Sildenafil Citrate

Name: Sildenafil Citrate
CAS: 139755-83-2
ATC Code: G04BE03
PubChem: 5281023
DrugBank: APRD00556
ChemSpider: 56586
Molecular Formula: C22H30N6O4S
Molecular Weight: 474.6g/mol
Bioavailability: 40%
Half Life: 3-4 Hours
Metabolism: Hepatic
Excretion: Fecal (80%) and renal (around 13%)
Major Functions:
Sildenafil citrate, sold as Viagra, Revatio and under various other trade names, is a drug used to treat erectile dysfunction (male impotence) and pulmonary arterial hypertension (PAH). It was developed and is being marketed by the pharmaceutical company Pfizer. It acts by inhibiting cGMP specific phosphodiesterase type 5, an enzyme that regulates blood flow in the penis. Since becoming available in 1998, sildenafil has been the prime treatment for erectile dysfunction; its primary competitors on the market are tadalafil (Cialis) and vardenafil (Levitra).
Dosage
The dose of sildenafil for erectile dysfunction is 25 mg to 150 mg taken not more than once per day between 30 minutes and 4 hours prior to sexual intercourse. It is usually recommended to start with a dosage of 50 mg (or even 25 mg) and then lower or raise the dosage as appropriate

The preparation steps for synthesis of sildenafil citrate are as follows
Methylation of 3-propylpyrazole-5-carboxylic acid ethyl ester with hot dimethyl sulfate.
Hydrolysis with aqueous NaOH to free acid.
Nitration with oleum/fuming nitric acid.
Carboxamide formation with refluxing thionyl chloride/NH4OH.
Reduction of nitro group to amino.
Acylation with 2-ethoxybenzoyl chloride.
Cyclization.
Sulfonation to the chlorosulfonyl derivative.
Condensation with 1-methylpiperazine.

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