Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Norelgestromin: Difference between pages

{{Short description|Pharmaceutical drug}}

| Verifiedfields = verified

| Watchedfields = verified

| verifiedrevid = 464196488

| IUPAC_name = (8''R'',9''S'',10''R'',13''S'',14''S'',17''R'')-13-ethyl-17-ethynyl-3-hydroxyimino-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[''a'']phenanthren-17-ol

| width = 250px

| image2 = Norelgestromin molecule ball.png

| width2 = 250px

| tradename = Evra, Ortho Evra, Xulane, others

| pregnancy_US =

| licence_EU = yes

| legal_status = Rx

| routes_of_administration = [[Transdermal patch]]

| class = [[Progestogen (medication)|Progestogen]]; [[Progestin]]

| bioavailability =

| protein_bound = 99% (to [[human serum albumin|albumin]] but not to {{abbrlink|SHBG|sex hormone-binding globulin}})<ref name="PrefestLabel" /><ref name="OrthoCyclenLabel">{{cite web | title = ORTHO-CYCLEN and ORTHO TRI-CYCLEN (norgestimate/ethinyl estradiol) tablets, for oral use | url = https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/019653s058,019697s054lbl.pdf | work = Janssen Pharmaceuticals, Inc. | date = August 2017 | publisher = U.S. Food and Drug Administration }}</ref><ref name="pmid16112947" />

| metabolism = [[Liver]] ([[oxime]] to [[ketone]] [[chemical reaction|reaction]], [[hydroxylation]], [[conjugation (biochemistry)|conjugation]])<ref name="OrthoEvraLabel" />

| metabolites = • [[Levonorgestrel]]<ref name="OrthoEvraLabel" />

| elimination_half-life = 17–37 hours<ref name="PrefestLabel">{{cite web | title = PREFEST (estradiol/norgestimate) tablets | url = https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/021040s013lbl.pdf | date = November 2017 | work = Teva Pharmaceuticals | publisher = U.S. Food and Drug Administration }}</ref><ref name="pmid16112947" />

| excretion = [[Urine]] and [[feces]]<ref name="OrthoEvraLabel" />

| CAS_number_Ref = {{cascite|correct|CAS}}

| CAS_number = 53016-31-2

| ATC_supplemental = (only combinations with [[estrogen (medication)|estrogen]]s)

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| KEGG_Ref = {{keggcite|correct|kegg}}

| ChEBI_Ref = {{ebicite|correct|EBI}}

| ChEBI = 135398

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 1200807

| synonyms = Norelgestromine; NGMN; RWJ-10553; Levonorgestrel 3-oxime; 17β-Deacetylnorgestimate; 17α-Ethynyl-18-methyl-19-nortestosterone 3-oxime; 17α-Ethynyl-18-methylestr-4-en-17β-ol-3-one 3-oxime

<!--Chemical data-->

| SMILES = ON=C4\C=C3/[C@@H]([C@H]2CC[C@]1([C@@H](CC[C@]1(C#C)O)[C@@H]2CC3)CC)CC4

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

<!-- Definition and medical uses -->

'''Norelgestromin''', or '''norelgestromine''', sold under the brand names '''Evra''' and '''Ortho Evra''' among others, is a [[progestin]] medication which is used as a method of [[birth control]] for women.<ref name="Drugs.com" /><ref name="Drugs.com-2">{{cite web | work = Drugs.com | url = https://www.drugs.com/cdi/norelgestromin-ethinyl-estradiol-patch.html | title = Norelgestromin/Ethinyl Estradiol Patch }}</ref><ref name="CrosignaniNappi2009">{{cite journal | vauthors = Crosignani PG, Nappi C, Ronsini S, Bruni V, Marelli S, Sonnino D | title = Satisfaction and compliance in hormonal contraception: the result of a multicentre clinical study on women's experience with the ethinylestradiol/norelgestromin contraceptive patch in Italy | journal = BMC Women's Health | volume = 9 | issue = 1 | pages = 18 | date = June 2009 | pmid = 19566925 | pmc = 2714834 | doi = 10.1186/1472-6874-9-18 | doi-access = free }}</ref> The medication is available in combination with an [[estrogen (medication)|estrogen]] and is not available alone.<ref name="Drugs.com" /> It is used as a [[transdermal patch|patch that is applied to the skin]].<ref name="Drugs.com-2" /><ref name="CrosignaniNappi2009" />

