Tadalafil

Base Information

• Chemical Name: Tadalafil
• CAS No.: 171596-29-5
• Molecular Formula: C22H19N3O4
• Molecular Weight: 389.411
• Hs Code.: 2934990002
• European Community (EC) Number: 687-782-2
• NSC Number: 759172,750236
• UNII: 742SXX0ICT
• DSSTox Substance ID: DTXSID9046786
• Nikkaji Number: J1.662.659G
• Wikipedia: Tadalafil
• Wikidata: Q424156
• NCI Thesaurus Code: C47743
• RXCUI: 358263
• Pharos Ligand ID: SN4U17L6RNNH
• Metabolomics Workbench ID: 43110
• ChEMBL ID: CHEMBL779
• Mol file: 171596-29-5.mol

Synonyms:Cialis;IC 351;IC-351;IC351;Pyrazino(1',2':1,6)pyrido(3,4-b)indole-1,4-dione, 6-(1,3- benzodioxol-5-yl)-2,3,6,7,12,12a-hexahydro-2-methyl-, (6R,12aR)-;tadalafil

Chemical Property of Tadalafil

Chemical Property:

• Appearance/Colour: white to off-white cyrstalline solid
• Vapor Pressure: 5.29E-13mmHg at 25°C
• Melting Point: 298-300 °C
• Refractive Index: 1.705
• Boiling Point: 679.1 °C at 760 mmHg
• PKA: 16.68±0.40(Predicted)
• Flash Point: 364.5 °C
• PSA: 74.87000
• Density: 1.51 g/cm³
• LogP: 2.08710
• Storage Temp.: Hygroscopic, -20?C Freezer, Under Inert Atmosphere
• Solubility.: DMSO: soluble20mg/mL, clear
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 389.13755610
• Heavy Atom Count: 29
• Complexity: 702

Purity/Quality:

99% ^*data from raw suppliers

Tadalafil ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F,Xn
• Hazard Codes: F,Xn
• Statements: 11-20/21/22-36
• Safety Statements: 16-36/37

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: PDE5 Inhibitors
• Canonical SMILES: CN1CC(=O)N2C(C1=O)CC3=C(C2C4=CC5=C(C=C4)OCO5)NC6=CC=CC=C36
• Isomeric SMILES: CN1CC(=O)N2[C@@H](C1=O)CC3=C([C@H]2C4=CC5=C(C=C4)OCO5)NC6=CC=CC=C36
• Recent ClinicalTrials: Endocrine Cardiomyopathy in Cushing Syndrome: Response to Cyclic GMP PDE5 inhibitOrs
• Recent EU Clinical Trials: Effects of single dose tadalafil on urethral and anal closure function and on urinary flow in healthy females: A randomised, controlled, double-blinded, two-period cross-over study
• Recent NIPH Clinical Trials: TADAFL
• Mechanism of Action: Tadalafil is a phosphodiesterase-5 (PDE-5) inhibitor, which works by increasing smooth muscle relaxation through the breakdown of cyclic guanosine monophosphate (cGMP).
• Vasodilator Properties: Tadalafil is widely used as a vasodilator due to its ability to increase smooth muscle relaxation. It has a relatively long plasma half-life of 16 hours in healthy adults, allowing for sustained effects.
• Treatment of Erectile Dysfunction: Tadalafil, along with other PDE5 inhibitors such as avanafil and sildenafil, is used to treat male erectile dysfunction (ED). It is available in tablet form under various brand names and has been recommended by regulatory agencies like the European Medicines Agency (EMA) and the Food and Drug Administration (FDA).
• Effect on Glucose Metabolism and Lipid Homeostasis: Tadalafil does not significantly affect lipid homeostasis or body composition, as demonstrated by studies showing no change in body mass index (BMI) or adipose tissue levels.
• Renal Hemodynamic Effects: Tadalafil treatment significantly modulates renal hemodynamic parameters, indicating its potential effects on kidney function.
• Detection Methods: Due to health and economic concerns, there is a need for a convenient, fast, cheap, and sensitive method for detecting tadalafil. Common detection methods include thin-layer chromatography, high-performance liquid chromatography, liquid chromatography-tandem mass spectrometry, and immunoassay methods, which are highly specific and sensitive for detecting analytes like tadalafil.

Technology Process of Tadalafil

There total 45 articles about Tadalafil which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.3%

C22H19ClN2O5*(x)ClH + methylamine (74-89-5) → (6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione (171596-29-5)

Guidance literature:

In dichloromethane; at 0 - 5 ℃; for 3h; Temperature; Solvent;

Reference yield: 95.4%

methylamine (74-89-5) + methyl (1R,3R)-1-(3,4-methylenedioxyphenyl)-2-chloroacetyl-2,3,4,9-tetrahydro-9H-pyrido[3,4-b]indol-3-carboxylate (171489-59-1) → (6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione (171596-29-5)

Guidance literature:

In water; N,N-dimethyl-formamide; at 20 ℃;

DOI:10.1016/j.tetasy.2007.12.017

Reference yield: 95.0%

(6R,12aR)-6-(3,4-dihydroxyphenyl)-2-methyl-2,3,6,7,12,12a-hexahydropyrazino[1',2'-1,6]-pyrido[3,4-b]indole-1,4-dione (171489-03-5) + 1,1-dibromomethane (74-95-3) → (6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione (171596-29-5)

Guidance literature:

With sodium hydroxide; In N,N-dimethyl-formamide; at 60 ℃; for 6h;

upstream raw materials:

methylamine

methyl (1R,3R)-1-(3,4-methylenedioxyphenyl)-2-chloroacetyl-2,3,4,9-tetrahydro-9H-pyrido[3,4-b]indol-3-carboxylate

1-benzo[1,3]dioxol-5-yl-2-{[(9H-fluoren-9-ylmethoxycarbonyl)-methyl-amino]-acetyl}-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester

(1R,3R)-1-(benzo[d][1,3]dioxol-5-yl)-2-(2-chloroacetyl)-N-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxamide

Downstream raw materials:

(6R,12aS)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione

(1R,3R)-1-(benzo[d][1,3]dioxol-5-yl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxamide

(6R,12aR)-6-(benzo[d][1,3]dioxol-5-yl)-2,7-dimethyl-2,3,6,7,12,12a-hexahydropyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione

C₉H₁₀O₂*C₂₂H₁₉N₃O₄

Refernces

• 1、 -. "Preparation method of tadalafil". . . Retrieved 2022/03/27.
• 2、 -. "TADALAFIL SYNTHESIS METHOD". Page/Page column 11-22. . Retrieved 2020/11/03.