Sandbox 45673: Difference between revisions

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==Function==

Finasteride is a synthetic 4-azasteroid compound that acts as a 5α-reductase inhibitor <ref name="one"> I.K. Morton; Judith M. Hall (6 December 2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 121, 246. ISBN 978-94-011-4439-1 </ref>. 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)<ref name="one"> I.K. Morton; Judith M. Hall (6 December 2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 121, 246. ISBN 978-94-011-4439-1 </ref>. 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 <ref name="two"> Yamana K, Labrie F, Luu-The V (January 2010). Human type 3 5α-reductase is expressed in peripheral tissues at higher levels than types 1 and 2 and its activity is potently inhibited by finasteride and dutasteride. Hormone Molecular Biology and Clinical Investigation. 2 (3). doi:10.1515/hmbci.2010.035 </ref>. Pattern hair loss, another condition in men, caused by the build up of DHT, can also be treated with Finasteride <ref name="three"> Varothai, S; Bergfeld, WF (Jul 2014). "Androgenetic alopecia: an evidence-based treatment update.". American journal of clinical dermatology. 15 (3): 217–30. doi:10.1007/s40257-014-0077-5. PMID 24848508 </ref~~>. 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 <ref name="one"> I.K. Morton; Judith M. Hall (6 December 2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 121, 246. ISBN 978-94-011-4439-1 </ref>. 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)<ref name="one"> I.K. Morton; Judith M. Hall (6 December 2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 121, 246. ISBN 978-94-011-4439-1 </ref>. 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 <ref name="two"> Yamana K, Labrie F, Luu-The V (January 2010). Human type 3 5α-reductase is expressed in peripheral tissues at higher levels than types 1 and 2 and its activity is potently inhibited by finasteride and dutasteride. Hormone Molecular Biology and Clinical Investigation. 2 (3). doi:10.1515/hmbci.2010.035 </ref>. Pattern hair loss, another condition in men, caused by the build up of DHT, can also be treated with Finasteride <ref name="three"> Varothai, S; Bergfeld, WF (Jul 2014). "Androgenetic alopecia: an evidence-based treatment update.". American journal of clinical dermatology. 15 (3): 217–30. doi:10.1007/s40257-014-0077-5. PMID 24848508 </ref>.

==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. Although gonane has 6 chirality centers, giving it 64 possible steroisomers, the majority of steroids 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 in the rings with different atoms.

To see what Finasteride looks like unbound, click this link: <scene name='74/745970/Finasteride_unbound/1'>FIT</scene>.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, the majority of steroids 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 in the rings with different atoms.

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.

Sandbox 45673: Difference between revisions

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@@ Line 5: / Line 5: @@
 ==Function==
-Finasteride is a synthetic 4-azasteroid compound that acts as a 5α-reductase inhibitor <ref name="one"> I.K. Morton; Judith M. Hall (6 December 2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 121, 246. ISBN 978-94-011-4439-1 </ref>. 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)<ref name="one"> I.K. Morton; Judith M. Hall (6 December 2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 121, 246. ISBN 978-94-011-4439-1 </ref>. 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 <ref name="two"> Yamana K, Labrie F, Luu-The V (January 2010). Human type 3 5α-reductase is expressed in peripheral tissues at higher levels than types 1 and 2 and its activity is potently inhibited by finasteride and dutasteride. Hormone Molecular Biology and Clinical Investigation. 2 (3). doi:10.1515/hmbci.2010.035 </ref>. Pattern hair loss, another condition in men, caused by the build up of DHT, can also be treated with Finasteride <ref name="three">  Varothai, S; Bergfeld, WF (Jul 2014). "Androgenetic alopecia: an evidence-based treatment update.". American journal of clinical dermatology. 15 (3): 217–30. doi:10.1007/s40257-014-0077-5. PMID 24848508 </ref>. 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 <ref name="one"> I.K. Morton; Judith M. Hall (6 December 2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 121, 246. ISBN 978-94-011-4439-1 </ref>. 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)<ref name="one"> I.K. Morton; Judith M. Hall (6 December 2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 121, 246. ISBN 978-94-011-4439-1 </ref>. 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 <ref name="two"> Yamana K, Labrie F, Luu-The V (January 2010). Human type 3 5α-reductase is expressed in peripheral tissues at higher levels than types 1 and 2 and its activity is potently inhibited by finasteride and dutasteride. Hormone Molecular Biology and Clinical Investigation. 2 (3). doi:10.1515/hmbci.2010.035 </ref>. Pattern hair loss, another condition in men, caused by the build up of DHT, can also be treated with Finasteride <ref name="three">  Varothai, S; Bergfeld, WF (Jul 2014). "Androgenetic alopecia: an evidence-based treatment update.". American journal of clinical dermatology. 15 (3): 217–30. doi:10.1007/s40257-014-0077-5. PMID 24848508 </ref>.
 ==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. Although gonane has 6 chirality centers, giving it 64 possible steroisomers, the majority of steroids 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 in the rings with different atoms.
+To see what Finasteride looks like unbound, click this link: <scene name='74/745970/Finasteride_unbound/1'>FIT</scene>.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, the majority of steroids 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 in the rings with different atoms.
 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.