Chemistry:Norgestrienone

Norgestrienone
Clinical data
Trade names	Ogyline, Planor, Miniplanor
Other names	RU-2010; A-301; 17α-Ethynyltrienolone; 17α-Ethynyltrenbolone; Δ9,11-Norethisterone; 17α-Ethynylestra-4,9,11-trien-17β-ol-3-one
Routes of; administration	By mouth
Drug class	Progestogen; Progestin; Androgen; Anabolic steroid
ATC code	G03AC07 (WHO) ;
Identifiers
	IUPAC name (8S,13S,14S,17R)-17-ethynyl-17-hydroxy-13-methyl-1,2,6,7,8,14,15,16-octahydrocyclopenta[a]phenanthren-3-one;
CAS Number	848-21-5 ;
PubChem CID	13313;
ChemSpider	12749 ;
UNII	89386PYU9O;
KEGG	D07220 ;
Chemical and physical data
Formula	C20H22O2
Molar mass	294.394 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C4\C=C3/C(=C2/C=C\[C@]1([C@@H](CC[C@]1(C#C)O)[C@@H]2CC3)C)CC4;
	InChI InChI=1S/C20H22O2/c1-3-20(22)11-9-18-17-6-4-13-12-14(21)5-7-15(13)16(17)8-10-19(18,20)2/h1,8,10,12,17-18,22H,4-7,9,11H2,2H3/t17-,18+,19+,20+/m1/s1 ; Key:GVDMJXQHPUYPHP-FYQPLNBISA-N ;
	(verify)

Short description: Chemical compound

Norgestrienone, sold under the brand names Ogyline, Planor, and Miniplanor, is a progestin medication which has been used in birth control pills, sometimes in combination with ethinylestradiol.^[1]^[2]^[3]^[4]^[5] It was developed by Roussel Uclaf and has been registered for use only in France .^[4]^[5]^[6] Under the brand name Planor, it has been marketed in France as 2 mg norgestrienone and 50 μg ethinylestradiol tablets.^[7] It is taken by mouth.^[5]

Norgestrienone is a progestin, or a synthetic progestogen, and hence is an agonist of the progesterone receptor, the biological target of progestogens like progesterone.^[8] It has some androgenic activity.^[9]^[10]^[11]^[12]

Norgestrienone was first described in the literature in 1965.^[10] It is sometimes referred to as a "second-generation" progestin.^[13] Norgestrienone is no longer available.^{[citation needed]}

Medical uses

Norgestrienone was used in hormonal contraception to prevent pregnancy.^[2]^[7] It has typically been used as an oral contraceptive at a dosage of 2 mg/day in combination with ethinylestradiol and 350 µ/day when used alone.^[5]

Side effects

Pharmacology

Pharmacodynamics

Norgestrienone has been found to possess similar affinity for the progesterone receptor and androgen receptor,^[8] and in accordance, has some androgenic activity.^[9]^[10]^[11]^[12] The androgenic activity of norgestrienone is greater than that of other 19-nortestosterone derivatives due to the presence of the C9(11) double bond, which enhances said activity.^[12] The ratio of progestogenic to androgenic activity appears to be much lower for norgestrienone that it is for other 19-nortestosterone progestins such as norethisterone and levonorgestrel.^[14]^[15]^[16]^[17] Gestrinone, the 18-methyl analogue of norgestrienone, has even greater androgenic activity than norgestrienone, as this modification increases androgenic activity similarly.^[12]

Relative affinities (%) of norgestrienone and related steroids
Compound	PR	AR	ER	GR	MR	SHBG	CBG
Norethisterone	155–156	43–45	<0.1	2.7–2.8	0.2	?	?
Norgestrienone	63–65	70	<0.1	11	1.8	?	?
Levonorgestrel	170	84–87	<0.1	14	0.6–0.9	?	?
Gestrinone	75–76	83–85	<0.1, 3–10	77	3.2	?	?

