-substituted-alpha-amino acid
- Alpha-amino acid or derivatives
- Phenylacetamide
- Penam
- Sulfonylurea
- Monocyclic benzene moiety
- Imidazolidinone
- Benzenoid
- Beta-lactam
- Imidazolidine
- Organic sulfonic acid or derivatives
- Organosulfonic acid or derivatives
- Sulfonyl
- Tertiary carboxylic acid amide
- Thiazolidine
- Urea
- Azetidine
- Secondary carboxylic acid amide
- Carbonic acid derivative
- Lactam
- Carboxamide group
- Hemithioaminal
- Dialkylthioether
- Thioether
- Organoheterocyclic compound
- Azacycle
- Monocarboxylic acid or derivatives
- Carboxylic acid
- Organic nitrogen compound
- Organic oxygen compound
- Hydrocarbon derivative
- Carbonyl group
- Organonitrogen compound
- Organopnictogen compound
- Organooxygen compound
- Organosulfur compound
- Organic oxide
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic heteropolycyclic compounds |
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External Descriptors | |
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Biological Properties |
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Status | Detected and Not Quantified |
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Origin | Not Available |
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Cellular Locations | Not Available |
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Biofluid Locations | Not Available |
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Tissue Locations | Not Available |
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Pathways | Not Available |
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Applications | Not Available |
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Biological Roles | Not Available |
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Chemical Roles | Not Available |
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Physical Properties |
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State | Not Available |
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Appearance | Not Available |
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Experimental Properties | Property | Value |
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Melting Point | Not Available | Boiling Point | Not Available | Solubility | Not Available |
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Predicted Properties | |
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Spectra |
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Spectra | Spectrum Type | Description | Splash Key | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0002-1090000000-30ba63db4797e4d4836d | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive | splash10-0002-1090000000-8356c0b1a87fcce856cf | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS ("Mezlocillin,1TMS,#1" TMS) - 70eV, Positive | Not Available | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-014i-0910010000-9de4bf02d7dd1cc9d377 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-00kr-7910000000-e06a9bd362ce4723bce2 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-014r-6900000000-f20f6eeb80ce786a597d | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0002-0109200000-4b61d69c53d74fe2e0a6 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-00kb-3908300000-41e54898cd272dbc82ec | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-004i-9311000000-fd81fa067ad63b9dc4d0 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0006-0432090000-edbf59d4f68de248dc62 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-00lr-3925010000-5a77477e443c073ce3f2 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-01q9-0913100000-38849f0b13c1ff924b58 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-03di-1902030000-431dbf04e41622d870c4 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-001i-9500000000-6bd2926f658df74e070e | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-00fu-7910000000-2183d83c42f1b7c12ac4 | Spectrum | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum |
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Toxicity Profile |
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Route of Exposure | Not Available |
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Mechanism of Toxicity | Not Available |
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Metabolism | Not Available |
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Toxicity Values | Not Available |
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Lethal Dose | Not Available |
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Carcinogenicity (IARC Classification) | Not Available |
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Uses/Sources | Not Available |
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Minimum Risk Level | Not Available |
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Health Effects | Not Available |
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Symptoms | Not Available |
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Treatment | Not Available |
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Concentrations |
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| Not Available |
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External Links |
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DrugBank ID | DB00948 |
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HMDB ID | HMDB0015083 |
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FooDB ID | Not Available |
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Phenol Explorer ID | Not Available |
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KNApSAcK ID | Not Available |
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BiGG ID | Not Available |
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BioCyc ID | Not Available |
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METLIN ID | Not Available |
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PDB ID | Not Available |
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Wikipedia Link | Mezlocillin |
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Chemspider ID | 570894 |
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ChEBI ID | 6919 |
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PubChem Compound ID | 656511 |
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Kegg Compound ID | C07221 |
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YMDB ID | Not Available |
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ECMDB ID | Not Available |
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References |
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Synthesis Reference | Not Available |
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MSDS | Not Available |
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General References | 1. https://www.ncbi.nlm.nih.gov/pubmed/?term=1701026 | 2. https://www.ncbi.nlm.nih.gov/pubmed/?term=29017833 | 3. https://www.ncbi.nlm.nih.gov/pubmed/?term=6460964 | 4. https://www.ncbi.nlm.nih.gov/pubmed/?term=9403281 | 5. McCormick PA, Greenslade L, Kibbler CC, Chin JK, Burroughs AK, McIntyre N: A prospective randomized trial of ceftazidime versus netilmicin plus mezlocillin in the empirical therapy of presumed sepsis in cirrhotic patients. Hepatology. 1997 Apr;25(4):833-6. | 6. Rohde B, Werner U, Hickstein H, Ehmcke H, Drewelow B: Pharmacokinetics of mezlocillin and sulbactam under continuous veno-venous hemodialysis (CVVHD) in intensive care patients with acute renal failure. Eur J Clin Pharmacol. 1997;53(2):111-5. | 7. Kristof RA, Clusmann H, Koehler W, Fink KB, Schramm J: Treatment of accidental high dose intraventricular mezlocillin application by cerebrospinal fluid exchange. J Neurol Neurosurg Psychiatry. 1998 Mar;64(3):379-81. |
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