Norethisterone enanthate

Last updated
Norethisterone enanthate
Norethindrone enanthate.svg
Norethisterone enanthate molecule ball.png
Clinical data
Trade names Noristerat, others
Other namesNETE; NET-EN; Norethindrone enanthate; SH-393; 17α-Ethynyl-19-nortestosterone 17β-enanthate; 17α-Ethynylestra-4-en-17β-ol-3-one 17β-enanthate
AHFS/Drugs.com International Drug Names
Routes of
administration 		Intramuscular injection
Drug class Progestogen; Progestin; Progestogen ester
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only)
Identifiers
  • [(9S,10R,13S,14S,17R)-17-ethynyl-13-methyl-3-oxo-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-yl] heptanoate
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.021.207 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C27H38O3
Molar mass 410.598 g·mol−1
3D model (JSmol)
  • CCCCCCC(=O)O[C@]1(CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CCC4=CC(=O)CC[C@H]34)C)C#C
  • InChI=1S/C27H38O3/c1-4-6-7-8-9-25(29)30-27(5-2)17-15-24-23-12-10-19-18-20(28)11-13-21(19)22(23)14-16-26(24,27)3/h2,18,21-24H,4,6-17H2,1,3H3/t21-,22+,23+,24-,26-,27-/m0/s1
  • Key:APTGJECXMIKIET-WOSSHHRXSA-N
   (verify)

Norethisterone enanthate (NETE), also known as norethindrone enanthate, is a form of hormonal birth control which is used to prevent pregnancy in women. [1] [2] [3] It is used both as a form of progestogen-only injectable birth control and in combined injectable birth control formulations. It may be used following childbirth, miscarriage, or abortion. [1] The failure rate per year in preventing pregnancy for the progestogen-only formulation is 2 per 100 women. [4] Each dose of this form lasts two months with only up to two doses typically recommended. [5] [1]

Contents

Side effects include breast pain, headaches, depression, irregular menstrual periods, and pain at the site of injection. [5] Use in those with liver disease is not recommended as is use during pregnancy due to risk of birth defects. [1] Use appears to be okay during breastfeeding. [1] It does not protect against sexually transmitted infections. [1] NETE is an ester and prodrug of norethisterone, [6] through which it works. [1] It works as a method of birth control by stopping ovulation. [1]

Norethisterone was patented in 1951 and NETE came into medical use in 1957. [7] [8] It is on the World Health Organization's List of Essential Medicines. [9] It has been approved by itself in more than 60 countries including the United Kingdom and some in Europe, Central America, and Africa, and in combination with estradiol valerate in at least 36 countries mainly in Latin America. [4] [10] [11] [12] It is not available in the United States. [10]

Medical uses

NETE is used on its own as a long-lasting progestogen-only injectable contraceptive in women. [1] [5] It is administered via intramuscular injection once every two months. [1] [5]

Contraindications

Side effects

Side effects of NETE may include breast pain, headaches, depression, irregular menstrual periods, and pain at the site of injection. [5] It can cause birth defects in the fetus if used during pregnancy. [1]

Overdose

Interactions

Pharmacology

Norethisterone, the active form of NETE. Norethisterone.svg
Norethisterone, the active form of NETE.

Pharmacodynamics

NETE is a prodrug of norethisterone in the body. [13] Upon reaching circulation, it is rapidly converted into norethisterone by esterases. Hence, as a prodrug of norethisterone, NETE has essentially the same effects as norethisterone, acting as a potent progestogen with additional weak androgenic and estrogenic activity (the latter via its metabolite ethinylestradiol). [14] NETA has some progestogenic activity of its own, but it is unclear if NETE does similarly. [13]

NETE is of about 38% higher molecular weight than norethisterone due to the presence of its C17β enanthate ester. [2]

