Noretynodrel information

Noretynodrel
Clinical data
Trade names	Enovid (with mestranol), others
Other names	Norethynodrel; Noretinodrel Norethinodrel; NYD; SC-4642; NSC-15432; 5(10)-Norethisterone; 17α-Ethinyl-19-nor-5(10)-testosterone; 17α-Ethynyl-δ5(10)-19-nortestosterone; 17α-Ethynylestr-5(10)-en-17β-ol-3-one; 19-Nor-17α-pregn-5(10)-en-20-yn-17β-ol-3-one
Routes of; administration	By mouth
Drug class	Progestogen; Progestin; Estrogen
ATC code	G03FA09 (WHO) ;
Pharmacokinetic data
Protein binding	Noretynodrel: to albumin and not to SHBGTooltip sex hormone-binding globulin or CBGTooltip corticosteroid-binding globulin
Metabolism	Liver, intestines (hydroxylation, isomerization, conjugation)
Metabolites	• 3α-Hydroxynoretynodrel; • 3β-Hydroxynoretynodrel; • Norethisterone; • Ethinylestradiol• Conjugates
Elimination half-life	Very short (< 30 minutes)
Excretion	Breast milk: 1%
Identifiers
	IUPAC name (8R,9S,13S,14S,17R)-17-ethynyl-17-hydroxy-13-methyl-1,2,4,6,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one;
CAS Number	68-23-5 ;
PubChem CID	6231;
DrugBank	DB09371 ;
ChemSpider	5995 ;
UNII	88181ACA0M;
KEGG	D05207;
ChEBI	CHEBI:34895 ;
ChEMBL	ChEMBL1387 ;
CompTox Dashboard (EPA)	DTXSID3021069 ;
ECHA InfoCard	100.000.620
Chemical and physical data
Formula	C20H26O2
Molar mass	298.426 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C4CCC\1=C(\CC[C@@H]2[C@@H]/1CC[C@]3([C@H]2CC[C@]3(C#C)O)C)C4;
	InChI InChI=1S/C20H26O2/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/h1,16-18,22H,4-12H2,2H3/t16-,17-,18+,19+,20+/m1/s1 ; Key:ICTXHFFSOAJUMG-SLHNCBLASA-N ;
	(verify)

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.^[3]^[6]^[7]^[8] It was available both alone and in combination with an estrogen.^[7]^[8]^[9] The medication is taken by mouth.^[7]

Noretynodrel is a progestin, or a synthetic progestogen, and hence is an agonist of the progesterone receptor, the biological target of progestogens like progesterone.^[3] It is a relatively weak progestogen.^[10] The medication has weak estrogenic activity, no or only very weak androgenic activity, and no other important hormonal activity.^[3]^[8]^[11]^[12] It is a prodrug of various active metabolites in the body, such as norethisterone among others.^[3]^[13]

Noretynodrel was introduced for medical use in 1957.^[8] It was specifically approved at this time in combination with mestranol for the treatment of gynecological and menstrual disorders.^[8] Subsequently, in 1960, this formulation was approved for use as a birth control pill.^[8]^[14] It was the first birth control pill to be introduced, and was followed by birth control pills containing norethisterone and other progestins shortly thereafter.^[8]^[14]^[15] Due to its nature as a relatively weak progestogen, noretynodrel is no longer used in medicine.^[10] As such, it is no longer marketed.^[6]^[16]