<!-- Side effects and mechanism -->

[[Side effect]]s of the combination of an estrogen and norelgestromin include [[menstrual irregularities]], [[headache]]s, [[nausea]], [[abdominal pain]], [[breast tenderness]], [[mood (psychology)|mood]] changes, and others.<ref name="OrthoEvraLabel" /> Norelgestromin is a progestin, or a [[synthetic compound|synthetic]] [[progestogen (medication)|progestogen]], and hence is an [[agonist]] of the [[progesterone receptor]], the [[biological target]] of progestogens like [[progesterone]].<ref name="Doherty2003" /><ref name="OffermannsRosenthal2008" /> It has very weak [[androgen]]ic activity and no other important [[hormonal agent|hormonal]] activity.<ref name="Doherty2003" /><ref name="OffermannsRosenthal2008" />

<!-- History, society, and culture -->

Norelgestromin was introduced for medical use in 2002.<ref name="Macor2012" /> It is sometimes referred to as a "third-generation" progestin.<ref name="Borgelt2010">{{cite book| vauthors = Borgelt LM |title=Women's Health Across the Lifespan: A Pharmacotherapeutic Approach|url=https://books.google.com/books?id=riP3pxq2jWAC&pg=PA294|year=2010|publisher=ASHP|isbn=978-1-58528-194-7|pages=294–}}</ref><ref name="VaamondePlessis2016">{{cite book| vauthors = Vaamonde D, du Plessis SS, Agarwal A |title=Exercise and Human Reproduction: Induced Fertility Disorders and Possible Therapies|url=https://books.google.com/books?id=d86zCwAAQBAJ&pg=PA288|date=7 March 2016|publisher=Springer|isbn=978-1-4939-3402-7|pages=288–}}</ref> Norelgestromin is marketed widely throughout the world.<ref name="Drugs.com" /> It is available as a [[generic drug|generic medication]].<ref name="MPR2014">{{cite web|url=https://www.empr.com/generics-news/first-generic-ortho-evra-patch-launched/article/343041/|title=First Generic Ortho Evra Patch Launched|date=17 April 2014 | work = Medical Professionals Reference (MPR) | publisher = Haymarket Media, Inc. }}</ref>

==Medical uses==

Norelgestromin is used in combination with [[ethinyl estradiol]] in [[contraceptive patch]]es.<ref name="Drugs.com-2" /><ref name="OrthoEvraLabel" /><ref name="CrosignaniNappi2009" /> These patches mediate their contraceptive effects by suppressing [[gonadotropin]] levels as well as by causing changes in the [[cervical mucus]] and [[endometrium]] that diminish the likelihood of [[pregnancy]].<ref name="OrthoEvraLabel" />

===Available forms===

Norelgestromin is available only as a transdermal contraceptive patch in combination with ethinyl estradiol.<ref name="Drugs.com-2" /> The Ortho Evra patch is a 20&nbsp;cm{{Sup|2}}, once-weekly adhesive that contains 6.0&nbsp;mg norelgestromin and 0.6&nbsp;mg ethinyl estradiol and delivers 200&nbsp;μg/day norelgestromin and 35&nbsp;μg/day ethinyl estradiol.<ref name="OrthoEvraLabel" /><ref name="pmid28553144">{{cite journal | vauthors = Galzote RM, Rafie S, Teal R, Mody SK | title = Transdermal delivery of combined hormonal contraception: a review of the current literature | journal = International Journal of Women's Health | volume = 9 | pages = 315–321 | date = 2017 | pmid = 28553144 | pmc = 5440026 | doi = 10.2147/IJWH.S102306 | doi-access = free }}</ref>