Relative affinities (%) of norethisterone, metabolites, and prodrugs
CompoundTypea PR Tooltip Progesterone receptor AR Tooltip Androgen receptor ER Tooltip Estrogen receptor GR Tooltip Glucocorticoid receptor MR Tooltip Mineralocorticoid receptor SHBG Tooltip Sex hormone-binding globulin CBG Tooltip Corticosteroid binding globulin
Norethisterone –67–751500–10–3160
5α-Dihydronorethisterone Metabolite252700 ? ? ?
3α,5α-TetrahydronorethisteroneMetabolite100–10 ? ? ?
3α,5β-TetrahydronorethisteroneMetabolite ?00 ? ? ? ?
3β,5α-TetrahydronorethisteroneMetabolite100–80 ? ? ?
Ethinylestradiol Metabolite15–251–31121–300.180
Norethisterone acetate Prodrug205100 ? ?
Norethisterone enanthateProdrug ? ? ? ? ? ? ?
Noretynodrel Prodrug6020000
Etynodiol Prodrug1011–180 ? ? ?
Etynodiol diacetate Prodrug10000 ? ?
Lynestrenol Prodrug11300 ? ?
Notes: Values are percentages (%). Reference ligands (100%) were promegestone for the PR Tooltip progesterone receptor, metribolone for the AR Tooltip androgen receptor, estradiol for the ER Tooltip estrogen receptor, dexamethasone for the GR Tooltip glucocorticoid receptor, aldosterone for the MR Tooltip mineralocorticoid receptor, dihydrotestosterone for SHBG Tooltip sex hormone-binding globulin, and cortisol for CBG Tooltip Corticosteroid-binding globulin. Footnotes:a = Active or inactive metabolite, prodrug, or neither of norethisterone. Sources: See template.
Parenteral potencies and durations of progestogens [a] [b]
CompoundFormDose for specific uses (mg) [c] DOA [d]
TFD [e] POICD [f] CICD [g]
Algestone acetophenide Oil soln.––75–15014–32 d
Gestonorone caproate Oil soln.25–50––8–13 d
Hydroxyprogest. acetate [h] Aq. susp.350––9–16 d
Hydroxyprogest. caproate Oil soln.250–500 [i] –250–5005–21 d
Medroxyprog. acetate Aq. susp.50–1001502514–50+ d
Megestrol acetate Aq. susp.––25>14 d
Norethisterone enanthateOil soln.100–2002005011–52 d
Progesterone Oil soln.200 [i] ––2–6 d
Aq. soln. ?––1–2 d
Aq. susp.50–200––7–14 d
Notes and sources:
  1. ↑ Sources: [15] [16] [17] [18] [19] [20] [21] [22] [23] [24] [25] [26] [27] [28] [29] [30] [31] [32] [33]
  2. ↑ All given by intramuscular or subcutaneous injection.
  3. ↑ Progesterone production during the luteal phase is ~25 (15–50) mg/day. The OID Tooltip ovulation-inhibiting dose of OHPC is 250 to 500 mg/month.
  4. ↑ Duration of action in days.
  5. ↑ Usually given for 14 days.
  6. ↑ Usually dosed every two to three months.
  7. ↑ Usually dosed once monthly.
  8. ↑ Never marketed or approved by this route.
  9. 1 2 In divided doses (2 × 125 or 250 mg for OHPC, 10 × 20 mg for P4).
Hormone levels following a single intramuscular injection of estradiol valerate/norethisterone enanthate (5 mg/50 mg) (Mesigyna) in healthy young men. Testosterone levels were maximally suppressed by about 94%, to ~30 ng/dL, when measured at day 7 post-injection. Hormone levels in men with a single intramuscular injection of 5 mg estradiol valerate and 50 mg norethisterone enanthate in oil.png
Hormone levels following a single intramuscular injection of estradiol valerate/norethisterone enanthate (5 mg/50 mg) (Mesigyna) in healthy young men. Testosterone levels were maximally suppressed by about 94%, to ~30 ng/dL, when measured at day 7 post-injection.