Pharmacokinetics

The metabolism of norgestrienone in humans has been studied.^[18]

Chemistry

Norgestrienone, also known as 17α-ethynyl-19-nor-δ^9,11-testosterone or as 17α-ethynylestra-4,9,11-trien-17β-ol-3-one, as well as δ^9,11-norethisterone or 17α-ethynyltrienolone (17α-ethynyltrenbolone), is a synthetic estrane steroid and a derivative of testosterone and 19-nortestosterone.^[1]^[4]^[19] It is structurally related to the anabolic steroid trenbolone (19-nor-δ^9,11-testosterone; the non-17α-ethynylated analogue of norgestrienone), the progestogenic and androgenic steroid gestrinone (the 13β-ethyl variant or 18-methyl derivative of norgestrienone), and the anabolic steroid tetrahydrogestrinone (the 18-methyl and 17α-ethyl variant of norgestrienone).^[1]^[4]^[20]

History

Norgestrienone was first described in the literature in 1965.^[10] It is sometimes referred to as a "second-generation" progestin based on its time of introduction.^[13]

Society and culture

Generic names

Norgestrienone is the generic name of the drug and its INN.^[1]^[2]^[4] It is also known by its developmental code names RU-2010 and A-301.^[1]^[2]^[4]

Brand names

Norgestrienone has been marketed under the brand names Ogyline, Planor, and Miniplanor.^[1]^[2]^[4]

Availability

Norgestrienone is no longer marketed and hence is no longer available in any country.^{[citation needed]} It was previously used in France .^[4] The medication was never marketed in the United States .^[21]

Research

Norgestrienone has been studied for use in male hormonal contraception.^[22]

References

↑ ^1.0 ^1.1 ^1.2 ^1.3 ^1.4 ^1.5 The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. 14 November 2014. pp. 887–. ISBN 978-1-4757-2085-3. https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA887.
↑ ^2.0 ^2.1 ^2.2 ^2.3 ^2.4 Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. 6 December 2012. pp. 202–. ISBN 978-94-011-4439-1. https://books.google.com/books?id=tsjrCAAAQBAJ&pg=PA202.
↑ "Clinical trial with subdermal implants containing norgestrienone". Contraception 18 (4): 429–440. October 1978. doi:10.1016/0010-7824(78)90027-6. PMID 720075.
↑ ^4.0 ^4.1 ^4.2 ^4.3 ^4.4 ^4.5 ^4.6 ^4.7 Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 751–. ISBN 978-3-88763-075-1. https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA751.
↑ ^5.0 ^5.1 ^5.2 ^5.3 "Sex hormones and their modulators". Martindale: The Complete Drug Reference (36th ed.). London: Pharmaceutical Press. 2009. p. 2122. ISBN 978-0-85369-840-1. https://www.medicinescomplete.com/. "Norgestrienone is a progestogen structurally related to norethisterone that has been used as an oral contraceptive. Typical doses have been 2 mg daily with an oestrogen, and 350 micrograms daily when used alone."
↑ Pharmaceuticals, 4 Volume Set. Wiley. 2000. p. 1580,1599. ISBN 978-3-527-29874-7. https://books.google.com/books?id=uG9qAAAAMAAJ.
↑ ^7.0 ^7.1 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. 455–. ISBN 978-92-832-1291-1. https://books.google.com/books?id=aGDU5xibtNgC&pg=PA455.
↑ ^8.0 ^8.1 "A comparison of progestin and androgen receptor binding using the CoMFA technique". Journal of Computer-Aided Molecular Design 6 (6): 569–581. December 1992. doi:10.1007/bf00126215. PMID 1291626. Bibcode: 1992JCAMD...6..569L.
↑ ^9.0 ^9.1 Biochemical Actions of Hormones. Academic Press. 1 January 1982. ISBN 978-0-12-452809-3. https://books.google.com/books?id=AxpPAQAAIAAJ.
↑ ^10.0 ^10.1 ^10.2 ^10.3 Current Management of the Menopause. CRC Press. 22 June 2005. pp. 45–. ISBN 978-0-203-48612-2. https://books.google.com/books?id=WD7S7677xUUC&pg=PA45.
↑ ^11.0 ^11.1 Interconnections Between Human and Ecosystem Health. Springer Science & Business Media. 6 December 2012. pp. 60–. ISBN 978-94-009-1523-7. https://books.google.com/books?id=dQ1JCAAAQBAJ&pg=PA60.
↑ ^12.0 ^12.1 ^12.2 ^12.3 "Relationships between chemical structure and biological properties of progestogens". American Journal of Obstetrics and Gynecology 142 (6 Pt 2): 719–724. March 1982. doi:10.1016/S0002-9378(16)32477-2. PMID 7065053.
↑ ^13.0 ^13.1 "Risk of venous thromboembolism with third-generation oral contraceptives: A review". American Journal of Obstetrics and Gynecology 180 (2 Pt 2): 295–301. February 1999. doi:10.1016/S0002-9378(99)70721-0. PMID 9988833.
↑ Cite error: Invalid <ref> tag; no text was provided for refs named pmid7382482
↑ Cite error: Invalid <ref> tag; no text was provided for refs named pmid7421203
↑ Cite error: Invalid <ref> tag; no text was provided for refs named pmid8136304
↑ Cite error: Invalid <ref> tag; no text was provided for refs named RaynaudOjasoo1979
↑ "Metabolism of contraceptive steroids in man.". Excerpta Medica International Congress Series 219: 915–922. 1970. https://www.popline.org/node/480947.
↑ Pediatric and Adolescent Obstetrics and Gynecology. Springer Science & Business Media. 6 December 2012. pp. 236–. ISBN 978-1-4612-5064-7. https://books.google.com/books?id=l9XTBwAAQBAJ&pg=PA236.
↑ Reconstructive and Reproductive Surgery in Gynecology. CRC Press. 27 September 2010. pp. 90–. ISBN 978-1-84184-757-3. https://books.google.com/books?id=C4TOBQAAQBAJ&pg=PA90.
↑ Strategies for Organic Drug Synthesis and Design. John Wiley & Sons. 4 March 2009. pp. 134–. ISBN 978-0-470-39959-0. https://books.google.com/books?id=fEwl6Qev-mUC&pg=PA134.
↑ "The use of progestins and androgens as a male contraceptive. Hormonal control of male fertility.". DHEW Publication No.(NIH).: 78–1097. 1978. https://www.popline.org/node/443605.

