Silodosin glucuronide sodium | CAS# 879292-24-7 | Metabolite

MedKoo Cat#: 574165 | Name: Silodosin glucuronide sodium

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Silodosin glucuronide sodium is an active metabolite of the α1A-adrenergic receptor antagonist silodosin. It is formed from silodosin by the UDP-glucuronosyltransferase (UGT) isoform UGT2B7.

Chemical Structure

Silodosin glucuronide sodium

CAS#879292-24-7

Theoretical Analysis

MedKoo Cat#: 574165

Name: Silodosin glucuronide sodium

CAS#: 879292-24-7

Chemical Formula: C31H39F3N3NaO10

Exact Mass: 0.0000

Molecular Weight: 693.65

Elemental Analysis: C, 53.68; H, 5.67; F, 8.22; N, 6.06; Na, 3.31; O, 23.06

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Size	Price	Availability	Quantity
1mg	USD 1,000.00	2 weeks

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Related CAS #

160970-54-7

Synonym

Silodosin β-D-glucuronide, Silodosin glucuronide sodium

IUPAC/Chemical Name

sodium (2S,3S,4S,5R,6R)-6-(3-(7-carbamoyl-5-((R)-2-((2-(2-(2,2,2-trifluoroethoxy)phenoxy)ethyl)amino)propyl)indolin-1-yl)propoxy)-3,4,5-trihydroxytetrahydro-2H-pyran-2-carboxylate

InChi Key

SSXDGVSHJRFUEJ-XNUWQVEGSA-M

InChi Code

InChI=1S/C31H40F3N3O10.Na/c1-17(36-8-12-44-21-5-2-3-6-22(21)46-16-31(32,33)34)13-18-14-19-7-10-37(23(19)20(15-18)28(35)41)9-4-11-45-30-26(40)24(38)25(39)27(47-30)29(42)43;/h2-3,5-6,14-15,17,24-27,30,36,38-40H,4,7-13,16H2,1H3,(H2,35,41)(H,42,43);/q;+1/p-1/t17-,24+,25+,26-,27+,30-;/m1./s1

SMILES Code

C[C@H](CC1=CC(C(N)=O)=C(N(CCCO[C@@H]2O[C@H](C([O-])=O)[C@@H](O)[C@H](O)[C@H]2O)CC3)C3=C1)NCCOC4=C(OCC(F)(F)F)C=CC=C4.[Na+]

Appearance

Solid powder

Purity

>95% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

To be determined

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Silodosin is a selective α1A adrenoceptor antagonist (Ki = 0.036 nM) that displays >55 fold selectivity for α1A over α1B and α1D. Silodosin inhibits norepinephrine-induced [Ca2+]I increase in α1A expressing CHO cells (IC50 = 0.32 nM) and inhibits norepinephrine-induced contraction of isolated human prostate tissue.

In vitro activity:

Silodosin inactivates ELK1 in prostate cancer cells and not only inhibits their growth, but also enhances the cytotoxic activity of gemcitabine. Silodosin treatment reduced ELK1 expression/activity, cell viability in AR-positive cells, and migration in both AR-positive and AR-negative cells. Silodosin increased sensitivity to gemcitabine, but not to cisplatin or docetaxel, in AR-negative cells. Reference: Prostate. 2016 Jun;76(8):744-56. https://pubmed.ncbi.nlm.nih.gov/26864615/

In vivo activity:

Silodosin improves functional consequences of lower urinary tract obstruction secondary to benign prostate hypertrophy. Chronic silodosin treatment relieved storage symptoms in spontaneously hypertensive rats (SHR) supplemented with testosterone and decreased the frequency of non-voiding detrusor contractions during the filling phase. Silodosin treated rats displayed a significant increase in prostate and bladder weights and a 15% increase in the detrusor wall area compared to the control rats. Reference: BMC Urol. 2020 Aug 27;20(1):132. https://pubmed.ncbi.nlm.nih.gov/32854676/

Preparing Stock Solutions

The following data is based on the product molecular weight 693.65 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Gond DP, Singh S, Agrawal NK. Norepinephrine augmented in vitro growth of uropathogenic E. coli in Type 2 diabetes mellitus and its suppression by silodosin (alpha blocker). Diagn Microbiol Infect Dis. 2018 Oct;92(2):85-89. doi: 10.1016/j.diagmicrobio.2018.05.005. Epub 2018 May 30. PMID: 29934070. 2. Kawahara T, Aljarah AK, Shareef HK, Inoue S, Ide H, Patterson JD, Kashiwagi E, Han B, Li Y, Zheng Y, Miyamoto H. Silodosin inhibits prostate cancer cell growth via ELK1 inactivation and enhances the cytotoxic activity of gemcitabine. Prostate. 2016 Jun;76(8):744-56. doi: 10.1002/pros.23164. Epub 2016 Feb 11. PMID: 26864615. 3. Assaly R, Faugeroux J, Laurin M, Compagnie S, Alexandre L, Giuliano F, Behr-Roussel D. Silodosin improves functional consequences of lower urinary tract obstruction secondary to benign prostate hypertrophy, a proof of concept study in the spontaneously hypertensive rat supplemented with testosterone. BMC Urol. 2020 Aug 27;20(1):132. doi: 10.1186/s12894-020-00699-y. PMID: 32854676; PMCID: PMC7453715. 4. Liu N, Shimizu S, Shimizu T, Nakamura K, Yamamoto M, Higashi Y, Saito M. Protective effects of the selective alpha1A-adrenoceptor antagonist silodosin against cyclophosphamide-induced cystitis in rats. J Pharmacol Sci. 2016 Sep;132(1):71-77. doi: 10.1016/j.jphs.2016.08.007. Epub 2016 Sep 9. PMID: 27654219.

In vitro protocol:

In vivo protocol:

1. Assaly R, Faugeroux J, Laurin M, Compagnie S, Alexandre L, Giuliano F, Behr-Roussel D. Silodosin improves functional consequences of lower urinary tract obstruction secondary to benign prostate hypertrophy, a proof of concept study in the spontaneously hypertensive rat supplemented with testosterone. BMC Urol. 2020 Aug 27;20(1):132. doi: 10.1186/s12894-020-00699-y. PMID: 32854676; PMCID: PMC7453715. 2. Liu N, Shimizu S, Shimizu T, Nakamura K, Yamamoto M, Higashi Y, Saito M. Protective effects of the selective alpha1A-adrenoceptor antagonist silodosin against cyclophosphamide-induced cystitis in rats. J Pharmacol Sci. 2016 Sep;132(1):71-77. doi: 10.1016/j.jphs.2016.08.007. Epub 2016 Sep 9. PMID: 27654219.

1. Keating, G.M. Silodosin: A review of its use in the treatment of the signs and symptoms of benign prostatic hyperplasia. Drugs 75(2), 207-217 (2015). 2. Vishnuvardhan, C., Baikadi, S., Borkar, R.M., et al. In vivo metabolic investigation of silodosin using UHPLC-QTOF-MS/MS and in silico toxicological screening of its metabolites. J. Mass. Spectrom. 51(10), 867-882 (2016).