Naftopidil | Flivas | BM-15275 | CAS#57149-07-2 | Alpha-1-D Adrenoceptor Antagonist

MedKoo Cat#: 328509 | Name: Naftopidil

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Description:

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

Naftopidil, also known as Flivas and BM-15275, is an alpha-1-D adrenoceptor antagonist used to treat dysuria in men with benign prostatic hypertrophy.

Chemical Structure

Naftopidil

CAS#57149-07-2

Theoretical Analysis

MedKoo Cat#: 328509

Name: Naftopidil

CAS#: 57149-07-2

Chemical Formula: C24H28N2O3

Exact Mass: 392.2100

Molecular Weight: 392.50

Elemental Analysis: C, 73.44; H, 7.19; N, 7.14; O, 12.23

Price and Availability

Size	Price	Availability	Quantity
25mg	USD 325.00
100mg	USD 830.00

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Synonym

Naftopidil; BM-15275; KT-611; BM 15275; KT 611; BM15275; KT611; Flivas

IUPAC/Chemical Name

1-(4-(2-methoxyphenyl)piperazin-1-yl)-3-(naphthalen-1-yloxy)propan-2-ol

InChi Key

HRRBJVNMSRJFHQ-UHFFFAOYSA-N

InChi Code

InChI=1S/C24H28N2O3/c1-28-24-11-5-4-10-22(24)26-15-13-25(14-16-26)17-20(27)18-29-23-12-6-8-19-7-2-3-9-21(19)23/h2-12,20,27H,13-18H2,1H3

SMILES Code

OC(COC1=C2C=CC=CC2=CC=C1)CN3CCN(C4=CC=CC=C4OC)CC3

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

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:

Naftopidil (KT-611) is is a selective alpha1-adrenoceptor antagonist, with Kis of 3.7 nM, 20 nM and 1.2 nM for the cloned human α1a-, α1b- and α1d-adrenoceptor subtypes.

In vitro activity:

In in vitro analyses, naftopidil and silodosin showed antiproliferative effects on PCa cells regardless of androgen sensitivity and α(1)-AR subtype expression. In PrSC, a strong growth inhibitory effect was observed with naftopidil but not silodosin. Flow cytometric analysis revealed that naftopidil, but not silodosin, induced G(1) cell-cycle arrest in both PCa cells and PrSC. In naftopidil-treated PrSC, total interleukin-6 protein was significantly reduced with increased suppression of cell proliferation. Reference: Cancer Prev Res (Phila). https://pubmed.ncbi.nlm.nih.gov/21205739/

In vivo activity:

This study investigated the effects of naftopidil on 5-hydroxytryptamine (5-HT)-induced rat bladder contraction (10(-8)-10(-4) M). Naftopidil (0.3, 1, and 3 μM) inhibited 5-HT-induced bladder contraction in a concentration-dependent manner. Naftopidil inhibited both the 5-HT(2A) and 5-HT(2) receptor agonists-induced bladder contractions. Naftopidil binds to the human 5-HT(2A) and 5-HT(2B) receptors with pKi values of 6.55 and 7.82, respectively. Reference: Eur J Pharmacol. 2013 Jan 30;700(1-3):194-200. https://pubmed.ncbi.nlm.nih.gov/23274492/

	Solvent	mg/mL	mM
Solubility
	DMSO	25.2	64.11

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 392.50 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. Hori Y, Ishii K, Kanda H, Iwamoto Y, Nishikawa K, Soga N, Kise H, Arima K, Sugimura Y. Naftopidil, a selective {alpha}1-adrenoceptor antagonist, suppresses human prostate tumor growth by altering interactions between tumor cells and stroma. Cancer Prev Res (Phila). 2011 Jan;4(1):87-96. doi: 10.1158/1940-6207.CAPR-10-0189. PMID: 21205739. 2. Kanda H, Ishii K, Ogura Y, Imamura T, Kanai M, Arima K, Sugimura Y. Naftopidil, a selective alpha-1 adrenoceptor antagonist, inhibits growth of human prostate cancer cells by G1 cell cycle arrest. Int J Cancer. 2008 Jan 15;122(2):444-51. doi: 10.1002/ijc.23095. PMID: 17918159. 3. Sakai T, Kasahara K, Tomita K, Ikegaki I, Kuriyama H. Naftopidil inhibits 5-hydroxytryptamine-induced bladder contraction in rats. Eur J Pharmacol. 2013 Jan 30;700(1-3):194-200. doi: 10.1016/j.ejphar.2012.12.022. Epub 2012 Dec 26. PMID: 23274492. 4. Takei R, Ikegaki I, Shibata K, Tsujimoto G, Asano T. Naftopidil, a novel alpha1-adrenoceptor antagonist, displays selective inhibition of canine prostatic pressure and high affinity binding to cloned human alpha1-adrenoceptors. Jpn J Pharmacol. 1999 Apr;79(4):447-54. doi: 10.1254/jjp.79.447. PMID: 10361884.

