desogestrel

Desogestrel
Systematic (IUPAC) name
	13-ethyl-17-ethynyl- 11-methylidene- 1,2,3,6,7,8,9,10,12,13,14,15, 16,17- tetradecahydrocyclopenta[a] phenanthren-17-ol
Clinical data
AHFS/Drugs.com	Micromedex Detailed Consumer Information
MedlinePlus	a601050
Legal status	?
Pharmacokinetic data
Protein binding	98.3%
Identifiers
CAS number	54024-22-5
ATC code	G03AC09
PubChem	CID 40973
DrugBank	DB00304
ChemSpider	37400
UNII	81K9V7M3A3
KEGG	D02367
ChEBI	CHEBI:4453
ChEMBL	CHEMBL1533
Chemical data
Formula	C22H30O
Mol. mass	310.473 g/mol
	SMILES C#C[C@@]4(O)[C@@]2([C@H]([C@@H]3CC/C1=C/CCC[C@@H]1[C@H]3C(=C)\C2)CC4)CC;
	InChI InChI=1S/C22H30O/c1-4-21-14-15(3)20-17-9-7-6-8-16(17)10-11-18(20)19(21)12-13-22(21,23)5-2/h2,8,17-20,23H,3-4,6-7,9-14H2,1H3/t17-,18-,19-,20+,21-,22-/m0/s1 ; Key:RPLCPCMSCLEKRS-BPIQYHPVSA-N ;
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デソゲストレル

Wikipedia preview

出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2014/01/28 13:27:01」(JST)

wiki en

[Wiki en表示]

Desogestrel is a molecule used in hormonal contraceptives. 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. Desogestrel-containing birth control pills are sometimes referred to as "third generation" oral contraceptives. In contrast, birth control pills that are considered "second generation" (Tri-Levlen, for example) contain an estrogen and a progestin, but the progestin is different, such as levonorgestrel.

Benefits[edit]

Third-generation oral contraceptives 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 synthetic estrogen dosage is lower than second-generation oral contraceptives, reducing the likelihood of weight gain, breast tenderness and migraine.

Controversy[edit]

In February 2007, the consumer advocacy 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.^[1] In 2009, Public Citizen released a list of recommendations that included numerous alternative, second-generation birth control pills that women could take in place of oral contraceptives containing desogestrel. Most of those second-generation medications have been on the market longer and have been shown to be as effective in preventing unwanted pregnancy, but with a lower risk of blood clots.^[2]

Drugs cited specifically in the petition include Apri-28, Cyclessa, Desogen, Kariva, Mircette, Ortho-Cept, Reclipsen, Velivet and some generic pills. ^[1]

References[edit]

^ ^a ^b 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
^ Public Citizen Think Twice About Third-Generation Oral Contraceptives and YASMIN Worst Pills, Best Pills, December, 2009

External links[edit]

Dr Lisa E. More, ClotCare.com: Should 3rd generation be banned? 2007

UpToDate Contents

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1. 避妊用のプロゲスチン単剤ピル（POP） progestin only pills pops for contraception
2. エストロゲン・プロゲスチン避妊剤と関連したリスクおよび副作用 risks and side effects associated with estrogen progestin contraceptives
3. エストロゲン・プロゲスチン避妊剤の使用に関する概要 overview of the use of estrogen progestin contraceptives
4. 避妊している女性におけるホルモン剤内服中の出血のマネージメント management of unscheduled bleeding in women using contraception
5. 避妊用膣内リング contraceptive vaginal ring

English Journal

Efavirenz, in contrast to nevirapine, is associated with unfavorable progesterone and antiretroviral levels when co-administered with combined oral contraceptives.

Landolt NK, Phanuphak N, Ubolyam S, Pinyakorn S, Kriengsinyot R, Ahluwalia J, Thongpaeng P, Gorowara M, Thammajaruk N, Chaithongwongwatthana S, Lange JM, Ananworanich J.Source1The HIV Netherlands Australia Thailand Research Collaboration (HIV-NAT), Bangkok, Thailand 2The Thai Red Cross AIDS Research Centre, Bangkok, Thailand 3SEARCH, Bangkok, Thailand 4Faculty of Medicine, Chulalongkorn University, Bangkok, Thailand 5Department of Global Health, Academic Medical Center, University of Amsterdam, Amsterdam Institute for Global Health and Development (AIGHD), Amsterdam, the Netherlands.
Journal of acquired immune deficiency syndromes (1999).J Acquir Immune Defic Syndr.2012 Nov 26. [Epub ahead of print]
BACKGROUND:: Effective contraception has been widely promoted for HIV-positive women. However, there are limited data on the interactions between combined hormonal contraceptives and non-nucleoside reverse transcriptase inhibitors (NNRTIs). METHODS:: The study assessed the steady-state contraceptive
PMID 23187949

The risk of venous thrombosis in women over 50 years old using oral contraception or postmenopausal hormone therapy.

Roach RE, Lijfering WM, Helmerhorst FM, Cannegieter SC, Rosendaal FR, van Hylckama Vlieg A.SourceDepartment of Clinical Epidemiology, Leiden University Medical Center, Leiden, The Netherlands Einthoven Laboratory for Experimental Vascular Medicine, Leiden, University Medical Center Department of Gynecology and Reproductive Medicine, Leiden University Medical Center Department of Thrombosis and Haemostasis, Leiden, University Medical Center.
Journal of thrombosis and haemostasis : JTH.J Thromb Haemost.2012 Nov 8. doi: 10.1111/jth.12060. [Epub ahead of print]
Background: Oral contraception (OC) and postmenopausal hormone therapy (HT) can be used to alleviate menopausal symptoms. However, the risk of venous thrombosis (VT) associated with OC use in women over 50 years old has never been assessed and the two preparations have not been directly compared.
PMID 23136837

Japanese Journal

臨床研究低用量ピルによるニキビ治療の効果

松本安代,山辺晋吾,浅原彩子 [他]
産科と婦人科 75(5), 640-645, 2008-05-00
NAID 40016019605

In Vivo Effects of Oral Contraceptives on Paraoxonase, Catalase and Carbonic Anhydrase Enzyme Activities on Mouse(Biochemistry)

Kiranoglu Selda,Sinan Selma,Gencer Nahit [他],KOCKAR Feray,ARSLAN Oktay
Biological & pharmaceutical bulletin 30(6), 1048-1051, 2007-06-01
… This study was carried out in order to determine the in vivo effect of three oral contraceptives containing ethinyl estradiol in combination with desogestrel and levonorgestrel on the paraoxonase (PON), catalase (CAT) and carbonic anhydrase (CA) activities in mice, which are model organisms for humans. … For these studies, a group of ten mice (25±2g) was selected for oral administration for 21 d of each drug (0.15 mg desogestrel+0.03 mg ethinylestradiol (A); …
NAID 110006278390