Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2012-09-06 15:16:50 UTC |
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Update Date | 2022-03-07 02:51:46 UTC |
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HMDB ID | HMDB0014898 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Meropenem |
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Description | Meropenem, also known as merrem I.V. or MEPM, belongs to the class of organic compounds known as thienamycins. These are beta-lactam antibiotics that differ from penicillins in having the thiazolidine sulfur atom replaced by carbon, the sulfur then becoming the first atom in the side chain. Meropenem is a drug which is used for use as single agent therapy for the treatment of the following infections when caused by susceptible isolates of the designated microorganisms: complicated skin and skin structure infections due to staphylococcus aureus (b-lactamase and non-b-lactamase producing, methicillin-susceptible isolates only), streptococcus pyogenes, streptococcus agalactiae, viridans group streptococci, enterococcus faecalis (excluding vancomycin-resistant isolates), pseudomonas aeruginosa, escherichia coli, proteus mirabilis, bacteroides fragilis and peptostreptococcus species; complicated appendicitis and peritonitis caused by viridans group streptococci, escherichia coli, klebsiella pneumoniae, pseudomonas aeruginosa, bacteroides fragilis, b. thetaiotaomicron, and peptostreptococcus species. also for use in the treatment of bacterial meningitis caused by streptococcus pneumoniae, haemophilus influenzae (b-lactamase and non-b-lactamase-producing isolates), and neisseria meningitidis. Based on a literature review a significant number of articles have been published on Meropenem. |
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Structure | [H][C@]1([C@@H](C)O)C(=O)N2C(C(O)=O)=C(S[C@@H]3CN[C@@H](C3)C(=O)N(C)C)[C@H](C)[C@]12[H] InChI=1S/C17H25N3O5S/c1-7-12-11(8(2)21)16(23)20(12)13(17(24)25)14(7)26-9-5-10(18-6-9)15(22)19(3)4/h7-12,18,21H,5-6H2,1-4H3,(H,24,25)/t7-,8-,9+,10+,11-,12-/m1/s1 |
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Synonyms | Value | Source |
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(1R,5S,6S)-2-[(3S,5S)-5-DIMETHYLAMINOCARBONYLPYRROLIDIN-3-ylthio]-6-[(R)-1-hydroxyethyl]-1-methylcarbapen-2-em-3-carboxylIC ACID | ChEBI | (4R,5S,6S)-3-{[(3S,5S)-5-(dimethylcarbamoyl)pyrrolidin-3-yl]thio}-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid | ChEBI | Antibiotic SM 7338 | ChEBI | MEPM | ChEBI | Meropenem anhydrous | ChEBI | Meropenemum | ChEBI | Merrem i.v. | Kegg | Meronem | Kegg | (1R,5S,6S)-2-[(3S,5S)-5-DIMETHYLAMINOCARBONYLPYRROLIDIN-3-ylthio]-6-[(R)-1-hydroxyethyl]-1-methylcarbapen-2-em-3-carboxylate | Generator | (4R,5S,6S)-3-{[(3S,5S)-5-(dimethylcarbamoyl)pyrrolidin-3-yl]thio}-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate | Generator | 3-(5-Dimethylcarbamoylpyrrolidin-3-ylthio)-6-(1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo(3.2.0)hept-2-ene-2-carboxylic acid | HMDB | Merrem | HMDB | Ronem | HMDB | Penem | HMDB |
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Chemical Formula | C17H25N3O5S |
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Average Molecular Weight | 383.463 |
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Monoisotopic Molecular Weight | 383.151491615 |
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IUPAC Name | (4R,5S,6S)-3-{[(3S,5S)-5-(dimethylcarbamoyl)pyrrolidin-3-yl]sulfanyl}-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid |
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Traditional Name | meropenem |
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CAS Registry Number | 119478-56-7 |
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SMILES | [H][C@]1([C@@H](C)O)C(=O)N2C(C(O)=O)=C(S[C@@H]3CN[C@@H](C3)C(=O)N(C)C)[C@H](C)[C@]12[H] |