In vitro protocol:

In vivo protocol:

1. Sakai T, Kasahara K, Tomita K, Ikegaki I, Kuriyama H. Naftopidil inhibits 5-hydroxytryptamine-induced bladder contraction in rats. Eur J Pharmacol. 2013 Jan 30;700(1-3):194-200. doi: 10.1016/j.ejphar.2012.12.022. Epub 2012 Dec 26. PMID: 23274492. 2. Takei R, Ikegaki I, Shibata K, Tsujimoto G, Asano T. Naftopidil, a novel alpha1-adrenoceptor antagonist, displays selective inhibition of canine prostatic pressure and high affinity binding to cloned human alpha1-adrenoceptors. Jpn J Pharmacol. 1999 Apr;79(4):447-54. doi: 10.1254/jjp.79.447. PMID: 10361884.

1: Yamamoto M, Shimizu T, Shimizu S, Higashi Y, Nakamura K, Fujieda M, Saito M. Effect of naftopidil on brain noradrenaline-induced decrease in arginine-vasopressin secretion in rats. J Pharmacol Sci. 2016 Sep 8. pii: S1347-8613(16)30117-7. doi: 10.1016/j.jphs.2016.09.002. [Epub ahead of print] PubMed PMID: 27666018. 2: Nakagawa YU, Nagaya H, Miyata T, Wada Y, Oyama T, Gotoh A. Piperazine-based Alpha-1 AR Blocker, Naftopidil, Selectively Suppresses Malignant Human Bladder Cells via Induction of Apoptosis. Anticancer Res. 2016 Apr;36(4):1563-70. PubMed PMID: 27069132. 3: Kohjimoto Y, Hagino K, Ogawa T, Inagaki T, Kitamura S, Nishihata M, Iba A, Matsumura N, Hara I. Naftopidil versus flopropione as medical expulsive therapy for distal ureteral stones: results of a randomized, multicenter, double-blind, controlled trial. World J Urol. 2015 Dec;33(12):2125-9. doi: 10.1007/s00345-015-1556-x. Epub 2015 Apr 14. PubMed PMID: 25869815. 4: Sugaya K, Nishijima S, Kadekawa K, Ashitomi K, Ueda T, Yamamoto H, Hattori T. Action of naftopidil on spinal serotonergic neurotransmission for inhibition of the micturition reflex in rats. Neurourol Urodyn. 2016 Apr 29. doi: 10.1002/nau.23028. [Epub ahead of print] PubMed PMID: 27128660. 5: Matsukawa Y, Funahashi Y, Takai S, Majima T, Ogawa T, Narita H, Kato M, Gotoh M. Comparison of silodosin and naftopidil for efficacy in the treatment of benign prostatic enlargement complicated by overactive bladder: A randomized, prospective study (SNIPER study). J Urol. 2016 Sep 8. pii: S0022-5347(16)31211-3. doi: 10.1016/j.juro.2016.08.111. [Epub ahead of print] PubMed PMID: 27615436. 6: Sugaya K, Nishijima S, Kadekawa K, Ashitomi K, Ueda T, Yamamoto H. Naftopidil improves locomotor activity and urinary frequency in rats with pelvic venous congestion. Biomed Res. 2016;37(4):221-6. doi: 10.2220/biomedres.37.221. PubMed PMID: 27544997. 7: Kadekawa K, Sugaya K, Mukoyama H, Sakumoto M, Shimabukuro H, Shimabukuro S, Matayoshi Y, Onaga T, Ashitomi K, Nishijima S. Influence of Naftopidil on Plasma Monoamine Levels and Lower Urinary Tract Symptoms Associated with Benign Prostatic Hyperplasia. Low Urin Tract Symptoms. 2016 May;8(2):100-5. doi: 10.1111/luts.12079. Epub 2014 Nov 6. PubMed PMID: 27111621. 8: Peng J, Xiao D, He H, Zhao H, Wang C, Shi T, Shi K. Molecularly imprinted polymeric stir bar: Preparation and application for the determination of naftopidil in plasma and urine samples. J Sep Sci. 2016 Jan;39(2):383-90. doi: 10.1002/jssc.201500751. PubMed PMID: 26541792. 9: Masumori N, Tsukamoto T, Shibuya A, Miyao N, Kunishima Y, Iwasawa A. Three-year outcome analysis of alpha 1-blocker naftopidil for patients with benign prostatic hyperplasia in a prospective multicenter study in Japan. Patient Prefer Adherence. 2016 Jul 22;10:1309-16. doi: 10.2147/PPA.S110440. eCollection 2016. PubMed PMID: 27524886; PubMed Central PMCID: PMC4966686. 10: Tanuma Y, Tanaka Y, Takeyama K, Okamoto T. Does prostate volume affect the efficacy of α1D/A: Adrenoceptor antagonist naftopidil? Urol Ann. 2016 Jan-Mar;8(1):20-5. doi: 10.4103/0974-7796.157979. PubMed PMID: 26834396; PubMed Central PMCID: PMC4719506.