A single intramuscular injection of estradiol valerate/norethisterone enanthate (5 mg/50 mg) (Mesigyna) has been found to strongly suppress testosterone levels in men. [34] Levels of testosterone decreased from ~503 ng/dL at baseline to ~30 ng/dL at the lowest point (–94%). [34]

Pharmacokinetics

Norethisterone and ethinylestradiol levels over 8 weeks after a single intramuscular injection of 200 mg NETE in premenopausal women. Norethisterone and ethinylestradiol levels after a single intramuscular injection of 200 mg norethisterone enanthate in premenopausal women.png
Norethisterone and ethinylestradiol levels over 8 weeks after a single intramuscular injection of 200 mg NETE in premenopausal women.

A single intramuscular injection of 50 to 200 mg NETE in oil solution has been found to have a duration of action of 11 to 52 days in terms of clinical biological effect in the uterus and on body temperature in women. [36]

Similarly to oral norethisterone and norethisterone acetate, intramuscular NETE has been found to form ethinylestradiol as an active metabolite. [35] With a single intramuscular injection of 200 mg NETE in premenopausal women, the mean maximum concentration of ethinylestradiol was 32% of that of a combined oral contraceptive containing 30 μg ethinylestradiol, the maximum equivalent oral dose of ethinylestradiol observed in the first few days of exposure was 20.3 μg/day, and the mean equivalent oral dose of ethinylestradiol over 8 weeks was 4.41 μg/day. [35] As such, the exposure to ethinylestradiol was described as markedly lower than that of an oral contraceptive containing 30 μg ethinylestradiol. [35] The estimated conversion rate of NETE into ethinylestradiol was 0.1%, which was much lower than that observed for oral norethisterone and norethisterone enanthate (0.2–1.0%), likely due to the lack of the first pass through the liver with parenteral administration. [35] In accordance with the low levels of ethinylestradiol produced, no increase rates of thromboembolism or hepatic adenoma have been observed in post-authorization data of intramuscular NETE, and the medication does not resemble combined oral contraceptives containing ethinylestradiol in its safety profile. [35]

Chemistry

NETE, also known as norethinyltestosterone enanthate, as well as 17α-ethynyl-19-nortestosterone 17β-enanthate or 17α-ethynylestr-4-en-17β-ol-3-one 17β-enanthate, is a progestin, or synthetic progestogen, of the 19-nortestosterone group, and a synthetic estrane steroid. [2] [37] It is the C17β enanthate ester of norethisterone. [2] [37] NETE is a derivative of testosterone with an ethynyl group at the C17α position, the methyl group at the C19 position removed, and an enanthate ester attached at the C17β position. [2] [37] In addition to testosterone, it is a combined derivative of nandrolone (19-nortestosterone) and ethisterone (17α-ethynyltestosterone). [2] [37] Esters related to NETE include norethisterone acetate and levonorgestrel butanoate. [2] [37]

History

NETE was introduced by Schering as Noristerat in 1957. [8] It was the second long-acting progestogen to be used clinically, after hydroxyprogesterone caproate. [38] The medication was the first progestogen-only injectable contraceptive, preceding medroxyprogesterone acetate (Depo-Provera). [8]

Society and culture

Generic names

Norethisterone enantate is the generic name of the drug and its INNM Tooltip International Nonproprietary Name and BANM Tooltip British Approved Name. [2] [37] [39] [40] [41] It is also spelled as norethisterone enanthate and is also known as norethindrone enanthate (the USAN Tooltip United States Adopted Name of norethisterone being norethindrone). [2] [37] [39] [40] [41] NETE is known by its former developmental code name SH-393 as well. [2] [37] [39] [40] [41]

