Quingestrone

Last updated
Quingestrone
Quingestrone.svg
Clinical data
Trade names Enol-Luteovis
Other namesW-3399; Progesterone 3-cyclopentyl enol ether; PCPE; 3-Cyclopentyloxypregna-3,5-dien-20-one
Routes of
administration 		By mouth
Drug class Progestogen; Progestin; Progestogen ether; Neurosteroid
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Identifiers
  • 1-[(8S,9S,10R,13S,14S,17S)-3-cyclopentyloxy-10,13-dimethyl-2,7,8,9,11,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-17-yl]ethanone
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
Formula C26H38O2
Molar mass 382.588 g·mol−1
3D model (JSmol)
  • CC(=O)C1CCC2C1(CCC3C2CC=C4C3(CCC(=C4)OC5CCCC5)C)C
  • InChI=1S/C26H38O2/c1-17(27)22-10-11-23-21-9-8-18-16-20(28-19-6-4-5-7-19)12-14-25(18,2)24(21)13-15-26(22,23)3/h8,16,19,21-24H,4-7,9-15H2,1-3H3/t21-,22+,23-,24-,25-,26+/m0/s1
  • Key:XAVRSHOUEXATJE-FBQZJRKBSA-N

Quingestrone, also known as progesterone 3-cyclopentyl enol ether (PCPE) and sold under the brand name Enol-Luteovis, is a progestin medication which was previously used in birth control pills in Italy but is now no longer marketed. [1] [2] [3] [4] [5] It is taken by mouth. [6]

Contents

Quingestrone is a progestin, or a synthetic progestogen, and hence is an agonist of the progesterone receptor, the biological target of progestogens like progesterone. [1] [7] [8] It has weak glucocorticoid activity. [9] [10] [11]

Quingestrone was introduced for medical use by 1962. [6] [12] It is no longer available. [13]

Medical uses

Quingestrone was formerly used in combination with ethinylestradiol or mestranol in combined birth control pills in Italy. [2] [3] The medication was studied in the clinical prevention of miscarriage during pregnancy, but insufficient efficacy was observed at the dosage assessed (100 mg/day orally). [14] [15] [16] [17]

Side effects

Pharmacology

Pharmacodynamics

Along with the retroprogesterone derivative dydrogesterone, quingestrone has been described as a "true" progesterone derivative or progestogen due to its close similarity to natural progesterone. [18] [12] Similarly to progesterone, dydrogesterone, and hydroxyprogesterone caproate, quingestrone is a pure progestogen and lacks any androgenic effects. [19] As such, it poses no risk of androgenic side effects or virilizing teratogenic effects on female fetuses. [19] Quingestrone is said to influence the hypothalamic–pituitary–adrenal axis similarly to progesterone and medroxyprogesterone acetate, producing adrenal suppression at sufficiently high doses, and this suggests that it possesses weak glucocorticoid activity similarly to progesterone. [9] [10] [11]

Quingestrone is a very weak progestogen. [8] [11] When administered orally or intraperitoneally in animals, the medication showed 1/80 and 1/20 the potency of subcutaneously injected progesterone, respectively. [8] Similarly, oral doses of quingestrone of 10 to 20 times those of subcutaneous progesterone were insufficient to maintain pregnancy in animals, and oral or intraperitoneal doses of quingestrone 20 to 40 times those of oral or intraperitoneal progesterone were unable to potentiate hexobarbital-induced anesthesia in animals (which progesterone does and is thought to do by inhibiting the hepatic metabolism of barbiturates). [8] With oral administration of equal doses of progesterone and quingestrone in animals, 3 to 4 times less pregnanediol was recovered from urine with quingestrone. [8] The fact that quingestrone is more potent by intraperitoneal than oral administration in animals suggests that it is transformed into a less active metabolite in the intestines. [8]

The effective dosage of quingestrone in the menstrual delay test has been studied. [20]

Quingestrone has no anesthetic effect in animals, in contrast to progesterone. [21] [22]

