Algestone: Difference between revisions
CSV import Tags: mobile edit mobile web edit |
CSV import Tags: mobile edit mobile web edit |
||
| Line 2: | Line 2: | ||
{{Drugbox | {{Drugbox | ||
| verifiedfields = changed | | verifiedfields = changed | ||
| verifiedrevid = | | verifiedrevid = 477318123 | ||
| IUPAC_name = (8S,9S,10R,13S,14S,17S)-17-acetyl-10,13-dimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-3-one | | IUPAC_name = (8S,9S,10R,13S,14S,17S)-17-acetyl-10,13-dimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-3-one | ||
| image = Algestone.svg | | image = Algestone.svg | ||
| Line 8: | Line 8: | ||
| width = 200 | | width = 200 | ||
| width2 = 200 | | width2 = 200 | ||
| tradename = | |||
| synonyms = 16α,17α-Dihydroxyprogesterone | |||
| CAS_number = 595-77-7 | |||
| ATC_prefix = | |||
| ATC_suffix = | |||
| PubChem = 68943 | |||
| ChemSpiderID = 62156 | |||
| UNII = 0F5N573A2Y | |||
| KEGG = D02899 | |||
| ChEMBL = 2104120 | |||
| C=21 | |||
| H=30 | |||
| O=3 | |||
| smiles = CC(=O)[C@H]1CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C | |||
| StdInChI = 1S/C21H30O3/c1-13(22)20-10-9-18-17-6-4-14-12-15(23)5-7-19(14,2)16(17)8-11-21(18,20)3/h12,16-18,20H,4-11H2,1-3H3/t16-,17-,18-,19-,20-,21-/m0/s1 | |||
| StdInChIKey = YQXJYQKZBIBWJQ-ZCPXKWAGSA-N | |||
}} | }} | ||
'''Algestone''' is a synthetic [[progestin]] | '''Algestone''', also known as 16α,17α-dihydroxyprogesterone, is a synthetic [[progestin]] of the [[17α-hydroxyprogesterone]] group. It is a derivative of [[progesterone]] and is used in [[hormonal contraception]] and [[hormone replacement therapy]]. | ||
==Chemical Structure== | ==Chemical Structure== | ||
[[File:Algestone.svg|Chemical structure of Algestone|thumb|right]] | [[File:Algestone.svg|Chemical structure of Algestone|thumb|right]] | ||
Algestone is characterized by its chemical structure as a 17α-hydroxyprogesterone derivative. The presence of hydroxyl groups at the 16α and 17α positions distinguishes it from other progestins. This modification enhances its progestogenic activity and influences its pharmacokinetic properties. | |||
==Pharmacology== | ==Pharmacology== | ||
Algestone acts primarily | Algestone acts primarily as a progestogen, binding to the [[progesterone receptor]] and exerting effects similar to those of natural progesterone. It is involved in the regulation of the [[menstrual cycle]], maintenance of [[pregnancy]], and development of the [[endometrium]]. | ||
===Mechanism of Action=== | |||
The mechanism of action of algestone involves its interaction with the progesterone receptor, leading to changes in gene expression that result in the suppression of [[ovulation]], thickening of the [[cervical mucus]], and alteration of the endometrial lining, making it less suitable for [[implantation (embryo)|implantation]]. | |||
== | ==Clinical Use== | ||
Algestone is used in various | Algestone is used in various hormonal therapies, including [[contraceptive]] formulations and [[hormone replacement therapy]] for menopausal symptoms. Its use is often combined with [[estrogens]] to enhance efficacy and reduce side effects. | ||
==Side Effects== | ==Side Effects== | ||
Common side effects of algestone include [[nausea]], [[headache]], [[breast tenderness]], and [[mood changes]]. Long-term use may be associated with an increased risk of [[thromboembolism]] and [[breast cancer]]. | |||
==Synthesis== | ==Synthesis== | ||
The synthesis of algestone involves the chemical modification of | The synthesis of algestone involves the chemical modification of progesterone, introducing hydroxyl groups at specific positions to enhance its progestogenic activity. This process requires precise control of reaction conditions to achieve the desired stereochemistry. | ||
==Related Compounds== | ==Related Compounds== | ||
Algestone is related to other synthetic progestins | Algestone is related to other synthetic progestins such as [[medroxyprogesterone acetate]] and [[norethisterone]], which are also used in hormonal therapies. These compounds share a common mechanism of action but differ in their pharmacokinetic profiles and side effect profiles. | ||
== | ==Related Pages== | ||
* [[Progestin]] | * [[Progestin]] | ||
* [[Hormonal contraception]] | * [[Hormonal contraception]] | ||
* [[Hormone replacement therapy]] | * [[Hormone replacement therapy]] | ||
* [[Progesterone]] | |||
* [[ | |||
[[Category:Progestogens]] | [[Category:Progestogens]] | ||
[[Category:Steroids]] | [[Category:Steroids]] | ||
[[Category:Hormonal contraception]] | [[Category:Hormonal contraception]] | ||
Latest revision as of 16:58, 5 March 2025
Synthetic progestin
| Algestone | |
|---|---|
| |
| INN | |
| Drug class | |
| Routes of administration | |
| Pregnancy category | |
| Bioavailability | |
| Metabolism | |
| Elimination half-life | |
| Excretion | |
| Legal status | |
| CAS Number | 595-77-7 |
| PubChem | 68943 |
| DrugBank | |
| ChemSpider | 62156 |
| KEGG | D02899 |
Algestone, also known as 16α,17α-dihydroxyprogesterone, is a synthetic progestin of the 17α-hydroxyprogesterone group. It is a derivative of progesterone and is used in hormonal contraception and hormone replacement therapy.
Chemical Structure[edit]
Algestone is characterized by its chemical structure as a 17α-hydroxyprogesterone derivative. The presence of hydroxyl groups at the 16α and 17α positions distinguishes it from other progestins. This modification enhances its progestogenic activity and influences its pharmacokinetic properties.
Pharmacology[edit]
Algestone acts primarily as a progestogen, binding to the progesterone receptor and exerting effects similar to those of natural progesterone. It is involved in the regulation of the menstrual cycle, maintenance of pregnancy, and development of the endometrium.
Mechanism of Action[edit]
The mechanism of action of algestone involves its interaction with the progesterone receptor, leading to changes in gene expression that result in the suppression of ovulation, thickening of the cervical mucus, and alteration of the endometrial lining, making it less suitable for implantation.
Clinical Use[edit]
Algestone is used in various hormonal therapies, including contraceptive formulations and hormone replacement therapy for menopausal symptoms. Its use is often combined with estrogens to enhance efficacy and reduce side effects.
Side Effects[edit]
Common side effects of algestone include nausea, headache, breast tenderness, and mood changes. Long-term use may be associated with an increased risk of thromboembolism and breast cancer.
Synthesis[edit]
The synthesis of algestone involves the chemical modification of progesterone, introducing hydroxyl groups at specific positions to enhance its progestogenic activity. This process requires precise control of reaction conditions to achieve the desired stereochemistry.
Related Compounds[edit]
Algestone is related to other synthetic progestins such as medroxyprogesterone acetate and norethisterone, which are also used in hormonal therapies. These compounds share a common mechanism of action but differ in their pharmacokinetic profiles and side effect profiles.