==Contraindications==

{{See also|Progestin#Contraindications}}

==Side effects==

{{See also|Progestin#Side effects}}

Norelgestromin has mostly been studied in combination with an estrogen, so the [[side effect]]s of norelgestromin specifically or on its own have not been well-defined.<ref name="OrthoEvraLabel" /> Side effects associated with the combination of ethinylestradiol and norelgestromin as a transdermal patch in premenopausal women, with greater than or equal to 2.5% incidence over 6 to 13 [[menstrual cycle]]s, include [[breast tension|breast symptom]]s (including [[breast discomfort|discomfort]], [[breast engorgement|engorgement]], and/or [[breast pain|pain]]; 22.4%), [[headache]]s (21.0%), [[application site reaction]]s (17.1%), [[nausea]] (16.6%), [[abdominal pain]] (8.1%), [[dysmenorrhea]] (7.8%), [[vaginal bleeding]] and [[menstrual disorder]]s (6.4%), [[mood disorder|mood]], [[affect disorder|affect]], and [[anxiety disorder]]s (6.3%), [[vomiting]] (5.1%), [[diarrhea]] (4.2%), [[vaginal yeast infection]]s (3.9%), [[dizziness]] (3.3%), [[acne]] (2.9%), [[migraine]] (2.7%), [[weight gain]] (2.7%), [[fatigue (medical)|fatigue]] (2.6%), and [[pruritus]] (2.5%).<ref name="OrthoEvraLabel" />

==Overdose==

{{See also|Progestin#Overdose}}

== Interactions ==

{{See also|Progestin#Interactions}}

==Pharmacology==

===Pharmacodynamics===

Norelgestromin is a [[progestogen (medication)|progestogen]].<ref name="pmid16112947" /><ref name="OrthoEvraLabel" /> It is one of the [[active metabolite]]s of [[norgestimate]].<ref name="Doherty2003">{{cite book| vauthors = Doherty AM |title=Annual Reports in Medicinal Chemistry|url=https://books.google.com/books?id=ECfQ6D5JLusC&pg=PA362|year=2003|publisher=Academic Press|isbn=978-0-12-040538-1|pages=362–}}</ref><ref name="OffermannsRosenthal2008">{{cite book| vauthors = Offermanns S, Rosenthal W |title=Encyclopedia of Molecular Pharmacology|url=https://books.google.com/books?id=iwwo5gx8aX8C&pg=PA391|date=14 August 2008|publisher=Springer Science & Business Media|isbn=978-3-540-38916-3|pages=391–}}</ref> Unlike many related progestins, norelgestromin reportedly has negligible [[androgen]]ic activity.<ref name="OffermannsRosenthal2008" /> However, it produces [[levonorgestrel]] as an active metabolite to some extent, which does have some androgenic activity.<ref name="OrthoEvraLabel" /><ref name="pmid16112947">{{cite journal | vauthors = Kuhl H | title = Pharmacology of estrogens and progestogens: influence of different routes of administration | journal = Climacteric | volume = 8 | issue = Suppl 1 | pages = 3–63 | date = August 2005 | pmid = 16112947 | doi = 10.1080/13697130500148875 | s2cid = 24616324 }}</ref> Nonetheless, transdermally-administered norelgestromin does not counteract the increase in [[sex hormone-binding globulin]] levels produced by ethinyl estradiol.<ref name="OrthoEvraLabel" />

{| class="wikitable mw-collapsible mw-collapsed" style="text-align:left; margin-left:auto; margin-right:auto; border:none;"

|+ class="nowrap" | Relative affinities (%) of norelgestromin and metabolites

|-

! Compound || {{abbrlink|PR|Progesterone receptor}} || {{abbrlink|AR|Androgen receptor}} || {{abbrlink|ER|Estrogen receptor}} || {{abbrlink|GR|Glucocorticoid receptor}} || {{abbrlink|MR|Mineralocorticoid receptor}} || {{abbrlink|SHBG|Sex hormone-binding globulin}} || {{abbrlink|CBG|Corticosteroid binding globulin}}

|-

| Norelgestromin || 10 || 0 || ? || ? || ? || 0 || ?

|-

| [[Levonorgestrel]] ({{abbr|3-keto-NGMN|3-ketonorelgestromin}}) || 150–162 || 45 || 0 || 1–8 || 17–75 || 50 || 0

|- class="sortbottom"

