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{{Drugbox|
{{Drugbox
|IUPAC_name = (17''S'')-13-ethyl-17-ethynyl-17-hydroxy-1,2,6,7,8,9,<br>10,11,12,14-decahydrocyclopenta[a]phenanthren-3-one
| Watchedfields = changed
| image=Gestodene.svg
| verifiedrevid = 443834989
| CAS_number=60282-87-3
| IUPAC_name = (8''R'',9''S'',10''R'',13''S'',14''S'',17''R'')-13-Ethyl-17-ethynyl-17-hydroxy-1,2,6,7,8,9,10,11,12,14-decahydrocyclopenta[a]phenanthren-3-one
| ATC_prefix=G03
| image =Gestodene.png
| ATC_suffix=AA10  
| image2 =Gestodeno3D.png
| ATC_supplemental=
 
| PubChem=43249
<!--Clinical data-->
| DrugBank=
| tradename = 
| C = 21 | H = 26 | O = 2  
| Drugs.com = {{drugs.com|international|gestodene}}
| pregnancy_category = X
| legal_status = Rx-only
| routes_of_administration = oral administration
 
<!--Pharmacokinetic data-->
| bioavailability = in vitro 99% using <sup>3</sup>H=R5020 / in vivo similar to progesterone
| elimination_half-life = 16 to 18 hrs.
| excretion = urinary tract mainly
 
<!--Identifiers-->
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 60282-87-3
| ATC_prefix = G03
| ATC_suffix = AA10
| ATC_supplemental = {{ATC|G03|AB06}} (only combinations with [[estrogen]]s)
| PubChem = 3033968
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB06730
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 2298532
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 1664P6E6MI
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D04316
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 1213583
 
<!--Chemical data-->
| C=21 | H=26 | O=2  
| molecular_weight = 310.430 g/mol
| molecular_weight = 310.430 g/mol
| bioavailability= in vitro 99% using <sup>3</sup>H=R5020 / in vivo similar to progesterone
| smiles = O=C4\C=C3/[C@@H]([C@H]2CC[C@]1([C@@H](/C=C\[C@]1(C#C)O)[C@@H]2CC3)CC)CC4
| metabolism =  
| InChI = 1/C21H26O2/c1-3-20-11-9-17-16-8-6-15(22)13-14(16)5-7-18(17)19(20)10-12-21(20,23)4-2/h2,10,12-13,16-19,23H,3,5-9,11H2,1H3/t16-,17+,18+,19-,20-,21-/m0/s1
| elimination_half-life= 16 to 18 hrs.
| InChIKey = SIGSPDASOTUPFS-XUDSTZEEBD
| excretion = urinary tract mainly
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| pregnancy_category =  
| StdInChI = 1S/C21H26O2/c1-3-20-11-9-17-16-8-6-15(22)13-14(16)5-7-18(17)19(20)10-12-21(20,23)4-2/h2,10,12-13,16-19,23H,3,5-9,11H2,1H3/t16-,17+,18+,19-,20-,21-/m0/s1
| legal_status =  
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| routes_of_administration= oral administration
| StdInChIKey = SIGSPDASOTUPFS-XUDSTZEESA-N
}}
}}
__Notoc__
{{SI}}
{{SI}}
'''Editor-in-Chief:''' Norman David Goldstuck  
{{CMG}}
==Overview==
 
'''Gestodene''' is a [[progestogen]] [[hormonal contraceptive]].  Products containing gestodene include:
*'''Melodene-15''', '''Mirelle''', and '''Minesse'''  which contain 15 mcg of [[ethinylestradiol]] and 60 mcg of gestodene;
*'''Meliane''', '''Sunya''', '''Femodette''', and '''Millinette 20/75''' which contain 20 mcg of ethinylestradiol and 75 mcg of gestodene; and
*'''Gynera''', '''Minulet''', '''Femoden''', '''Femodene''', '''Katya''' and '''Millinette 30/75''' which contain 30 mcg of ethinylestradiol and 75 mcg of gestodene.<ref>http://www.bayerscheringpharma.es/ebbsc/cms/es/_galleries/download/s_mujer/prospectos/MelodeneS.pdf</ref>
 
==Benefits==
 
Gestodene is androgenically neutral, meaning that contraceptive pills containing gestodene do not exhibit the androgenic side effects (e.g. acne, hirsutism, weight gain) often associated with second-generation contraceptive pills, such as those containing [[levonorgestrel]].<ref>http://dermnetnz.org/treatments/antiandrogens.html</ref>
 
The synthetic estrogen dosage in third-generation contraceptive pills (including those containing gestodene) is lower than that in second-generation oral contraceptives, reducing the likelihood of weight gain, breast tenderness and migraine.<ref>{{ cite journal | author = Festin | title = Progestogens in combined oral contraceptives for contraception | journal = The WHO Reproductive Health Library | year = 2006 }}</ref>
 
Third-generation oral contraceptives are also suitable for use in patients with diabetes or lipid disorders because they have minimal impact on blood glucose levels and the lipid profile.<ref>{{ cite journal | author = Cerel-Suhl | title = Update on Oral Contraceptive Pills | journal = American Family Physician | volume = 60 | issue = 7 | pages = 2073–2084 | year = 1999 }}</ref>


