LYNESTRENOL

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C20H28O
Molecular Weight	284.4357
Optical Activity	UNSPECIFIED
Defined Stereocenters	6 / 6
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]12CC[C@@](O)(C#C)[C@@]1(C)CC[C@]3([H])[C@@]4([H])CCCC=C4CC[C@@]23[H]

InChI

InChIKey=YNVGQYHLRCDXFQ-XGXHKTLJSA-N

InChI=1S/C20H28O/c1-3-20(21)13-11-18-17-9-8-14-6-4-5-7-15(14)16(17)10-12-19(18,20)2/h1,6,15-18,21H,4-5,7-13H2,2H3/t15-,16+,17+,18-,19-,20-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C20H28O
Molecular Weight	284.4357
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	6 / 6
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.dokteronline.com/en/orgametril

Lynestrenol is a progestogen structurally related to norethisterone; it is used singularly, or as the progestogenic component of oral contraceptives. It is also used in treatments for menstrual disorders. Lynestrenol is typically used as an oral contraceptive, but also for the treatment of menstrual disorders like: Oligo-menorrhea and hypo-menorrhea; Polymenorrhoea; Fibrocystic mastopathy; Endometriosis; Endometrial carcinoma and/or metastases etc. As a synthetic oral progestogen, Lynestrenol has similar effects as that of the natural progesterone hormone. It has a strong progestational effect on the uterine endometrium by transforming the proliferative endometrium into a secretory one. It also inhibits the secretion of gonadotropin, suppresses maturation of follicles in the ovaries and ovulation, and reduces menstrual bleeding. Lynestrenol has minimal estrogenic, androgenic and anabolic effects.

