Naftopidil-d5 | CAS#2747918-58-5 | Naftopidil quantification internal standard

MedKoo Cat#: 464482 | Name: Naftopidil-d5

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Description:

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

Naftopidil-d5 is intended for use as an internal standard for the quantification of naftopidil by GC- or LC-MS. Naftopidil is an antagonist of α1-adrenergic receptors (α1-ARs; Kis = 3.7, 20, and 1.2 nM for α1A-, α1B-, and α1D-ARs, respectively). It is selective for α1-ARs over α2-ARs (Ki = 1,793 nM). Naftopidil inhibits norepinephrine-induced contractions in various blood vessels isolated from dog, rabbit, guinea pig, or rat with pA2 values ranging from 6.73 to 8.15. It reduces prostatic pressure and mean blood pressure in anesthetized dogs when administered at doses of 100 or 1,000 µg/kg. Naftopidil also inhibits the growth of androgen-sensitive LNCaP cells and androgen-insensitive PC3 cancer cells with IC50 values of 22.2 and 33.2 µM, respectively.4 Formulations containing naftopidil have been used in the treatment of benign prostatic hyperplasia.

Chemical Structure

Naftopidil-d5

CAS#2747918-58-5

Theoretical Analysis

MedKoo Cat#: 464482

Name: Naftopidil-d5

CAS#: 2747918-58-5

Chemical Formula: C24H23D5N2O3

Exact Mass: 397.2414

Molecular Weight: 397.53

Elemental Analysis: C, 72.51; H, 8.37; N, 7.05; O, 12.07

Price and Availability

Size	Price	Availability	Quantity
1mg	USD 750.00	2 Weeks

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Synonym

Naftopidil-d5; Naftopidil d5;

IUPAC/Chemical Name

1-(4-(2-methoxyphenyl)piperazin-1-yl)-3-(naphthalen-1-yloxy)propan-1,1,2,3,3-d5-2-ol

InChi Key

HRRBJVNMSRJFHQ-XOYZCUSZSA-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/i17D2,18D2,20D

SMILES Code

COC1=C(C=CC=C1)N2CCN(CC2)C([2H])(C([2H])(O)C([2H])(OC3=CC=CC4=C3C=CC=C4)[2H])[2H]

Appearance

Solid powder

Purity

>99% (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

>2 years if stored properly

Drug Formulation

To be determined

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-d5 is intended for use as an internal standard for the quantification of naftopidil by GC- or LC-MS.

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/

Preparing Stock Solutions

The following data is based on the product molecular weight 397.53 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.

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