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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 of LYNESTRENOL

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
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 6 / 6
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

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

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Primary
Unknown
Primary
Unknown
Primary
Unknown
Primary
Unknown

Cmax

ValueDoseCo-administeredAnalytePopulation
14.6 ng/mL
1 mg single, oral
NORETHINDRONE serum
Homo sapiens
19.5 ng/mL
2 mg single, oral
NORETHINDRONE serum
Homo sapiens
26.3 ng/mL
5 mg single, oral
NORETHINDRONE serum
Homo sapiens
3.7 ng/mL
150 μg single, oral
LYNESTRENOL plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
64.1 ng × h/mL
1 mg single, oral
NORETHINDRONE serum
Homo sapiens
114.4 ng × h/mL
2 mg single, oral
NORETHINDRONE serum
Homo sapiens
164.2 ng × h/mL
5 mg single, oral
NORETHINDRONE serum
Homo sapiens
47 ng × h/mL
150 μg single, oral
LYNESTRENOL plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
2.5 h
1 mg single, oral
NORETHINDRONE serum
Homo sapiens
4 h
2 mg single, oral
NORETHINDRONE serum
Homo sapiens
4.3 h
5 mg single, oral
NORETHINDRONE serum
Homo sapiens
28.9 h
150 μg single, oral
LYNESTRENOL plasma
Homo sapiens

Doses

AEs

PubMed

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
Record UNII
N2Z8ALG4U5
Record Status Validated (UNII)
Record Version