Novel Pharmaceutical Cocrystal of Voxelotor, a Hemoglobin Oxygen Affinity Modulator: Synthesis, Crystal Structure, and Physicochemical Properties

Article Chemistry, Physical

Physicochemical aspects and comparative analysis of Voxelotor and its salt and cocrystal

Uday Kumar Neelam et al.

Summary: This study investigated the crystal forms of Voxelotor using crystallographic and solid-state characterization techniques, revealing the improved solubility and stability of VOX-HCl salt and VOX-SC cocrystal.

JOURNAL OF MOLECULAR STRUCTURE (2023)

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Review Chemistry, Applied

Opportunities and Challenges in Mechanochemical Cocrystallization toward Scaled-Up Pharmaceutical Manufacturing

Sithmi Nimashi Madanayake et al.

Summary: Pharmaceutical cocrystals have attracted significant interest due to their potential in modifying the properties of active pharmaceutical ingredients while maintaining therapeutic efficacy. This review focuses on cocrystallization as a viable strategy for commercial pharmaceutical manufacturing, discussing solid-state cocrystal preparation methods and the opportunities and challenges in overall product and process development. The review also presents a comparative study of mechanochemical cocrystallization methods, highlighting remedies and alternatives for the challenges in this area and emphasizing the commercial perspectives of sustainable and eco-friendly approaches.

ORGANIC PROCESS RESEARCH & DEVELOPMENT (2023)

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Article Chemistry, Multidisciplinary

Novel Pharmaceutical Cocrystal of Apalutamide, a Nonsteroidal Antiandrogen Drug: Synthesis, Crystal Structure, Dissolution, Stress, and Excipient Compatibility

Venkata Narasayya Saladi et al.

Summary: The novel 1:1 cocrystal of Apalutamide (APA) with methylparaben (MP) improves solubility and dissolution rate due to strong hydrogen bonds, demonstrating stability under stress conditions and compatibility with excipients used in the drug product of APA.

CRYSTAL GROWTH & DESIGN (2022)

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Review Chemistry, Multidisciplinary

Crystal Engineering of Pharmaceutical Cocrystals in the Discovery and Development of Improved Drugs

Geetha Bolla et al.

Summary: Crystal engineering is a discipline that started in the 1970s, focusing on the study of topochemical reactions in the solid state. One important application of crystal engineering is in the design of pharmaceutical cocrystals, which can systematically tune the physicochemical properties of drugs without altering their molecular structure. This review traces the development of supramolecular synthons as robust hydrogen bond patterns for pharmaceutical cocrystal design, and discusses recent advancements in the field that have led to the launch of several drugs with improved efficacy and bioavailability. The importance of pharmaceutical cocrystals lies in their ability to bridge the gap between drug discovery and development, and their potential to provide high-value pharmaceuticals with economic and environmental benefits.

CHEMICAL REVIEWS (2022)

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Article Chemistry, Multidisciplinary

Synthesis of Ternary Cocrystals, Salts, and Hydrates of Acefylline with Enhanced Dissolution and High Permeability

Suryanarayana Allu et al.

Summary: This study synthesized binary and ternary cocrystals, salts-cocrystals, and polymorphs of ACF with different coformers. Two methods were used for the assembly of ternary systems, and the former method was found to be superior. Crystal structures were determined by X-ray diffraction, and the intermolecular interactions were analyzed. The permeability of ACF was found to increase in binary and ternary systems with selected coformers, making ACF-PIP an improved crystalline formulation of acefylline.

CRYSTAL GROWTH & DESIGN (2022)

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Article Chemistry, Multidisciplinary

Solubility and permeability enhancement of BCS class IV drug ribociclib through cocrystallization

M. K. Chaitanya Mannava et al.

Summary: This study successfully synthesized a novel salt and cocrystal of Ribociclib and reported its crystal structure as hydrate for the first time. The salt and cocrystal forms showed a 1:1 stoichiometry between the components. The cocrystal form exhibited enhanced permeability compared to pure Ribociclib.

