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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
MDL Number:
MFCD07771966
MOL File:
171596-29-5.mol
MSDS File:
SDS
Last updated:2024-03-18 11:47:05

Tadalafil Properties

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)
NCI Dictionary of Cancer Terms Cialis; tadalafil
FDA UNII 742SXX0ICT
NCI Drug Dictionary Cialis
ATC code G04BE08

Pharmacokinetic data

Protein binding 94%
Excreted unchanged in urine 36%
Volume of distribution 63 Litres
Biological half-life 17.5 / Increased

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
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
0
3 0

Tadalafil price More Price(33)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich T-072 Tadalafil solution 1.0?mg/mL in acetonitrile, ampule of 1?mL, certified reference material, Cerilliant? 171596-29-5 1mL $183 2024-03-01 Buy
Sigma-Aldrich PHR1810 Tadalafil Pharmaceutical Secondary Standard; Certified Reference Material 171596-29-5 500mg $179 2024-03-01 Buy
Sigma-Aldrich 1642879 Tadalafil United States Pharmacopeia (USP) Reference Standard 171596-29-5 200mg $590 2024-03-01 Buy
Cayman Chemical 14024 Tadalafil ≥98% 171596-29-5 10mg $44 2024-03-01 Buy
Cayman Chemical 14024 Tadalafil ≥98% 171596-29-5 25mg $61 2024-03-01 Buy
Product number Packaging Price Buy
T-072 1mL $183 Buy
PHR1810 500mg $179 Buy
1642879 200mg $590 Buy
14024 10mg $44 Buy
14024 25mg $61 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

Originator

Lilly/ICOS (US)

Uses

Tadalafil is used for the treatment of erectile dysfunction. A phosphodiesterase 5 inhibitor.

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.

Preparation

Tadalafil is synthesized in three steps starting from D-tryptophan methyl ester, by first condensing with piperonal in a Pictet-Spengler cyclization reaction to form the tetrahydro-β-carboline derivative, which is followed by chloroacetylation of the piperidine ring nitrogen and cyclization with methylamine.

brand name

Cialis (Lilly).

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.

Clinical Use

Tadalafil is one of the two new PDE5 inhibitors launched for the oral treatment of male erectile dysfunction. Tadalafil is a b-carboline derivative and it is structurally distinct from vardenafil (Levitraw) and sildenafil (Viagraw), both of which are PDE5 inhibitors based on a fused pyrimidine core structure.

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.

Synthesis

D-(-)-Tryptophan methyl ester (175) and 1,3- benzodioxole-5-carboxaldehyde (176) were subjected to a modified Pictet-Spengler reaction to form cis- and transtetrahydro- |?-carboline tricyclic compounds. The ciscompound 177 was isolated as a white solid in 42% yield. The basic nitrogen in the piperidine ring of 177 was acylated with chloroacetyl chloride (179) to give compound 180 in 93% yield. Finally, the diketonepiperazine ring was formed by adding 180 to 33% methylamine in ethanol under refluxing conditions and yielded tadalafil (XXII) in 77% as a white solid.

Synthesis_171596-29-5

Drug interactions

Potentially hazardous interactions with other drugs
Alpha-blockers: enhanced hypotensive effect - avoid concomitant use.
Antibacterials: concentration possibly increased by clarithromycin and erythromycin; concentration reduced by rifampicin - avoid.
Antifungals: concentration increased by ketoconazole - avoid; concentration possibly increased by itraconazole.
Antivirals: concentration possibly increased by fosamprenavir and indinavir; increased by ritonavir - avoid; increased risk of ventricular arrhythmias with saquinavir - avoid; avoid high doses of tadalafil with telaprevir.
Cobicistat: concentration of tadalafil possibly increased - reduce dose of tadalafil.
Nicorandil: possibly enhanced hypotensive effect - avoid concomitant use.
Nitrates: enhanced hypotensive effect - avoid concomitant use.
Riociguat: enhanced hypotensive effect - avoid concomitant use.

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).

storage

Store at -20°C

Clinical claims and research

In a study of 348 cases of mild to severe erectile dysfunction, patients were randomly given 20mg of Cialis or a placebo. Results showed that in comparison to the placebo group, patients who took Cialis experienced improved intercourse success in the 24-36 hours following medication, with many patients achieving successful sexual intercourse twice in 36 hours. Side effect rate and severity were also no different from those of the placebo group. Over 5% of patients in the Cialis group experienced headaches and indigestion.

Precautions

Patients currently taking nitrates, experiencing angina pectoris, suffering from heart disease, patients who have unregulated hypertension or hypotension, or patients who have had a stroke in the past 6 months should not take Cialis.