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InChI Identifier | InChI=1S/C17H25N3O5S/c1-7-12-11(8(2)21)16(23)20(12)13(17(24)25)14(7)26-9-5-10(18-6-9)15(22)19(3)4/h7-12,18,21H,5-6H2,1-4H3,(H,24,25)/t7-,8-,9+,10+,11-,12-/m1/s1 |
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InChI Key | DMJNNHOOLUXYBV-PQTSNVLCSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as thienamycins. These are beta-lactam antibiotics that differ from penicillins in having the thiazolidine sulfur atom replaced by carbon, the sulfur then becoming the first atom in the side chain. |
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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 | Thienamycins |
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Alternative Parents | |
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Substituents | - Thienamycin
- Proline or derivatives
- Alpha-amino acid amide
- Alpha-amino acid or derivatives
- Pyrrolidine carboxylic acid or derivatives
- Pyrrolidine-2-carboxamide
- Pyrroline carboxylic acid
- Pyrroline carboxylic acid or derivatives
- Azepine
- Vinylogous thioester
- Pyrrolidine
- Pyrroline
- Tertiary carboxylic acid amide
- Amino acid or derivatives
- Azetidine
- Carboxamide group
- Amino acid
- Thioenolether
- Secondary alcohol
- Secondary amine
- Sulfenyl compound
- Azacycle
- Carboxylic acid derivative
- Carboxylic acid
- Secondary aliphatic amine
- Monocarboxylic acid or derivatives
- Amine
- Alcohol
- Organic nitrogen compound
- Carbonyl group
- Hydrocarbon derivative
- Organopnictogen compound
- Organonitrogen compound
- Organooxygen compound
- Organosulfur compound
- Organic oxide
- Organic oxygen compound
- Aliphatic heteropolycyclic compound
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Molecular Framework | Aliphatic heteropolycyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | Not Available |
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Disposition | |
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Process | Not Available |
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Role | Not Available |
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Physical Properties |
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State | Solid |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 5.63 g/L | Not Available | LogP | -0.6 | Not Available |
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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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Meropenem,1TMS,isomer #1 | C[C@@H](O[Si](C)(C)C)[C@H]1C(=O)N2C(C(=O)O)=C(S[C@@H]3CN[C@H](C(=O)N(C)C)C3)[C@H](C)[C@H]12 | 2955.5 | Semi standard non polar | 33892256 | Meropenem,1TMS,isomer #2 | C[C@@H](O)[C@H]1C(=O)N2C(C(=O)O[Si](C)(C)C)=C(S[C@@H]3CN[C@H](C(=O)N(C)C)C3)[C@H](C)[C@H]12 | 2934.5 | Semi standard non polar | 33892256 | Meropenem,1TMS,isomer #3 | C[C@@H](O)[C@H]1C(=O)N2C(C(=O)O)=C(S[C@H]3C[C@@H](C(=O)N(C)C)N([Si](C)(C)C)C3)[C@H](C)[C@H]12 | 2852.8 | Semi standard non polar | 33892256 | Meropenem,2TMS,isomer #1 | C[C@@H](O[Si](C)(C)C)[C@H]1C(=O)N2C(C(=O)O[Si](C)(C)C)=C(S[C@@H]3CN[C@H](C(=O)N(C)C)C3)[C@H](C)[C@H]12 | 2879.5 | Semi standard non polar | 33892256 | Meropenem,2TMS,isomer #2 | C[C@@H](O[Si](C)(C)C)[C@H]1C(=O)N2C(C(=O)O)=C(S[C@H]3C[C@@H](C(=O)N(C)C)N([Si](C)(C)C)C3)[C@H](C)[C@H]12 | 2824.6 | Semi standard non polar | 33892256 | Meropenem,2TMS,isomer #3 | C[C@@H](O)[C@H]1C(=O)N2C(C(=O)O[Si](C)(C)C)=C(S[C@H]3C[C@@H](C(=O)N(C)C)N([Si](C)(C)C)C3)[C@H](C)[C@H]12 | 2816.3 | Semi standard non polar | 33892256 | Meropenem,3TMS,isomer #1 | C[C@@H](O[Si](C)(C)C)[C@H]1C(=O)N2C(C(=O)O[Si](C)(C)C)=C(S[C@H]3C[C@@H](C(=O)N(C)C)N([Si](C)(C)C)C3)[C@H](C)[C@H]12 | 2849.4 | Semi standard non polar | 33892256 | Meropenem,3TMS,isomer #1 | C[C@@H](O[Si](C)(C)C)[C@H]1C(=O)N2C(C(=O)O[Si](C)(C)C)=C(S[C@H]3C[C@@H](C(=O)N(C)C)N([Si](C)(C)C)C3)[C@H](C)[C@H]12 | 3256.0 | Standard non polar | 33892256 | Meropenem,3TMS,isomer #1 | C[C@@H](O[Si](C)(C)C)[C@H]1C(=O)N2C(C(=O)O[Si](C)(C)C)=C(S[C@H]3C[C@@H](C(=O)N(C)C)N([Si](C)(C)C)C3)[C@H](C)[C@H]12 | 3776.3 | Standard polar | 