| colspan="9" style="width:1px; background:#eaecf0; text-align:center;"| '''Notes:''' Values are percentages (%). Reference [[ligand (biochemistry)|ligand]]s (100%) were [[promegestone|prome- gestone]] for the {{abbrlink|PR|progesterone receptor}}, [[metribolone]] for the {{abbrlink|AR|androgen receptor}}, [[estradiol (medication)|{{abbr|E2|estradiol}}]] for the {{abbrlink|ER|estrogen receptor}}, {{abbrlink|DEXA|dexamethasone}} for the {{abbrlink|GR|glucocorticoid receptor}}, [[aldosterone]] for the {{abbrlink|MR|mineralocorticoid receptor}}, {{abbrlink|DHT|dihydrotestosterone}} for {{abbrlink|SHBG|sex hormone-binding globulin}}, and [[hydrocortisone|cortisol]] for {{abbrlink|CBG|Corticosteroid-binding globulin}}. '''Sources:''' <ref name="pmid2170822">{{cite journal | vauthors = Kuhl H | title = Pharmacokinetics of oestrogens and progestogens | journal = Maturitas | volume = 12 | issue = 3 | pages = 171–197 | date = September 1990 | pmid = 2170822 | doi = 10.1016/0378-5122(90)90003-o }}</ref><ref name="pmid16112947" /><ref name="pmid10599548">{{cite journal | vauthors = Philibert D, Bouchoux F, Degryse M, Lecaque D, Petit F, Gaillard M | title = The pharmacological profile of a novel norpregnance progestin (trimegestone) | journal = Gynecological Endocrinology | volume = 13 | issue = 5 | pages = 316–326 | date = October 1999 | pmid = 10599548 | doi = 10.3109/09513599909167574 }}</ref>

|}

===Pharmacokinetics===

Upon application of a transdermal patch containing norelgestromin and ethinyl estradiol, [[Cmax (pharmacology)|plateau levels]] of both are reached by approximately 48&nbsp;hours, and [[steady state (pharmacokinetics)|steady-state levels]] are reached within 2&nbsp;weeks of application.<ref name="OrthoEvraLabel" /> Absorption following application to the buttock, upper outer arm, abdomen, and upper torso was assessed and, while absorption from the abdomen was slightly lower, it was considered to be therapeutically equivalent for the various areas.<ref name="OrthoEvraLabel" /> Mean levels of norelgestromin at steady-state ranged from 0.305&nbsp;ng/mL to 1.53&nbsp;ng/mL, with an average of about 0.725&nbsp;ng/mL.<ref name="OrthoEvraLabel" /> The [[plasma protein binding]] of norelgestromin is 99%, and it is bound to [[human serum albumin|albumin]] but not to [[sex hormone-binding globulin]].<ref name="PrefestLabel" /><ref name="OrthoCyclenLabel" /><ref name="pmid16112947" />

The [[metabolism]] of norelgestromin takes place in the [[liver]] and is via [[biotransformation|transformation]] into [[levonorgestrel]] (conversion of the C3 [[oxime]] into a [[ketone]]) as well as [[hydroxylation]] and [[conjugation (biochemistry)|conjugation]].<ref name="OrthoEvraLabel">{{cite web | title = ORTHO EVRA (norelgestromin / ethinyl estradiol TRANSDERMAL SYSTEM) | url = https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021180s043lbl.pdf | work = Janssen Pharmaceuticals, Inc. | publisher = U.S. Food and Drug Administration | date = August 2012 }}</ref> However, because norelgestromin is used [[parenteral]]ly, [[first-pass metabolism]] in the liver and [[gastrointestinal tract]] that normally occurs with [[oral administration]] are avoided.<ref name="OrthoEvraLabel" /> The [[biological half-life]] of norelgestromin is 17 to 37&nbsp;hours.<ref name="PrefestLabel" /><ref name="pmid16112947" /> The [[metabolite]]s of norelgestromin, along with those of ethinyl estradiol, are [[elimination (pharmacology)|eliminated]] in the [[urine]] and [[feces]].<ref name="OrthoEvraLabel" />

