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

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

MedKoo CAT#: 328509

CAS#: 57149-07-2

Description: 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

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 328509
Name: Naftopidil
CAS#: 57149-07-2
Chemical Formula: C24H28N2O3
Exact Mass: 392.21
Molecular Weight: 392.499
Elemental Analysis: C, 73.44; H, 7.19; N, 7.14; O, 12.23

Price and Availability

Size	Price	Availability	Quantity
25mg	USD 325
100mg	USD 830
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

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/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMSO	25.2	64.11

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:	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.
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.

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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.

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