Quingestanol acetate

Last updated
Quingestanol acetate
Quingestanol acetate.svg
Clinical data
Trade names Demovis, Pilomin, others
Other namesW-4540; Norethisterone acetate 3-cyclopentyl enol ether; 17α-Ethynyl-19-nortestosterone acetate 3-cyclopentyl enol ether; ENTACP; (17β)-3-(Cyclopentyloxy)-17-ethynylestra-3,5-dien-17-yl acetate
Routes of
administration 		By mouth
Drug class Progestogen; Progestin; Progestogen ester
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Identifiers
  • [(8R,9S,10R,13S,14S,17R)-3-cyclopentyloxy-17-ethynyl-13-methyl-2,7,8,9,10,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-17-yl] acetate
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.019.163 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C27H36O3
Molar mass 408.582 g·mol−1
3D model (JSmol)
  • O=C(O[C@@]5(C#C)CC[C@@H]4[C@]5(C)CC[C@@H]3[C@@H]2C(\C=C(\OC1CCCC1)CC2)=C/C[C@H]34)C
  • InChI=1S/C27H36O3/c1-4-27(30-18(2)28)16-14-25-24-11-9-19-17-21(29-20-7-5-6-8-20)10-12-22(19)23(24)13-15-26(25,27)3/h1,9,17,20,22-25H,5-8,10-16H2,2-3H3/t22-,23+,24+,25-,26-,27-/m0/s1
  • Key:FLGJKPPXEKYCBY-AKCFYGDASA-N

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. [1] It is taken by mouth. [2] [3] [4]

Contents

Quingestanol acetate is a progestin, or a synthetic progestogen, and hence is an agonist of the progesterone receptor, the biological target of progestogens like progesterone. [2] [3] [4] It has weak androgenic and estrogenic activity and no other important hormonal activity. [2] [3] [4] The medication is a prodrug of norethisterone in the body, with quingestanol and norethisterone acetate occurring as intermediates. [5] [6]

Quingestanol acetate was patented in 1963 and was introduced for medical use in 1972. [7] [8] It was marketed in Italy. [8]

Medical uses

Quingestanol acetate was used as an oral, once-a-month, or postcoital hormonal contraceptive. [2] [3] [4]

Side effects

Pharmacology

Quingestanol acetate is a progestogen, and also has weak androgenic and estrogenic activity. [2] [3] [4] It is a prodrug of norethisterone, with both quingestanol and norethisterone acetate serving as intermediates in the transformation. [5] [6] Unlike penmesterol (methyltestosterone 3-cyclopentyl enol ether) and quinestrol (ethinylestradiol 3-cyclopentyl ether), quingestanol acetate is not stored in fat and does not have a prolonged duration of action. [2]

Chemistry

Quingestanol acetate, also known as norethisterone 17β-acetate 3-cyclopentyl enol ether or as 17α-ethynyl-19-nortestosterone 17β-acetate 3-cyclopentyl enol ether (ENTACP), as well as 3-(cyclopentyloxy)-17α-ethynylestra-3,5-dien-17β-yl acetate, is a synthetic estrane steroid and a derivative of testosterone. [1] It is specifically a derivative of 19-nortestosterone and 17α-ethynyltestosterone, or of norethisterone (17α-ethynyl-19-nortestosterone), in which a cyclopentyl enol ether group has been attached at the C3 position and an acetate ester has been attached at the C17β position. [1] Quingestanol acetate is the C17β acetate ester of quingestanol (norethisterone 3-cyclopentyl enol ether). [1]

History

Quingestanol acetate was patented in 1963 [7] and marketed in Italy in 1972. [8] [9]

Society and culture

Generic names

Quingestanol acetate is the generic name of the drug and its INN Tooltip International Nonproprietary Name and USAN Tooltip United States Adopted Name. [1]

Brand names

Quingestanol acetate was marketed under the brand names Demovis, Pilomin, Riglovis, and Unovis. [1] [7]

Related Research Articles

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<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">Norelgestromin</span> Pharmaceutical drug

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. The medication is available in combination with an estrogen and is not available alone. It is used as a patch that is applied to the skin.

<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">Etynodiol diacetate</span> Chemical compound

Etynodiol diacetate, or ethynodiol diacetate, sold under the brand names Demulen and Femulen 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.

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

Gestodene, sold under the brand names Femodene and Minulet among others, is a progestin medication which is used in birth control pills for women. It is also used in menopausal hormone therapy. The medication is available almost exclusively in combination with an estrogen. It is taken by mouth.

<span class="mw-page-title-main">Lynestrenol</span> Androgen and anabolic steroid

Lynestrenol, sold under the brand names Exluton and Ministat among others, is a progestin medication which is used in birth control pills and in the treatment of gynecological disorders. The medication is available both alone and in combination with an estrogen. It is taken by mouth.

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

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.