Brand names

NETE has been marketed alone as a progestogen-only injectable contraceptive under the brand names Depocon, Doryxas, NET-EN, Noristat, Noristerat, Norigest, and Nur-Isterate, and in combination with estradiol valerate as a combined injectable contraceptive under the brand names Chinese Injectable No. 3, Efectimes, Ginediol, Mesigyna, Mesilar, Meslart, Mesocept, Mesygest, Nofertyl, Nofertyl Lafrancol, Noregyna, Norestrin, Norifam, Norigynon, Nostidyn, Sexseg, and Solouna. [37] [40] [41] [42]

Formulations and brand names of norethisterone and esters
CompositionDoseBrand namesUse
NET onlyLow (e.g., 0.35 mg)Multiple [a] Progestogen-only oral contraceptive
NET or NETA onlyHigh (e.g., 5 mg, 10 mg)Multiple [b] Gynecological disorders and other uses
NETE onlyInjection (e.g., 200 mg)Multiple [c] Progestogen-only injectable contraceptive
NET or NETA with ethinylestradiol Low (e.g., 0.4 mg, 0.5 mg, 0.75 mg, 1 mg, 1.5 mg)Multiple [d] Combined oral contraceptive
NET with mestranol Low (e.g., 1 mg, 2 mg)Multiple [e] Combined oral contraceptive
NETA with estradiol Low (e.g., 0.1 mg, 0.5 mg)Multiple [f] Combined menopausal hormone therapy
NETE with estradiol valerate Injection (e.g., 50 mg)Multiple [g] Combined injectable contraceptive
Abbreviations: NET = Norethisterone. NETA = Norethisterone acetate. NETE = Norethisterone enanthate.
Sources: [43] [44] [37] [45]
Notes:
  1. ↑ Camila, Errin, Heather, Jencycla, Jolivette, Locilan, Micro-Novum, Micronovum, Micronor, Nor-QD, Nora, Noriday, Ortho Micronor
  2. ↑ Aygestin, Lupaneta Pack (combination pack with leuprorelin), Norcolut, Norlutate, Primolut N, Primolut Nor, SH-420, Utovlan
  3. ↑ Depocon, Doryxas, NET-EN, Noristerat, Norigest, Nur-Isterate
  4. ↑ Aranelle, Balziva, Binovum, Brevicon, Brevinor, Briellyn, Cyclafem, Dasetta, Estrostep, Femcon, Generess, Gildagia, Gildess, Jinteli, Junel, Larin, Leena, Lo Loestrin, Lo Minastrin, Loestrin, Lolo, Lomedia, Microgestin, Minastrin, Modicon, Nelova, Norimin, Norinyl, Nortrel, Ortho, Ortho-Novum, Ovcon, Ovysmen, Philith, Primella, Select, Synphase, Synphasic, Tilia, Tri-Legest, Tri-Norinyl, Trinovum, Vyfemla, Wera, Wymzya, Zenchent, Zeosa
  5. ↑ Norethin, Noriday, Norinyl, Norquen, Ortho-Novum, Sophia
  6. ↑ Activella, Activelle, Alyacen, Cliane, Climagest, Climesse, Cliovelle, CombiPatch, Elleste Duet, Estalis, Estropause, Eviana, Evorel, Kliane, Kliofem, Kliogest, Kliovance, Mesigyna, Mesygest, Mimvey, Necon, Novofem, Nuvelle, Sequidot, Systen, Trisequens
  7. ↑ Chinese Injectable No. 3, Efectimes, Ginediol, Mesigyna, Mesilar, Meslart, Mesocept, Mesygest, Nofertyl, Nofertyl Lafrancol, Noregyna, Norestrin, Norifam, Norigynon, Nostidyn, Sexseg, Solouna

Availability

NETE has been approved for use alone as a progestogen-only injectable contraceptive in more than 60 countries throughout the world including in Europe, Latin America, Asia, and Africa. [4] [10] [11] Specific countries in which NETE as a standalone medication is or has been available include Bangladesh, France, Germany, India, Italy, Malaysia, Mexico, the Philippines, Singapore, South Africa, Thailand, and the United Kingdom. [37] [40] [41] [42]

