Show simple item record

dc.contributor.authorRanjan, S.
dc.contributor.authorDevarapalli, R.
dc.contributor.authorKundu, S.
dc.contributor.authorSaha, S.
dc.contributor.authorDeolka, S.
dc.contributor.authorVangala, Venu R.
dc.contributor.authorReddy, C.M.
dc.date.accessioned2020-04-22T18:58:35Z
dc.date.accessioned2020-05-06T13:00:41Z
dc.date.available2020-04-22T18:58:35Z
dc.date.available2020-05-06T13:00:41Z
dc.date.issued2020-03
dc.identifier.citationRanjan S, Devarapalli R, Kundu S et al (2020) Isomorphism: 'Molecular similarity to crystal structure similarity' in multicomponent forms of analgesic drugs tolfenamic and mefenamic acid. IUCrJ. 7(2): 173-183.en_US
dc.identifier.urihttp://hdl.handle.net/10454/17774
dc.descriptionYesen_US
dc.description.abstractThe non-steroidal anti-inflammatory drugs mefenamic acid (MFA) and tolfenamic acid (TFA) have a close resemblance in their molecular scaffold, whereby a methyl group in MFA is substituted by a chloro group in TFA. The present study demonstrates the isomorphous nature of these compounds in a series of their multicomponent solids. Furthermore, the unique nature of MFA and TFA has been demonstrated while excavating their alternate solid forms in that, by varying the drug (MFA or TFA) to coformer [4-dimethylaminopyridine (DMAP)] stoichiometric ratio, both drugs have produced three different types of multicomponent crystals, viz. salt (1:1; API to coformer ratio), salt hydrate (1:1:1) and cocrystal salt (2:1). Interestingly, as anticipated from the close similarity of TFA and MFA structures, these multicomponent solids have shown an isomorphous relation. A thorough characterization and structural investigation of the new multicomponent forms of MFA and TFA revealed their similarity in terms of space group and structural packing with isomorphic nature among the pairs. Herein, the experimental results are generalized in a broader perspective for predictably identifying any possible new forms of comparable compounds by mapping their crystal structure landscapes. The utility of such an approach is evident from the identification of polymorph VI of TFA from hetero-seeding with isomorphous MFA form I from acetone–methanol (1:1) solution. That aside, a pseudopolymorph of TFA with dimethylformamide (DMF) was obtained, which also has some structural similarity to that of the solvate MFA:DMF. These new isostructural pairs are discussed in the context of solid form screening using structural landscape similarityen_US
dc.description.sponsorshipDepartment of Science and Technology (DST/SJF/CSA-02/2014–15); Royal Pharmaceutical Society of Great Britain for seed corn funding (2018–19); INSPIRE fellowship from Department of Science and Technology, Government of India; IISER-Kolkata (instrumental facilities and fellowships)en_US
dc.language.isoenen_US
dc.relation.isreferencedbyhttps://doi.org/10.1107/S205225251901604Xen_US
dc.rights(c) 2020 The Authors. This is an Open Access article distributed under the Creative Commons CC-BY license (https://creativecommons.org/licenses/by/4.0/)en_US
dc.subjectCo-crystalsen_US
dc.subjectCrystal engineeringen_US
dc.subjectPolymorphismen_US
dc.subjectIsomorphismen_US
dc.titleIsomorphism: 'Molecular similarity to crystal structure similarity' in multicomponent forms of analgesic drugs tolfenamic and mefenamic aciden_US
dc.status.refereedYesen_US
dc.date.Accepted2019-11-28
dc.typeArticleen_US
dc.type.versionPublished versionen_US
dc.date.updated2020-04-22T17:58:36Z
refterms.dateFOA2020-05-06T13:02:25Z


Item file(s)

Thumbnail
Name:
ranjan_et_al_2020.pdf
Size:
1.603Mb
Format:
PDF

This item appears in the following Collection(s)

Show simple item record