Ethinylestradiol/norethisterone acetate

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Ethinylestradiol/norethisterone acetate
Combination of
Ethinylestradiol Estrogen
Norethisterone acetate Progestogen
Clinical data
Trade names Estrostep, Loestrin, Microgestin, others [1]
Other namesEE/NETA
AHFS/Drugs.com Professional Drug Facts
License data
Routes of
administration 		By mouth
ATC code
Legal status
Legal status
Identifiers
PubChem CID
KEGG
Chemical and physical data
3D model (JSmol)
  • CC(=O)OC1(CCC2C1(CCC3C2CCC4=CC(=O)CCC34)C)C#C.CC12CCC3C(C1CCC2(C#C)O)CCC4=C3C=CC(=C4)O
  • InChI=1S/C22H28O3.C20H24O2/c1-4-22(25-14(2)23)12-10-20-19-7-5-15-13-16(24)6-8-17(15)18(19)9-11-21(20,22)3;1-3-20(22)11-9-18-17-6-4-13-12-14(21)5-7-15(13)16(17)8-10-19(18,20)2/h1,13,17-20H,5-12H2,2-3H3;1,5,7,12,16-18,21-22H,4,6,8-11H2,2H3/t17-,18+,19+,20-,21-,22-;16-,17-,18+,19+,20+/m01/s1
  • Key:GEONECATAKDDLT-JDSZYESASA-N

Ethinylestradiol/norethisterone acetate (EE/NETA), or ethinylestradiol/norethindrone acetate, is a combination of ethinylestradiol (EE) and norethisterone acetate (NETA) which is used as birth control and menopausal hormone therapy. [1] [2] EE is an estrogen, while norethisterone acetate (NETA) is a progestin. [1] It is taken by mouth. [1] Some preparations of EE/NETA used in birth control additionally contain an iron supplement in the form of ferrous fumarate. [3]

Contents

Norethindrone acetate and ethinyl estradiol have been approved in the US for the prevention of pregnancy as a swallowable tablet since 1968. [4] In 2021, it was the 52nd most commonly prescribed medication in the United States, with more than 12 million prescriptions. [5] [6] It is available as a generic medication. [7]

Medical uses

Ethinylestradiol/norethisterone acetate is indicated for use by females of reproductive potential to prevent pregnancy. [8]

Ethinylestradiol/norethisterone acetate is also indicated in women with an intact uterus for the treatment of moderate to severe vasomotor symptoms associated with the menopause; and for prevention of postmenopausal osteoporosis.ref name="pmid16860174" /> [9] [10]

Society and culture

In July 2024, the US Food and Drug Administration (FDA) approved Femlyv, the first orally disintegrating tablet for the prevention of pregnancy. [4] Norethindrone acetate and ethinyl estradiol have been approved in the US for the prevention of pregnancy as a swallowable tablet since 1968. [4]

Brand names

Brand names include Anovlar, Blisovi, Cumorit, Estrostep, Femhrt, Femlyv, Fyavolv, Gildess, Junel, [11] Larin, Leribane, Loestrin, Lo Loestrin (Lo Lo), Mibelas, Microgestin, Minastrin, Norlestrin, Primodos, Taytulla, and Tri-Legest, among others. [7] [12]

See also

Related Research Articles

<span class="mw-page-title-main">Ethinylestradiol</span> Estrogen medication

Ethinylestradiol (EE) is an estrogen medication which is used widely in birth control pills in combination with progestins. In the past, EE was widely used for various indications such as the treatment of menopausal symptoms, gynecological disorders, and certain hormone-sensitive cancers. It is usually taken by mouth but is also used as a patch and vaginal ring.

<span class="mw-page-title-main">Desogestrel</span> Medication

Desogestrel is a progestin medication which is used in birth control pills. It is also used in the treatment of menopausal symptoms in women. The medication is available and used alone or in combination with an estrogen. It is taken by mouth.

<span class="mw-page-title-main">Drospirenone</span> Medication drug

Drospirenone is a progestin and antiandrogen medication which is used in birth control pills to prevent pregnancy and in menopausal hormone therapy, among other uses. It is available both alone under the brand name Slynd and in combination with an estrogen under the brand name Yasmin among others. The medication is an analog of the drug spironolactone. Drospirenone is taken by mouth.

<span class="mw-page-title-main">Norethisterone acetate</span> Chemical compound

Norethisterone acetate (NETA), also known as norethindrone acetate and sold under the brand name Primolut-Nor among others, is a progestin medication which is used in birth control pills, menopausal hormone therapy, and for the treatment of gynecological disorders. The medication available in low-dose and high-dose formulations and is used alone or in combination with an estrogen. It is ingested orally.