NETE has been approved for use in combination with estradiol valerate as a combined injectable contraceptive in at least 36 countries, mostly in Latin America but also in Africa. [11] [12] It is or has been available in combination with estradiol valerate in Argentina, the Bahamas, Barbados, Bolivia, Brazil, Chile, Colombia, Costa Rica, the Dominican Republic, Ecuador, Egypt, El Salvador, Ghana, Grenada, Guatemala, Guyana, Haiti, Honduras, Jamaica, Kenya, Mexico, Nicaragua, Panama, Paraguay, Peru, St. Lucia, Turkey, Uruguay, Venezuela, and Zimbabwe. [40] [41] [42] [14]

NETE is not available in any form in the United States. [10]

Research

NETE was studied by Schering for use as a progestogen-only injectable contraceptive at a dose of 25 mg once a month but produced poor cycle control with this regimen and was not marketed. [46]

NETE has been studied for use as a potential male hormonal contraceptive in combination with testosterone in men. [47]

See also

Related Research Articles

<span class="mw-page-title-main">Progestogen (medication)</span> Medication producing effects similar to progesterone

A progestogen, also referred to as a progestagen, gestagen, or gestogen, is a type of medication which produces effects similar to those of the natural female sex hormone progesterone in the body. A progestin is a synthetic progestogen. Progestogens are used most commonly in hormonal birth control and menopausal hormone therapy. They can also be used in the treatment of gynecological conditions, to support fertility and pregnancy, to lower sex hormone levels for various purposes, and for other indications. Progestogens are used alone or in combination with estrogens. They are available in a wide variety of formulations and for use by many different routes of administration. Examples of progestogens include natural or bioidentical progesterone as well as progestins such as medroxyprogesterone acetate and norethisterone.

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

Estradiol valerate (EV), sold for use by mouth under the brand name Progynova and for use by injection under the brand names Delestrogen and Progynon Depot among others, is an estrogen medication. It is used in hormone therapy for menopausal symptoms and low estrogen levels, hormone therapy for transgender people, and in hormonal birth control. It is also used in the treatment of prostate cancer. The medication is taken by mouth or by injection into muscle or fat once every 1 to 4 weeks.

<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">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">Norethisterone</span> Progestin medication

Norethisterone, also known as norethindrone and sold under the brand name Norlutin among others, 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.

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

Gestonorone caproate, also known as gestronol hexanoate or norhydroxyprogesterone caproate and sold under the brand names Depostat and Primostat, is a progestin medication which is used in the treatment of enlarged prostate and cancer of the endometrium. It is given by injection into muscle typically once a week.

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

Dienogest, sold under the brand name Visanne among others, is a progestin medication which is used in birth control pills and in the treatment of endometriosis. It is also used in menopausal hormone therapy and to treat heavy periods. Dienogest is available both alone and in combination with estrogens. It is taken by mouth.

Combined injectable contraceptives (CICs) are a form of hormonal birth control for women. They consist of monthly injections of combined formulations containing an estrogen and a progestin to prevent pregnancy.

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

Algestone acetophenide, also known more commonly as dihydroxyprogesterone acetophenide (DHPA) and sold under the brand names Perlutal and Topasel among others, is a progestin medication which is used in combination with an estrogen as a form of long-lasting injectable birth control. It has also been used alone, but is no longer available as a standalone medication. DHPA is not active by mouth and is given once a month by injection into muscle.

<span class="mw-page-title-main">Medroxyprogesterone acetate</span> Injectable form of birth control

Medroxyprogesterone acetate (MPA), also known as depot medroxyprogesterone acetate (DMPA) in injectable form and sold under the brand name Depo-Provera among others, is a hormonal medication of the progestin type. It is used as a method of birth control and as a part of menopausal hormone therapy. It is also used to treat endometriosis, abnormal uterine bleeding, paraphilia, and certain types of cancer. The medication is available both alone and in combination with an estrogen. It is taken by mouth, used under the tongue, or by injection into a muscle or fat.

