Encyclopedia / Anti-Allergic Agents / Cardiovascular Agents / Pharmaceutical

Silodosin

CAS：160970-54-7
MW:495.53
MF：C25H32F3N3O4

Silodosin, an a1A adrenoceptor (a1A-AR) antagonist selective for prostaticreceptors, was launched as an oral treatment for dysuria associated withbenign prostatic hypertrophy (BPH). The regulation of smooth muscle tone in thebladder neck and prostate is thought to be primarily mediated by a1A-AR.Blockade of these receptors can cause smooth muscle relaxation in these areas,resulting in improved symptoms and urinary flow rates. Conversely, a1B-AR arelargely located on vascular smooth muscle, and antagonism of these receptorscan cause tissue relaxation and potentially decrease cardiac compensation mechanismsinvolved in regulating blood pressure. View more+

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Names and ldentifier
Properties
Use and Manufacturing
Safety and Handling
Msds
NMR Spectrum
Other Information
Computational chemical data
Related Questions
Realated Product Infomation

1. Names and Identifiers

1.1 Name: Silodosin

1.2 Synonyms: [14C]-Silodosin; [3H]-Silodosin; 1-(3-hydroxypropyl)-5-[(2R)-({2-[2-[2-(2,2,2-trifluoroethoxy)phenoxy]ethyl}aMino)propyl]indoline-7-carboxaMide; 1-(3-hydroxypropyl)-5-[(2R)-2-({2-[2-(2,2,2-trifluoroethoxy)phenoxy]ethyl}amino)propyl]-2,3-dihydro-1H-indole-7-carboxamide; 1-(3-Hydroxypropyl)-5-[(2R)-2-({2-[2-(2,2,2-trifluoroethoxy)phenoxy]ethyl}amino)propyl]-7-indolinecarboxamide; 1H-Indole-7-carboxamide, 2,3-dihydro-1-(3-hydroxypropyl)-5-[(2R)-2-[[2-[2-(2,2,2-trifluoroethoxy)phenoxy]ethyl]amino]propyl]-; 1H-Indole-7-carboxaMide,2,3-dihydro-1-(3-hydroxypropyl)-5-[(2R)-2-[[2-[2-(2,2,2-trifluoroethoxy)phenoxy]ethyl]aMino]propyl]-; KAD 3213; KMD 3213; KMD-3213; Rapaflo; Silodosin API; Silodosin-d4; Silodoxin; Silodyx; UNII-CUZ39LUY82; Urief;

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1.3 CAS No.: 160970-54-7

1.4 CID: 5312125

1.5 EINECS: 1308068-626-2

1.6 Molecular Formula: C25H32F3N3O4

1.7 Inchi: InChI=1S/C25H32F3N3O4/c1-17(30-8-12-34-21-5-2-3-6-22(21)35-16-25(26,27)28)13-18-14-19-7-10-31(9-4-11-32)23(19)20(15-18)24(29)33/h2-3,5-6,14-15,17,30,32H,4,7-13,16H2,1H3,(H2,29,33)/t17-/m1/s1

1.8 InChkey: PNCPYILNMDWPEY-QGZVFWFLSA-N

1.9 Canonical Smiles: CC(CC1=CC2=C(C(=C1)C(=O)N)N(CC2)CCCO)NCCOC3=CC=CC=C3OCC(F)(F)F

1.10 Isomers Smiles: C[C@H](CC1=CC2=C(C(=C1)C(=O)N)N(CC2)CCCO)NCCOC3=CC=CC=C3OCC(F)(F)F

2. Properties

2.1 Appearance: White to off-white solid

2.2 Chemical Properties: White Solid

2.3 Color/Form: Powder

2.4 pKa: 14.85±0.10(Predicted)

2.5 Water Solubility: H2O: Very slightly soluble

2.6 StorageTemp: Keep in dark place,Inert atmosphere,2-8°C

3. Use and Manufacturing

3.1 Description

White SolidSilodosin, an a1A adrenoceptor (a1A-AR) antagonist selective for prostatic receptors, was launched as an oral treatment for dysuria associated with benign prostatic hypertrophy (BPH). The regulation of smooth muscle tone in the bladder neck and prostate is thought to be primarily mediated by a1A-AR. Blockade of these receptors can cause smooth muscle relaxation in these areas, resulting in improved symptoms and urinary flow rates. Conversely, a1B-AR are largely located on vascu

