LYNESTRENOL

Possibly Marketed Outside US

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

C[C@]12CC[C@H]3[C@@H](CCC4=CCCC[C@H]34)[C@@H]1CC[C@@]2(O)C#C

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 8583	Unknown Approved Use Unknown
Dysmenorrhoea, premenstrual syndrome 1 Sources: https://www.dokteronline.com/en/orgametril	Primary	Approved 8583	Unknown Approved Use Unknown
Oligomenorrhea 1 Sources: https://www.dokteronline.com/en/orgametril	Primary	Approved 8583	Unknown Approved Use Unknown
Amenorrhea 18 Sources: https://www.dokteronline.com/en/orgametril	Primary	Approved 8583	Unknown Approved Use Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
14.6 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7172676/	1 mg single, oral dose: 1 mg route of administration: Oral experiment type: SINGLE co-administered:		NORETHINDRONE serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN
19.5 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7172676/	2 mg single, oral dose: 2 mg route of administration: Oral experiment type: SINGLE co-administered:		NORETHINDRONE serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN
26.3 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7172676/	5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered:		NORETHINDRONE serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN
3.7 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23570863/	150 μg single, oral dose: 150 μg route of administration: Oral experiment type: SINGLE co-administered: ETHINYL ESTRADIOL	ETHINYL ESTRADIOL	LYNESTRENOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED

AUC

Value	Dose	Co-administered	Analyte	Population
64.1 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7172676/	1 mg single, oral dose: 1 mg route of administration: Oral experiment type: SINGLE co-administered:		NORETHINDRONE serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN
114.4 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7172676/	2 mg single, oral dose: 2 mg route of administration: Oral experiment type: SINGLE co-administered:		NORETHINDRONE serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN
164.2 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7172676/	5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered:		NORETHINDRONE serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN
47 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23570863/	150 μg single, oral dose: 150 μg route of administration: Oral experiment type: SINGLE co-administered: ETHINYL ESTRADIOL	ETHINYL ESTRADIOL	LYNESTRENOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
2.5 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7172676/	1 mg single, oral dose: 1 mg route of administration: Oral experiment type: SINGLE co-administered:		NORETHINDRONE serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN
4 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7172676/	2 mg single, oral dose: 2 mg route of administration: Oral experiment type: SINGLE co-administered:		NORETHINDRONE serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN
4.3 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7172676/	5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered:		NORETHINDRONE serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN
28.9 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23570863/	150 μg single, oral dose: 150 μg route of administration: Oral experiment type: SINGLE co-administered: ETHINYL ESTRADIOL	ETHINYL ESTRADIOL	LYNESTRENOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED

Doses

Dose	Population	Adverse events
250 mg single, oral Highest studied dose Dose: 250 mg Route: oral Route: single Dose: 250 mg Sources: https://pubmed.ncbi.nlm.nih.gov/5731790/	healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/5731790/	Sources: https://pubmed.ncbi.nlm.nih.gov/5731790/
5 mg 1 times / day multiple, oral Studied dose Dose: 5 mg, 1 times / day Route: oral Route: multiple Dose: 5 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/5332557/	healthy, ADULT Health Status: healthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/5332557/	Disc. AE: Nausea, Nervousness... AEs leading to discontinuation/dose reduction: Nausea (0.3%) Nervousness (0.3%) Fatigue extreme (0.3%) Sources: https://pubmed.ncbi.nlm.nih.gov/5332557/

AEs

AE	Significance	Dose	Population
Fatigue extreme	0.3% Disc. AE	5 mg 1 times / day multiple, oral Studied dose Dose: 5 mg, 1 times / day Route: oral Route: multiple Dose: 5 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/5332557/	healthy, ADULT Health Status: healthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/5332557/
Nausea	0.3% Disc. AE	5 mg 1 times / day multiple, oral Studied dose Dose: 5 mg, 1 times / day Route: oral Route: multiple Dose: 5 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/5332557/	healthy, ADULT Health Status: healthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/5332557/
Nervousness	0.3% Disc. AE	5 mg 1 times / day multiple, oral Studied dose Dose: 5 mg, 1 times / day Route: oral Route: multiple Dose: 5 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/5332557/	healthy, ADULT Health Status: healthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/5332557/

