User:Cody J Cubbage: Difference between revisions
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==Structure== | ==Structure== | ||
Finasteride belongs to the subclass of steroids called azasteroids. All steroids contain a core structure called gonane, a structure composed of 3 cyclohexane rings and 1 cyclopentane ring "fused" together. The function and naming of | Finasteride belongs to the subclass of steroids called azasteroids. All steroids contain a core structure called gonane, a structure composed of 3 cyclohexane rings and 1 cyclopentane ring "fused" together. Although gonane has 6 chirality centers, giving it 64 possible steroisomers, most steroids found in organisms contain the 5α-gonane stereoisomer. The function and naming of steroids are determined by what functional groups are attached to the rings of gonane and by the substitution of carbon atoms with in the rings with different atoms. | ||
In the case of Finasteride, two methyl groups have | In the case of Finasteride, two methyl groups have been attached to carbons 10 and 13, placing it in the androstane classification of steroids. A the presence of a double bond | ||
==Mechanism== | ==Mechanism== | ||
Revision as of 09:59, 16 November 2016
FinasterideFinasteride
FunctionFunction
StructureStructure
Finasteride belongs to the subclass of steroids called azasteroids. All steroids contain a core structure called gonane, a structure composed of 3 cyclohexane rings and 1 cyclopentane ring "fused" together. Although gonane has 6 chirality centers, giving it 64 possible steroisomers, most steroids found in organisms contain the 5α-gonane stereoisomer. The function and naming of steroids are determined by what functional groups are attached to the rings of gonane and by the substitution of carbon atoms with in the rings with different atoms.
In the case of Finasteride, two methyl groups have been attached to carbons 10 and 13, placing it in the androstane classification of steroids. A the presence of a double bond
MechanismMechanism
Finasteride is a 5-alpha reductase inhibitor. There are two isoforms of the 5alpha-reductase enzyme, type I and II, and while the drug has a higher affinity for the type II enzyme, it also inhibits the function of the type I. (.....) Typically 5 alpha-redcutase turns testosterone into Dihydrotestosterone(DHT), but the enzyme will accept Finasteride as an alternate substrate; turning it into dihydrofinasteride through an enzyme bound, NADP-dihydrofinasteride adduct. Finasteride is similar in structure to testosterone and 5alpha-reductase has almost the same affinity for both molecules. However, Finasteride , having a high affinity for 5 alpha-reductase, covalently binds to the enzyme as a Michael acceptor, through a functionally irreversible reaction. However, the NADP-dihydrofinasteride complex breaks down with a half life of about 1 month at 37˚C., which is why patients must continue taking the drug.(.....)
=Medical Uses=Medical Uses
Finasteride is used to shrink an enlarged prostate, also known as benign prostatic hyperplasia (BPH), in adult men. This medication works by inhibiting 5a-reductase, which prevents conversion of testosterone to the natural body hormone, dihydrosestosterone (DHT) that causes growth of the prostate. Finasteride is specific for type II isoenzymes, resulting in a decline in serum DHT levels by 65-70% and in prostate DHT levels by up to 80-90% (source).