==Chemistry==

{{See also|List of progestogens}}

Norelgestromin, also known as 17α-ethynyl-18-methyl-19-nortestosterone 3-oxime or as 17α-ethynyl-18-methylestr-4-en-17β-ol-3-one 3-oxime, is a [[synthetic compound|synthetic]] [[estrane]] [[steroid]] and a [[chemical derivative|derivative]] of [[testosterone]].<ref name="Drugs.com" /> It is a [[racemic mixture]] of [[cis–trans isomerism|''E'' and ''Z'' isomer]]s, which have approximately the same activity.<ref name="US7345183">{{cite patent |url=https://www.google.com/patents/US7345183 | country = US | number = 7345183|title = Process for obtaining norelgestromin in different relations of isomers E and Z | inventor = Tombari DG, Vecchioli A | assign1 = Gador SA | gdate = 18 March 2008 | postscript = . }}</ref> Norelgestromin is more specifically a derivative of [[norethisterone]] (17α-ethynyl-19-nortestosterone) and is a member of the [[gonane]] (18-methylestrane) subgroup of the [[19-nortestosterone]] family of progestins.<ref name="BruckerKing2015">{{cite book| vauthors = Brucker MC, King TL |title=Pharmacology for Women's Health|url=https://books.google.com/books?id=AniUCgAAQBAJ&pg=PA368|date=8 September 2015|publisher=Jones & Bartlett Publishers|isbn=978-1-284-05748-5|pages=368–}}</ref><ref name="Shoupe2007">{{cite book| vauthors = Shoupe D |title=The Handbook of Contraception: A Guide for Practical Management|url=https://books.google.com/books?id=sczb0Tk_2IwC&pg=PA16|date=7 November 2007|publisher=Springer Science & Business Media|isbn=978-1-59745-150-5|pages=16–}}</ref> It is the C3 [[oxime]] derivative of [[levonorgestrel]] and the C17β [[acetyl|deacetyl]] derivative of [[norgestimate]] and is also known as levonorgestrel 3-oxime and as 17β-deacetylnorgestimate.<ref name="HumansOrganization2007">{{cite book|author1=IARC Working Group on the Evaluation of Carcinogenic Risks to Humans|author2=World Health Organization|author3=International Agency for Research on Cancer|title=Combined Estrogen-progestogen Contraceptives and Combined Estrogen-progestogen Menopausal Therapy|url=https://books.google.com/books?id=aGDU5xibtNgC&pg=PA150|year=2007|publisher=World Health Organization|isbn=978-92-832-1291-1|pages=150–151}}</ref> A related progestin is [[norethisterone acetate oxime]] (17α-ethynyl-19-nortestosterone 3-oxime 17β-acetate).<ref name="Elks2014-NAO">{{cite book| vauthors = Elks J |title=The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies|url=https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA886|date=14 November 2014|publisher=Springer|isbn=978-1-4757-2085-3|pages=886–}}</ref>

==History==

Norelgestromin was introduced for medical use in 2002.<ref name="Macor2012">{{cite book| vauthors = Macor JE |title=Annual Reports in Medicinal Chemistry|url=https://books.google.com/books?id=xpe9Mk50BGsC&pg=PA620|year=2012|publisher=Academic Press|isbn=978-0-12-396492-2|pages=620–}}</ref>

==Society and culture==

===Generic names===

''Norelgestromin'' is the [[generic term|generic name]] of the drug and its {{abbrlink|INN|International Nonproprietary Name}}, {{abbrlink|USAN|United States Adopted Name}}, and {{abbrlink|BAN|British Approved Name}}.<ref name="Drugs.com">{{cite web|url=https://www.drugs.com/international/norelgestromin.html |title=Norelgestromin - brand name list from |publisher=Drugs.com |date= |access-date=2022-09-17}}</ref> The combined ethinyl estradiol and norelgestromin contraceptive patch is also known by its developmental code name ''RWJ-10553''.<ref name="AdisInsight-Patch">{{cite web|url=http://adisinsight.springer.com/drugs/800013168|title = Ethinylestradiol/Norelgestromin transdermal - Johnson & Johnson | work = AdisInsight | publisher = Springer Nature Switzerland AG }}</ref>

===Brand names===

Norelgestromin is marketed under the brand names Evra, Ortho Evra, Xulane, and others, all in combination with [[ethinylestradiol]].<ref name="Drugs.com" /><ref name="MPR2014" />

===Availability===

Norelgestromin is marketed widely throughout the world, including in the [[United States]], [[Canada]], the [[United Kingdom]], [[Ireland]], elsewhere throughout [[Europe]], [[South Africa]], [[Latin America]], [[Asia]], and elsewhere in the world.<ref name="Drugs.com" /> It is not listed as being marketed in [[Australia]], [[New Zealand]], [[Japan]], [[South Korea]], [[China]], [[India]], or certain other countries.<ref name="Drugs.com" />