33892256 | Meropenem,1TBDMS,isomer #1 | C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1C(=O)N2C(C(=O)O)=C(S[C@@H]3CN[C@H](C(=O)N(C)C)C3)[C@H](C)[C@H]12 | 3158.9 | Semi standard non polar | 33892256 | Meropenem,1TBDMS,isomer #2 | C[C@@H](O)[C@H]1C(=O)N2C(C(=O)O[Si](C)(C)C(C)(C)C)=C(S[C@@H]3CN[C@H](C(=O)N(C)C)C3)[C@H](C)[C@H]12 | 3164.0 | Semi standard non polar | 33892256 | Meropenem,1TBDMS,isomer #3 | C[C@@H](O)[C@H]1C(=O)N2C(C(=O)O)=C(S[C@H]3C[C@@H](C(=O)N(C)C)N([Si](C)(C)C(C)(C)C)C3)[C@H](C)[C@H]12 | 3074.9 | Semi standard non polar | 33892256 | Meropenem,2TBDMS,isomer #1 | C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1C(=O)N2C(C(=O)O[Si](C)(C)C(C)(C)C)=C(S[C@@H]3CN[C@H](C(=O)N(C)C)C3)[C@H](C)[C@H]12 | 3316.8 | Semi standard non polar | 33892256 | Meropenem,2TBDMS,isomer #2 | C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1C(=O)N2C(C(=O)O)=C(S[C@H]3C[C@@H](C(=O)N(C)C)N([Si](C)(C)C(C)(C)C)C3)[C@H](C)[C@H]12 | 3236.9 | Semi standard non polar | 33892256 | Meropenem,2TBDMS,isomer #3 | C[C@@H](O)[C@H]1C(=O)N2C(C(=O)O[Si](C)(C)C(C)(C)C)=C(S[C@H]3C[C@@H](C(=O)N(C)C)N([Si](C)(C)C(C)(C)C)C3)[C@H](C)[C@H]12 | 3240.9 | Semi standard non polar | 33892256 | Meropenem,3TBDMS,isomer #1 | C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1C(=O)N2C(C(=O)O[Si](C)(C)C(C)(C)C)=C(S[C@H]3C[C@@H](C(=O)N(C)C)N([Si](C)(C)C(C)(C)C)C3)[C@H](C)[C@H]12 | 3456.1 | Semi standard non polar | 33892256 | Meropenem,3TBDMS,isomer #1 | C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1C(=O)N2C(C(=O)O[Si](C)(C)C(C)(C)C)=C(S[C@H]3C[C@@H](C(=O)N(C)C)N([Si](C)(C)C(C)(C)C)C3)[C@H](C)[C@H]12 | 3942.3 | Standard non polar | 33892256 | Meropenem,3TBDMS,isomer #1 | C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1C(=O)N2C(C(=O)O[Si](C)(C)C(C)(C)C)=C(S[C@H]3C[C@@H](C(=O)N(C)C)N([Si](C)(C)C(C)(C)C)C3)[C@H](C)[C@H]12 | 3981.4 | Standard polar | 33892256 |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - Meropenem GC-MS (Non-derivatized) - 70eV, Positive | splash10-0g6r-9165000000-bfa50046e33decc913f0 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Meropenem GC-MS (2 TMS) - 70eV, Positive | splash10-00dl-9320210000-71603485baf0ee1f92c6 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Meropenem GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Meropenem 10V, Positive-QTOF | splash10-01ox-0936000000-857a771e636fb53260ae | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Meropenem 20V, Positive-QTOF | splash10-02tc-1977000000-43d0012adc5dc96ecabd | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Meropenem 40V, Positive-QTOF | splash10-0hfx-9840000000-2ccf21d5dcd32f3989c7 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Meropenem 10V, Negative-QTOF | splash10-000i-0229000000-f9d8bdfc2564aeca32ae | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Meropenem 20V, Negative-QTOF | splash10-000i-9521000000-83bc2070b161829e83c8 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Meropenem 40V, Negative-QTOF | splash10-0002-2900000000-e17d924d7e7692764373 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Meropenem 10V, Positive-QTOF | splash10-001i-0009000000-5e44660aff42cac149bd | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Meropenem 20V, Positive-QTOF | splash10-00lr-0009000000-4dd3b9244a8243c4b20d | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Meropenem 40V, Positive-QTOF | splash10-0udi-4911000000-def7d662e5166c4d5e94 | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Meropenem 10V, Negative-QTOF | splash10-001i-0009000000-d7eed5c18e5f3c6f6f92 | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Meropenem 20V, Negative-QTOF | splash10-017l-1289000000-11238b0e8232b05612fc | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Meropenem 40V, Negative-QTOF | splash10-08nc-3294000000-363e013578d0e013c800 | 2021-10-11 | Wishart Lab | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Predicted 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum |
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