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

Estradiol cypionate (EC), sold under the brand name Depo-Estradiol among others, is an estrogen medication which is used in hormone therapy for menopausal symptoms and low estrogen levels in women, in hormone therapy for trans women, and in hormonal birth control for women. It is given by injection into muscle once every 1 to 4 weeks.

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

Estradiol enantate, also spelled estradiol enanthate and sold under the brand names Perlutal and Topasel among others, is an estrogen medication which is used in hormonal birth control for women. It is formulated in combination with dihydroxyprogesterone acetophenide, a progestin, and is used specifically as a combined injectable contraceptive. Estradiol enantate is not available for medical use alone. The medication, in combination with DHPA, is given by injection into muscle once a month.

<span class="mw-page-title-main">Progestogen ester</span> Drug class

A progestogen ester is an ester of a progestogen or progestin. The prototypical progestogen is progesterone, an endogenous sex hormone. Esterification is frequently employed to improve the pharmacokinetics of steroids, including oral bioavailability, lipophilicity, and elimination half-life. In addition, with intramuscular injection, steroid esters are often absorbed more slowly into the body, allowing for less frequent administration. Many steroid esters function as prodrugs.

Combined birth control pills that contain natural estradiol or an estradiol ester include:

<span class="mw-page-title-main">Estradiol benzoate/progesterone</span> Drug combination

Estradiol benzoate/progesterone (EB/P4), sold under the brand names Duogynon and Sistocyclin among others, is a combination medication of estradiol benzoate (EB), an estrogen, and progesterone (P4), a progestogen. It has been formulated both as short-acting oil solutions and long-acting microcrystalline aqueous suspensions and is given by injection into muscle either once or continuously at regular intervals.

<span class="mw-page-title-main">Estradiol valerate/norethisterone enantate</span> Combination drug

Estradiol valerate/norethisterone enantate (EV/NETE), sold under the brand name Mesigyna among others, is a form of combined injectable birth control which is used to prevent pregnancy in women. It contains estradiol valerate (EV), an estrogen, and norethisterone enantate (NETE), a progestin. The medication is given once a month by injection into muscle.

<span class="mw-page-title-main">Estradiol valerate/hydroxyprogesterone caproate</span> Pharmaceutical combination

Estradiol valerate/hydroxyprogesterone caproate (EV/OHPC), sold under the brand names Gravibinon and Injectable No. 1 among others, is a combined estrogen and progestogen medication which is used in the treatment of threatened miscarriage and other indications and as a form of combined injectable birth control to prevent pregnancy. It contains estradiol valerate (EV), an estrogen, and hydroxyprogesterone caproate (OHPC), a progestin. The medication is given by injection into muscle once a day to once a month depending on the indication.

<span class="mw-page-title-main">Estradiol enantate/algestone acetophenide</span> Pharmaceutical combination

Estradiol enantate/algestone acetophenide, also known as estradiol enantate/dihydroxyprogesterone acetophenide (E2-EN/DHPA) and sold under the brand names Perlutal and Topasel among others, is a form of combined injectable birth control which is used to prevent pregnancy. It contains estradiol enantate (E2-EN), an estrogen, and algestone acetophenide, a progestin. The medication is given once a month by injection into muscle.

<span class="mw-page-title-main">Estradiol undecylate/norethisterone enanthate</span> Combination drug

Estradiol undecylate/norethisterone enanthate (EU/NETE) is a combination medication of estradiol undecylate (EU), an estrogen, and norethisterone enanthate (NETE), a progestin, which was developed by Schering for potential use as a combined injectable contraceptive in women but was ultimately never marketed. It contained 5 to 10 mg EU and 50 to 70 mg NETE in oil solution and was intended for use by intramuscular injection at regular intervals. Although never commercialized, EU/NETE was found to be effective and well tolerated.

