Desogestrel
From DrugPedia: A Wikipedia for Drug discovery
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| + | [http://crdd.osdd.net/raghava/hmrbase/test_extract.php?db=arun&table=nphormonet&id=1038&show=SHOW-3D Show 3-D Structure] | ||
| + | {{Drugbox | ||
| + | | IUPAC_name = (8S,9S,10R,13S,14S,17R)-13-ethyl-17-ethynyl-11-methylidene-1,2,3,6,7,8,9,10,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-ol | ||
| + | | CAS_number = 54024-22-5 | ||
| + | | CAS_supplemental = | ||
| + | | ATC_suffix = | ||
| + | | ATC_supplemental = | ||
| + | | PubChem = | ||
| + | | ChemSpiderID = | ||
| + | | DrugBank= APRD00762 | ||
| + | | chemical_formula =C<sub>2</sub><sub>2</sub>H<sub>3</sub><sub>0</sub>O | ||
| + | | molecular_weight = 310.47 | ||
| + | | smiles = CCC12CC(=C)C3C(C1CCC2(C#C)O)CCC4=CCCCC34 | ||
| + | | synonyms = | ||
| + | | density = | ||
| + | | melting_point = | ||
| + | | boiling_point = | ||
| + | | solubility = | ||
| + | | specific_rotation = | ||
| + | | sec_combustion = | ||
| + | | bioavailability = | ||
| + | | protein_bound = 98.3% | ||
| + | | metabolism = | ||
| + | | elimination_half-life = | ||
| + | | excretion = | ||
| + | | pregnancy_category= | ||
| + | | dependency_liability = | ||
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| + | }} | ||
A synthetic progestational hormone used often as the progestogenic component of combined oral contraceptive agents. | A synthetic progestational hormone used often as the progestogenic component of combined oral contraceptive agents. | ||
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| + | '''Desogestrel''' is a molecule used in [[hormonal]] [[contraceptives]]. | ||
==General Properties== | ==General Properties== | ||
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| + | ==Benefits== | ||
| + | Third generation pills have been shown to resolve or to reduce acne and hirsutism. They are suitable for use in patients with diabetes or lipid disorders because they have minimal impact on blood glucose levels and the lipid profile. Their dosage is lower than other oral contraceptives. | ||
| + | |||
| + | ==Controversy== | ||
| + | In February 2007, the consumer adovcacy group [[Public Citizen]] released a petition requesting that the [[Food and Drug Administration|FDA]] ban oral contraceptives containing desogestrel, citing studies going as far back as 1995 that suggest the risk of dangerous [[thrombus|blood clots]] is doubled for women on such pills in comparison to other oral contraceptives. The scare of 1995 caused 9% increase in abortions and significant unwanted pregnancies. Ironically, the benefits of contraception outweigh the risk of VTE, especially considering that pregnancy itself is a much larger cause of fatal blood clots. | ||
| + | |||
| + | Most [[combined oral contraceptive pill]]s (COCPs, or simply OCs) on the market today contain both an estrogen compound ([[ethinyl estradiol]] is common) plus a [[progestin]] (a [[progesterone]]-like compound) such as desogestrel. | ||
| + | |||
| + | As such, desogestrel-containing birth control pills are sometimes referred to as "third generation" oral contraceptives. Drugs cited specifically in the petition include Apri-28, [[Cyclessa]], [[Desogen]], [[Kariva]], [[Mircette]], [[Ortho-Cept]], Reclipsen, [[Velivet]] and some generic pills. Birth control pills that are considered "second generation" ([[Ortho Tri-Cyclen]], for example) contain an [[estrogen]] and a [[progestin]], but the [[progestin]] is different, such as [[levonorgestrel]]. | ||
| + | |||
| + | The dispute is whether third generation OCs are less safe than the second generations OCs, which are considered the current "gold standard" in terms of oral contraceptive safety. | ||
| + | ==See also== | ||
| + | * [[Progestin]] | ||
| + | |||
| + | ==References== | ||
| + | * Public Citizen’s Health Research Group: [http://www.citizen.org/publications/release.cfm?ID=7503 Petition to the U.S. Food and Drug Administration to Ban Third Generation Oral Contraceptives Containing Desogestrel due to Increased Risk of Venous Thrombosis] HRG Publication #1799, 2007 | ||
