Quingestanol acetate

Quingestanol acetate
Clinical data
Routes of; administration	Oral
ATC code	G03AC04 (WHO); G03AA02 (WHO) (with an estrogen);
Legal status
Legal status	In general: ℞ (Prescription only);
Identifiers
	IUPAC name (17β)-3-(Cyclopentyloxy)-17-ethynylestra-3,5-dien-17-yl acetate;
Synonyms	W-4540
CAS Number	3000-39-3;
PubChem CID	18142;
ChemSpider	17136;
ECHA InfoCard	100.019.163
Chemical and physical data
Formula	C27H36O3
Molar mass	408.573 g/mol
3D model (JSmol)	Interactive image;
	SMILES 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 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 (INN, USAN) (brand names Demovis, Pilomin, Riglovis, Unovis), also known as norethisterone acetate 3-cyclopentyl enol ether, is a steroidal progestin of the 19-nortestosterone group with additional weak androgenic and estrogenic activity which is used as an oral, once-a-month, or postcoital hormonal contraceptive.^[1]^[2]^[3]^[4] It is a prodrug of norethisterone, with both quingestanol and norethisterone acetate serving as intermediates in the transformation.^[5]^[6] The drug was patented in 1963^[7] and marketed in Italy in 1972.^[8]^[9]

References[edit]

^ 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.
^ 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. Society for Experimental Biology and Medicine (New York, N.Y.). 131 (3): 781–9. PMID 5815452. doi:10.3181/00379727-131-33977.
^ 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. PMID 4613534. doi:10.1016/0010-7824(74)90013-4.
^ Donde UM, Virkar KD (June 1975). "Biochemical studies with once-a-month contraceptive pill containing quinestrol-quingestanol acetate". Contraception. 11 (6): 681–8. PMID 1137940. doi:10.1016/0010-7824(75)90065-7.
^ Raynaud JP, Ojasoo T (1986). "The design and use of sex-steroid antagonists". J. Steroid Biochem. 25 (5B): 811–33. PMID 3543501. Similar androgenic potential is inherent to norethisterone and its prodrugs (norethisterone acetate, ethynodiol diacetate, lynestrenol, norethynodrel, quingestanol).
^ Di Carlo FJ, Loo JC, Aceto T, Zuleski FR, Barr WH (1974). "Quingestanol acetate metabolism in women". Pharmacology. 11 (5): 287–303. PMID 4853997. doi:10.1159/000136501.
^ Lara Marks (2010). Sexual Chemistry: A History of the Contraceptive Pill. Yale University Press. pp. 73–. ISBN 978-0-300-16791-7.
^ 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.

This drug article relating to the genito-urinary system is a stub. You can help Wikipedia by expanding it.

This article about a steroid is a stub. You can help Wikipedia by expanding it.

[Elks2014-1] 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.

[pmid5815452-2] 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. Society for Experimental Biology and Medicine (New York, N.Y.). 131 (3): 781–9. PMID 5815452. doi:10.3181/00379727-131-33977.

[pmid4613534-3] 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. PMID 4613534. doi:10.1016/0010-7824(74)90013-4.

[pmid1137940-4] Donde UM, Virkar KD (June 1975). "Biochemical studies with once-a-month contraceptive pill containing quinestrol-quingestanol acetate". Contraception. 11 (6): 681–8. PMID 1137940. doi:10.1016/0010-7824(75)90065-7.

[pmid3543501-5] Raynaud JP, Ojasoo T (1986). "The design and use of sex-steroid antagonists". J. Steroid Biochem. 25 (5B): 811–33. PMID 3543501. Similar androgenic potential is inherent to norethisterone and its prodrugs (norethisterone acetate, ethynodiol diacetate, lynestrenol, norethynodrel, quingestanol).

[pmid4853997-6] Di Carlo FJ, Loo JC, Aceto T, Zuleski FR, Barr WH (1974). "Quingestanol acetate metabolism in women". Pharmacology. 11 (5): 287–303. PMID 4853997. doi:10.1159/000136501.

[Marks2010-7] Lara Marks (2010). Sexual Chemistry: A History of the Contraceptive Pill. Yale University Press. pp. 73–. ISBN 978-0-300-16791-7.

[8] Population Reports: Oral contraceptives. Department of Medical and Public Affairs, George Washington Univ. Medical Center. 1975. p. A-64.

[Kowalski1988-9] Janne S. Kowalski (1 August 1988). Drug companies & products world guide. Sittig & Noyes. p. 388.

[1]

[2]

[3]

[4]

[5]

[6]

[7]

[8]

[9]

Quingestanol acetate

See also[edit]

References[edit]

Navigation menu

Personal tools

Namespaces

Variants

Views

More

Search

Navigation

Interaction

Tools

Print/export

Languages

Clinical data

Routes of administration	Oral
ATC code	G03AC04 (WHO) G03AA02 (WHO) (with an estrogen)
Legal status
Legal status	In general: ℞ (Prescription only)
Identifiers
IUPAC name (17β)-3-(Cyclopentyloxy)-17-ethynylestra-3,5-dien-17-yl acetate
Synonyms	W-4540
CAS Number	3000-39-3
PubChem CID	18142
ChemSpider	17136
ECHA InfoCard	100.019.163
Chemical and physical data
Formula	C₂₇H₃₆O₃
Molar mass	408.573 g/mol
3D model (JSmol)	Interactive image
SMILES 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 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