CRYSTENGCOMM (2022)

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Article Chemistry, Physical

The role of solvation in proton transfer reactions: implications for predicting salt/co-crystal formation using the ΔpKa rule

Aurora J. Cruz-Cabeza et al.

Summary: The Delta pK(a) rule is a guideline commonly used by chemists and crystal engineers to design molecular salts and co-crystals. Empirical evidence shows that different Delta pK(a) values lead to different forms of salts and co-crystals. Solvation plays a crucial role in the proton transfer process, and the solvation strength of the lattice has a significant impact on ion stabilization.

FARADAY DISCUSSIONS (2022)

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Review Pharmacology & Pharmacy

Voxelotor: A Novel Treatment for Sickle Cell Disease

Leah B. Herity et al.

Summary: The study reviewed the pharmacological characteristics and clinical evidence of voxelotor for the treatment of sickle cell disease. Voxelotor is a targeted therapy that can increase Hb levels and is well-tolerated. It may be considered for some SCD patients, especially those with anemia and hemolysis despite hydroxyurea therapy.

ANNALS OF PHARMACOTHERAPY (2021)

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Article Chemistry, Multidisciplinary

New Salts and Cocrystals of Pymetrozine with Improvements on Solubility and Humidity Stability: Experimental and Theoretical Study

Di Wu et al.

Summary: Novel multicomponent crystals were developed to enhance the solubility and humidity stability of pymetrozine, a highly active but nonbiocidal pesticide, utilizing crystal engineering and advanced analytical techniques. The new crystals exhibited improved physicochemical properties and preserved insecticidal activity.

CRYSTAL GROWTH & DESIGN (2021)

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Article Chemistry, Physical

Cocrystal versus salt, a matter of hydrogen bonds in two benzoic acid crystals

Antonio Santoro et al.

Summary: This study compares the crystallization properties, structural distribution, and basicity of salts and cocrystals, showing that different crystallization partners can lead to the formation of crystals with different structures and ratios.

JOURNAL OF MOLECULAR STRUCTURE (2021)

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Review Pharmacology & Pharmacy

Pharmaceutical cocrystals: A review of preparations, physicochemical properties and applications

Minshan Guo et al.

Summary: Pharmaceutical cocrystals are multicomponent systems where at least one component is an active pharmaceutical ingredient. Cocrystallization with a coformer is a promising approach to enhance pharmaceutical performance. This review provides a comprehensive overview of pharmaceutical cocrystals, their preparation methods, properties, and applications, offering guidance for more efficient design and manufacturing.

ACTA PHARMACEUTICA SINICA B (2021)

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Article Pharmacology & Pharmacy

Improving physicochemical properties of Ibrutinib with cocrystal strategy based on structures and natures of the carboxylic acid co-formers

Xiangjun Shi et al.

Summary: The study successfully improved the physicochemical properties of Ibrutinib through co-crystallization with co-formers such as hydroxy-2-naphthoic acids, mono-hydroxybenzoic acids, and aliphatic acids. The solubility and dissolution of the prepared cocrystals were significantly increased compared to the original form of Ibrutinib, showing enhanced stability as well.

JOURNAL OF DRUG DELIVERY SCIENCE AND TECHNOLOGY (2021)

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Article Chemistry, Multidisciplinary

Pharmaceutical Cocrystals: Formulation Approaches to Develop Robust Drug Products

Naga Kiran Duggirala et al.

CRYSTAL GROWTH & DESIGN (2020)

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Review Pharmacology & Pharmacy

Voxelotor: First Approval

Hannah A. Blair

DRUGS (2020)

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Article Chemistry, Multidisciplinary

Influence of Excipients on Cocrystal Stability and Formation

Marwah Aljohani et al.

