Treatment of prostatic hyperplasia Benign prostatic hyperplasia Uses
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Silodosin

Treatment of prostatic hyperplasia Benign prostatic hyperplasia Uses
Product Name
Silodosin
CAS No.
160970-54-7
Chemical Name
Silodosin
Synonyms
Rapaflo;Silodosin-d4;1-(3-hydroxypropyl)-5-[(2R)-({2-[2-[2-(2,2,2-trifluoroethoxy)phenoxy]ethyl}aMino)propyl]indoline-7-carboxaMide;Urief;CS-288;KMD 3213;KAD 3213;Silodosin;Silodoxin;celodosin
CBNumber
CB42129460
Molecular Formula
C25H32F3N3O4
Formula Weight
495.53
MOL File
160970-54-7.mol
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Silodosin Property

Melting point:
>104°C (dec.)
alpha 
D25 -14.0° (c = 1.01 in methanol)
Boiling point:
601.4±55.0 °C(Predicted)
Density 
1.249±0.06 g/cm3(Predicted)
storage temp. 
under inert gas (nitrogen or Argon) at 2–8 °C
solubility 
Aqueous Base (Slightly, Heated Sonicated), DMSO (Slightly, Sonicated), Methanol
form 
Solid
pka
14.85±0.10(Predicted)
color 
White to Off-White
CAS DataBase Reference
160970-54-7(CAS DataBase Reference)
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Safety

HS Code 
29339900
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

Precautionary statements

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P337+P313IF eye irritation persists: Get medical advice/attention.

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N-Bromosuccinimide Price

Cayman Chemical
Product number
14866
Product name
Silodosin
Purity
≥98%
Packaging
1mg
Price
$49
Updated
2024/03/01
Cayman Chemical
Product number
14866
Product name
Silodosin
Purity
≥98%
Packaging
5mg
Price
$190
Updated
2024/03/01
Cayman Chemical
Product number
14866
Product name
Silodosin
Purity
≥98%
Packaging
10mg
Price
$356
Updated
2024/03/01
Cayman Chemical
Product number
14866
Product name
Silodosin
Purity
≥98%
Packaging
25mg
Price
$830
Updated
2024/03/01
Tocris
Product number
6663
Product name
Silodosin
Purity
≥98%(HPLC)
Packaging
50
Price
$432
Updated
2021/12/16
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Silodosin Chemical Properties,Usage,Production

Treatment of prostatic hyperplasia

Silodosin is a kind of α-adrenergic receptor antagonists developed by Japanese Kissei pharmaceutical company. It has a very good therapeutic efficacy on treating the dysuria related to benign prostatic hyperplasia. The selective effect on urethra of Silodosin is 12 times and 7.4 times as high as that of prazosin and tamsulosin, respectively, which can significantly inhibit norepinephrine-induced contraction of the prostate; it has dose-dependent inhibition bladder activity excitation in the benign prostatic hypertrophy models of rats, and can also improve the pressure threshold of bladder contraction. These data have suggested that, in addition to helping improve bladder function, silodosin is also effective in alleviating the related symptoms associated with benign prostatic hypertrophy.
Compared with similar drugs such as prazosin and tamsulosin, silodosin has a high selectivity onn theα1A-receptors located in the prostate and bladder neck, while having a low affinity to theα1B-and α1D-receptor. It can block theα1A-receptors in these sites, and relax the smooth muscle, and thus leading to the improvement of urinary flow rate and the alleviation of BPH symptoms.
The selective binding to the α1A-receptor by silodosin has a higher selectivity compared to the binding to the cardiovascular associated receptors α1B, thus maximizing the activity of the target organ as well as minimizing the potential effect on blood pressure.
The above information is edited by the chemicalbook of Dai Xiongfeng.

