Tadalafil
- CAS No.
- 171596-29-5
- Chemical Name:
- Tadalafil
- Synonyms
- CIALIS;Tadanafil;Tadalafei;tadanafei;Calais;Taladafil;Tadalafil CRS;Tildenafil;TadaL;Adcirca
- CBNumber:
- CB2236841
- Molecular Formula:
- C22H19N3O4
- Molecular Weight:
- 389.4
- MOL File:
- 171596-29-5.mol
- MSDS File:
- SDS
- Modify Date:
- 2024/8/13 12:20:35
| Melting point | 298-300°C |
|---|---|
| alpha | D20 +71.0° |
| Boiling point | 679.1±55.0 °C(Predicted) |
| Density | 1.51±0.1 g/cm3(Predicted) |
| Flash point | 2℃ |
| storage temp. | Sealed in dry,2-8°C |
| solubility | DMSO: soluble20mg/mL, clear |
| form | powder |
| pka | 16.68±0.40(Predicted) |
| color | white to beige |
| optical activity | [α]/D +68 to +78°, c = 1 in chloroform-d |
| BCS Class | 4 |
| Stability | Unstable in Methanol |
| InChI | InChI=1S/C22H19N3O4/c1-24-10-19(26)25-16(22(24)27)9-14-13-4-2-3-5-15(13)23-20(14)21(25)12-6-7-17-18(8-12)29-11-28-17/h2-8,16,21,23H,9-11H2,1H3/t16-,21-/m1/s1 |
| InChIKey | WOXKDUGGOYFFRN-IIBYNOLFSA-N |
| SMILES | N1C2=C(C=CC=C2)C2C[C@]3([H])C(=O)N(C)CC(=O)N3[C@H](C3=CC=C4OCOC4=C3)C1=2 |
| CAS DataBase Reference | 171596-29-5(CAS DataBase Reference) |
SAFETY
Risk and Safety Statements
| Symbol(GHS) |  GHS07 |
|||||||||
|---|---|---|---|---|---|---|---|---|---|---|
| Signal word | Warning | |||||||||
| Hazard statements | H315-H319-H335 | |||||||||
| Precautionary statements | P302+P352-P305+P351+P338 | |||||||||
| Hazard Codes | F,Xn | |||||||||
| Risk Statements | 11-20/21/22-36 | |||||||||
| Safety Statements | 16-36/37 | |||||||||
| WGK Germany | 3 | |||||||||
| RTECS | UQ4431050 | |||||||||
| HS Code | 2934990002 | |||||||||
| NFPA 704 |
|
Tadalafil price More Price(5)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| Sigma-Aldrich(India) | SML1877 | Tadalafil ≥98% (HPLC) | 171596-29-5 | 10MG | ₹7934.73 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | T-072 | Tadalafil solution 1.0?mg/mL in acetonitrile, ampule of 1?mL, certified reference material, Cerilliant? | 171596-29-5 | 1ML | ₹16837.8 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | SML1877 | Tadalafil ≥98% (HPLC) | 171596-29-5 | 50MG | ₹26748.58 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | PHR1810 | Tadalafil Pharmaceutical Secondary Standard; Certified Reference Material | 171596-29-5 | 500MG | ₹16215.85 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | NMID941 | Tadalafil | 171596-29-5 | 20MG | ₹25536.18 | 2022-06-14 | Buy |
Tadalafil Chemical Properties,Uses,Production
Description
Tadalafil (market name “Cialis” or “Adcirca”) was developed by American pharmaceutical company Lilly. It is a kind of PDE5 inhibitor used for the treatment of erectile dysfunction, benign prostatic hypertrophy and pulmonary arterial hypertension.The effect of Tadalafil is relaxing the blood vessels muscles and increasing the blood flow into the corpus cavernosum. Studies show that Cialis works very quickly, taking effect in around 15-20 minutes, and has a prolonged effect that can last for up to 36 hours. T1/2 is 17.5h.
Chemical Properties
White to Off-White Cyrstalline Solid
Definition
ChEBI: Tadalafil is a pyrazinopyridoindole that is 2,3,6,7,12,12a-hexahydropyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione substituted at position 2 by a methyl group and at position 6 by a 1,3-benzodioxol-5-yl group (the 6R,12aR-diastereomer). A phosphodiesterase V inhibitor inhibitor, currently marketed in pill form for treating erectile dysfunction under the name Cialis; and under the name Adcirca for the treatment of pulmonary arterial hypertension. It has a role as an EC 3.1.4.35 (3',5'-cyclic-GMP phosphodiesterase) inhibitor and a vasodilator agent. It is a pyrazinopyridoindole and a member of benzodioxoles.
