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MedKoo Cat#: 319611 | Name: Silodosin
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Description:

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

Silodosin, also known as KMD-3213, is an α1-adrenoceptor antagonist approved for the symptomatic treatment of benign prostatic hyperplasia. It acts as an α1-adrenoceptor antagonist with high uroselectivity (selectivity for the prostate). Since silodosin has high affinity for the α1A adrenergic receptor, it causes practically no orthostatic hypotension (in contrast to other α1 blockers).

Chemical Structure

Silodosin
Silodosin
CAS#160970-54-7

Theoretical Analysis

MedKoo Cat#: 319611

Name: Silodosin

CAS#: 160970-54-7

Chemical Formula: C25H32F3N3O4

Exact Mass: 495.2345

Molecular Weight: 495.54

Elemental Analysis: C, 60.60; H, 6.51; F, 11.50; N, 8.48; O, 12.91

Price and Availability

Size Price Availability Quantity
50mg USD 150.00 2 Weeks
100mg USD 250.00 2 Weeks
500mg USD 450.00 2 Weeks
1g USD 950.00 2 Weeks
2g USD 1,650.00 2 Weeks
5g USD 2,950.00 2 Weeks
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Related CAS #
879292-24-7
Synonym
KMD-3213; KMD3213; KMD 3213; KAD 3213; KAD 3213; KAD3213; Silodosin. trade names Rapaflo, Silodyx, Rapilif, Silodal, Urief, Urorec.
IUPAC/Chemical Name
2,3-dihydro-1-(3-hydroxypropyl)-5-[(2R)-2-[[2-[2-(2,2,2-trifluoroethoxy)phenoxy]ethyl]amino]propyl]-1H-indole-7-carboxamide
InChi Key
PNCPYILNMDWPEY-QGZVFWFLSA-N
InChi Code
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
SMILES Code
O=C(C1=CC(C[C@H](NCCOC2=CC=CC=C2OCC(F)(F)F)C)=CC3=C1N(CCCO)CC3)N
Appearance
Solid powder
Purity
>98% (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
Soluble in DMSO and ethanol
Shelf Life
>2 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/
Solvent mg/mL mM
Solubility
DMSO 49.6 100.00
Ethanol 49.6 100.00
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 495.54 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.