Pharmacokinetics

Quingestrone has been suggested to act as a prodrug of progesterone via slow hydrolysis in the body. [14] [23] Indeed, it produces similar metabolites (e.g., pregnanediols and allopregnanediols) as progesterone, [14] [24] although with differing ratios, [25] [4] and notably is the only progestin that is known to produce pregnanediol as a metabolite. [6] Subsequent research has cast doubt on the notion that quingestrone is a prodrug of progesterone however, and indicates that it instead is directly metabolized into pregnanediols without intermediate conversion into progesterone. [8] Based on its chemical structure, quingestrone may be transformed into 3α-dihydroprogesterone and/or 3β-dihydroprogesterone and then further metabolized into pregnanolones and pregnanediols. 3β-Dihydroprogesterone has been reported to possess about the same progestogenic potency as progesterone in the Clauberg test, whereas 3α-dihydroprogesterone was not assessed. [26] [27]

Relative to progesterone, quingestrone shows improved pharmacokinetics, including higher potency, [25] oral activity, [28] and a longer terminal half-life and hence duration of action. [23] This is considered to be due to its higher lipophilicity, [23] being stored into and slowly released from fat. [5] [14] Quingestrone also shows slower metabolism and more stable blood levels, with a longer time to peak concentrations and a less intense peak compared to progesterone. [7] The bioavailability of quingestrone is highest when it is given as a sesame seed oil solution (compared to an oil suspension (~2-fold less) or micronization (~7-fold less)). [24]

The C3 enol ethers of progesterone are less suited for use via depot injection relative to progestogen esters like hydroxyprogesterone caproate due to their susceptibility to oxidative metabolism. [29]

The pharmacokinetics of quingestrone have been reviewed. [21]

Chemistry

Quingestrone, also known as progesterone 3-cyclopentyl enol ether (PCPE) or as 3-cyclopentyloxypregna-3,5-dien-20-one, is a synthetic pregnane steroid and a derivative of progesterone. [1] It is specifically the 3-cyclopentyl enol ether of progesterone. [1] Quingestrone is closely related to progesterone 3-acetyl enol ether and pentagestrone acetate (17α-acetoxyprogesterone 3-cyclopentyl enol ether). [1]

Synthesis

Chemical syntheses of quingestrone have been published. [21]

History

Quingestrone appears to have been first synthesized in 1936. [30] It was introduced for medical use in Italy by 1962. [6] [12]

Society and culture

Generic names

Quingestrone is the generic name of the drug and its INN and USAN. [1] It is also known by its developmental code name W-3399. [1]

Brand names

Quingestrone was marketed under the brand name Enol-Luteovis. [1] [13]

Availability

Quingestrone is no longer marketed and hence is no longer available in any country. [13] It was previously available in Italy. [13]

Related Research Articles

Progestogen Steroid hormone that activates the progesterone receptor

Progestogens, also sometimes written progestagens or gestagens, are a class of steroid hormones that bind to and activate the progesterone receptor (PR). Progesterone is the major and most important progestogen in the body. The progestogens are named for their function in maintaining pregnancy, although they are also present at other phases of the estrous and menstrual cycles.

Progestogen (medication) 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.

17α-Hydroxyprogesterone Chemical compound

17α-Hydroxyprogesterone (17α-OHP), also known as 17-OH progesterone (17-OHP), or hydroxyprogesterone (OHP), is an endogenous progestogen steroid hormone related to progesterone. It is also a chemical intermediate in the biosynthesis of many other endogenous steroids, including androgens, estrogens, glucocorticoids, and mineralocorticoids, as well as neurosteroids.

Maternal use of androgens or high doses of certain weakly androgenic synthetic progestogens (progestins) structurally related to testosterone can masculinize (virilize) the external genitalia of a female fetus during susceptible times in pregnancy.

Dydrogesterone

Dydrogesterone, sold under the brand name Duphaston, Zuviston, Dydrofem, Dydroboon, and Femoston, is a progestin medication which is used for a variety of indications, including threatened or recurrent miscarriage during pregnancy, dysfunctional bleeding, infertility due to luteal insufficiency, dysmenorrhea, endometriosis, secondary amenorrhea, irregular cycles, premenstrual syndrome, and as a component of menopausal hormone therapy. It is taken by mouth.

Ethisterone

Ethisterone, also known as ethinyltestosterone, pregneninolone, and anhydrohydroxyprogesterone and formerly sold under the brand names Proluton C and Pranone among others, is a progestin medication which was used in the treatment of gynecological disorders but is now no longer available. It was used alone and was not formulated in combination with an estrogen. The medication is taken by mouth.

