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Mar . 18, 2024 10:39 Back to list

tadalafil cas 171596-29-5Physical and chemical properties



Overview
Tadalafil (Tadalafil) has a molecular formula of C22H19N3O4 and a molecular weight of 389.4. It has been widely used to treat male erectile dysfunction since 2003, and its trade name is Cialis. In 2008, Eli Lilly and Company sold the commercial development rights of this product for PAH treatment to United Therapeutics. In June 2009, the FDA approved tadalafil for the treatment of patients with pulmonary arterial hypertension (PAH) in the United States, under the trade name Adcirca. Tadalafil was launched in 2003 as a drug to treat ED. It takes effect 30 minutes after administration, but its best effect is 2 hours after the onset of effect. The effect can last for 36 hours, and its effect is not affected by food. The dosage of tadalafil is 10 or 20 mg. The recommended initial dose is 10 mg. The dose adjustment is based on the patient's response and adverse reactions. Preliminary market research shows that after 12 weeks of oral administration of 10 or 20 mg of tadalafil, the effective rates are 67% and 81% respectively. Many studies have shown that tadalafil is effective in treating ED.
Indications
Tadalafil is used to treat erectile dysfunction (ED) and pulmonary hypertension in men.
Mechanism
Erectile dysfunction: Tadalafil and sildenafil both belong to the selective phosphodiesterase type 5 (PDE5), but their structure is different from the latter, and high-fat diet will not interfere with its absorption. Under the action of sexual stimulation, nitric oxide synthase (NOS) in penile nerve endings and vascular endothelial cells catalyzes the synthesis of nitric oxide (NO) from the substrate L-arginine. NO activates guanylyl cyclase, which converts guanosine triphosphate into cyclic guanosine monophosphate (cGMP), thereby activating cyclic guanosine monophosphate-dependent protein kinase, resulting in a decrease in calcium ion concentration in smooth muscle cells, causing the corpus cavernosum to Smooth muscles relax and erection occurs. Phosphodiesterase type 5 (PDE5) degrades cGMP into physiologically inactive products, causing the penis to enter a weak state. Tadalafil inhibits the degradation of PDE5, causing the accumulation of cGMP and relaxing the smooth muscles of the corpus cavernosum, leading to penile erection. Since nitrates are NO donors, their combined use with tadalafil will significantly increase cGMP levels and cause severe hypotension. Therefore, the combined use of the two is contraindicated in clinical practice.
medicine interactions
Tadalafil affects PDES by inhibiting it. GMP degrades, so when used in combination with nitrates, it may cause an extreme drop in blood pressure and increase the risk of syncope. CY3PA4 inducers will reduce the bioavailability of tadalafil, and combined use with rifampicin, cimetidine, erythromycin, clarithromycin, itracanvail, ketoconvail, HVI protease inhibitors, etc. may increase the bioavailability of this product. blood concentration, attention should be paid to adjusting the dose. So far, there are no reports that the human pharmacokinetic parameters of this product are affected by diet and alcohol.
preparation

Using D-tryptophan as raw material, methyl esterification reaction is performed first, and the generated D-tryptophan methyl ester hydrochloride undergoes Pictet-spengler reaction with piperonal in isopropanol to obtain cis-tetrahydrocarboline compound. It was then reacted with chloroacetyl chloride and methylamine in sequence, with a total yield of 56%. After screening, glacial acetic acid was used as a recrystallization solvent for further purification. The specific reaction equation is as follows:

Synthesis of 171596-29-5

Drugs to Treat Male Erectile Dysfunction
Cialis is Tadalafil. It is an oral drug for the treatment of male erectile dysfunction developed by Eli Lilly and Company of the United States. It is a second-generation phosphodiesterase 5 inhibitor. Research reports show that it is comparable to sildenafil. Compared with Cialis, Cialis takes effect very quickly, taking effect in about 15 to 20 minutes, and has long-lasting effects, up to 36 hours. T1/2 is 17.5h. In a study involving 348 men with mild to severe erectile dysfunction, the patients were randomized to take tadalafil 20 mg or a placebo. The results showed that compared with placebo, sexual intercourse was more successful 24 and 36 hours after taking the drug. Sexual intercourse was improved, and most men were able to successfully have sexual intercourse twice within 36 hours. There was no difference in the incidence and severity of adverse drug reactions compared with placebo. More than 5% of men in the Tadalafil group experienced headaches and indigestion.
[Adverse Reactions] There are no serious adverse reactions, including facial flushing and visual abnormalities after taking it. Occasionally, headache and indigestion may occur.
[Precautions] It is contraindicated for patients who are taking nitrate drugs, have angina pectoris, heart disease, uncontrolled high blood pressure or hypotension, and those who have had a stroke in the past 6 months.
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