Darifenacin Hydrobromide
Basic information
- CAS
133099-07-7- Standard SMILES
Br.NC(=O)C(c1ccccc1)(c1ccccc1)[C@@H]1CCN(CCc2ccc3c(c2)CCO3)C1- InChIKey
UQAVIASOPREUIT-VQIWEWKSSA-N- Molecular formula
- C28H31BrN2O2
- Average molar mass
- 507.5 g/mol
- Monoisotopic mass
- 506.15689
Overview
Darifenacin hydrobromide is the hydrobromide salt of darifenacin. A selective antagonist for the M3 muscarinic acetylcholine receptor, which is primarily responsible for bladder muscle contractions, it is used in the management of urinary incontinence. It has a role as a muscarinic antagonist. It contains a darifenacin.
Names & identifiers
- Preferred name
- Darifenacin Hydrobromide
- IUPAC
- 2-[(3S)-1-[2-(2,3-dihydro-1-benzofuran-5-yl)ethyl]pyrrolidin-3-yl]-2,2-diphenylacetamide;hydrobromide
- English name
- Darifenacin hydrobromide
- Molecular formula
- C28H31BrN2O2
- Molecular weight
- 507.47
Names & synonyms
Darifenacin hydrobromide133099-07-7darifenacin HBrUK 88525-04 hydrobromideDTXSID9046780CR02EYQ8GVUK-88525-04 (HYDROBROMIDE)Uk-88525-04 (hbr)DTXCID7026780CHEBI:31455(S)-2-{1-(2-(2,3-Dihydrobenzofuran-5-yl)ethyl)-3-pyrrolidnyl}-2,2-diphenylacetamide hydrobromide(S)-2-(1-(2-(2,3-DIHYDROBENZOFURAN-5-YL)ETHYL)-3-PYRROLIDNYL)-2,2-DIPHENYLACETAMIDE HYDROBROMIDE
Show more names
EmseleUK 88525-04Darifenacin HClDarifenacin hydrobroDARFENACIN HYDROBROMIDEDarifenacin Hydrobromid
(S)-2-{1-[2-(2,3-Dihydrobenzofuran-5-yl)ethyl]-3-pyrrolidnyl}-2,2-diphenylacetamide hydrobromideDarifenacin 15 mgDarifenacin 7.5 mgRefChem:57151EnablexEmselexMFCD08141803Darifenacin hydrobromide [USAN]
Database identifiers
Properties
Computed structural properties
- Topological polar surface area
- 55.6 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 7
- Heavy atoms
- 33
- Formal charge
- 0
- Complexity
- 607
Experimental & physicochemical properties
Human Drugs
FDA approved drugs -> Active ingredient
EMA approved medicines: Human medicine
FDA approved drugs -> Active ingredient
Physicochemical properties
- Melting point
- 228 · 228-2300C
- alpha
- 25 D · 25D -30.3° (c = 1.0 in methylene chloride)
- storage temp.
- -20 °C · -20°C
- solubility
- 20 mg/mL, · DMSO: soluble20mg/mL, clear
- form
- powder
- color
- white to beige
- optical activity
- 41 to · [α]/D +41 to +49°, c = 1 in methylene chloride
- InChIKey
- UQAVIASOPREUIT-YEZAQYPZNA-N
- SMILES
- C(C1C=CC=CC=1)(C1C=CC=CC=1)([C@@H]1CCN(CCC2=CC=C3OCCC3=C2)C1)C(=O)N.Br |&1:13,r|
- CAS DataBase Reference
- 133099 · 133099-07-7(CAS DataBase Reference)
- FDA UNII
- 2 EYQ8GV · CR02EYQ8GV
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H315 (95.1%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 41 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesSkin Irrit. 2 (95.1%)
Toxicology
Drug Induced Liver Injury
Drug Induced Liver Injury Rank (DILIrank 2.0)
Darifenacin hydrobromide
vNo-DILI-concern
0
No match
DOI:10.1016/j.drudis.2016.02.015
Safety data
- wgk
- 3
- hs_code
- 2934990002
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Storage Class
- 11 - Combustible Solids
- target organs
- Respiratory system
- Hazard statements
- H315-H319-H335
- Hazard Classifications
- Eye Irrit. 2Skin Irrit. 2STOT SE 3
- Precautionary statements
Chemistry & industry
Pharmacology
FDA Pharmacological Classification
DARIFENACIN HYDROBROMIDE
Cholinergic Muscarinic Antagonist [EPC]; Cholinergic Muscarinic Antagonists [MoA]
MeSH Pharmacological Classification
Drugs that bind to but do not activate MUSCARINIC RECEPTORS, thereby blocking the actions of endogenous ACETYLCHOLINE or exogenous agonists. Muscarinic antagonists have widespread effects including actions on the iris and ciliary muscle of the eye, the heart and blood vessels, secretions of the respiratory tract, GI system, and salivary glands, GI motility, urinary bladder tone, and the central nervous system.
Drugs used in the treatment of urological conditions and diseases such as URINARY INCONTINENCE and URINARY TRACT INFECTIONS.
Applications
DescriptionDarifenacin, an orally active, once a day selective M3 receptor antagonist, was launched for the treatment of overactive bladder in patients with symptoms of urge urinary incontinence, urgency and frequency. The drug selectively inhibits M3 receptor in the detrusor muscle while sparing the M1 and M2 receptors that are believed to be involved in central nervous system and cardiovascular function respectively. The compound was originally developed by Pfizer and licensed to Novartis and Bayer.
DescriptionDarifenacin is an antagonist of M3 muscarinic acetylcholine receptors (mAChRs; Ki = 0.76 nM). It is selective for M3 over M1, M2, M4, and M5 mAChRs (Kis = 7.08, 44.67, 45.71, and 9.33 nM, respectively). Darifenacin selectively inhibits contractions in isolated guinea pig ileum, bladder, and trachea (pA2s = 9.44, 8.66, and 8.7, respectively), tissues that endogenously express high levels of M3 mAChRs, over isolated rabbit vas deferens and isolated guinea pig atria (pA2s = 7.9 and 7.48, respectively), which endogenously express M1 and M2 mAChRs, respectively. It inhibits micturition pressure (ED50 = 0.089 mg/kg, i.v.), as well as micturition interval and volume in rats. Formulations containing darifenacin have been used in the treatment of overactive bladder.
Usescalcium replenisher
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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