| + | * Dr Lisa E. More, ClotCare.com: [http://www.clotcare.com/clotcare/oralcontraceptivebloodclots2.aspx Should 3rd generation be banned?] 2007 | ||
==External Links== | ==External Links== | ||
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*[http://www.drugbank.ca/drugs/DB00304]Drugbank | *[http://www.drugbank.ca/drugs/DB00304]Drugbank | ||
| - | [[ | + | [[Category:Hormones]] |
| + | [[Category:Hormonal contraception]] | ||
| + | [[Category:Progestagens]] | ||
Current revision
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| Desogestrel
| |
| Systematic (IUPAC) name | |
| (8S,9S,10R,13S,14S,17R)-13-ethyl-17-ethynyl-11-methylidene-1,2,3,6,7,8,9,10,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-ol | |
| Identifiers | |
| CAS number | |
| ATC code | ? |
| PubChem | ? |
| DrugBank | |
| Chemical data | |
| Formula | C22H30O |
| Mol. mass | 310.47 |
| SMILES | & |
| Pharmacokinetic data | |
| Bioavailability | ? |
| Protein binding | 98.3% |
| Metabolism | ? |
| Half life | ? |
| Excretion | ? |
| Therapeutic considerations | |
| Pregnancy cat. |
? |
| Legal status | |
| Routes | ? |
A synthetic progestational hormone used often as the progestogenic component of combined oral contraceptive agents.
Desogestrel is a molecule used in hormonal contraceptives.
Contents |
[edit] General Properties
*Molecular Weight
310.47
*Molecular Formula
C22H30O
*IUPAC NAME
(8S,9S,10R,13S,14S,17R)-13-ethyl-17-ethynyl-11-methylidene-1,2,3,6,7,8,9,10,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-ol
*Canonical Smiles
CCC12CC(=C)C3C(C1CCC2(C#C)O)CCC4=CCCCC34
*Isomeric Smiles
CC[C@]12CC(=C)[C@H]3[C@H]([C@@H]1CC[C@]2(C#C)O)CCC4=CCCC[C@H]34
[edit] PhysioChemical Properties
*Melting Point
109.5(EXP)
*LogP
5.65(EST)
*Water Solubility
[edit] Benefits
Third generation pills have been shown to resolve or to reduce acne and hirsutism. They are suitable for use in patients with diabetes or lipid disorders because they have minimal impact on blood glucose levels and the lipid profile. Their dosage is lower than other oral contraceptives.
[edit] Controversy
In February 2007, the consumer adovcacy group Public Citizen released a petition requesting that the FDA ban oral contraceptives containing desogestrel, citing studies going as far back as 1995 that suggest the risk of dangerous blood clots is doubled for women on such pills in comparison to other oral contraceptives. The scare of 1995 caused 9% increase in abortions and significant unwanted pregnancies. Ironically, the benefits of contraception outweigh the risk of VTE, especially considering that pregnancy itself is a much larger cause of fatal blood clots.
Most combined oral contraceptive pills (COCPs, or simply OCs) on the market today contain both an estrogen compound (ethinyl estradiol is common) plus a progestin (a progesterone-like compound) such as desogestrel.
As such, desogestrel-containing birth control pills are sometimes referred to as "third generation" oral contraceptives. Drugs cited specifically in the petition include Apri-28, Cyclessa, Desogen, Kariva, Mircette, Ortho-Cept, Reclipsen, Velivet and some generic pills. Birth control pills that are considered "second generation" (Ortho Tri-Cyclen, for example) contain an estrogen and a progestin, but the progestin is different, such as levonorgestrel.
The dispute is whether third generation OCs are less safe than the second generations OCs, which are considered the current "gold standard" in terms of oral contraceptive safety.
[edit] See also
[edit] References
- Public Citizen’s Health Research Group: Petition to the U.S. Food and Drug Administration to Ban Third Generation Oral Contraceptives Containing Desogestrel due to Increased Risk of Venous Thrombosis HRG Publication #1799, 2007
- Dr Lisa E. More, ClotCare.com: Should 3rd generation be banned? 2007