Benign prostatic hyperplasia

Benign prostatic hyperplasia (referred as BPH) is one of the most common diseases in older male with the non-malignant prostate being the character. It can cause the obstructive urination symptoms and other irritation symptoms which have brought significant negative impact on the life of older people. In recent years, with the increasing level of industrialization of China, the annual intake of animal protein intake gradually increased and life expectancy increases, the incidence of benign prostatic hyperplasia also has increased year by year. Over 50 percent in elderly people at age 60 or above has got this disease. This ratio increases to over 90% for elderly people over 85 years-old. Its triggering factor has not been totally elucidated. It is generally believed that this is related to the secretion of sex hormones and cholesterol as well as other kinds of metabolic disorders. Some people think that, for elder people, their weakened pituitary-gonadotropin-pathway or endogenous change cause degeneration of testicles decreased sexual function, reduced testosterone value, as well as the change of glandular epithelium and enlarged prostate caused by the increased connected tissue of prostate.
The enlargement of prostate will compress the urethra, resulting in poor urine flow of bladder and even blocked bladder outlet. There is α1A-adrenergic receptor located in the human prostate. The activation of the receptor will deteriorate the symptoms of dysuria and urethral obstruction. Therefore, by blocking the binding α1A-adrenergic receptor, we can relax the obstructed prostate smooth muscle relaxation, and thereby alleviating the symptoms. In recent years, people has achieved excellent efficacy by clinically applying 5α-reductase inhibitors and α1-adrenergic receptors (α1-AR) blocker (silodosin). This is considered as a major breakthrough in drug treatment of benign prostatic hyperplasia.

Uses

It can be used for treatment of benign prostatic hyperplasia.

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.

Chemical Properties

White Solid

Originator

Kissei (Japan)

Uses

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

Uses

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

Uses

Silodosin(Rapaflo) is an α1-adrenoceptor antagonist with high uroselectivity. It causes practically no orthostatic hypotension (in contrast to other α1 blockers). Since Silodosin is a highly selective inhibitor of the α1A adrenergic receptor, it causes pr

Definition

ChEBI: Silodosin is an indolecarboxamide.

brand name

Urief

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.

target

Adrenergic Receptor

storage

Store at -20°C

Silodosin Preparation Products And Raw materials

Raw materials

Preparation Products

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Silodosin Suppliers

AnHui HaiKang Pharmaceutical Co., Ltd.
Tel
0556-5800026 17709662922
Email
melrose@worldpharma.cn
Country
China
ProdList
212
Advantage
55
Changzhou Fulangke Chemical Technology Co., Ltd.
Tel
13776872728
Email
amwpl888@sina.cn
Country
China
ProdList
15
Advantage
58
Hubei Chenxin Pharmaceutical Co., Ltd.
Tel
17362916295 17362916295
Fax
QQ:840947394
Email
w17362916295@163.com
Country
China
ProdList
3029
Advantage
58
Sichuan Qingmu Pharmaceutical Co., Ltd.
Tel
+86-28-87827187 +86-15258599553
Email
sales@eastonpharma.cn
Country
China
ProdList
76
Advantage
60
Beijing Lianben Pharm-Chemicals Tech. Co.,Ltd
Tel
010-83386559 18810831598
Fax
010-83386758
Email
sales@lianben.com
Country
China
ProdList
92
Advantage
58
J & K SCIENTIFIC LTD.
Tel
010-82848833 400-666-7788
Fax
86-10-82849933
Email
jkinfo@jkchemical.com
Country
China
ProdList
96815
Advantage
76
Chembest Research Laboratories Limited
Tel
021-20908456
Fax
021-58180499
Email
sales@BioChemBest.com
Country
China
ProdList
6013
Advantage
61
Jia Xing Isenchem Co.,Ltd
Tel
0573-85285100 18627885956
Fax
0573-85285100
Email
isenchem@163.com
Country
China
ProdList
9555
Advantage
66
Adamas Reagent, Ltd.
Tel
400-6009262 16621234537
Fax
021-64823266
Email
zhangsn@titansci.com
Country
China
ProdList
14113
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59
LGM Pharma
Tel
1-(800)-881-8210
Fax
615-250-9817
Email
inquiries@lgmpharma.com
Country
United States
ProdList
2127
Advantage
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View Lastest Price from Silodosin manufacturers

Hebei Dangtong Import and export Co LTD
Product
Silodosin 160970-54-7
Price
US $50.00-40.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
20
Release date
2023-10-09
Hebei Lingding Biotechnology Co., Ltd.
Product
Silodosin 160970-54-7
Price
US $90.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
9000kg/per week
Release date
2024-02-03
Henan Bao Enluo International TradeCo.,LTD
Product
Silodosin 160970-54-7
Price
US $100.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
1000tons
Release date
2023-07-25

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