Product Name

Finasteride

Name: Finasteride
SKU: 98319-26-7

CAS Number

98319-26-7

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Product Name:

Finasteride

CAS Number:

98319-26-7

Indication:

For the treatment of symptomatic benign prostatic hyperplasia (BPH) in men with an enlarged prostate to: Improve symptoms, reduce the risk of acute urinary retention, reduce the risk of the need for surgery including transurethral resection of the prostate. Also used for the stimulation of regrowth of hair in men with mild to moderate androgenetic alopecia (male pattern alopecia, hereditary alopecia, common male baldness).

Mode of Action:

The mechanism of action of Finasteride is based on its preferential inhibition of Type II 5a-reductase through the formation of a stable complex with the enzyme. Inhibition of Type II 5a-reductase blocks the peripheral conversion of testosterone to DHT, resulting in significant decreases in serum and tissue DHT concentrations, minimal to moderate increase in serum testosterone concentrations, and substantial increases in prostatic testosterone concetrations. As DHT appears to be the principal androgen responsible for stimulation of prostatic growth, a decrease in DHT concentrations will result in a decrease in prostatic volume (approximately 20-30% after 6-24 months of continued therapy). In men with androgenic alopecia, the mechanism of action has not been fully determined, but finasteride has shown to decrease scalp DHT concentration to the levels found in hairy scalp, reduce serum DHT, increase hair regrowth, and slow hair loss.

Pharmacodynamics:

Finasteride is a synthetic 4-azasteroid compound. This drug is a competitive and specific inhibitor of Type II 5a-reductase, an intracellular enzyme that converts the androgen testosterone into 5_-dihydrotestosterone (DHT). Two distinct isozymes are found in mice, rats, monkeys, and humans: Type I and II. Each of these isozymes is differentially expressed in tissues and developmental stages. In humans, Type I 5a-reductase is predominant in the sebaceous glands of most regions of skin, including scalp, and liver. Type I 5a-reductase is responsible for approximately one-third of circulating DHT. The Type II 5a-reductase isozyme is primarily found in prostate, seminal vesicles, epididymides, and hair follicles as well as liver, and is responsible for two-thirds of circulating DHT. Although finasteride is 100-fold more selective for type II 5a-reductase than for the type I isoenzyme, chronic treatment with this drug may have some effect on type I 5a-reductase.

Metabolism:

Drug is extensively metabolized, primarily in the liver via CYP3A4. Two metabolites have been identified with _20% of the activity of finasteride.

IUPAC:

(1S, 2R, 7R, 10S, 11S, 14S, 15S)-N-tert-butyl-2, 15-dimethyl-5-oxo-6-azatetracyclo[8.7.0.0, {2, 7}.0, {11, 15}]heptadec-3-ene-14-carboxamide

ATC:

D11AX10 G04CB01

PubChem:

194453

DrugBank:

DB01216 (APRD00632, DB07774)

Formula:

C₁₅H₁₄FN₃O₃

Molecular Mass:

372.5441

Synonyms:

Finasterida [INN-Spanish] Finasteridum [INN-Latin]

SMILES:

CC(C)(C)NC(=O)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4NC(=O)C=C[C@]4(C)[C@H]3CC[C@]12C

AHFS Code:

84:92.00 92:00.00

InChi:

DBEPLOCGEIEOCV-WSBQPABSSA-N

General Reference:

Suzuki R, Satoh H, Ohtani H, Hori S, Sawada Y: Saturable binding of finasteride to steroid 5alpha-reductase as determinant of nonlinear pharmacokinetics. Drug Metab Pharmacokinet. 2010;25(2):208-13. Pubmed
Smith AB, Carson CC: Finasteride in the treatment of patients with benign prostatic hyperplasia: a review. Ther Clin Risk Manag. 2009 Jun;5(3):535-45. Epub 2009 Jul 12. Pubmed

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Finasteride

98319-26-7

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