CRYSTAL GROWTH & DESIGN (2020)

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Review Pharmacology & Pharmacy

Systematic Review of Voxelotor: A First-in-Class Sickle Hemoglobin Polymerization Inhibitor for Management of Sickle Cell Disease

Jin Han et al.

PHARMACOTHERAPY (2020)

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Review Chemistry, Multidisciplinary

Crystalline Multicomponent Solids: An Alternative for Addressing the Hygroscopicity Issue in Pharmaceutical Materials

Tejender S. Thakur et al.

CRYSTAL GROWTH & DESIGN (2020)

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Article Pharmacology & Pharmacy

Pharmacokinetics and pharmacodynamics of voxelotor (GBT440) in healthy adults and patients with sickle cell disease

Athiwat Hutchaleelaha et al.

BRITISH JOURNAL OF CLINICAL PHARMACOLOGY (2019)

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Article Chemistry, Applied

Cocrystal Dissociation under Controlled Humidity: A Case Study of Caffeine-Glutaric Acid Cocrystal Polymorphs

Ranjit Thakuria et al.

ORGANIC PROCESS RESEARCH & DEVELOPMENT (2019)

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Article Medicine, General & Internal

A Phase 3 Randomized Trial of Voxelotor in Sickle Cell Disease

Elliott Vichinsky et al.

NEW ENGLAND JOURNAL OF MEDICINE (2019)

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Article Hematology

A phase 1/2 ascending dose study and open-label extension study of voxelotor in patients with sickle cell disease

Jo Howard et al.

BLOOD (2019)

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Article Chemistry, Multidisciplinary

Mechanochemical Synthesis of Olanzapine Salts and Their Hydration Stability Study Using Powder X-ray Diffraction

Kashyap Kumar Sarmah et al.

CRYSTAL GROWTH & DESIGN (2018)

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Review Pharmacology & Pharmacy

Pharmaceutical cocrystallization techniques. Advances and challenges

Marisa Rodrigues et al.

INTERNATIONAL JOURNAL OF PHARMACEUTICS (2018)

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Article Medicine, Research & Experimental

Drug-Excipient Interactions: Effect on Molecular Mobility and Physical Stability of Ketoconazole-Organic Acid Coamorphous Systems

Michelle H. Fung et al.

MOLECULAR PHARMACEUTICS (2018)

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Review Chemistry, Multidisciplinary

Creating Cocrystals: A Review of Pharmaceutical Cocrystal Preparation Routes and Applications

Maryam Karimi-Jafari et al.

CRYSTAL GROWTH & DESIGN (2018)

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Review Chemistry, Multidisciplinary

Pharmaceutical cocrystallization: an effective approach to modulate the physicochemical properties of solid-state drugs

Xia-Lin Dai et al.

CRYSTENGCOMM (2018)

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Review Chemistry, Multidisciplinary

From Molecules to Interactions to Crystal Engineering: Mechanical Properties of Organic Solids

Subhankar Saha et al.

ACCOUNTS OF CHEMICAL RESEARCH (2018)

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Article Medicine, Research & Experimental

Mechanistic Insight into Caffeine-Oxalic Cocrystal Dissociation in Formulations: Role of Excipients

Naga Kiran Duggirala et al.

MOLECULAR PHARMACEUTICS (2017)

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Review Pharmacology & Pharmacy

Pharmaceutical cocrystals, salts and multicomponent systems; intermolecular interactions and property based design

David J. Berry et al.

ADVANCED DRUG DELIVERY REVIEWS (2017)

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Article Chemistry, Multidisciplinary

Cocrystal and Salt Forms of Furosemide: Solubility and Diffusion Variations

Manas Banik et al.

CRYSTAL GROWTH & DESIGN (2016)

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Article Chemistry, Multidisciplinary

Enhancing Bioavailability of Dihydromyricetin through Inhibiting Precipitation of Soluble Cocrystals by a Crystallization Inhibitor

Chenguang Wang et al.