Hydroxyprogesterone caproate

Hydroxyprogesterone caproate (OHPC), sold under the brand names Proluton and Makena among others, is a progestin medication which is used to prevent preterm birth in pregnant women with a history of the condition and to treat gynecological disorders. It has also been formulated in combination with estrogens for various indications and as a form of long-lasting injectable birth control. It is not used by mouth and is instead given by injection into muscle or fat, typically once per week to once per month depending on the indication.

5α-Dihydroprogesterone Chemical compound

5α-Dihydroprogesterone is an endogenous progestogen and neurosteroid that is synthesized from progesterone. It is also an intermediate in the synthesis of allopregnanolone and isopregnanolone from progesterone.

Quingestanol acetate

Quingestanol acetate, sold under the brand names Demovis and Pilomin among others, is a progestin medication which was used in birth control pills but is no longer marketed. It is taken by mouth.

Hydroxyprogesterone acetate

Hydroxyprogesterone acetate (OHPA), sold under the brand name Prodox, is an orally active progestin related to hydroxyprogesterone caproate (OHPC) which has been used in clinical and veterinary medicine. It has reportedly also been used in birth control pills.

20α-Dihydroprogesterone Chemical compound

20α-Dihydroprogesterone (20α-DHP), also known as 20α-hydroxyprogesterone (20α-OHP), is a naturally occurring, endogenous progestogen. It is a metabolite of progesterone, formed by the 20α-hydroxysteroid dehydrogenases (20α-HSDs) AKR1C1, AKR1C2, and AKR1C3 and the 17β-hydroxysteroid dehydrogenase (17β-HSD) HSD17B1. 20α-DHP can be transformed back into progesterone by 20α-HSDs and by the 17β-HSD HSD17B2. HSD17B2 is expressed in the human endometrium and cervix among other tissues. In animal studies, 20α-DHP has been found to be selectively taken up into and retained in target tissues such as the uterus, brain, and skeletal muscle.

3β-Dihydroprogesterone Chemical compound

3β-Dihydroprogesterone (3β-DHP), also known as 3β-hydroxyprogesterone, or pregn-4-en-3β-ol-20-one, is an endogenous steroid. It is biosynthesized by 3β-hydroxysteroid dehydrogenase from progesterone. Unlike 3α-dihydroprogesterone (3α-DHP), 3β-DHP does not act as a positive allosteric modulator of the GABAA receptor, which is in accordance with the fact that other 3β-hydroxylated progesterone metabolites such as isopregnanolone and epipregnanolone similarly do not act as potentiators of this receptor and instead inhibit it as well as reverse the effects of potentiators like allopregnanolone. 3β-DHP has been reported to possess about the same potency as progesterone in a bioassay of progestogenic activity, whereas 3α-DHP was not assessed.

Hydroxyprogesterone heptanoate

Hydroxyprogesterone heptanoate (OHPH), also known as hydroxyprogesterone enanthate (OHPE) and sold under the brand names H.O.P., Lutogil A.P., and Lutogyl A.P. among others, is a progestin medication used for progestogenic indications. It has been formulated both alone and in together with estrogens, androgens/anabolic steroids, and other progestogens in several combination preparations. OHPH is given by injection into muscle at regular intervals.

Retroprogesterone

Retroprogesterone, also known as 9β,10α-progesterone or as 9β,10α-pregn-4-ene-3,20-dione, is a progestin which was never marketed. It is a stereoisomer of the naturally occurring progestogen progesterone, in which the hydrogen atom at the 9th carbon is in the α-position instead of the β-position and the methyl group at the 10th carbon is in the β-position instead of the α-position. In other words, the atom positions at the two carbons have been reversed relative to progesterone, hence the name retroprogesterone. This reversal results in a "bent" configuration in which the plane of rings A and B is orientated at a 60° angle below the rings C and D. This configuration is ideal for interaction with the progesterone receptor, with retroprogesterone binding with high affinity to this receptor. However, the configuration is not as ideal for binding to other steroid hormone receptors, and as a result, retroprogesterone derivatives have increased selectivity for the progesterone receptor relative to progesterone.

Progestogen ester

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.

Pentagestrone acetate

Pentagestrone acetate (PGA), sold under the brand names Gestovis and Gestovister, is a progestin which was described in the literature in 1960 and was introduced by Vister in Italy in 1961. It is the 3-cyclopentyl enol ether of 17α-hydroxyprogesterone acetate. PGA, along with quingestrone, is said to have very similar properties to those of dydrogesterone, a pure progestogen and close analogue of progesterone.

