Efficient and single pot process for the preparation of enantiomerically pure solifenacin succinate, an antimuscarinic agent

Niphade, Navnath C.; Jagtap, Kunal M.; Mali, Anil C.; Solanki, Pavankumar V.; Jachak, Madhukar N.; Mathad, Vijayavitthal T.

doi:10.1007/s00706-011-0610-7

Cited by 7 publications

(3 citation statements)

References 5 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…According to the first strategy, the racemic (14.3.53) was reacted with ethyl chloroformate to yield dihydroisoquinoline-carboxylate (14.3.54). According to the second strategy, racemic 1-phenyl-1,2,3,4-tetrahydroisoquinoline Other published patents are based on these two approaches [40][41][42][43][44][45][46][47][48][49] with minor changes, like asymmetric hydrogenation of 1-phenyl-3,4-dihydroisoquinoline [47] or enantioselective synthesis of1-phenyl-tetrahydroisoquinoline [48,49]. According to the second strategy, racemic 1-phenyl-1,2,3,4-tetrahydroisoquinoline Other published patents are based on these two approaches [40][41][42][43][44][45][46][47][48][49] with minor changes, like asymmetric hydrogenation of 1-phenyl-3,4-dihydroisoquinoline [47] or enantioselective synthesis of1-phenyl-tetrahydroisoquinoline [48,49].…”

Section: Solifenacin-vesicarementioning

confidence: 99%

Anticholinergic Drugs

Vardanyan

Hruby

2016

Synthesis of Best-Seller Drugs

View full text Add to dashboard Cite

Section: Solifenacin-vesicarementioning

confidence: 99%

Anticholinergic Drugs

Vardanyan

Hruby

2016

Synthesis of Best-Seller Drugs

View full text Add to dashboard Cite

“…After a 12-week phase III study, patients who orally received 5 or 10 mg of SOL showed marked reductions in the number of voids, incontinence episodes, and urgency episodes per 24 h [ 4 ]. Although the muscarinic antagonist is lipophilic (log p value of 1.69, at pH 7.0), its succinate salt is sparingly soluble (10 mg/mL, pH 7.2) in aqueous media [ 5 ]. The plasma SOL levels peaked 3–8 h after oral administration (5 or 10 mg tablets).…”

Section: Introductionmentioning

confidence: 99%

Novel Bioequivalent Tablet of Solifenacin Succinate Prepared Using Direct Compression Technique for Improved Chemical Stability

Kim

Jeong

et al. 2023

Pharmaceutics

View full text Add to dashboard Cite

We designed a bioequivalent tablet form of solifenacin succinate (SOL) with an improved storage stability using a direct compression (DC) technique. An optimal direct compressed tablet (DCT) containing an active substance (10 mg), lactose monohydrate, and silicified microcrystalline cellulose as diluents, crospovidone as a disintegrant, and hydrophilic fumed silica as an anti-coning agent was constructed by evaluating the drug content uniformity, mechanical properties, and in vitro dissolution. The physicochemical and mechanical properties of the DCT were as follows: drug content 100.1 ± 0.7%, disintegration time of 6.7 min, over 95% release within 30 min in dissolution media (pH 1.2, 4.0, 6.8, and distilled water), hardness > 107.8 N, and friability ~0.11%. The SOL-loaded tablet fabricated via DC showed an improved stability at 40 °C and RH 75%, exhibiting markedly reduced degradation products compared to those fabricated using ethanol or water-based wet granulation or a marketed product (Vesicare®, Astellas Pharma). Moreover, in a bioequivalence study in healthy subjects (n = 24), the optimized DCT offered a pharmacokinetic profile comparable to that of the marketed product, with no statistical differences in the pharmacokinetic parameters. The 90% CIs for the geometric mean ratios of the test to the reference formulation for the area under the curve and the maximum drug concentration in plasma were 0.98–1.05 and 0.98–1.07, respectively, and satisfied the FDA regulatory criteria for bioequivalence. Thus, we conclude that DCT is a beneficial oral dosage form of SOL with an improved chemical stability.

show abstract

“…Stereoiso-mers of racemic drugs often differ in pharmacokinetic behavior or pharmacological action, and among the four stereoisomers, the pharmacological action of (SR)-stereoisomer, that is, solifenacin shows high affinity and selectivity for the M3 receptor and hence has been approved as the drug [8]. Recently, we reported the novel process for making highly stereoisomerically pure solifenacin succinate from our laboratory [9]. During the development, we felt the need for an efficient analytical method for the determination of stereoisomerical purity and the results of the same are reported here.…”

Section: Introductionmentioning

confidence: 99%

Development and Validation of New Chromatographic Method for the Determination of Enantiomeric and Diastereomeric Purity of Solifenacin Succinate: An Antimuscarinic Agent

Landge

Jadhav

Dahale

et al. 2011

Chromatography Research International

Self Cite

View full text Add to dashboard Cite

A new, simple, and rapid stereoselective normal phase-liquid chromatographic (NP-LC) method was developed to separate and quantify the solifenacin succinate and its three stereoisomers. The stereoisomeric separation was achieved on Chiralpak IC ( mm ID) column. The mobile phase was consisting of n-hexane, ethanol, isopropyl alcohol, and diethylamine in the ratio (60 : 15 : 25 : 0.1, v/v/v/v), and the flow rate was maintained at 1.0 mL min−1. UV detection was carried out at 220 nm. In addition, chiroptical detection was carried out using laser polarimeter to understand the elution orders. Resolution between all the stereoisomers was not less than 3. Effect of column temperature on resolution between the stereoisomers was studied. The method was validated as per ICH guideline and found to be robust. The proposed NP-LC method was successfully applied to the analysis of commercial formulation. The method could be of use not only for routine evaluation of the quality of solifenacin succinate in bulk drug manufacturing unit but also for detection of impurities in pharmaceutical formulations.

show abstract

Efficient and single pot process for the preparation of enantiomerically pure solifenacin succinate, an antimuscarinic agent

Cited by 7 publications

References 5 publications

Anticholinergic Drugs

Anticholinergic Drugs

Novel Bioequivalent Tablet of Solifenacin Succinate Prepared Using Direct Compression Technique for Improved Chemical Stability

Development and Validation of New Chromatographic Method for the Determination of Enantiomeric and Diastereomeric Purity of Solifenacin Succinate: An Antimuscarinic Agent

Contact Info

Product

Resources

About