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D₂ receptor antagonists (prolactin releasers) (e.g., domperidone, metoclopramide, risperidone, haloperidol, chlorpromazine, sulpiride)
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Progestogens (incl., chlormadinone acetate, [[cyproterone acetate, hydroxyprogesterone caproate, gestonorone caproate, [[Chemistry:Medroxyprogesterone medroxyprogesterone acetate, Chemistry:Megestrol acetate|megestrol acetate]])

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^#WHO-EM
^‡Withdrawn from market
Clinical trials:
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See also: Androgen receptor modulators; Estrogens and antiestrogens; Progestogens and antiprogestogens; List of androgens/anabolic steroids

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Original source: https://en.wikipedia.org/wiki/Norgestrienone. Read more

[Elks2014-1] 1.0 ^1.1 ^1.2 ^1.3 ^1.4 ^1.5 The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. 14 November 2014. pp. 887–. ISBN 978-1-4757-2085-3. https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA887.

[MortonHall2012-2] 2.0 ^2.1 ^2.2 ^2.3 ^2.4 Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. 6 December 2012. pp. 202–. ISBN 978-94-011-4439-1. https://books.google.com/books?id=tsjrCAAAQBAJ&pg=PA202.

[DiazPavez1978-3] "Clinical trial with subdermal implants containing norgestrienone". Contraception 18 (4): 429–440. October 1978. doi:10.1016/0010-7824(78)90027-6. PMID 720075.

[IndexNominum2000-4] 4.0 ^4.1 ^4.2 ^4.3 ^4.4 ^4.5 ^4.6 ^4.7 Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 751–. ISBN 978-3-88763-075-1. https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA751.

[Martindale-5] 5.0 ^5.1 ^5.2 ^5.3 "Sex hormones and their modulators". Martindale: The Complete Drug Reference (36th ed.). London: Pharmaceutical Press. 2009. p. 2122. ISBN 978-0-85369-840-1. https://www.medicinescomplete.com/. "Norgestrienone is a progestogen structurally related to norethisterone that has been used as an oral contraceptive. Typical doses have been 2 mg daily with an oestrogen, and 350 micrograms daily when used alone."