17α-Methylprogesterone Chemical compound

17α-Methylprogesterone (17α-MP), or 17α-methylpregn-4-ene-3,20-dione, is a steroidal progestin related to progesterone that was synthesized and characterized in 1949 but was never marketed. Along with ethisterone (1938) and 19-norprogesterone (1951), 17α-MP was one of the earliest derivatives of progesterone to be identified as possessing progestogenic activity. Similarly to progesterone and derivatives like 17α-hydroxyprogesterone and 19-norprogesterone, 17α-MP was found to possess poor oral bioavailability, but showed improved progestogenic activity relative to progesterone when administered via other routes. In addition to its activity as a progestogen, 17α-MP has also been found to possess some antiglucocorticoid activity.

Cymegesolate

Cymegesolate, also known as cypionyl megestrol acetate or as megestrol acetate 3β-cypionate, is a progestin medication which was never marketed. It was developed in China in the late 1970s and early to mid 1980s for use as a hormonal contraceptive. The medication was formulated at a dose of 50–100 mg in combination with a "trace" dose of 0.25–0.5 mg quinestrol as a long-lasting, once-a-month combined oral contraceptive pill. This combination has been studied in 1,213 women across a total of 9,651 menstrual cycles, with contraceptive effectiveness of over 99.13% and "very few side effects." At the high dose, it showed an anovulation rate of only about 60%, and instead mediated its contraceptive effects via a marked anti-implantation effect.

Progesterone 3-acetyl enol ether

Progesterone 3-acetyl enol ether, also known as progesterone acetate, as well as 3-acetoxypregna-3,5-dien-20-one, is a progestin which was never marketed. It was reported to possess similar potency to progesterone and hydroxyprogesterone caproate in the rabbit endometrial carbonic anhydrase test, a bioassay of progestogenic activity. In addition, it was able to maintain pregnancy in animals. Progesterone 3-acetyl enol ether is closely related to quingestrone, which is also known as progesterone 3-cyclopentyl enol ether and was formerly marketed as an oral contraceptive.

Estradiol valerate/gestonorone caproate

Estradiol valerate/gestonorone caproate (EV/GC), known by the developmental code names SH-834 and SH-8.0834, is a high-dose combination medication of estradiol valerate (EV), an estrogen, and gestonorone caproate, a progestin, which was developed and studied by Schering in the 1960s and 1970s for potential use in the treatment of breast cancer in women but was ultimately never marketed. It contained 90 mg EV and 300 mg GC in each 3 mL of oil solution and was intended for use by intramuscular injection once a week. The combination has also been studied incidentally in the treatment of ovarian cancer.

References

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  25. 1 2 "POPLINE retirement". 2019-09-06.
  26. ↑ Junkermann H, Runnebaum B, Lisboa BP (July 1977). "New progesterone metabolites in human myometrium". Steroids. 30 (1): 1–14. doi:10.1016/0039-128X(77)90131-3. PMID   919010. S2CID   28420255. In the Clauberg bioassay the 3β-hydroxy-4-pregnen-20-one shows about the same potency as progesterone (34). In regard to the biological activity of the 3α epimer no data are available.
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  28. ↑ Joseph Bolivar De Lee (1965). "The ... Year Book of Obstetrics and Gynecology". Yearbook of Obstetrics and Gynecology (O). Year Book Publishers: 150. ISSN   0084-3911. LCCN   cdr38000020.
  29. ↑ Junkmann, Karl (1954). "Gestagens of prolonged action". Naunyn-Schmiedebergs Archiv für Pharmakologie und Experimentelle Pathologie. 223: 244–53. ISSN   0365-5423. Among a large no. of pregnane derivs. the esters of 17-α-hydroxyprogesterone (I), itself of weak lutein hormone action, have a strong and long-lasting gestagen action. The optimal results are obtained with I caproate. It permits the administration of depot doses in clear solns. Within the range of dosage used no androgenic effect was noted. It has no influence on growth and on the secondary sex characteristics in infantile and adult castrate male rats. The 3-enol esters of progesterone, which have a somewhat prolonged action, are less suited for depot administration because of their oxidizability.
  30. ↑ Westphal, Ulrich (1936). "Über Enolacetate des Progesterons und Testosterons". Die Naturwissenschaften. 24 (44): 696–697. Bibcode:1936NW.....24..696W. doi:10.1007/BF01491541. ISSN   0028-1042. S2CID   41442733.
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