==Research==

A [[transdermal]] [[gel]] formulation of norgelstromin and [[ethinyl estradiol]] was under development by Antares Pharma for use as a method of birth control with the code name AP-1081 but development was discontinued.<ref name="AdisInsight-Gel">{{cite web|url=http://adisinsight.springer.com/drugs/800022316|title = Ethinylestradiol/Norelgestromin | work = AdisInsight | publisher = Springer Nature Switzerland AG }}</ref>

== See also ==

* [[Ethinylestradiol/norelgestromin]]

== References ==

{{Reflist}}

== Further reading ==

{{refbegin|30em}}

* {{cite journal | vauthors = Creasy GW, Abrams LS, Fisher AC | title = Transdermal contraception | journal = Seminars in Reproductive Medicine | volume = 19 | issue = 4 | pages = 373–380 | date = December 2001 | pmid = 11727179 | doi = 10.1055/s-2001-18645 | s2cid = 40939944 }}

* {{cite journal | vauthors = Burkman RT | title = The transdermal contraceptive patch: a new approach to hormonal contraception | journal = International Journal of Fertility and Women's Medicine | volume = 47 | issue = 2 | pages = 69–76 | date = 2002 | pmid = 11991433 }}

* {{cite journal | vauthors = Henzl MR, Loomba PK | title = Transdermal delivery of sex steroids for hormone replacement therapy and contraception. A review of principles and practice | journal = The Journal of Reproductive Medicine | volume = 48 | issue = 7 | pages = 525–540 | date = July 2003 | pmid = 12953327 }}

* {{cite journal | vauthors = Goa KL, Warner GT, Easthope SE | title = Transdermal ethinylestradiol/norelgestromin: a review of its use in hormonal contraception | journal = Treatments in Endocrinology | volume = 2 | issue = 3 | pages = 191–206 | date = 2003 | pmid = 15966567 | doi = 10.2165/00024677-200302030-00005 | s2cid = 68166901 }}

* {{cite journal | vauthors = Sigridov I, Dikov I, Ivanov S | title = [Transdermal contraception--a new beginning] | language = bg | journal = Akusherstvo I Ginekologiia | volume = 43 | issue = Suppl 1 | pages = 19–27 | date = 2004 | pmid = 15323313 }}

* {{cite journal | vauthors = Taneepanichskul S | title = Norelgestromin/ethinyl estradiol transdermal system | journal = Journal of the Medical Association of Thailand = Chotmaihet Thangphaet | volume = 88 | issue = Suppl 2 | pages = S82–S84 | date = October 2005 | pmid = 17722322 | citeseerx = 10.1.1.598.3979 }}

* {{cite journal | vauthors = McNamee K | title = The vaginal ring and transdermal patch: new methods of contraception | journal = Sexual Health | volume = 3 | issue = 3 | pages = 135–142 | date = September 2006 | pmid = 17044218 | doi = 10.1071/sh05060 }}

* {{cite journal | vauthors = Graziottin A | title = A review of transdermal hormonal contraception : focus on the ethinylestradiol/norelgestromin contraceptive patch | journal = Treatments in Endocrinology | volume = 5 | issue = 6 | pages = 359–365 | date = 2006 | pmid = 17107221 | doi = 10.2165/00024677-200605060-00004 | s2cid = 21033630 }}

* {{cite journal | vauthors = Swica Y | title = The transdermal patch and the vaginal ring: two novel methods of combined hormonal contraception | journal = Obstetrics and Gynecology Clinics of North America | volume = 34 | issue = 1 | pages = 31–42, viii | date = March 2007 | pmid = 17472863 | doi = 10.1016/j.ogc.2007.01.005 }}

* {{cite journal | vauthors = Nelson AL | title = Transdermal contraception methods: today's patches and new options on the horizon | journal = Expert Opinion on Pharmacotherapy | volume = 16 | issue = 6 | pages = 863–873 | date = April 2015 | pmid = 25800084 | doi = 10.1517/14656566.2015.1022531 | s2cid = 6209967 }}

* {{cite journal | vauthors = Galzote RM, Rafie S, Teal R, Mody SK | title = Transdermal delivery of combined hormonal contraception: a review of the current literature | journal = International Journal of Women's Health | volume = 9 | pages = 315–321 | date = 2017 | pmid = 28553144 | pmc = 5440026 | doi = 10.2147/IJWH.S102306 | doi-access = free }}

{{refend}}

{{Progestogens and antiprogestogens}}

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