General Description
Tadalafil, 171596-29-5, is a potent PDE5 inhibitor.It received FDA approval for the treatment of erectiledysfunction in December 2003. Because of its half-life of17.5 hours, it is marketed as a 36-hour treatment. Tadalafil ispredominantly metabolized by hepatic enzymes, includingCYP3A4. The concomitant use of CYP3A4 inhibitors suchas ritonavir, indinavir, ketoconazole, as well as moderateCYP3A inhibitors such as erythromycin have been shown toresult in significant increases in tadalafil plasma levels.Much like sildenafil, tadalafil is under clinical investigationfor managing PAH.
Mechanism of action
The mechanism of action of tadalafil is through inhibiting the activity of the cGMP specific phosphodiesterase type 5 (PDE5). PDE5 degrades cGMP in the corpus cavernosum located around the penis. Therefore, tadalafi leads to the increased concentration of cGMP which further causes the smooth muscle relaxation and increased blood flow into the corpus cavernosum. Some clinical studies also implied that tadalafil could improve endothelia function in men with increased cardiovascular risk and lower the urinary tract symptoms secondary to benign prostatic hyperplasia.
Pharmacokinetics
Tadalafil is different in structure from both sildenafil and vardenafil. It is rapidly absorbed and peaks in concentration (378 μg/L after a 20-mg dose) after 2 hours, displaying a long half-life of 17.5 hours. It also is metabolized by the liver (CYP3A4). Notably, its pharmacokinetics is not clinically influenced by alcohol or food intake or by factors such as diabetes or impaired hepatic or renal function.
Side effects
The most common drug-related adverse events are headache, back pain, dyspepsia, and myalgia. At 10 and 20 mg doses, Tadalafil does not have a significant effect on blood pressure and heart rate and does not result in increased instances of myocardial infarction. Rare reports of prolonged erections greater than 4 h and priapism have been noted with the use of tadalafil. Priapism, if not treated properly, can result in irreversible damage to the erectile tissue. Patients who have an erection lasting greater than 4 h are advised to seek emergency medical attention.
Metabolism
Tadalafil(171596-29-5) is metabolised in the liver mainly by the cytochrome P450 isoenzyme CYP3A4. The major metabolite, the methylcatechol glucuronide, is inactive. Tadalafil is excreted, mainly as metabolites, in the faeces (61% of the dose), and to a lesser extent the urine (36% of the dose).
References
https://www.drugs.com/tadalafil.html
https://www.drugbank.ca/drugs/DB00820
Roehrborn, C. G., et al. "Tadalafil administered once daily for lower urinary tract symptoms secondary to benign prostatic hyperplasia: a dose finding study." Journal of Urology 180.4(2008):1228.
Rosano, Giuseppe M. C., et al. "Chronic Treatment with Tadalafil Improves Endothelial Function in Men with Increased Cardiovascular Risk." European Urology 47.2(2005):214-222.
Tadalafil Preparation Products And Raw materials
| Supplier | Tel | Country | ProdList | Advantage | Inquiry |
|---|---|---|---|---|---|
| Jigs Chemical ltd | +919099003427 | Gujarat, India | 239 | 58 | Inquiry |
| SGMR PHARMACEUTICALS PVT LTD | +91-9032001889 +91-9032001889 | Telangana, India | 83 | 58 | Inquiry |
| ANWITA APIS | +919000311012 | Hyderabad, India | 198 | 58 | Inquiry |
| ChemBioReas Life Sciences | +91-7989264158 +91-7989264158 | Hyderabad, India | 82 | 58 | Inquiry |
| AARTIA KEM SCIENCE | +91-8291072530 +91-8291072530 | Maharashtra, India | 70 | 58 | Inquiry |
| GLP Pharma Standards | +91 9866074638 | Hyderabad, India | 1644 | 58 | Inquiry |
| Reenold Enterprises | +91-8208173540 +91-8208173540 | Maharashtra, India | 28 | 58 | Inquiry |
| Gonane Pharma | +91-9819380043 +91-9819380043 | NaviMumbai, India | 192 | 58 | Inquiry |
| Shree HariKrishna Pharmaceuticals | +91-9925611910 +91-9925611910 | Gujarat, India | 16 | 58 | Inquiry |
| KARPSCHEM LABORATORIES | +91-7249203006 +91-7249203006 | Maharashtra, India | 786 | 58 | Inquiry |
| Supplier | Advantage |
|---|---|
| Jigs Chemical ltd | 58 |
| SGMR PHARMACEUTICALS PVT LTD | 58 |
| ANWITA APIS | 58 |
| ChemBioReas Life Sciences | 58 |
| AARTIA KEM SCIENCE | 58 |
| GLP Pharma Standards | 58 |
| Reenold Enterprises | 58 |
| Gonane Pharma | 58 |
| Shree HariKrishna Pharmaceuticals | 58 |
| KARPSCHEM LABORATORIES | 58 |
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