CRYSTAL GROWTH & DESIGN (2016)

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Article Chemistry, Multidisciplinary

Co-crystallization and small molecule crystal form diversity: from pharmaceutical to materials applications

Suryanarayan Cherukuvada et al.

CRYSTENGCOMM (2016)

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Article Chemistry, Multidisciplinary

Correlation Among Crystal Structure, Mechanical Behavior, and Tabletability in the Co-Crystals of Vanillin Isomers

G. Rama Krishna et al.

CRYSTAL GROWTH & DESIGN (2015)

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Article Medicine, Research & Experimental

Cocrystals of Hydrochlorothiazide: Solubility and Diffusion/Permeability Enhancements through Drug-Coformer Interactions

Palash Sanphui et al.

MOLECULAR PHARMACEUTICS (2015)

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Article Chemistry, Multidisciplinary

Structures of benzoic acids with substituted pyridines and quinolines: salt versus co-crystal formation

Gaelle Ramon et al.

CRYSTENGCOMM (2014)

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Article Chemistry, Medicinal

Cocrystal Dissociation in the Presence of Water: A General Approach for Identifying Stable Cocrystal Forms

Mark D. Eddleston et al.

JOURNAL OF PHARMACEUTICAL SCIENCES (2014)

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Article Chemistry, Multidisciplinary

Crystal Engineering: From Molecule to Crystal

Gautain R. Desiraju

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2013)

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Article Chemistry, Multidisciplinary

Acid-base crystalline complexes and the pKa rule

Aurora J. Cruz-Cabeza

CRYSTENGCOMM (2012)

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Article Chemistry, Medicinal

Nitrofurantoin-p-Aminobenzoic Acid Cocrystal: Hydration Stability and Dissolution Rate Studies

Suryanarayan Cherukuvada et al.

JOURNAL OF PHARMACEUTICAL SCIENCES (2011)

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Review Chemistry, Applied

Crystal Polymorphism in Chemical Process Development

Alfred Y. Lee et al.

ANNUAL REVIEW OF CHEMICAL AND BIOMOLECULAR ENGINEERING, VOL 2 (2011)

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Article Chemistry, Multidisciplinary

The growing world of crystal forms

Dario Braga et al.

CHEMICAL COMMUNICATIONS (2010)

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Review Pharmacology & Pharmacy

Benefits of cocrystallisation in pharmaceutical materials science: an update

Tomislav Friscic et al.

JOURNAL OF PHARMACY AND PHARMACOLOGY (2010)

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Article Chemistry, Multidisciplinary

Hirshfeld surface analysis

Mark A. Spackman et al.

CRYSTENGCOMM (2009)

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Software Review Chemistry, Multidisciplinary

OLEX2: a complete structure solution, refinement and analysis program

Oleg V. Dolomanov et al.

JOURNAL OF APPLIED CRYSTALLOGRAPHY (2009)

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Review Pharmacology & Pharmacy

Crystal engineering of active pharmaceutical ingredients to improve solubility and dissolution rates

N. Blagden et al.

ADVANCED DRUG DELIVERY REVIEWS (2007)

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Article Medicine, Research & Experimental

The salt-cocrystal continuum: The influence of crystal structure on ionization state

Scott L. Childs et al.

MOLECULAR PHARMACEUTICS (2007)

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Review Pharmacology & Pharmacy

Drug polymorphism and dosage form design: a practical perspective

D Singhal et al.

ADVANCED DRUG DELIVERY REVIEWS (2004)

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Article Chemistry, Multidisciplinary

Crystal engineering of the composition of pharmaceutical phases. Do pharmaceutical co-crystals represent a new path to improved medicines?

O Almarsson et al.

CHEMICAL COMMUNICATIONS (2004)

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Novel Pharmaceutical Cocrystal of Voxelotor, a Hemoglobin Oxygen Affinity Modulator: Synthesis, Crystal Structure, and Physicochemical Properties

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