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Darifenacin Hydrobromide

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2-[(3S)-1-[2-(2,3-Dihydro-1-benzofuran-5-yl)ethyl]pyrrolidin-3-yl]-2,2-diphenylacetamide hydrobromide
133099-04-4 (net), 133099-07-7 (hydrobromide)
Molecular Formula
Long-term Storage Conditions
Overactive bladder
Darifenacin hydrobromide is used to treat people who have urinary problems such as urinary incontinence, urinary urgency or urinary frequency which are caused by an overactive bladder. It works by preventing spasms of the bladder muscle. This can help to reduce the episodes of urinary incontinence, the frequency of urination or reduce the feeling of urgency that bladder spasms can cause.
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Darifenacin hydrobromide is an antispasmodic muscarinic antagonist, selective for blocking the M3 muscarinic acetylcholine receptor, which is primarily responsible for bladder muscle contractions. Darifenacin hydrobromide has 9 and 12-fold greater affinity for M3 compared to M1 and M5, respectively, and 59-fold greater affinity for M3 compared to both M2 and M4. Darifenacin is used clinically to treat urinary incontinence and overactive bladder syndrome.

CAS: 201530-41-8
Sequence: ---
M.W: 373.3615
Molecular Formula: C21H15N3O4
CAS: 60731-46-6 (net)
Sequence: Cyclo(-Ser-Asn-Leu-Ser-Thr-Asu)-Val-Leu-Gly-Lys-Leu-Ser-Gln-Glu-Leu-His-Lys-Leu-Gln-Thr-Tyr-Pro-Arg-Thr-Asp-Val-Gly-Ala-Gly-Thr-Pro-NH2 acetate salt
M.W: 3363.8
Molecular Formula: C148H244N42O47
CAS: 17035-90-4 (net), 53308-83-1 (acetate)
Sequence: H-Arg(Me)-OH acetate salt
M.W: 248.28
Molecular Formula: C9H20N4O4
CAS: 163913-87-9
Sequence: Met-Glu-Val-Gly-Trp-Tyr-Arg-Ser-Pro-Phe-Ser-Arg-Val-Val-His-Leu -Tyr-Arg-Asn-Gly-Lys
M.W: 2581.99
Molecular Formula: C118H177N35O29S
CAS: 73385-60-1
Sequence: Tyr-Met(O)-Gly-(4-nitrophenyl)-Ala-ProNH2
M.W: 673.74
Molecular Formula: C30H39N7O9S

Darifenacin hydrobromide is a selective muscarinic M(3) receptor antagonist that is indicated for use in treatment of overactive bladder disorder. Darifenacin was found to have a short terminal elimination half-life after intravenous and immediate-release oral dosage forms (3-4 hours) but this increased with a prolonged-release (PR) formulation (14-16 hours). The absolute bioavailability of darifenacin from 7.5 and 15 mg PR tablets was estimated to be 15.4% and 18.6%, respectively. With repeated once-daily oral administration of the PR formulation, peak plasma concentrations of darifenacin are achieved approximately 7 hours post-dose. After oral administration, darifenacin is well absorbed from the gastrointestinal tract and very little unchanged drug (<2%) is recovered in the faeces. Steady state is achieved after 6 days of once-daily administration of the PR formulation. As expected, values of peak plasma concentration (C(max)) and area under the plasma concentration-time curve are dose dependent, although the increase in plasma concentrations is proportionally greater than the increase in dose owing to saturation of presystemic metabolism. From intravenous administration, it has been established that darifenacin possesses a moderate-to-high hepatic extraction ratio, with high plasma clearance (36-52 L/h) and a volume of distribution (165-276L) that exceeds total body water.

Skerjanec, A. (2006). The clinical pharmacokinetics of darifenacin. Clinical pharmacokinetics, 45(4), 325-350.

The present study describes the identification and characterization of two process impurities and major stress degradants in darifenacin hydrobromide using high performance liquid chromatography (HPLC) analysis. Forced degradation studies confirmed that the drug substance was stable under acidic, alkaline, aqueous hydrolysis, thermal and photolytic conditions and susceptible only to oxidative degradation. Impurities were identified using liquid chromatography coupled with ion trap mass spectrometry (LC-MS/MS(n)). Proposed structures were unambiguously confirmed by synthesis followed by characterization using nuclear magnetic resonance spectroscopy (NMR), infrared spectroscopy (IR) and elemental analysis (EA). Based on the spectroscopic, spectrometric and elemental analysis data, the unknown impurities were characterized as 2-{1-[2-(2,3-dihydrobenzofuran-5-yl)-2-oxo-ethyl]-pyrrolidin-3-yl}-2,2-diphenylacetamide (Imp-A), 2-[1-(2-benzofuran-5-yl-ethyl)-pyrrolidin-3-yl]-2,2-diphenylacetamide (Imp-B), 2-{1-[2-(2,3-dihydrobenzofuran-5-yl)-ethyl]-1-oxy-pyrrolidin-3-yl}-2,2-diphenylacetamide (Imp-C) and 2-{1-[2-(7-bromo-2,3-dihydrobenzofuran-5-yl)-ethyl]-pyrrolidin-3-yl}-2,2-diphenylacetamide (Imp-D). Plausible mechanisms for the formation and control of these impurities have also been proposed. The method was validated as per regulatory guidelines to demonstrate specificity, sensitivity, linearity, precision, accuracy and the stability-indicating nature. Regression analysis showed a correlation coefficient value greater than 0.99 for darifenacin hydrobromide and its impurities. The accuracy of the method was established based on the recovery obtained between 86.6 and 106.7% for all impurities.

Thomas, S., Paul, S. K., Shandilya, S., Agarwal, A., Saxena, N., Awasthi, A. K., ... & Mathela, C. S. (2012). Identification and structural elucidation of two process impurities and stress degradants in darifenacin hydrobromide active pharmaceutical ingredient by LC-ESI/MS n. Analyst, 137(15), 3571-3582.

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