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Nortadalafil

PDE5 inhibitor CAS# 171596-36-4

Nortadalafil

Catalog No. BCC1806----Order now to get a substantial discount!

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Chemical structure

Nortadalafil

3D structure

Chemical Properties of Nortadalafil

Cas No. 171596-36-4 SDF Download SDF
PubChem ID 9820973 Appearance Powder
Formula C21H17N3O4 M.Wt 375.38
Type of Compound N/A Storage Desiccate at -20°C
Solubility DMSO : 50 mg/mL (133.20 mM; Need ultrasonic)
H2O : < 0.1 mg/mL (insoluble)
SMILES C1C2C(=O)NCC(=O)N2C(C3=C1C4=CC=CC=C4N3)C5=CC6=C(C=C5)OCO6
Standard InChIKey XHDLVMPUSXRZOS-FOIQADDNSA-N
Standard InChI InChI=1S/C21H17N3O4/c25-18-9-22-21(26)15-8-13-12-3-1-2-4-14(12)23-19(13)20(24(15)18)11-5-6-16-17(7-11)28-10-27-16/h1-7,15,20,23H,8-10H2,(H,22,26)/t15-,20-/m1/s1
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Biological Activity of Nortadalafil

DescriptionNortadalafil is a inhibitor of PDE5.
TargetsPDE5    

Nortadalafil Dilution Calculator

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Nortadalafil Molarity Calculator

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Preparing Stock Solutions of Nortadalafil

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.664 mL 13.3198 mL 26.6397 mL 53.2793 mL 66.5992 mL
5 mM 0.5328 mL 2.664 mL 5.3279 mL 10.6559 mL 13.3198 mL
10 mM 0.2664 mL 1.332 mL 2.664 mL 5.3279 mL 6.6599 mL
50 mM 0.0533 mL 0.2664 mL 0.5328 mL 1.0656 mL 1.332 mL
100 mM 0.0266 mL 0.1332 mL 0.2664 mL 0.5328 mL 0.666 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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Background on Nortadalafil

IC50: N/A for Nortadalafil; 5 nM for Tadalafil

The cGMP-specific PDE5 is the major PDE isozyme in the corpus cavernosum, and controls penile erection. The PDE5 inhibitors used in the clinic amplify the NO-cCMP pathway and enhance the normal process leading to penile erection.

Nortadalafil is demethyl Tadalafil, which is a PDE5 inhibitor currently marketed in pill form for treating erectile dysfunction under the name Cialis and for the treatment of pulmonary arterial hypertension under the name Adcirca.

In vitro: Tadalafil has been identified as a highly potent PDE5 inhibitor (IC50 = 5 nM) with high selectivity for PDE5 vs PDE1-4 and PDE6. It displays 85-fold greater selectivity vs PDE6 than sildenafil [1].

In vivo: Tadalafil showed profound and long-lasting blood pressure lowering activity (30 mmHg/>7 h) in the spontaneously hypertensive rat model after oral administration (5 mg/kg) [1].

Clinical trial: Tadalafil once-daily provides efficacy comparable to on-demand dosing regimens with PDE-5 inhibitors, is well tolerated and allows patients and their partners to disconnect the administration of medication from sexual activity, thereby enabling them to return to the sex-life they had before the onset of erectile dysfunction [2].

References:
[1] Daugan A, Grondin P, Ruault C, Le Monnier de Gouville AC, Coste H, Linget JM, Kirilovsky J, Hyafil F, Labaudinière R.  The discovery of tadalafil: a novel and highly selective PDE5 inhibitor. 2: 2,3,6,7,12,12a-hexahydropyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione analogues. J Med Chem. 2003;46(21):4533-42.
[2] Porst H, Hell-Momeni K, Büttner H.   Chronic PDE-5 inhibition in patients with erectile dysfunction - a treatment approach using tadalafil once-daily. Expert Opin Pharmacother. 2012 Jul;13(10):1481-94. doi: 10.1517/14656566.2012.693162.

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References on Nortadalafil

Isolation and characterization of a tadalafil analogue, N-cyclopentyl nortadalafil in health supplement.[Pubmed:26580820]

J Pharm Biomed Anal. 2016 Jan 25;118:235-241.

A tadalafil analogue was detected for the first time during the screening of a health supplement for undeclared sexual enhancement drugs. The compound had been isolated and purified by preparative high-pressure liquid chromatography (HPLC). Its chemical structure was elucidated using high-resolution mass spectrometry (HRMS), electrospray ionization tandem mass spectrometry (ESI-MS/MS) and nuclear magnetic resonance (NMR) spectroscopy. The compound had a protonated molecular ion at m/z 444 with a chemical formula of C26H25N3O4. The data obtained from the MS analysis of the compound suggested that the N-methyl group on the piperazinedione moiety of tadalafil was substituted with a -C5H9 group. Analysis using NMR was performed and the -C5H9 group was characterized as a cyclopentyl moiety. The analogue was named N-cyclopentyl Nortadalafil.

Description

Nortadalafil is demethyl Tadalafil, which is a PDE5 inhibitor, currently marketed in pill form for treating erectile dysfunction (ED) under the name Cialis; and under the name Adcirca for the treatment of pulmonary arterial hypertension.

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