An internal standard for the quantification of naftopidil
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Unlabeled Version(s)
21122Naftopidil (hydrochloride)
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Naftopidil-d5

Item No. 33811

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
4-(2-methoxyphenyl)-α-[(1-naphthalenyloxy)methyl-d2]-1-piperazineethan-α,β,β-d3-ol
CAS Number
2747918-58-5
Molecular Formula
C24H23D5N2O3
Formula Weight
397.5
Purity
≥99% deuterated forms (d1-d5)
Formulation
A solid
Solubility(Learn about Variance in Solubility)
Methanol: soluble
SMILES
COC1=C(N2CCN(C([2H])([2H])C(C([2H])([2H])OC3=CC=CC4=C3C=CC=C4)([2H])O)CC2)C=CC=C1
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
InChi Key
HRRBJVNMSRJFHQ-XOYZCUSZSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    500 µg

    $229

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    1 mg

    $431

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    Product Description

    Naftopidil-d5 is intended for use as an internal standard for the quantification of naftopidil (Item No. 21122) 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).1 It is selective for α1-ARs over α2-ARs (Ki = 1,793 nM).2 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 8.15.2 It reduces prostatic pressure and mean blood pressure in anesthetized dogs when administered at doses of 100 or 1,000 µg/kg.3 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.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Masumori, N. Naftopidil for the treatment of urinary symptoms in patients with benign prostatic hyperplasia. Ther. Clin. Risk Manag. 7, 227-238 (2011).

    2. Muramatsu, I., Yamanaka, K., and Kigoshi, S. Pharmacological profile of the novel α-adrenoceptor antagonist KT-611 (naftopidil). Jpn. J. Pharmacol. 55(3), 391-398 (1991).

    3. Takei, R.-i., Ikegaki, I., Shibata, K., et al. Naftopidil, a novel α1-adrenoceptor antagonist, displays selective inhibition of canine prostatic pressure and high affinity binding to cloned human α1-adrenoceptors. Jpn. J. Pharmacol. 79(4), 447-454 (1999).

    4. Kanda, H., Ishii, K., Ogura, Y., et al. Naftopidil, a selective α-1 adrenoceptor antagonist, inhibits growth of human prostate cancer cells by G1 cell cycle arrest. Int. J. Cancer 122(2), 444-451 (2008).