<span class="mw-page-title-main">Norgestimate</span> Chemical compound

Norgestimate, sold under the brand names Ortho Tri-Cyclen and Previfem among others, is a progestin medication which is used in birth control pills for women and in menopausal hormone therapy. The medication is available in combination with an estrogen and is not available alone. It is taken by mouth.

<span class="mw-page-title-main">Norgestrel</span> Progestin medication used for birth control

Norgestrel is a progestin which is used in birth control pills sold under the brand name Ovral in combination with the estrogen ethinylestradiol and Opill by itself. It is also used in menopausal hormone therapy. It is taken by mouth.

<span class="mw-page-title-main">Etynodiol diacetate</span> Chemical compound

Etynodiol diacetate, or ethynodiol diacetate, sold under the brand name Ovulen among others, is a progestin medication which is used in birth control pills. The medication is available only in combination with an estrogen. It is taken by mouth.

<span class="mw-page-title-main">Norethisterone</span> Progestin medication

Norethisterone, also known as norethindrone and sold under many brand names, is a progestin medication used in birth control pills, menopausal hormone therapy, and for the treatment of gynecological disorders. The medication is available in both low-dose and high-dose formulations and both alone and in combination with an estrogen. It is used by mouth or, as norethisterone enanthate, by injection into muscle.

Estradiol/norethisterone acetate (E2/NETA), sold under the brand name Activella among others, is a combination of estradiol (E2) and norethisterone acetate (NETA) which is used in the treatment of vasomotor symptoms, vulvar and vaginal atrophy, and osteoporosis associated with menopause. Activella specifically is marketed by Novo Nordisk and is supplied as film-coated tablets containing 1 mg estradiol and 0.5 mg norethisterone acetate. CombiPatch is a combination of estradiol and NETA provided as a transdermal patch.

Birth control pills come in a variety of formulations. The main division is between combined oral contraceptive pills, containing both estrogens and synthetic progestogens (progestins), and progestogen only pills. Combined oral contraceptive pills also come in varying types, including varying doses of estrogen, and whether the dose of estrogen or progestogen changes from week to week.

Ethinylestradiol/norethisterone (EE/NET), or ethinylestradiol/norethindrone, is a combination birth control pill which contains ethinylestradiol (EE), an estrogen and norethisterone (NET), a progestin. It is used for birth control, symptoms of menstruation, endometriosis, and menopausal symptoms. Other uses include acne. It is taken by mouth. Some preparations of EE/NET additionally contain an iron supplement in the form of ferrous fumarate.

<span class="mw-page-title-main">Drospirenone/ethinylestradiol/levomefolic acid</span> Pharmaceutical combination

Drospirenone/ethinylestradiol/levomefolic acid (EE/DRSP/LMF), sold under the brand name Beyaz among others, is a combination of ethinylestradiol (EE), an estrogen, drospirenone (DRSP), a progestogen, antimineralocorticoid, and antiandrogen, and levomefolic acid (LMF), a form of vitamin B9, which is used as a birth control pill to prevent pregnancy in women. The formulation contains folate as the calcium salt of levomefolic acid to lower the risk of complications such as fetal neural tube defects should the medication fail as a form of birth control. EE/DRSP/LMF was approved for use by the US Food and Drug Administration (FDA) in September 2010.

<span class="mw-page-title-main">Ethinylestradiol/levonorgestrel</span> Pharmaceutical combination

Ethinylestradiol/levonorgestrel (EE/LNG) is a combined birth control pill made up of ethinylestradiol, an estrogen and levonorgestrel a progestin. It is used for birth control, symptoms of menstruation, endometriosis, and as emergency contraception. It is taken by mouth. Some preparations of EE/LNG additionally contain an iron supplement in the form of ferrous bisglycinate or ferrous fumarate.

<span class="mw-page-title-main">Estrogen (medication)</span> Type of medication

An estrogen (E) is a type of medication which is used most commonly in hormonal birth control and menopausal hormone therapy, and as part of feminizing hormone therapy for transgender women. They can also be used in the treatment of hormone-sensitive cancers like breast cancer and prostate cancer and for various other indications. Estrogens are used alone or in combination with progestogens. They are available in a wide variety of formulations and for use by many different routes of administration. Examples of estrogens include bioidentical estradiol, natural conjugated estrogens, synthetic steroidal estrogens like ethinylestradiol, and synthetic nonsteroidal estrogens like diethylstilbestrol. Estrogens are one of three types of sex hormone agonists, the others being androgens/anabolic steroids like testosterone and progestogens like progesterone.