^ ^a ^b ^c Cite error: The named reference pmid2170822 was invoked but never defined (see the help page).
^ ^a ^b ^c Cite error: The named reference pmid22210085 was invoked but never defined (see the help page).
^ ^a ^b ^c ^d ^e ^f ^g ^h Kuhl H (2005). "Pharmacology of estrogens and progestogens: influence of different routes of administration" (PDF). Climacteric. 8 (Suppl 1): 3–63. doi:10.1080/13697130500148875. PMID 16112947. S2CID 24616324.
^ Cite error: The named reference Kuhl2011 was invoked but never defined (see the help page).
^ Cite error: The named reference pmid2256526 was invoked but never defined (see the help page).
^ ^a ^b ^c Sweetman SC, ed. (2009). "Sex hormones and their modulators". Martindale: The Complete Drug Reference (36th ed.). London: Pharmaceutical Press. pp. 2120–2121. ISBN 978-0-85369-840-1.
^ ^a ^b ^c Jucker E, ed. (21 December 2013). Progress in Drug Research / Fortschritte der Arzneimittelforschung / Progrès des recherches pharmaceutiques. Birkhäuser. pp. 85–88. ISBN 978-3-0348-7065-8.
^ ^a ^b ^c ^d ^e ^f ^g Marks L (2010). Sexual Chemistry: A History of the Contraceptive Pill. Yale University Press. pp. 74–75. ISBN 978-0-300-16791-7.
^ Cite error: The named reference WHO1974 was invoked but never defined (see the help page).
^ ^a ^b Williams DA, Foye WO, Lemke TL (January 2002). Foye's Principles of Medicinal Chemistry. Lippincott Williams & Wilkins. pp. 700–. ISBN 978-0-683-30737-5.
^ Runnebaum BC, Rabe T, Kiesel L (6 December 2012). Female Contraception: Update and Trends. Springer Science & Business Media. pp. 36–. ISBN 978-3-642-73790-9.
^ Sloane E (2002). Biology of Women. Cengage Learning. pp. 426–. ISBN 978-0-7668-1142-3.
^ Cite error: The named reference pmid12215716 was invoked but never defined (see the help page).
^ ^a ^b Hollinger MA (19 October 2007). Introduction to Pharmacology, Third Edition. CRC Press. pp. 160–. ISBN 978-1-4200-4742-4.
^ Cite error: The named reference Ravina2011 was invoked but never defined (see the help page).
^ Cite error: The named reference Drugs.com was invoked but never defined (see the help page).

[pmid2170822-1] Cite error: The named reference pmid2170822 was invoked but never defined (see the help page).

[pmid22210085-2] Cite error: The named reference pmid22210085 was invoked but never defined (see the help page).

[pmid16112947-3] ^ ^a ^b ^c ^d ^e ^f ^g ^h Kuhl H (2005). "Pharmacology of estrogens and progestogens: influence of different routes of administration" (PDF). Climacteric. 8 (Suppl 1): 3–63. doi:10.1080/13697130500148875. PMID 16112947. S2CID 24616324.

[Kuhl2011-4] Cite error: The named reference Kuhl2011 was invoked but never defined (see the help page).

[pmid2256526-5] Cite error: The named reference pmid2256526 was invoked but never defined (see the help page).

[Martindale-6] Sweetman SC, ed. (2009). "Sex hormones and their modulators". Martindale: The Complete Drug Reference (36th ed.). London: Pharmaceutical Press. pp. 2120–2121. ISBN 978-0-85369-840-1.

[Jucker2013-7] Jucker E, ed. (21 December 2013). Progress in Drug Research / Fortschritte der Arzneimittelforschung / Progrès des recherches pharmaceutiques. Birkhäuser. pp. 85–88. ISBN 978-3-0348-7065-8.

[Marks2010-8] ^ ^a ^b ^c ^d ^e ^f ^g Marks L (2010). Sexual Chemistry: A History of the Contraceptive Pill. Yale University Press. pp. 74–75. ISBN 978-0-300-16791-7.

[WHO1974-9] Cite error: The named reference WHO1974 was invoked but never defined (see the help page).

[WilliamsFoye2002-10] Williams DA, Foye WO, Lemke TL (January 2002). Foye's Principles of Medicinal Chemistry. Lippincott Williams & Wilkins. pp. 700–. ISBN 978-0-683-30737-5.

[RunnebaumRabe2012-11] Runnebaum BC, Rabe T, Kiesel L (6 December 2012). Female Contraception: Update and Trends. Springer Science & Business Media. pp. 36–. ISBN 978-3-642-73790-9.

[Sloane2002-12] Sloane E (2002). Biology of Women. Cengage Learning. pp. 426–. ISBN 978-0-7668-1142-3.

[pmid12215716-13] Cite error: The named reference pmid12215716 was invoked but never defined (see the help page).

[Hollinger2007-14] Hollinger MA (19 October 2007). Introduction to Pharmacology, Third Edition. CRC Press. pp. 160–. ISBN 978-1-4200-4742-4.

[Ravina2011-15] Cite error: The named reference Ravina2011 was invoked but never defined (see the help page).

[Drugs.com-16] Cite error: The named reference Drugs.com was invoked but never defined (see the help page).

Noretynodrel information

and 25 Related for: Noretynodrel information

Noretynodrel

Syntex

Combined oral contraceptive pill

Progesterone

Triamcinolone acetonide

Norethisterone

Estrogen

Enclomifene

Birth control

Testosterone

Nicotinamide

Hormone therapy

Quercetin

Progestogen

Dydrogesterone

Oxymetholone

Feminizing hormone therapy

Letrozole

Alkyne

Apigenin

Mifepristone

Trenbolone

Dihydrotestosterone

Nandrolone

Metandienone