Silodosin is an indolecarboxamide.|Silodosin is an α1-adrenoceptor antagonist that is selective for the prostate. Silodosin is for symptomatic treatment of benign prostatic hyperplasia. FDA approved Oct 9, 2008.|Silodosin is an alpha-Adrenergic Blocker. The mechanism of action of silodosin is as an Adrenergic alpha-Antagonist.|Silodosin is a selective alpha-1a adrenergic antagonist used in the therapy of benign prostatic hypertrophy. Silodosin is associated with a low rate of serum aminotransferase elevations and to rare instances of clinically apparent acute liver injury.|Silodosin is an orally available, alpha-1 adrenoreceptor (alpha-1a) selective antagonist that can be used to relieve symptoms of benign prostate hyperplasia (BPH). Upon administration, silodosin selectively binds alpha-1a receptors located in the human prostate and bladder with high affinity and blocks signaling pathways mediated by alpha-1a. Blockade of these receptors causes smooth muscle relaxation, lowers intraurethral pressure, and results in improved urine flow and a reduction in the symptoms of BPH, such as difficulty with urinating, painful urination, urinary frequency and incomplete bladder emptying. In addition, silodosin may be used to improve lower urinary tract symptoms, which can occur after receiving radiation therapy for prostate cancer.

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3.2 Usage: It can be used for treatment of benign prostatic hyperplasia.

4. Safety and Handling

4.1 Specification: Silodosin (CAS NO.160970-64-9) is also named as Rapaflo ; Rapflo ; UNII-CUZ39LUY82 ; (-)-1-(3-Hydroxypropyl)-5-((2R)-2-((2-(2-(2,2,2-trifluoroethoxy)phenoxy)ethyl)amino)propyl)-2,3-dihydro-1H-indole-7-carboxamide ; 160970-54-7 .

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

no data available

2.2 GHS label elements, including precautionary statements

Pictogram(s)	no data available
Signal word	no data available
Hazard statement(s)	no data available
Precautionary statement(s)
Prevention	no data available
Response	no data available
Storage	no data available
Disposal	no data available

2.3 Other hazards which do not result in classification

no data available

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6. NMR Spectrum

13C NMR : Predict

1H NMR : Predict

7. Synthesis Route

160970-54-7Total: 48 Synthesis Route

90-05-1 331 Suppliers

160970-54-7 224 Suppliers

120-80-9 10 Suppliers

160970-54-7 224 Suppliers

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8. Precursor and Product

precursor:

350797-53-4

885340-13-6

90-05-1

496-15-1

160969-00-6

160969-03-9

120-80-9

350797-51-2

160969-20-0

175870-34-5

9. Computed Properties

Molecular Weight：495.53g/mol
Molecular Formula：C₂₅H₃₂F₃N₃O₄
Compound Is Canonicalized：True
Exact Mass：3.6
XLogP3-AA：495.23449100
Monoisotopic Mass：495.23449100
Complexity：654
Rotatable Bond Count：13
Hydrogen Bond Donor Count：3
Hydrogen Bond Acceptor Count：9
Topological Polar Surface Area：97
Heavy Atom Count：：35
Defined Atom Stereocenter Count：1
Undefined Atom Stereocenter Count：0
Defined Bond Stereocenter Count：0
Undefined Bond Stereocenter Count：0
Isotope Atom Count：0
Covalently-Bonded Unit Count：1
CACTVS Substructure Key Fingerprint：AAADcfB7OYAAAAAAAAAAAAAAAAAAAWAAAAAwYAAAAAAAAFgBQAAAHwAQCAAADCzhmBYyxoPABgCIAiVSUACCCAAlIAAIiIEOzMgPNjrE9ZuHearm0BHa6ceYyMCOCAACAAACQAAQAAQAAASAAAAAAAAAAA==

10.Other Information

Uses: It can be used for treatment of benign prostatic hyperplasia.

Chemical Properties: White Solid

Uses: An α1a-adrenoceptor antagonist. It is used in treatment of benign prostatic hypertophy.

Target: Value

Description: Silodosin, an a1A adrenoceptor (a1A-AR) antagonist selective for prostatic receptors, was launched as an oral treatment for dysuria associated with benign prostatic hypertrophy (BPH). The regulation of smooth muscle tone in the bladder neck and prostate is thought to be primarily mediated by a1A-AR. Blockade of these receptors can cause smooth muscle relaxation in these areas, resulting in improved symptoms and urinary flow rates. Conversely, a1B-AR are largely located on vascular smooth muscle, and antagonism of these receptors can cause tissue relaxation and potentially decrease cardiac compensation mechanisms involved in regulating blood pressure.

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Originator: Kissei (Japan)

Uses: Silodosin is an α1a-adrenoceptor antagonist. It is used in treatment of benign prostatic hypertrophy.

