Sandbox 45673: Difference between revisions
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==Function== | ==Function== | ||
Finasteride is a synthetic 4-azasteroid compound that acts as a 5α-reductase inhibitor. The 5α-reductase enzyme is very important in the metabolism of many of the steroids produced by the body, in particular the conversion of testosterone to dihydrotestosterone (DHT). For this reason, Finasteride is used as a treatment for benign prostate hyperplasia (BPH), which is caused by an overproduction of DHT in the male prostate. Pattern hair loss, another condition in men, caused by the build up of DHT, can also be treated with Finasteride. To see what Finasteride looks like unbound, click this link: <scene name='74/745970/Finasteride_unbound/1'>FIT</scene>. | Finasteride is a synthetic 4-azasteroid compound that acts as a 5α-reductase inhibitor. The 5α-reductase enzyme is very important in the metabolism of many of the steroids produced by the body, in particular the conversion of testosterone to dihydrotestosterone (DHT). For this reason, Finasteride is used as a treatment for benign prostate hyperplasia (BPH), which is caused by an overproduction of DHT in the male prostate. Pattern hair loss, another condition in men, caused by the build up of DHT, can also be treated with Finasteride. To see what Finasteride looks like unbound, click this link: <scene name='74/745970/Finasteride_unbound/1'>FIT</scene>. | ||
==Structure== | ==Structure== | ||
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In the case of Finasteride, two methyl groups have been attached to carbons 10 and 13 of the gonane structure, placing it in the androstane classification of steroids. The gonane ring is further modified by the addition of a double bond at carbon 1 and a ketone to carbon 3. Carbon 4 in Finasteride has been substituted with a nitrogen atom, making Finasteride a 4-azasteroid. Finally, a carboxamide has been added onto the carbon 17. The nitrogen present in the carboxamide has been with a tert-butyl group. | In the case of Finasteride, two methyl groups have been attached to carbons 10 and 13 of the gonane structure, placing it in the androstane classification of steroids. The gonane ring is further modified by the addition of a double bond at carbon 1 and a ketone to carbon 3. Carbon 4 in Finasteride has been substituted with a nitrogen atom, making Finasteride a 4-azasteroid. Finally, a carboxamide has been added onto the carbon 17. The nitrogen present in the carboxamide has been with a tert-butyl group. | ||
==Mechanism== | ==Mechanism== | ||
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. (Schieck,1998.) | 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. (Schieck,1998.) | ||
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.(Bull ''et. al,1995'') | 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.(Bull ''et. al,1995'') | ||
==Medical== | ==Medical== | ||
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1.) Hyperlink to other articles | 1.) Hyperlink to other articles | ||
2.) Go into more depth with each section, especially structure and function | 2.) Go into more depth with each section, especially structure and function | ||
3.) Add synthesis | |||