Approval Year

Conditions

Condition	Modality	Highest Phase	Product
Endometrial hyperplasia without atypia 1 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24488582	Primary	Preclinical	Unknown Approved Use Unknown
Endometriosis 32 Sources: https://www.dokteronline.com/en/orgametril	Primary	Approved 8429	Unknown Approved Use Unknown
Dysmenorrhoea, premenstrual syndrome 1 Sources: https://www.dokteronline.com/en/orgametril	Primary	Approved 8429	Unknown Approved Use Unknown
Oligomenorrhea 1 Sources: https://www.dokteronline.com/en/orgametril	Primary	Approved 8429	Unknown Approved Use Unknown
Amenorrhea 18 Sources: https://www.dokteronline.com/en/orgametril	Primary	Approved 8429	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
[Arterial hypertension during treatment with estro-progestative drugs].	1971 Sep-Oct	5153254
[Lipoprotein changes during hormonal treatment of endometriosis with lynestrenol and danazol].	1984 Mar	6562983
Camptocormia, a new side effect of sodium valproate.	1987 Jul	3143551
[Coronary disease and hormonal treatment during the perimenopausal period].	1998 Jan	9553405
Pre-operative GnRH analogue therapy before hysterectomy or myomectomy for uterine fibroids.	2001	11405968
Leuprorelin and triptorelin: new indication. Preoperative treatment of uterine leiomyoma: no proven value.	2001 Jun	11718167
Prospective randomized study comparing the GnRH-agonist leuprorelin acetate and the gestagen lynestrenol in the treatment of severe endometriosis.	2001 Jun	11447732
[Endometriosis of the abdominal wall: diagnosis and treatment techniques].	2001 May	11526776
Variegate porphyria with coexistent decrease in porphobilinogen deaminase activity.	2001 Oct-Nov	11800145
FSH and ovarian response: spontaneous recovery of pituitary-ovarian activity during the pill-free period vs. exogenous recombinant FSH during high-dose combined oral contraceptives.	2002 Apr	11966744
Use of progestogen-only contraceptives/medications and lipid parameters in women age 40 to 42 years: results of a population-based cross-sectional Norwegian Survey.	2002 Jul	12169374
The effect of ethinyloestradiol and levonorgestrel on the CYP2C19-mediated metabolism of omeprazole in healthy female subjects.	2003 Aug	12895199
Classification and pharmacology of progestins.	2003 Dec 10	14670641
A 3-year double-blind, randomized, controlled study on the influence of two oral contraceptives containing either 20 microg or 30 microg ethinylestradiol in combination with levonorgestrel on bone mineral density.	2004 Mar	14969664
Contraceptive vaginal rings releasing Nestorone and ethinylestradiol: a 1-year dose-finding trial.	2005 Feb	15707562
Venous thromboembolism after high-dose chemotherapy in a patient with Hodgkin's lymphoma receiving the new oral contraceptive ethinylestradiol and drospirenone ("Yasmine").	2005 Jan	15531905
In vivo induction of sister chromatid exchanges (SCEs) and chromosomal aberrations (CAs) by lynestrenol.	2005 Mar	15816420
[Multiple endometrial polyps in patient undergoing long-term gestagen therapy].	2005 Sep-Oct	16640190
[Ectopia of cervix of the uterus and hormonal contraception].	2006 Dec	17261880
Two routes of hormonal replacement therapy in symptomatic menopausal women after kidney transplantation.	2006 Jun	16816826
Birth control pills and nonprofessional voice: acoustic analyses.	2006 Oct	17077219
Breast cancer risk associated with different HRT formulations: a register-based case-control study.	2006 Sep 12	16965641
Effects of intranasal 17beta-estradiol administration on serum bioactive interleukin-6 and C-reactive protein levels in healthy postmenopausal women.	2006 Sep-Oct	16894332
[Hormonal contraception and cervix of the uterus pathology].	2007 Apr	17525492
Benefits and risks of hormonal contraception for women.	2007 Aug 10	21289940
Regressive liver adenomatosis following androgenic progestin therapy withdrawal: a case report with a 10-year follow-up and a molecular analysis.	2007 Jun	17535860
Oral progestagens before menopause and breast cancer risk.	2007 Mar 12	17299388
[State of the hypothalamo-hypophyseal-ovarian system in young nullipara women with ectopia of the cervix of uterus during taking the hormonal contraceptives].	2007 Oct	18071207
Laparoscopic hysterectomy of large uteri with uterine artery coagulation at its origin.	2008 Jan-Mar	18402735
Identification of the human cytochrome P450 enzymes involved in the in vitro biotransformation of lynestrenol and norethindrone.	2008 May	18356043
Evaluation of extended and continuous use oral contraceptives.	2008 Oct	19209272
Classification and pharmacology of progestins.	2008 Sep-Oct	19434889
The venous thrombotic risk of oral contraceptives, effects of oestrogen dose and progestogen type: results of the MEGA case-control study.	2009 Aug 13	19679614
Safety, efficacy and patient satisfaction with continuous daily administration of levonorgestrel/ethinylestradiol oral contraceptives.	2009 Nov 3	19936155
Protrhombotic effects of contraceptives.	2010	20858187
Oxidation of lynestrenol by the fungus Cunninghamella elegans.	2010	20013465
Gene expression signatures of breast tissue before and after cross-sex hormone therapy in female-to-male transsexuals.	2010 Dec	20537635

Patents

Sample Use Guides

In Vivo Use Guide

lynestrenol (LYN) in a dose of 15 mg/d

Route of Administration: Oral

In Vitro Use Guide

Lynestrenol markedly enhanced the lymphocyte response to phytohemagglutinin, the mixed lymphocyte culture, the active T-rosette test, the autologous red cell rosettes, and the number of nonadherent cells in the leukocyte adherence inhibition test. Lynestrenol also increased monocyte phagocytosis.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:11:03 GMT 2023` Edited by `admin` on `Fri Dec 15 15:11:03 GMT 2023`
Record UNII	N2Z8ALG4U5
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

LYNESTRENOL

Official Name

English

LYNOESTRENOL

Common Name

English

LYNESTRENOL [MART.]

Common Name

English

LYNESTRENOL [MI]

Common Name

English

19-Nor-17α-pregn-4-en-20-yn-17-ol

Common Name

English

LYNESTRENOL [USAN]

Common Name

English

lynestrenol [INN]

Common Name

English

LYNESTRENOL [USP-RS]

Common Name

English

19 NORPREGN-4-EN-20-YN-17-OL, (17.ALPHA.)-

Common Name

English

LYNESTRENOL [JAN]

Common Name

English

LYNESTRENOL [EP MONOGRAPH]

Common Name

English

Lynestrenol [WHO-DD]

Common Name

English

NSC-37725

Code

English

Classification Tree Code System Code

WHO-VATC

QG03AB02