A1R antagonists(Adenosine A1 receptor antagonists), A2aR antagonists(Adenosine A2a receptor antagonists), cGMP-PDE inhibitors(3',5'-cyclic phosphodiesterase inhibitors)

Therapeutic Areas

Immune System DiseasesInfectious DiseasesCardiovascular Diseases+ [1]

Active Indication

AsthmaAsthmatic bronchitisHeart Failure

Inactive Indication-

Originator Organization

Nichi-Iko Pharmaceutical Co., Ltd.

Active Organization

Nichi-Iko Pharmaceutical Co., Ltd.

Inactive Organization-

Drug Highest PhaseApproved

First Approval Date

JP (20 Feb 1959),

AsthmaAsthmatic bronchitisHeart Failure

Regulation-

Structure

Molecular FormulaC10H14N4O3

InChIKeyKYHQZNGJUGFTGR-UHFFFAOYSA-N

CAS Registry603-00-9

100 Clinical Results associated with Proxyphylline

100 Translational Medicine associated with Proxyphylline

100 Patents (Medical) associated with Proxyphylline

Literatures (Medical) associated with Proxyphylline

01 Jul 2024·YAKUGAKU ZASSHI

Investigation of Mechanism of Creming-down Phenomenon and Development of High-order Functions Using Tea Catechins

Review

Author: Ishizu, Takashi

An aqueous solution of 2,3-cis gallate type catechin (-)-epigallocatechin-3-O-gallate (EGCg) and caffeine afforded a precipitate of Creaming-down Phenomenon, which crystallized slowly for about three months to give a colorless block crystal. By X-ray crystallographic analysis, the crystal was determined to be a 2 : 2 complex of EGCg and caffeine, in which caffeine molecules were captured in a hydrophobic space formed with three aromatic A, B, and B' rings of EGCg. It was considered that the solubility of the 2 : 2 complex in water rapidly decreased and the 2 : 2 complex precipitated from aqueous solution. The hydrophobic spaces of EGCg captured a variety of heterocyclic compounds, and the molecular capture abilities of heterocyclic compounds using EGCg from the aqueous solutions were evaluated. Since the C ring of EGCg has two chiral carbon atoms, C₂ and C₃, the hydrophobic space of EGCg was a chiral space. EGCg captured diketopiperazine cyclo(Pro-Xxx) (Xxx=Phe, Tyr) and pharmaceuticals with a xanthine skeleton, proxyphylline and diprophylline, in the hydrophobic space, and recognized their chirality.

05 Feb 2024·Molecular Pharmaceutics

Investigation of the Binary System of Proxyphylline Enantiomers: Structural Resolution and Phase Diagram Determination

Article

Author: Bendeif, El-Eulmi ; Cartigny, Yohann ; Harfouche, Lina ; Dupray, Valérie ; Pinetre, Clément ; Brandel, Clément ; Couvrat, Nicolas ; Sanselme, Morgane

The solid-state landscape of proxyphylline (PXL), a chiral derivative of theophylline crystallizing as a racemic compound, was extensively investigated by means of thermal analyses and diffraction techniques. This study revealed the presence of five distinct polymorphic forms that were characterized: two polymorphs of the racemic mixture and three polymorphs of the pure enantiomer. The nature of each solid phase was confirmed by combining the different analytical techniques, revealing the presence of a thermodynamically stable racemic compound, RI (T_Fus= 134 °C), in equilibrium with the stable enantiopure crystal form, EI (T_Fus = 148.3 °C). Additionally, other crystal forms could be evidenced: a polymorph of the racemic compound, RII (T_Fus= 111.5 °C), as well as two metastable conglomerates, cEI and cEII, and two other polymorphs of the pure enantiomer, EII and EIII. The crystal structures of RI and EI are reported and discussed, highlighting the diversity of molecular conformations that can be adopted by the PXL molecule, which accounts for the versatility of the crystallization behaviors observed in this system. These findings enhance our understanding of the crystallization behavior of chiral pharmaceutical compounds and have implications for optimizing their crystallization processes in the pharmaceutical industry.

01 Oct 2022·Bioorganic Chemistry

Biocatalytic hydrogen-transfer to access enantiomerically pure proxyphylline, xanthinol, and diprophylline

Article

Author: Rudzka, Aleksandra ; Reiter, Tamara ; Kroutil, Wolfgang ; Borowiecki, Paweł

Alcohol dehydrogenases (ADHs; EC 1.1.1.1) have been widely used for the reversible redox reactions of carbonyl compounds (i.e., aldehydes and ketones) and primary or secondary alcohols, often resulting in optically pure hydroxyl products with high added value. In this work, we report a concise chemoenzymatic route toward xanthine-based enantiomerically pure active pharmaceutical ingredients (API) - proxyphylline, xanthinol, and diprophylline employing various recombinant short-chain ADHs with (R)- or (S)-selectivity as key biocatalysts. By choosing the appropriate ADH, the (R)- as well as the (S)-enantiomer of proxyphylline was prepared in excellent enantiomeric excess (99-99.9% ee), >99% conversion, and the isolated yield ranging from 65% to 74%, depending on the used biocatalyst (ADH-A from Rhodococcus ruber or a variant derived from Lactobacillus kefir, Lk-ADH-Lica). In turn, E. coli/ADH-catalyzed bioreduction of the carbonylic precursor of xanthinol and diprophylline furnished the corresponding (S)-chlorohydrin in >99% ee, >99% conversion, and 80% yield (in the case of Lk-ADH-Lica); while the (R)-counterpart was afforded in 94% ee, 64% conversion, and 41% yield (in the case of SyADH from Sphingobium yanoikuyae). After further chemical functionalization of the key (S)-chlorohydrin intermediate, the desired homochiral (R)-xanthinol (>99% ee) was obtained in 97% yield and (S)-diprophylline (>99% ee) in 90% yield. The devised biocatalytic method is straightforward and thus might be considered practical in the manufacturing of title pharmaceuticals.

100 Deals associated with Proxyphylline

External Link

KEGG	Wiki	ATC	Drug Bank
D01771	Proxyphylline	R03DA03	DB13449

R&D Status

10 top approved records.

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Indication	Country/Location	Organization	Date
Asthma	JP	Nichi-Iko Pharmaceutical Co., Ltd.	20 Feb 1959
Asthmatic bronchitis	JP	Nichi-Iko Pharmaceutical Co., Ltd.	20 Feb 1959
Heart Failure	JP	Nichi-Iko Pharmaceutical Co., Ltd.	20 Feb 1959

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