Recalculate based on batch purity %
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:
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.
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: Tan S, Ludwig KC, Müller A, Schneider T, Nodwell JR. The Lasso Peptide Siamycin-I Targets Lipid II at the Gram-Positive Cell Surface. ACS Chem Biol. 2019 May 17;14(5):966-974. doi: 10.1021/acschembio.9b00157. Epub 2019 May 3. PMID: 31026131. 2: Kaweewan I, Hemmi H, Komaki H, Harada S, Kodani S. Isolation and structure determination of a new lasso peptide specialicin based on genome mining. Bioorg Med Chem. 2018 Dec 15;26(23-24):6050-6055. doi: 10.1016/j.bmc.2018.11.007. Epub 2018 Nov 9. PMID: 30448257. 3: Daniel-Ivad M, Hameed N, Tan S, Dhanjal R, Socko D, Pak P, Gverzdys T, Elliot MA, Nodwell JR. An Engineered Allele of afsQ1 Facilitates the Discovery and Investigation of Cryptic Natural Products. ACS Chem Biol. 2017 Mar 17;12(3):628-634. doi: 10.1021/acschembio.6b01002. Epub 2017 Jan 19. PMID: 28075554. 4: Yamamoto T, Matsui H, Yamaji K, Takahashi T, Øverby A, Nakamura M, Matsumoto A, Nonaka K, Sunazuka T, Ōmura S, Nakano H. Narrow-spectrum inhibitors targeting an alternative menaquinone biosynthetic pathway of Helicobacter pylori. J Infect Chemother. 2016 Sep;22(9):587-92. doi: 10.1016/j.jiac.2016.05.012. Epub 2016 Jun 23. PMID: 27346378. 5: Phillips-Jones MK, Patching SG, Edara S, Nakayama J, Hussain R, Siligardi G. Interactions of the intact FsrC membrane histidine kinase with the tricyclic peptide inhibitor siamycin I revealed through synchrotron radiation circular dichroism. Phys Chem Chem Phys. 2013 Jan 14;15(2):444-7. doi: 10.1039/c2cp43722h. Epub 2012 Nov 26. PMID: 23183669. 6: Ma P, Nishiguchi K, Yuille HM, Davis LM, Nakayama J, Phillips-Jones MK. Anti- HIV siamycin I directly inhibits autophosphorylation activity of the bacterial FsrC quorum sensor and other ATP-dependent enzyme activities. FEBS Lett. 2011 Sep 2;585(17):2660-4. doi: 10.1016/j.febslet.2011.07.026. Epub 2011 Jul 26. PMID: 21803040. 7: Nakayama J, Tanaka E, Kariyama R, Nagata K, Nishiguchi K, Mitsuhata R, Uemura Y, Tanokura M, Kumon H, Sonomoto K. Siamycin attenuates fsr quorum sensing mediated by a gelatinase biosynthesis-activating pheromone in Enterococcus faecalis. J Bacteriol. 2007 Feb;189(4):1358-65. doi: 10.1128/JB.00969-06. Epub 2006 Oct 27. PMID: 17071762; PMCID: PMC1797363. 8: De Clercq E. Current lead natural products for the chemotherapy of human immunodeficiency virus (HIV) infection. Med Res Rev. 2000 Sep;20(5):323-49. doi: 10.1002/1098-1128(200009)20:5<323::aid-med1>3.0.co;2-a. PMID: 10934347. 9: Lin PF, Samanta H, Bechtold CM, Deminie CA, Patick AK, Alam M, Riccardi K, Rose RE, White RJ, Colonno RJ. Characterization of siamycin I, a human immunodeficiency virus fusion inhibitor. Antimicrob Agents Chemother. 1996 Jan;40(1):133-8. doi: 10.1128/AAC.40.1.133. PMID: 8787894; PMCID: PMC163071. 10: Yano K, Toki S, Nakanishi S, Ochiai K, Ando K, Yoshida M, Matsuda Y, Yamasaki M. MS-271, a novel inhibitor of calmodulin-activated myosin light chain kinase from Streptomyces sp.--I. Isolation, structural determination and biological properties of MS-271. Bioorg Med Chem. 1996 Jan;4(1):115-20. doi: 10.1016/0968-0896(95)00175-1. PMID: 8689231. 11: Detlefsen DJ, Hill SE, Volk KJ, Klohr SE, Tsunakawa M, Furumai T, Lin PF, Nishio M, Kawano K, Oki T, et al. Siamycins I and II, new anti-HIV-1 peptides: II. Sequence analysis and structure determination of siamycin I. J Antibiot (Tokyo). 1995 Dec;48(12):1515-7. doi: 10.7164/antibiotics.48.1515. PMID: 8557614. 12: Tsunakawa M, Hu SL, Hoshino Y, Detlefson DJ, Hill SE, Furumai T, White RJ, Nishio M, Kawano K, Yamamoto S, et al. Siamycins I and II, new anti-HIV peptides: I. Fermentation, isolation, biological activity and initial characterization. J Antibiot (Tokyo). 1995 May;48(5):433-4. doi: 10.7164/antibiotics.48.433. PMID: 7797448. 13: Constantine KL, Friedrichs MS, Detlefsen D, Nishio M, Tsunakawa M, Furumai T, Ohkuma H, Oki T, Hill S, Bruccoleri RE, et al. High-resolution solution structure of siamycin II: novel amphipathic character of a 21-residue peptide that inhibits HIV fusion. J Biomol NMR. 1995 Apr;5(3):271-86. doi: 10.1007/BF00211754. PMID: 7787424.