[McGuire2000-6] Pharmaceuticals, 4 Volume Set. Wiley. 2000. p. 1580,1599. ISBN 978-3-527-29874-7. https://books.google.com/books?id=uG9qAAAAMAAJ.

[HumansOrganization2007-7] 7.0 ^7.1 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. 455–. ISBN 978-92-832-1291-1. https://books.google.com/books?id=aGDU5xibtNgC&pg=PA455.

[pmid1291626-8] 8.0 ^8.1 "A comparison of progestin and androgen receptor binding using the CoMFA technique". Journal of Computer-Aided Molecular Design 6 (6): 569–581. December 1992. doi:10.1007/bf00126215. PMID 1291626. Bibcode: 1992JCAMD...6..569L.

[Axelrod1982-9] 9.0 ^9.1 Biochemical Actions of Hormones. Academic Press. 1 January 1982. ISBN 978-0-12-452809-3. https://books.google.com/books?id=AxpPAQAAIAAJ.

[LauritzenStudd2005-10] 10.0 ^10.1 ^10.2 ^10.3 Current Management of the Menopause. CRC Press. 22 June 2005. pp. 45–. ISBN 978-0-203-48612-2. https://books.google.com/books?id=WD7S7677xUUC&pg=PA45.

[GiulioMonosson2012-11] 11.0 ^11.1 Interconnections Between Human and Ecosystem Health. Springer Science & Business Media. 6 December 2012. pp. 60–. ISBN 978-94-009-1523-7. https://books.google.com/books?id=dQ1JCAAAQBAJ&pg=PA60.

[pmid7065053-12] 12.0 ^12.1 ^12.2 ^12.3 "Relationships between chemical structure and biological properties of progestogens". American Journal of Obstetrics and Gynecology 142 (6 Pt 2): 719–724. March 1982. doi:10.1016/S0002-9378(16)32477-2. PMID 7065053.

[pmid9988833-13] 13.0 ^13.1 "Risk of venous thromboembolism with third-generation oral contraceptives: A review". American Journal of Obstetrics and Gynecology 180 (2 Pt 2): 295–301. February 1999. doi:10.1016/S0002-9378(99)70721-0. PMID 9988833.

[pmid7382482-14] Cite error: Invalid <ref> tag; no text was provided for refs named pmid7382482

[pmid7421203-15] Cite error: Invalid <ref> tag; no text was provided for refs named pmid7421203

[pmid8136304-16] Cite error: Invalid <ref> tag; no text was provided for refs named pmid8136304

[RaynaudOjasoo1979-17] Cite error: Invalid <ref> tag; no text was provided for refs named RaynaudOjasoo1979

[Raynaud1971-18] "Metabolism of contraceptive steroids in man.". Excerpta Medica International Congress Series 219: 915–922. 1970. https://www.popline.org/node/480947.

[LaverySanfilippo2012-19] Pediatric and Adolescent Obstetrics and Gynecology. Springer Science & Business Media. 6 December 2012. pp. 236–. ISBN 978-1-4612-5064-7. https://books.google.com/books?id=l9XTBwAAQBAJ&pg=PA236.

[GomelBrill2010-20] Reconstructive and Reproductive Surgery in Gynecology. CRC Press. 27 September 2010. pp. 90–. ISBN 978-1-84184-757-3. https://books.google.com/books?id=C4TOBQAAQBAJ&pg=PA90.

[Lednicer2009-21] Strategies for Organic Drug Synthesis and Design. John Wiley & Sons. 4 March 2009. pp. 134–. ISBN 978-0-470-39959-0. https://books.google.com/books?id=fEwl6Qev-mUC&pg=PA134.

[Scheater1978-22] "The use of progestins and androgens as a male contraceptive. Hormonal control of male fertility.". DHEW Publication No.(NIH).: 78–1097. 1978. https://www.popline.org/node/443605.

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