PubMed

Title	Date	PubMed
Gene expression signatures of breast tissue before and after cross-sex hormone therapy in female-to-male transsexuals.	2010-12	20537635
Protrhombotic effects of contraceptives.	2010	20858187
Oxidation of lynestrenol by the fungus Cunninghamella elegans.	2010	20013465
Safety, efficacy and patient satisfaction with continuous daily administration of levonorgestrel/ethinylestradiol oral contraceptives.	2009-11-03	19936155
The venous thrombotic risk of oral contraceptives, effects of oestrogen dose and progestogen type: results of the MEGA case-control study.	2009-08-13	19679614
Classification and pharmacology of progestins.	2009-05-13	19434889
Evaluation of extended and continuous use oral contraceptives.	2008-10	19209272
Identification of the human cytochrome P450 enzymes involved in the in vitro biotransformation of lynestrenol and norethindrone.	2008-05	18356043
Laparoscopic hysterectomy of large uteri with uterine artery coagulation at its origin.	2008-04-12	18402735
[State of the hypothalamo-hypophyseal-ovarian system in young nullipara women with ectopia of the cervix of uterus during taking the hormonal contraceptives].	2007-10	18071207
Benefits and risks of hormonal contraception for women.	2007-08-10	21289940
Regressive liver adenomatosis following androgenic progestin therapy withdrawal: a case report with a 10-year follow-up and a molecular analysis.	2007-06	17535860
[Hormonal contraception and cervix of the uterus pathology].	2007-04	17525492
Oral progestagens before menopause and breast cancer risk.	2007-03-12	17299388
[Ectopia of cervix of the uterus and hormonal contraception].	2006-12	17261880
Birth control pills and nonprofessional voice: acoustic analyses.	2006-10	17077219
Breast cancer risk associated with different HRT formulations: a register-based case-control study.	2006-09-12	16965641
Effects of intranasal 17beta-estradiol administration on serum bioactive interleukin-6 and C-reactive protein levels in healthy postmenopausal women.	2006-08-09	16894332
Two routes of hormonal replacement therapy in symptomatic menopausal women after kidney transplantation.	2006-06	16816826
[Multiple endometrial polyps in patient undergoing long-term gestagen therapy].	2006-04-28	16640190
In vivo induction of sister chromatid exchanges (SCEs) and chromosomal aberrations (CAs) by lynestrenol.	2005-03	15816420
Contraceptive vaginal rings releasing Nestorone and ethinylestradiol: a 1-year dose-finding trial.	2005-02	15707562
Venous thromboembolism after high-dose chemotherapy in a patient with Hodgkin's lymphoma receiving the new oral contraceptive ethinylestradiol and drospirenone ("Yasmine").	2005-01	15531905
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.	2004-03	14969664
Classification and pharmacology of progestins.	2003-12-10	14670641
The effect of ethinyloestradiol and levonorgestrel on the CYP2C19-mediated metabolism of omeprazole in healthy female subjects.	2003-08	12895199
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.	2002-07	12169374
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.	2002-04	11966744
Variegate porphyria with coexistent decrease in porphobilinogen deaminase activity.	2002-01-22	11800145
Leuprorelin and triptorelin: new indication. Preoperative treatment of uterine leiomyoma: no proven value.	2001-06	11718167
Prospective randomized study comparing the GnRH-agonist leuprorelin acetate and the gestagen lynestrenol in the treatment of severe endometriosis.	2001-06	11447732
[Endometriosis of the abdominal wall: diagnosis and treatment techniques].	2001-05	11526776
Pre-operative GnRH analogue therapy before hysterectomy or myomectomy for uterine fibroids.	2001	11405968
[Coronary disease and hormonal treatment during the perimenopausal period].	1998-01	9553405
Camptocormia, a new side effect of sodium valproate.	1987-07	3143551
[Lipoprotein changes during hormonal treatment of endometriosis with lynestrenol and danazol].	1984-03	6562983
[Arterial hypertension during treatment with estro-progestative drugs].	1971-09-01	5153254

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 `Mon Mar 31 17:49:19 GMT 2025` Edited by `admin` on `Mon Mar 31 17:49:19 GMT 2025`
Record UNII	N2Z8ALG4U5
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

LYNESTRENOL

Official Name

English

NSC-37725

Preferred Name

English

LYNOESTRENOL

Common Name

English

LYNESTRENOL [MART.]

Common Name

English

LYNESTRENOL [MI]

Common Name

English

19-Nor-17?-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

Classification Tree Code System Code

WHO-VATC

QG03AB02