Crystal structure of tebipenem pivoxil
The molecular structure of the first orally active carbapenem antibacterial agent, tebipenem pivoxil (systematic name: (2,2-dimethylpropanoyloxy)methyl (4R,5S,6S)-3-{[1-(4,5-dihydro-1,3-thiazol-2-yl)azetidin-3-yl]sulfanyl}-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carbox...
| Main Authors: | , , , , , , |
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| Format: | Article |
| Language: | English |
| Published: |
International Union of Crystallography
2018-09-01
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| Series: | Acta Crystallographica Section E: Crystallographic Communications |
| Subjects: | |
| Online Access: | http://scripts.iucr.org/cgi-bin/paper?S2056989018010770 |
| _version_ | 1798019082166992896 |
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| author | Chao Tang Li Cai Shuai Liu Zhiwei Zheng Gen Li Jianli Chen Qiang Sui |
| author_facet | Chao Tang Li Cai Shuai Liu Zhiwei Zheng Gen Li Jianli Chen Qiang Sui |
| author_sort | Chao Tang |
| collection | DOAJ |
| description | The molecular structure of the first orally active carbapenem antibacterial agent, tebipenem pivoxil (systematic name: (2,2-dimethylpropanoyloxy)methyl (4R,5S,6S)-3-{[1-(4,5-dihydro-1,3-thiazol-2-yl)azetidin-3-yl]sulfanyl}-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate), C22H31N3O6S2, has been determined and the configurations of the four chiral centers validated. The title compound crystallizes in the triclinic space group P1 with one molecule in the unit cell. Three out of the four rings adopt planar conformations while the thiazolinyl ring adopts an enveloped conformation. In the crystal, O—H...N hydrogen bonds link the molecules into chains along [1\overline{1}0]. |
| first_indexed | 2024-04-11T16:34:46Z |
| format | Article |
| id | doaj.art-7685b5d627684c41b8a74ea564471c11 |
| institution | Directory Open Access Journal |
| issn | 2056-9890 |
| language | English |
| last_indexed | 2024-04-11T16:34:46Z |
| publishDate | 2018-09-01 |
| publisher | International Union of Crystallography |
| record_format | Article |
| series | Acta Crystallographica Section E: Crystallographic Communications |
| spelling | doaj.art-7685b5d627684c41b8a74ea564471c112022-12-22T04:13:52ZengInternational Union of CrystallographyActa Crystallographica Section E: Crystallographic Communications2056-98902018-09-017491215121710.1107/S2056989018010770ex2010Crystal structure of tebipenem pivoxilChao Tang0Li Cai1Shuai Liu2Zhiwei Zheng3Gen Li4Jianli Chen5Qiang Sui6China State Institute of Pharmaceutical Industry, 285 Gebaini Rd, Shanghai 201203, People's Republic of ChinaUniversity of South Carolina Lancaster, 476 Hubbard Drive, Lancaster, SC 29720, USAChina State Institute of Pharmaceutical Industry, 285 Gebaini Rd, Shanghai 201203, People's Republic of ChinaChina State Institute of Pharmaceutical Industry, 285 Gebaini Rd, Shanghai 201203, People's Republic of ChinaChina State Institute of Pharmaceutical Industry, 285 Gebaini Rd, Shanghai 201203, People's Republic of ChinaChina State Institute of Pharmaceutical Industry, 285 Gebaini Rd, Shanghai 201203, People's Republic of ChinaChina State Institute of Pharmaceutical Industry, 285 Gebaini Rd, Shanghai 201203, People's Republic of ChinaThe molecular structure of the first orally active carbapenem antibacterial agent, tebipenem pivoxil (systematic name: (2,2-dimethylpropanoyloxy)methyl (4R,5S,6S)-3-{[1-(4,5-dihydro-1,3-thiazol-2-yl)azetidin-3-yl]sulfanyl}-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate), C22H31N3O6S2, has been determined and the configurations of the four chiral centers validated. The title compound crystallizes in the triclinic space group P1 with one molecule in the unit cell. Three out of the four rings adopt planar conformations while the thiazolinyl ring adopts an enveloped conformation. In the crystal, O—H...N hydrogen bonds link the molecules into chains along [1\overline{1}0].http://scripts.iucr.org/cgi-bin/paper?S2056989018010770crystal structurecarbapenemantibioticstebipenemprodrughydrogen bonding |
| spellingShingle | Chao Tang Li Cai Shuai Liu Zhiwei Zheng Gen Li Jianli Chen Qiang Sui Crystal structure of tebipenem pivoxil Acta Crystallographica Section E: Crystallographic Communications crystal structure carbapenem antibiotics tebipenem prodrug hydrogen bonding |
| title | Crystal structure of tebipenem pivoxil |
| title_full | Crystal structure of tebipenem pivoxil |
| title_fullStr | Crystal structure of tebipenem pivoxil |
| title_full_unstemmed | Crystal structure of tebipenem pivoxil |
| title_short | Crystal structure of tebipenem pivoxil |
| title_sort | crystal structure of tebipenem pivoxil |
| topic | crystal structure carbapenem antibiotics tebipenem prodrug hydrogen bonding |
| url | http://scripts.iucr.org/cgi-bin/paper?S2056989018010770 |
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