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.

74-89-5
171489-59-1
171596-29-5
Synthesis of Tadalafil from Methylamine and Chloropretadalafil

Tadalafil Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from Tadalafil manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Tadalafil API pictures 2024-03-19 Tadalafil API
171596-29-5
US $280.00 / KG 1KG 99% 6000KG Shandong Luning Pharmaceutical Co., Ltd.
Cialis pictures 2024-03-19 Cialis
171596-29-5
US $280.00 / KG 1KG 99% 6000KG Shandong Luning Pharmaceutical Co., Ltd.
Cialis-API pictures 2024-03-19 Cialis-API
171596-29-5
US $280.00 / KG 1KG 99% 6000KG Shandong Luning Pharmaceutical Co., Ltd.
  • Tadalafil API pictures
  • Tadalafil API
    171596-29-5
  • US $280.00 / KG
  • 99%
  • Shandong Luning Pharmaceutical Co., Ltd.
  • Cialis pictures
  • Cialis
    171596-29-5
  • US $280.00 / KG
  • 99%
  • Shandong Luning Pharmaceutical Co., Ltd.
  • Cialis-API pictures
  • Cialis-API
    171596-29-5
  • US $280.00 / KG
  • 99%
  • Shandong Luning Pharmaceutical Co., Ltd.

Tadalafil Spectrum

ICOS 351 UK 336017 TADALAFIL(CIALIS) Taladafil (cialis) Cialis/taladafil (6r,12ar)-6-(1,3-benzodioxol-5-yl)-2,3,6,7,12,12a-hexahydro-2-methyl-pyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione Cialis ,98% 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)- Africa and Ghana tadalafil powder extract (6R,12aR)-6-(1,3-Benzodioxol-5-yl)-2,3,6,7,12,12a-hexahydro-2-methyl-pyrazino[1',2':1,6]pyridol[3,4-b]indole-1,4-dione 6-Benzo[1,3]dioxol-5-yl-2-Methyl-2,3,6,7,12,12a-hexahydro-pyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione (6R,12aR)-6-(Benzo[d][1,3]dioxol-5-yl)-2-Methyl-2,3,12,12a-tetrahydropyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4(6H,7H)-dione (2R,8R)-2-(2H-1,3-benzodioxol-5-yl)-6-Methyl-3,6,17-triazatetracyclo[8.7.0.0^{3,8}.0^{11,16}]heptadeca-1(10),11(16),12,14-tetraene-4,7-dione Tadalafil Citrate(Cialis) Tadalafil (Cliais) hanyuanjian Cialis(IC351) TADALAFIL 99 % TADALAFIL (CIALIS,USP) CIALIS/TADALAFIL Tadalafil WS Cialis (6R,12aR)-6-(1,3-Benzodioxol-5-yl)-2,3,6,7,12,12a-hexahydro-2-methyl-pyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione Tadalafil solution Tadalafil (200 mg) Yang also base Cialis solution,1000ppm Huanyang Base tadinafei Calais BPC TADALAFIL IC 351 (6R,12AR)-6-(benzo[d][1,3]dioxol-5-yl)-2-methyl-2,3,12,12a-tetrahydropyrazino[1',2':1,6]pyrido GF 196960 Tadalafil (1642879) 90 anti test aphrodisiac raw materials Anti detection of kidney tonifying and Yang strengthening raw materials Tadalafil (Tadanafil) Tadalafil 171596-29-5 TadalafilQ: What is Tadalafil Q: What is the CAS Number of Tadalafil Q: What is the storage condition of Tadalafil Q: What are the applications of Tadalafil Tadalafil (Y0001417) Tadalafil(Cialis, CLS)-1 gram(27) Stanolon Test E Tren Acetate cialisr Tadala?l- EP/USP 99.88% cialis raw powder tadalafil Hot selling high purity Tadanafil Tadalafil powder 99% (2R,8R)-2-(1,3-dioxaindan-5-yl)-6-methyl-3,6,17-tri azatetracyclo[8.7.0.0^{3,8}.0^{11,16}]heptadeca-1( 10),11(16),12,14-tetraene-4,7-dione China Factroy Supply 99% Pure Tadalafil Powder Tadalafil (Calais) Tadalafil USP/EP/BP Cialis white powder He is a darnafil (6R,12aR)-6-(benzo[d][1,3]dioxol-5-yl)-2-methyl-2,3,6,7,12,12a-hexahydropyrazino[1,2:1,6]pyrido[3,4-b]indole-1,4-dione Tadanafil powder for men Calai He reached the non Tadanafil Powder Pharmaceutical Grade 99%Tadalafil