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Chemical compound
Quingestanol acetate
Trade names Demovis, Pilomin, others Other names W-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
In general: ℞ (Prescription only)
[(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
Formula C 27 H 36 O 3
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]
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]
References
^
a
b
c
d
e
f 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 .
^
a
b
c
d
e
f 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 .
^
a
b
c
d
e 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 .
^
a
b
c
d
e 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 .
^
a
b 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).
^
a
b 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 .
^
a
b
c Lara Marks (2010).
Sexual Chemistry: A History of the Contraceptive Pill . Yale University Press. pp. 73–.
ISBN
978-0-300-16791-7 .
^
a
b
c
Population Reports: Oral contraceptives . Department of Medical and Public Affairs, George Washington Univ. Medical Center. 1975. p. A-64.
^ Janne S. Kowalski (1 August 1988).
Drug companies & products world guide . Sittig & Noyes. p. 388.
ISBN
9780800242398 .
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RU-16117
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