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

Trestolone, also known as 7α-methyl-19-nortestosterone (MENT), is an experimental androgen/anabolic steroid (AAS) and progestogen medication which has been under development for potential use as a form of hormonal birth control for men and in androgen replacement therapy for low testosterone levels in men but has never been marketed for medical use. It is given as an implant that is placed into fat. As trestolone acetate, an androgen ester and prodrug of trestolone, the medication can also be given by injection into muscle.

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

Norethisterone enanthate (NETE), also known as norethindrone enanthate, is a form of hormonal birth control which is used to prevent pregnancy in women. 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. The failure rate per year in preventing pregnancy for the progestogen-only formulation is 2 per 100 women. Each dose of this form lasts two months with only up to two doses typically recommended.

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

Quingestanol, also known as norethisterone 3-cyclopentyl enol ether, is a progestin of the 19-nortestosterone group which was never marketed. It is a prodrug of norethisterone. An acylated derivative, quingestanol acetate, is used as a pharmaceutical drug.

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

Noretynodrel, or norethynodrel, sold under the brand name Enovid among others, is a progestin medication which was previously used in birth control pills and in the treatment of gynecological disorders but is now no longer marketed. It was available both alone and in combination with an estrogen. The medication is taken by mouth.

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

Norgesterone, also known as norvinodrel or vinylestrenolone and sold under the brand name Vestalin, is a progestin medication which was formerly used in birth control pills for women but is now no longer marketed. It was used in combination with the estrogen ethinylestradiol. It is taken by mouth.

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

Methylestradiol, sold under the brand names Ginecosid, Ginecoside, Mediol, and Renodiol, is an estrogen medication which is used in the treatment of menopausal symptoms. It is formulated in combination with normethandrone, a progestin and androgen/anabolic steroid medication. Methylestradiol is taken by mouth.

<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.

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

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. It is taken by mouth.

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

Dimethandrolone undecanoate (DMAU), also known by its developmental code name CDB-4521, is an experimental androgen/anabolic steroid (AAS) and progestogen medication which is under development as a potential birth control pill for men. It is taken by mouth, but can also be given by injection into muscle.

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

Levonorgestrel acetate (LNG-A), or levonorgestrel 17β-acetate, also known as 3-ketonorgestimate, is a progestin which was never marketed. It is a progestogen ester and is the C17β acetate ester and a prodrug of levonorgestrel. Norgestimate is the C3 oxime of LNG-A. The drug is a minor active metabolite of norgestimate, which is a prodrug of norelgestromin and to a lesser extent of levonorgestrel and LNG-A. LNG-A has high affinity for the progesterone receptor, about 135% of that of promegestone. Along with levonorgestrel butanoate, LNG-A was investigated as a hormonal contraceptive by the Population Council.

References

  1. 1 2 3 4 5 6 J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 1058–. ISBN   978-1-4757-2085-3.
  2. 1 2 3 4 5 6 Giannina T, Steinetz BG, Rassaert CL, McDougall EA, Meli A (July 1969). "Biological profile of quingestanol acetate". Proceedings of the Society for Experimental Biology and Medicine. 131 (3): 781–9. doi:10.3181/00379727-131-33977. PMID   5815452. S2CID   12433167.
  3. 1 2 3 4 5 Mischler TW, Rubio B, Larranaga A, Guiloff E, Moggia AV (March 1974). "Further experience with quingestanol acetate as a postcoital oral contraceptive". Contraception. 9 (3): 221–5. doi:10.1016/0010-7824(74)90013-4. PMID   4613534.
  4. 1 2 3 4 5 Donde UM, Virkar KD (June 1975). "Biochemical studies with once-a-month contraceptive pill containing quinestrol-quingestanol acetate". Contraception. 11 (6): 681–8. doi:10.1016/0010-7824(75)90065-7. PMID   1137940.
  5. 1 2 Raynaud JP, Ojasoo T (1986). "The design and use of sex-steroid antagonists". J. Steroid Biochem. 25 (5B): 811–33. doi:10.1016/0022-4731(86)90313-4. PMID   3543501. Similar androgenic potential is inherent to norethisterone and its prodrugs (norethisterone acetate, ethynodiol diacetate, lynestrenol, norethynodrel, quingestanol).
  6. 1 2 Di Carlo FJ, Loo JC, Aceto T, Zuleski FR, Barr WH (1974). "Quingestanol acetate metabolism in women". Pharmacology. 11 (5): 287–303. doi:10.1159/000136501. PMID   4853997.
  7. 1 2 3 Lara Marks (2010). Sexual Chemistry: A History of the Contraceptive Pill. Yale University Press. pp. 73–. ISBN   978-0-300-16791-7.
  8. 1 2 3 Population Reports: Oral contraceptives. Department of Medical and Public Affairs, George Washington Univ. Medical Center. 1975. p. A-64.
  9. ↑ Janne S. Kowalski (1 August 1988). Drug companies & products world guide. Sittig & Noyes. p. 388. ISBN   9780800242398.
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