<span class="mw-page-title-main">Ethinylestradiol sulfonate/norethisterone acetate</span> Combination drug

Ethinylestradiol sulfonate/norethisterone acetate (EES/NETA), sold under the brand name Deposiston, is a combination medication of ethinylestradiol sulfonate (EES), an estrogen, and norethisterone acetate (NETA), a progestin, which was used as a combined birth control pill for women. It was formulated as oral tablets and contained 1 mg EES and 5 mg NETA per tablet. The medication had a long-lasting depot effect and was taken only once per week, for a total of four tablets per cycle. It was developed and marketed by Jenapharm and was previously available in Germany. EES/NETA was introduced for medical use in 1978.

<span class="mw-page-title-main">Ethinylestradiol/drospirenone</span> Combination drug

Ethinylestradiol/drospirenone (EE/DRSP), sold under the brand name Yasmin among others, is a combination of ethinylestradiol (EE), an estrogen, and drospirenone (DRSP), a progestin, antimineralocorticoid, and antiandrogen, which is used as a birth control pill to prevent pregnancy in women. It is also indicated for the treatment of moderate acne, premenstrual syndrome (PMS), premenstrual dysphoric disorder (PMDD), and dysmenorrhea (painful menstruation) in women. The medication is taken by mouth and contains 30 μg EE and 3 mg DRSP per tablet (brand names Yasmin, others) or 20 μg EE and 3 mg DRSP per tablet (brand names Yaz, Yasminelle, Nikki, others). A formulation with levomefolic acid (vitamin B9) has also been marketed (brand names Beyaz, Safyral, others), with similar indications. EE/DRSP is marketed widely throughout the world.

<span class="mw-page-title-main">Ethinylestradiol/desogestrel</span> Progestogens and estrogens systemic contraceptives, sequential preparations

Ethinylestradiol/desogestrel (EE/DSG), sold under the brand name Marvelon among others, is a fixed-dose combination of ethinylestradiol (EE), an estrogen, and desogestrel (DSG), a progestin, which is used as a birth control pill to prevent pregnancy in women. It is taken by mouth.

<span class="mw-page-title-main">Relugolix/estradiol/norethisterone acetate</span> Combination medication

Relugolix/estradiol/norethisterone acetate, sold under the brand names Myfembree and Ryeqo, is a fixed-dose combination hormonal medication which is used for the treatment of heavy menstrual bleeding associated with uterine leiomyomas (fibroids) and for moderate to severe pain associated with endometriosis. It contains relugolix, an orally active gonadotropin-releasing hormone antagonist, estradiol, an estrogen, and norethisterone acetate, a progestin. The medication is taken by mouth.

References

  1. 1 2 3 4 "Estrogen-Progestin Combinations Monograph for Professionals". Drugs.com. AHFS. Retrieved 28 December 2018.
  2. ↑ Rowan JP, Simon JA, Speroff L, Ellman H (June 2006). "Effects of low-dose norethindrone acetate plus ethinyl estradiol (0.5 mg/2.5 microg) in women with postmenopausal symptoms: updated analysis of three randomized, controlled trials". Clin Ther. 28 (6): 921–32. doi:10.1016/j.clinthera.2006.06.013. PMID   16860174.
  3. ↑ Willihnganz M, Clayton AD (1 May 2014). Basic Pharmacology for Nurses - E-Book. Elsevier Health Sciences. pp. 648–. ISBN   978-0-323-29309-9.
  4. 1 2 3 "FDA Roundup: July 23, 2024". U.S. Food and Drug Administration (FDA) (Press release). 23 July 2024. Retrieved 25 July 2024.PD-icon.svg This article incorporates text from this source, which is in the public domain .
  5. ↑ "The Top 300 of 2021". ClinCalc. Archived from the original on 15 January 2024. Retrieved 14 January 2024.
  6. ↑ "Ethinyl Estradiol; Norethindrone - Drug Usage Statistics". ClinCalc. Retrieved 14 January 2024.
  7. 1 2 "Competitive Generic Therapy Approvals". U.S. Food and Drug Administration (FDA). 29 June 2023. Archived from the original on 29 June 2023. Retrieved 29 June 2023.
  8. ↑ https://www.accessdata.fda.gov/drugsatfda_docs/label/2024/218718s000lbl.pdf
  9. ↑ "Femhrt- norethindrone acetate/ethinyl estradiol tablet". DailyMed. 14 November 2017. Retrieved 31 December 2019.
  10. ↑ "Drug Approval Package: Femhrt (Norethindrone Acetate & Ethinyl Estradiol) NDA #21065". U.S. Food and Drug Administration (FDA). Retrieved 28 December 2018.
  11. ↑ "Junel 21 Day- norethindrone acetate and ethinyl estradiol tablet; Junel Fe 28 Day- norethindrone acetate and ethinyl estradiol and ferrous fumarate kit". DailyMed. 14 August 2023. Retrieved 27 February 2024.
  12. ↑ "Ethinyl Estradiol and Norethindrone (Professional Patient Advice)". Drugs.com. 13 July 2019. Retrieved 10 April 2020.
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