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Erythromycin A dimethyl sulfoxide disolvate 1.43-hydrate

The title compound, C(37)H(67)NO(13)·2C(2)H(6)OS·1.43H(2)O, is a macrolide anti­biotic with better solubility and better dermal penetration abilities than erythromycin A itself. The asymmetric unit of this form contains one erythromycin A mol­ecule, two dimethyl sulfoxide (DMSO) solvent mol­ecules,...

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Autores principales: Brüning, Jürgen, Trepte, Tanja K., Bats, Jan W., Schmidt, Martin U.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2012
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3295479/
https://www.ncbi.nlm.nih.gov/pubmed/22412590
http://dx.doi.org/10.1107/S1600536812005223
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author Brüning, Jürgen
Trepte, Tanja K.
Bats, Jan W.
Schmidt, Martin U.
author_facet Brüning, Jürgen
Trepte, Tanja K.
Bats, Jan W.
Schmidt, Martin U.
author_sort Brüning, Jürgen
collection PubMed
description The title compound, C(37)H(67)NO(13)·2C(2)H(6)OS·1.43H(2)O, is a macrolide anti­biotic with better solubility and better dermal penetration abilities than erythromycin A itself. The asymmetric unit of this form contains one erythromycin A mol­ecule, two dimethyl sulfoxide (DMSO) solvent mol­ecules, a fully occupied water mol­ecule and a partially occupied water mol­ecule with an occupancy factor of 0.432 (11). The 14-membered ring of the erythronolide fragment has a conformation which differs considerably from that in erythromycin A dihydrate [Stephenson, Stowell, Toma, Pfeiffer & Byrn (1997 ▶). J. Pharm. Sci. 86, 1239–1244]. One of the two DMSO mol­ecules is disordered over two orientations; the orientation depends on the presence or absence of the second, partially occupied, water mol­ecule. In the crystal, erythromycin mol­ecules are connected by O—H⋯O hydrogen bonds involving the hy­droxy groups and the fully occupied water mol­ecule to form layers parallel to (010). These layers are connected along the b-axis direction only by a possible hydrogen-bonding contact involving the partially occupied water mol­ecule.
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spelling pubmed-32954792012-03-12 Erythromycin A dimethyl sulfoxide disolvate 1.43-hydrate Brüning, Jürgen Trepte, Tanja K. Bats, Jan W. Schmidt, Martin U. Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound, C(37)H(67)NO(13)·2C(2)H(6)OS·1.43H(2)O, is a macrolide anti­biotic with better solubility and better dermal penetration abilities than erythromycin A itself. The asymmetric unit of this form contains one erythromycin A mol­ecule, two dimethyl sulfoxide (DMSO) solvent mol­ecules, a fully occupied water mol­ecule and a partially occupied water mol­ecule with an occupancy factor of 0.432 (11). The 14-membered ring of the erythronolide fragment has a conformation which differs considerably from that in erythromycin A dihydrate [Stephenson, Stowell, Toma, Pfeiffer & Byrn (1997 ▶). J. Pharm. Sci. 86, 1239–1244]. One of the two DMSO mol­ecules is disordered over two orientations; the orientation depends on the presence or absence of the second, partially occupied, water mol­ecule. In the crystal, erythromycin mol­ecules are connected by O—H⋯O hydrogen bonds involving the hy­droxy groups and the fully occupied water mol­ecule to form layers parallel to (010). These layers are connected along the b-axis direction only by a possible hydrogen-bonding contact involving the partially occupied water mol­ecule. International Union of Crystallography 2012-02-17 /pmc/articles/PMC3295479/ /pubmed/22412590 http://dx.doi.org/10.1107/S1600536812005223 Text en © Brüning et al. 2012 http://creativecommons.org/licenses/by/2.0/uk/ This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
spellingShingle Organic Papers
Brüning, Jürgen
Trepte, Tanja K.
Bats, Jan W.
Schmidt, Martin U.
Erythromycin A dimethyl sulfoxide disolvate 1.43-hydrate
title Erythromycin A dimethyl sulfoxide disolvate 1.43-hydrate
title_full Erythromycin A dimethyl sulfoxide disolvate 1.43-hydrate
title_fullStr Erythromycin A dimethyl sulfoxide disolvate 1.43-hydrate
title_full_unstemmed Erythromycin A dimethyl sulfoxide disolvate 1.43-hydrate
title_short Erythromycin A dimethyl sulfoxide disolvate 1.43-hydrate
title_sort erythromycin a dimethyl sulfoxide disolvate 1.43-hydrate
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3295479/
https://www.ncbi.nlm.nih.gov/pubmed/22412590
http://dx.doi.org/10.1107/S1600536812005223
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