Brand name: Urief

Chemical Synthesis: The synthesis of silodosin has been disclosed in several patents. The latest synthetic route disclosed in the 2006 patent is highlighted in the scheme. The synthesis started with Grignard generation from readily available bromoindoline 65 by treating it with Mg in the presence of a catalytic dibromoethane in THF. After initiation of the reaction with some heat and refluxing at a steady rate, CBZ protected oxazolidinone 66 [39b] was added over 1 h, refluxed for 4 h and then stirred at room temperature for 2 days. The reaction was quenched with 6 M aqueous HCl and stirred for 12 h after which time the reaction was worked up to provide product 67 in 53% yield. Ketone 67 was then treated with triethylsilane in TFA at 0oC and stirred at room temperature for 10 h to provide amine 68 in 61% yield. Bromination of the indoline 68 with bromine in warm acetic acid furnished bromide 69 in 53% yield which was reacted with copper cyanide in DMF at 130oC to give the cyano indoline 70 in 82% yield. Selective deprotection of the benzyloxycarbonyl over the benzyl group was accomplished by reacting indoline 70 with 1 atm hydrogen in the presence of 5% Pd/C in ethanol at room temperature. The resulting free amine 71 was then reacted with mesylate 72 in t-butanol with sodium carbonate as base at 80-90oC for 46 h to provide 73 in 67% yield. Removal of the benzyl ether was accomplished by reacting 73 with 1 atm hydrogen in the presence of 10%Pd/C to give alcohol 74, which upon hydrolysis provided the desired silodosin (X). No yield for the final reaction was given.

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Livertox Summary: Silodosin is a selective alpha-1a adrenergic antagonist used in the therapy of benign prostatic hypertrophy. Silodosin is associated with a low rate of serum aminotransferase elevations and to rare instances of clinically apparent acute liver injury.

Drug Classes: Benign Prostatic Hypertrophy Agents

Mesh: Drugs used in the treatment of urogenital conditions and diseases such as URINARY INCONTINENCE; PROSTATIC HYPERPLASIA; and ERECTILE DYSFUNCTION. (See all compounds classified as Urological Agents.)|Drugs that bind to and block the activation of ADRENERGIC ALPHA-1 RECEPTORS. (See all compounds classified as Adrenergic alpha-1 Receptor Antagonists.)

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Absorption: Quickly absorbed and has a bioavailability of 32% at 8mg/day (therapeutic dose). When 8 mg of silodosin is taken once daily with food, the pharmacokinetic parameters are as follows: Cmax = 61.6 ± 27.54 ng/mL; Tmax = 2.6 ± 0.90 hours; AUC (0h-24h) = 373 ng?hr/ml. The AUC of its metabolite, KMD3213G, is four times greater than silodosin.|Fecal (54.9%); Renal (33.5%)|49.5 L|Plasma clearance = 10 L/h

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Metabolism: Extensively metabolized in the liver. The main metabolite is generated via glucuronidation (KMD-3213G) by UDP-2B7. Oxidation by alcohol and aldehyde dehydrogenases produces the second major metabolite, KMD-3293. KMD-3213G accumulates in the plasma as it is very hydrophilic. KMD-3213G is also an active metabolite in which it has 50% of silodosin's inhibitory activity. KMD-3293 is inactive. Cytochrome P450 CYP 3A4 also generates some metabolites.

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Biological Half Life: Silodosin = 13.3 ± 8.07 hours; KMD-3213G = 24 hours;

Mesh Entry Terms: 1-(3-hydroxypropyl)-5-(2-(2-(2-(2,2,2-trifluoroethoxy)phenoxy)ethylamino)propyl)indoline-7-carboxamide

Use Classification: Human drugs -> Silodyx -> EMA Drug Category|Urologicals -> Human pharmacotherapeutic group|Human drugs -> Urorec -> EMA Drug Category|Human drugs -> Silodosin Recordati -> EMA Drug Category|Urologicals, Alpha-adrenoreceptor antagonists -> Human pharmacotherapeutic group|Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients

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11. Toltal 206 Suppliers View more

1H-Indole-7-carboxamide,2,3-dihydro-1-(3-hydroxypropyl)-5-[(2R)-2-[[2-[2-(2,2,2-trifluoroethoxy)phenoxy]ethyl]amino]propyl]-

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12. Related Questions

: Can Silodosin be the Solution for BPH Patients?Background and Overview Watson Pharmaceuticals has officially launched its oral, effective treatment for benign prostatic hyperplasia (BPH) - the selective a1A-adrenergic receptor antagonist Silodosin..; What should be noted when taking Silodosin?Silodosin is primarily used to treat benign prostatic hyperplasia in men. It is pale yellow-white in color and comes in powder form, which is easily soluble in acetic acid but insoluble in water. Silo..; What is Silodosin and how does it work?Overview Silodosin is an α-1 adrenergic receptor antagonist used to treat symptoms associated with benign prostatic hyperplasia (BPH). It has the highest affinity for the α1A subtype. α1-adrenergic..

13. Realated Product Infomation