Co-crystals of the antiretroviral nevirapine: crystal structures, thermal analysis and dissolution behaviour

Caira, Mino R.; Bourne, Susan A.; Samsodien, Halima; Engel, Emile R.; Liebenberg, Wilna; Stieger, Nicóle; Aucamp, Marique

doi:10.1039/c2ce06507j

Cited by 46 publications

(52 citation statements)

References 20 publications

(26 reference statements)

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“…All co-crystals, pure NV and co-formers were donated by the original research group responsible for their preparation Caira et al [1]. The integrity and purity of all co-crystals were verified using hot stage microscopy (HSM) prior to experimentation.…”

Section: Hot Stage Microscopymentioning

confidence: 99%

“…To ensure reproducibility these studies were conducted using the rotating basket method previously used by Caira et al [1]. The powder mixtures and co-crystals were ground for 5 minutes before encapsulation to ensure a particle size range of 65-200 µm.…”

Section: Dissolution Testingmentioning

confidence: 99%

“…NVSC and NVSLI formed co-crystals with a 2:1 ratio of NV to the relevant co-former. NVTTA, NVMLE and NVGLT formed co-crystals with a 1:1 ratio of NV to the relevant co-former [1].…”

Section: Introductionmentioning

confidence: 99%

“…A single dose of NV administered to the mother at the onset of labour and to the baby within 72 hours of delivery nearly halved the rate of HIV transmission. Since NV is given only once to the mother and baby it is relatively cheap and easy to administer [1][2][3].…”

Section: Introductionmentioning

confidence: 99%

“…According to the Biopharmaceutical Classification Index, NV is a Class II drug i.e. it has a high permeability and a low solubility [1]. The low rate of dissolution of NV is assumed to be the rate-limiting step for absorption of the drug [4].…”

Section: Introductionmentioning

confidence: 99%

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FTIR, Dissolution and Anti-viral Activity of Nevirapine Co-crystals

Samsodien¹,

Bapoo²,

Tl³

et al. 2017

Pharm Anal Acta

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The study uses Fourier Transform Infrared (FTIR) spectroscopy to identify five Nevirapine (NV) co-crystals, determines the dissolution profile of the co-crystals and the antiviral activity comparative to pure NV.Hot stage microscopy measured the purity and integrity of each co-crystal. FTIR analysis was used to identify the co-crystals to make recommendations regarding the future use of the technique to identify the NV co-crystals. Dissolution studies of the NV co-crystals prepared with maleic acid, salicylic acid and glutaric acid (NVMLE, NVSLI and NVGLT, respectively) were completed using the rotating basket method. Assays were conducted using High Performance Liquid Chromatography and compared to pure NV and the five NV: co-former mixtures. The antiviral activity was tested to determine whether the co-crystals had an improved activity against HIV -1 compared to pure NV.All co-crystals, except NVTTA (a NV co-crystal prepared with rac-tartaric acid), were pure and maintained their integrity for approximately one year. NVGLT, NVMLE and NVTTA, 1:1 molar ratio co-crystals were identified by FTIR. The C=O stretching frequency of the carboxylic acid groups of NV and GLT were observed at 1638.15 cm -1 and 1719.23 cm -1 in the NVGLT co-crystal which corresponded with spectra of NVMLE and NVTTA. In NVMLE the C=O stretching frequency of the C=O of NV and MLE were observed at 1640.58 cm -1 and 1694.10 cm -1 and in NVTTA it was at 1637.25 cm -1 and 1708.50 cm -1 , suggesting the presence of both parent molecules in the new phase for NVGLT, NVMLE and NVTTA.Dissolution studies suggested that NVGLT was the only co-crystal that yielded better results than both NV and its physical mixture. The antiviral activity of the NVSC (an NV co-crystal prepared with saccharin) and NVSLI cocrystals in DMSO was significantly different to pure NV, demonstrating an improvement in anti-viral activity.

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Section: Hot Stage Microscopymentioning

confidence: 99%

Section: Dissolution Testingmentioning

confidence: 99%

“…NVSC and NVSLI formed co-crystals with a 2:1 ratio of NV to the relevant co-former. NVTTA, NVMLE and NVGLT formed co-crystals with a 1:1 ratio of NV to the relevant co-former [1].…”

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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FTIR, Dissolution and Anti-viral Activity of Nevirapine Co-crystals

Samsodien¹,

Bapoo²,

Tl³

et al. 2017

Pharm Anal Acta

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Inclusion Compounds Containing Polymers

Zhong

Gao

Guo

et al. 2016

Kirk-Othmer Encyclopedia of Chemical Technology

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Inclusion compounds formed between host and guest molecules via noncovalent interaction exhibit novel properties and functions compared to the constituting species. The focus in this encyclopedia article is on the inclusion compounds containing polymers, as either hosts or guests. Among the hosts, the small molecular hosts can be divided into two categories: the small molecular hosts with intramolecular cavity, such as cyclodextrins (CDs) and cucurbiturils (CBs); the others with intermolecular cavity, such as urea, thiourea, choleic acids, deoxycholic acids, perhydrotriphenylene, tris(o‐phenylenedioxy)cyclotriphosphazene, some small molecular drugs, etc. Depending on the size of the cavity and the intermolecular interactions, chains of polyolefins, polyethers, polyesters, conjugated polymers, and ionic polymers can be accommodated in the cavities to form inclusion compounds. Besides the small molecular host, there are also many inclusion compounds with polymer chains as hosts, among them amylose, poly( l ‐lactic acid), stereoregular polystyrene, linear d,l ‐peptides, oligophenylacetylenes, and poly(ethylene oxide) are reviewed. Finally, applications of inclusion compounds containing polymers in the fields of separation, stereocontrolled polymerization, sensors, drug and gene delivery, nucleating agents, gels, self healing materials, molecular rotor, and molecular wires, are introduced.

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