Estradiol benzoate/estradiol valerate/norethisterone acetate/testosterone enanthate (EB/EV/NETA/TE), sold under the brand name Ablacton, is an injectable combination medication of estradiol benzoate (EB), an estrogen, estradiol valerate (EV), an estrogen, norethisterone acetate (NETA), a progestin, and testosterone enanthate (TE), an androgen/anabolic steroid, which has been used to suppress lactation in women. It contains 5 mg EB, 8 mg EV, 20 mg NETA, and 180 mg TE in oil solution and is provided in the form of ampoules. It is given as a single intramuscular injection following childbirth. The medication was manufactured by Schering and was previously marketed in Italy and Spain, but is no longer available.

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  13. 1 2 Hapgood JP, Koubovec D, Louw A, Africander D (November 2004). "Not all progestins are the same: implications for usage". Trends Pharmacol. Sci. 25 (11): 554–7. doi:10.1016/j.tips.2004.09.005. PMID   15491776.
  14. 1 2 IARC Working Group on the Evaluation of Carcinogenic Risks to Humans; World Health Organization; International Agency for Research on Cancer (2007). Combined Estrogen-progestogen Contraceptives and Combined Estrogen-progestogen Menopausal Therapy. World Health Organization. pp. 417, 432. ISBN   978-92-832-1291-1. Archived from the original on 2017-11-05. Norethisterone and its acetate and enanthate esters are progestogens that have weak estrogenic and androgenic properties.
  15. ↑ Knörr K, Beller FK, Lauritzen C (17 April 2013). Lehrbuch der Gynäkologie. Springer-Verlag. pp. 214–. ISBN   978-3-662-00942-0.
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  18. ↑ Horský J, Presl J (1981). "Hormonal Treatment of Disorders of the Menstrual Cycle". In Horsky J, Presl K (eds.). Ovarian Function and its Disorders: Diagnosis and Therapy. Springer Science & Business Media. pp. 309–332. doi:10.1007/978-94-009-8195-9_11. ISBN   978-94-009-8195-9.
  19. ↑ Ufer J (1969). The Principles and Practice of Hormone Therapy in Gynaecology and Obstetrics. de Gruyter. p. 49. ISBN   9783110006148. 17α-Hydroxyprogesterone caproate is a depot progestogen which is entirely free of side actions. The dose required to induce secretory changes in primed endometrium is about 250 mg. per menstrual cycle.
  20. ↑ Pschyrembel W (1968). Praktische Gynäkologie: für Studierende und Ärzte. Walter de Gruyter. pp. 598, 601. ISBN   978-3-11-150424-7.
  21. ↑ Ferin J (September 1972). "Effects, Duration of Action and Metabolism in Man". In Tausk M (ed.). Pharmacology of the Endocrine System and Related Drugs: Progesterone, Progestational Drugs and Antifertility Agents. Vol. II. Pergamon Press. pp. 13–24. ISBN   978-0080168128. OCLC   278011135.
  22. ↑ Henzl MR, Edwards JA (10 November 1999). "Pharmacology of Progestins: 17α-Hydroxyprogesterone Derivatives and Progestins of the First and Second Generation". In Sitruk-Ware R, Mishell DR (eds.). Progestins and Antiprogestins in Clinical Practice. Taylor & Francis. pp. 101–132. ISBN   978-0-8247-8291-7.
  23. ↑ Brotherton J (1976). Sex Hormone Pharmacology. Academic Press. p. 114. ISBN   978-0-12-137250-7.
  24. ↑ Sang GW (April 1994). "Pharmacodynamic effects of once-a-month combined injectable contraceptives". Contraception. 49 (4): 361–385. doi:10.1016/0010-7824(94)90033-7. PMID   8013220.
  25. ↑ Toppozada MK (April 1994). "Existing once-a-month combined injectable contraceptives". Contraception. 49 (4): 293–301. doi:10.1016/0010-7824(94)90029-9. PMID   8013216.