{{Editor Help}}
==Adverse effects==


'''Gestodene''' is a [[progestogen]] [[hormonal contraceptive]]. Products containing gestoden include Meliane which contains 20 mcg of [[ethinylestradiol]] and 75 mcg of gestodene and is used as a contraceptive. Gynera pills is an example of this.
Women who take oral contraceptives containing gestodene are 5.6 times as likely to develop thromboembolism than women who do not take any contraceptive pill, and 1.6 times as likely to develop thromboembolism compared to women taking oral contraceptives containing [[levonorgestrel]].<ref>{{cite journal | author = Lidegaard et al. | title = Risk of venous thromboembolism from use of oral contraceptives containing different progestogens and oestrogen doses | journal = BMJ | volume = 343 | pages = 1–15 | year = 2011 | doi= 10.1136/bmj.d6423 | pmid=22027398 | pmc=3202015}}</ref>


==See also==
==See also==
{| class="wikitable"  style="margin:auto 1em auto 1em; float:center;"
|-
! [[Tigestol]] || [[Ethynerone]] 
|-
| <center>[[Image:Tigestol.svg|200px|Tigestol]]</center> || <center>[[Image:Ethynerone.svg|200px|Ethynerone]]</center>
|}
*[[Etonogestrel]]
*[[Ethynerone]]<ref>Fried, J.; Bry, T. S.; 1968, {{US Patent|3,374,226}}.</ref>
*[[Tigestol]]<ref>DeWinter, M. S.; Siegman, C. M.; Szpilfogel, C. A.; Chem. Ind. (London) 1959, 905.</ref>


* [[Progestin]]
==Footnotes==
{{Reflist|2}}




{{SIB}}


[[Category:Progestagens]]
[[Category:Alkynes]]
[[Category:Endocrinology]]
[[Category:Drug]]
{{Sex hormones}}
{{WikiDoc Help Menu}}
{{WikiDoc Sources}}

Latest revision as of 17:38, 10 April 2015

Gestodene
Clinical data
AHFS/Drugs.comInternational Drug Names
Pregnancy
category
  • X
Routes of
administration		oral administration
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailabilityin vitro 99% using 3H=R5020 / in vivo similar to progesterone
Elimination half-life16 to 18 hrs.
Excretionurinary tract mainly
Identifiers
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
E number{{#property:P628}}
ECHA InfoCard{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
FormulaC21H26O2
Molar mass310.430 g/mol
3D model (JSmol)
  (verify)

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Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]

Overview

Gestodene is a progestogen hormonal contraceptive. Products containing gestodene include:

  • Melodene-15, Mirelle, and Minesse which contain 15 mcg of ethinylestradiol and 60 mcg of gestodene;
  • Meliane, Sunya, Femodette, and Millinette 20/75 which contain 20 mcg of ethinylestradiol and 75 mcg of gestodene; and
  • Gynera, Minulet, Femoden, Femodene, Katya and Millinette 30/75 which contain 30 mcg of ethinylestradiol and 75 mcg of gestodene.[1]

Benefits

Gestodene is androgenically neutral, meaning that contraceptive pills containing gestodene do not exhibit the androgenic side effects (e.g. acne, hirsutism, weight gain) often associated with second-generation contraceptive pills, such as those containing levonorgestrel.[2]

The synthetic estrogen dosage in third-generation contraceptive pills (including those containing gestodene) is lower than that in second-generation oral contraceptives, reducing the likelihood of weight gain, breast tenderness and migraine.[3]

Third-generation oral contraceptives are also suitable for use in patients with diabetes or lipid disorders because they have minimal impact on blood glucose levels and the lipid profile.[4]

Adverse effects

Women who take oral contraceptives containing gestodene are 5.6 times as likely to develop thromboembolism than women who do not take any contraceptive pill, and 1.6 times as likely to develop thromboembolism compared to women taking oral contraceptives containing levonorgestrel.[5]

See also

Tigestol Ethynerone
Tigestol
Ethynerone

Footnotes

  1. ↑ http://www.bayerscheringpharma.es/ebbsc/cms/es/_galleries/download/s_mujer/prospectos/MelodeneS.pdf
  2. ↑ http://dermnetnz.org/treatments/antiandrogens.html
  3. ↑ Festin (2006). "Progestogens in combined oral contraceptives for contraception". The WHO Reproductive Health Library.
  4. ↑ Cerel-Suhl (1999). "Update on Oral Contraceptive Pills". American Family Physician. 60 (7): 2073–2084.
  5. ↑ Lidegaard; et al. (2011). "Risk of venous thromboembolism from use of oral contraceptives containing different progestogens and oestrogen doses". BMJ. 343: 1–15. doi:10.1136/bmj.d6423. PMC 3202015. PMID 22027398.
  6. ↑ Fried, J.; Bry, T. S.; 1968, Template:US Patent.
  7. ↑ DeWinter, M. S.; Siegman, C. M.; Szpilfogel, C. A.; Chem. Ind. (London) 1959, 905.
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