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Details

Stereochemistry ABSOLUTE
Molecular Formula C21H28O2
Molecular Weight 312.4458
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DYDROGESTERONE

SMILES

CC(=O)[C@H]1CC[C@H]2[C@@H]3C=CC4=CC(=O)CC[C@@]4(C)[C@@H]3CC[C@]12C

InChI

InChIKey=JGMOKGBVKVMRFX-HQZYFCCVSA-N
InChI=1S/C21H28O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h4-5,12,16-19H,6-11H2,1-3H3/t16-,17+,18-,19+,20+,21+/m0/s1

HIDE SMILES / InChI

Molecular Formula C21H28O2
Molecular Weight 312.4458
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

Dydrogesterone is an orally active progestogen which acts directly on the uterus, producing a complete secretory endometrium in an estrogen-primed uterus. At therapeutic levels, dydrogesterone has no contraceptive effect as it does not inhibit or interfere with ovulation or the corpus luteum. Furthermore, dydrogesterone is non-androgenic, non-estrogenic, non-corticoid, non-anabolic and is not excreted as pregnanediol. Dydrogesterone helps to regulate the healthy growth and normal shedding of the uterus lining. Therefore, it may be useful in the treatment of menstrual disorders such as absent, irregular or painful menstrual periods, infertility, premenstrual syndrome and endometriosis. Dydrogesterone works by regulating the healthy growth and normal shedding of the womb lining by acting on progesterone receptors in the uterus. Used to treat irregular duration of cycles and irregular occurrence and duration of periods caused by progesterone deficiency. Also used to prevent natural abortion in patients who have a history of habitual abortions. Dydrogesterone was first introduced to the market in 1961, and is currently approved in over 100 countries world-wide. Banned in the USA and wthdrawn from the UK, but still used in other countries.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
1.9 µM [IC50]
0.5 µM [Ki]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
DUPHASTON
Primary
DUPHASTON
Primary
DUPHASTON

Cmax

ValueDoseCo-administeredAnalytePopulation
2.1 ng/mL
10 mg single, oral
DYDROGESTERONE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
7.7 ng × h/mL
10 mg single, oral
DYDROGESTERONE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
7 h
10 mg single, oral
DYDROGESTERONE plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
10%
10 mg single, oral
DYDROGESTERONE plasma
Homo sapiens

Doses

Overview

OverviewOther

Other InhibitorOther SubstrateOther Inducer







Drug as perpetrator​

Drug as victim

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
Drug dosage varies as per the medical condition. Painful menstruation and irregular menstrual periods: 10 mg twice daily from starting from the 5th day of the menstrual cycle to the 25th day. Endometriosis: 10 mg twice or thrice daily starting from the 5th day of the menstrual cycle to the 25th day. Dysfunctional bleeding/ unexpected bleeding: 10 mg twice daily for a week for stopping bleeding. 10 mg twice daily starting from the 11th day of the menstrual cycle to 25th day to prevent heavy bleeding. Secondary Amenorrhea: Should be given in combination with estrogen therapy. 10 mg twice daily starting from the 11th day of the menstrual cycle to the 25th day.
Route of Administration: Oral
In Vitro Use Guide
Dydrogesterone and its 20-dihydro-metabolite, at concentrations of 5x10(-7) and 5x10(-5)M, inhibited the conversion of E1S to E2 by 14% and 63%, 65% and 74%, respectively, in MCF-7 cells; the values were 15% and 48% and 31% and 51%, respectively, in T-47D cells.
Substance Class Chemical
Record UNII
90I02KLE8K
Record Status Validated (UNII)
Record Version