  26. ↑ Goebelsmann U (1986). "Pharmacokinetics of Contraceptive Steroids in Humans". In Gregoire AT, Blye RP (eds.). Contraceptive Steroids: Pharmacology and Safety. Springer Science & Business Media. pp. 67–111. doi:10.1007/978-1-4613-2241-2_4. ISBN   978-1-4613-2241-2.
  27. ↑ Becker H, Düsterberg B, Klosterhalfen H (1980). "[Bioavailability of cyproterone acetate after oral and intramuscular application in men (author's transl)]" [Bioavailability of Cyproterone Acetate after Oral and Intramuscular Application in Men]. Urologia Internationalis. 35 (6): 381–385. doi:10.1159/000280353. PMID   6452729.
  28. ↑ Moltz L, Haase F, Schwartz U, Hammerstein J (May 1983). "[Treatment of virilized women with intramuscular administration of cyproterone acetate]" [Efficacy of Intra muscularly Applied Cyproterone Acetate in Hyperandrogenism]. Geburtshilfe und Frauenheilkunde. 43 (5): 281–287. doi:10.1055/s-2008-1036893. PMID   6223851.
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  31. ↑ Runnebaum BC, Rabe T, Kiesel L (6 December 2012). Female Contraception: Update and Trends. Springer Science & Business Media. pp. 429–. ISBN   978-3-642-73790-9.
  32. ↑ Artini PG, Genazzani AR, Petraglia F (11 December 2001). Advances in Gynecological Endocrinology. CRC Press. pp. 105–. ISBN   978-1-84214-071-0.
  33. ↑ King TL, Brucker MC, Kriebs JM, Fahey JO (21 October 2013). Varney's Midwifery. Jones & Bartlett Publishers. pp. 495–. ISBN   978-1-284-02542-2.
  34. 1 2 3 4 del Cisne Valle Alvarez D (11 May 2011). Efecto de una Dosis de 50 mg de Enantato de Noretisterona y 5 mg de Valerato de Estradiol en los Niveles de Testosterona Total en Hombres Mexicanos Sanos [Effect of a Dose of 50 mg of Norethisterone Enanthate and 5 mg of Estradiol Valerate on Total Testosterone Levels in Healthy Mexican Men] (MSc). National Polytechnic Institute of Mexico.
  35. 1 2 3 4 5 6 Friedrich C, Berse M, Klein S, Rohde B, Höchel J (March 2018). "In Vivo Formation of Ethinylestradiol After Intramuscular Administration of Norethisterone Enantate". J Clin Pharmacol. 58 (6): 781–789. doi:10.1002/jcph.1079. PMID   29522253. S2CID   3813229.
  36. ↑ Ferin J (September 1972). "Effects, Duration of Action and Metabolism in Man". In Tausk M (ed.). Pharmacology of the Endocrine System and Related Drugs: Progesterone, Progestational Drugs and Antifertility Agents. Vol. II. Pergamon Press. pp. 13–24. ISBN   978-0080168128. OCLC   278011135.
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  41. 1 2 3 4 5 6 Sweetman SC, ed. (2009). "Sex hormones and their modulators". Martindale: The Complete Drug Reference (36th ed.). London: Pharmaceutical Press. p. 2082. ISBN   978-0-85369-840-1.
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  43. ↑ "Norethisterone". Drugs.com.
  44. ↑ "Drugs@FDA: FDA Approved Drug Products". United States Food and Drug Administration. Archived from the original on 16 November 2016. Retrieved 27 November 2016.
  45. ↑ IARC Working Group on the Evaluation of Carcinogenic Risks to Humans; International Agency for Research on Cancer (1 January 1999). Hormonal Contraception and Post-menopausal Hormonal Therapy (PDF). IARC. p. 65. ISBN   978-92-832-1272-0.
  46. ↑ Toppozada M (June 1977). "The clinical use of monthly injectable contraceptive preparations". Obstet Gynecol Surv. 32 (6): 335–47. doi:10.1097/00006254-197706000-00001. PMID   865726.
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