yingweiwo

Nortadalafil

Alias: Nortadalafil; 171596-36-4; Demethyltadalafil; N-Desmethyl Tadalafil; Demethyl Tadalafil; (+)-Nortadalafil; 5W59DMB3LD; CHEMBL342008;
Cat No.:V32319 Purity: ≥98%
Nortadalafil (Demethyl Tadalafil) is thedemethylated metabolite/impurity of Tadalafil, which is a potent PDE5 inhibitor approved as an oral drug for treating erectile dysfunction (ED).
Nortadalafil
Nortadalafil Chemical Structure CAS No.: 171596-36-4
Product category: Phosphodiesterase(PDE)
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
100mg
250mg
500mg
1g
Other Sizes

Other Forms of Nortadalafil:

  • Tadalafil (IC 351; Cialis)
  • Tadalafil, (6R ,12aS)-
  • ent-Tadalafil
  • cis-ent-Tadalafil (cis-ent-IC-351; Tadalafil, (6S,12aR)-)
  • Tadalafil-d3 (IC-351-d3)
Official Supplier of:
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Top Publications Citing lnvivochem Products
Product Description

Nortadalafil (Demethyl Tadalafil) is the demethylated metabolite/impurity of Tadalafil, which is a potent PDE5 inhibitor approved as an oral drug for treating erectile dysfunction (ED).

Biological Activity I Assay Protocols (From Reference)
Targets
PDE5
ln Vitro
To identify an unknown tadalafil analogue illegally adulterated in health foods. METHODS An unknown tadalafil analogue was observed in a routine screening for compounds illegally adulterated in heath foods by HPLC-DAD. The compound of interest was isolated by silica gel thin layer chromatography. Its molecular weight and structural fragments were obtained by UPLC-MS/MS, and its 1H-NMR spectum was also obtained using nuclear magnetic resonance. Its structure is elucidated by analysis of these data in combination of the literature. RESULTS A new tadalafil analogue, nortadalafil, was detected in health foods.CONCLUSION This is the first time to disclose that nortadalafil was illegally adulterated in health foods. It′s necessary to supplement the current inspection standard, which lists 11 target compounds but not including nortadalafil, to punish the illegal producers in time[4].
References

[1]. 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 analogue. Journal of Medicinal Chemistry (2003), 46(21), 4533-4542.

[2]. 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.

[3]. Frey MK, Lang I. Tadalafil for the treatment of pulmonary arterial hypertension. Expert Opin Pharmacother. 2012 Apr;13(5):747-55.

[4]. Discovery of Nortadalafil in Health Foods. Chinese Pharmaceutical Journal, 2015, 50(4): 371-374.

[5]. [The Configuration of Tadalafil and Tadalafil Analogues Found in Dietary Supplements]. Shokuhin Eiseigaku Zasshi. 2021;62(2):65-72.

[6]. PDE5 inhibitors: An original access to novel potent arylated analogues of tadalafil. Bioorg Med Chem Lett. 2007 Feb 1;17(3):789-92.

Additional Infomation
This study determined the configuration of the isomers of tadalafil, nortadalafil, and homotadalafil in dietary supplements. The products purchased over the Internet studied included a honey product and a tablet, which contained tadalafil, and a candy, which contained nortadalafil and homotadalafil. Each of the pharmaceutical ingredients isolated from the products was measured with circular dichroism (CD).As a result, the CD spectrum of each isolated pharmaceutical ingredient was found to align with the standard CD spectrum of the 6R,12aR isomer, confirmed that each isolated tadalafil or tadalafil analogue included in a 6R,12aR isomer. According to a report, among the stereoisomers of tadalafil, the 6R,12aR isomers have the most potent inhibitory activities of phosphodiesterase-type-5. From the report, the potential strength of the inhibitory activity of the 6R,12aR isomers of nortadalafil and homotadalafil was suggested. Therefore, it seemed that the 6R,12aR isomer often used in the product.[5]
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C21H17N3O4
Molecular Weight
375.3774
Exact Mass
375.121
Elemental Analysis
C, 67.19; H, 4.56; N, 11.19; O, 17.05
CAS #
171596-36-4
Related CAS #
Tadalafil;171596-29-5;cis-Tadalafil;171596-27-3;ent-Tadalafil;629652-72-8;cis-ent-Tadalafil;171596-28-4;Tadalafil-d3;960226-55-5
PubChem CID
9820973
Appearance
White to off-white solid powder
Density
1.6±0.1 g/cm3
Boiling Point
718.6±60.0 °C at 760 mmHg
Flash Point
388.4±32.9 °C
Vapour Pressure
0.0±2.3 mmHg at 25°C
Index of Refraction
1.772
LogP
0.38
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
4
Rotatable Bond Count
1
Heavy Atom Count
28
Complexity
672
Defined Atom Stereocenter Count
2
SMILES
C1[C@@H]2C(=O)NCC(=O)N2[C@@H](C3=C1C4=CC=CC=C4N3)C5=CC6=C(C=C5)OCO6
InChi Key
XHDLVMPUSXRZOS-FOIQADDNSA-N
InChi Code
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
Chemical Name
(2R,8R)-2-(1,3-benzodioxol-5-yl)-3,6,17-triazatetracyclo[8.7.0.03,8.011,16]heptadeca-1(10),11,13,15-tetraene-4,7-dione
Synonyms
Nortadalafil; 171596-36-4; Demethyltadalafil; N-Desmethyl Tadalafil; Demethyl Tadalafil; (+)-Nortadalafil; 5W59DMB3LD; CHEMBL342008;
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO : ~50 mg/mL (~133.20 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (6.66 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 2.5 mg/mL (6.66 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 2.6640 mL 13.3198 mL 26.6397 mL
5 mM 0.5328 mL 2.6640 mL 5.3279 mL
10 mM 0.2664 mL 1.3320 mL 2.6640 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

Calculator

Molarity Calculator allows you to calculate the mass, volume, and/or concentration required for a solution, as detailed below:

  • Calculate the Mass of a compound required to prepare a solution of known volume and concentration
  • Calculate the Volume of solution required to dissolve a compound of known mass to a desired concentration
  • Calculate the Concentration of a solution resulting from a known mass of compound in a specific volume
An example of molarity calculation using the molarity calculator is shown below:
What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
  • Enter 350.26 in the Molecular Weight (MW) box
  • Enter 10 in the Concentration box and choose the correct unit (mM)
  • Enter 5 in the Volume box and choose the correct unit (mL)
  • Click the “Calculate” button
  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
  • Enter 10 into the Concentration (Start) box and choose the correct unit (mM)
  • Enter 25 into the Concentration (End) box and select the correct unit (mM)
  • Enter 25 into the Volume (End) box and choose the correct unit (mL)
  • Click the “Calculate” button
  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
g/mol

Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
Instructions to calculate molar mass (molecular weight) of a chemical compound:
  • To calculate molar mass of a chemical compound, please enter the chemical/molecular formula and click the “Calculate’ button.
Definitions of molecular mass, molecular weight, molar mass and molar weight:
  • Molecular mass (or molecular weight) is the mass of one molecule of a substance and is expressed in the unified atomic mass units (u). (1 u is equal to 1/12 the mass of one atom of carbon-12)
  • Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.
/

Reconstitution Calculator allows you to calculate the volume of solvent required to reconstitute your vial.

  • Enter the mass of the reagent and the desired reconstitution concentration as well as the correct units
  • Click the “Calculate” button
  • The answer appears in the Volume (to add to vial) box
In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
+
+
+

Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

Contact Us