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Details

Stereochemistry ABSOLUTE
Molecular Formula C21H30O3
Molecular Weight 330.4611
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of HYDROXYPROGESTERONE

SMILES

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

InChI

InChIKey=DBPWSSGDRRHUNT-CEGNMAFCSA-N
InChI=1S/C21H30O3/c1-13(22)21(24)11-8-18-16-5-4-14-12-15(23)6-9-19(14,2)17(16)7-10-20(18,21)3/h12,16-18,24H,4-11H2,1-3H3/t16-,17+,18+,19+,20+,21+/m1/s1

HIDE SMILES / InChI

Molecular Formula C21H30O3
Molecular Weight 330.4611
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

17α-Hydroxyprogesterone (17α-OHP), or hydroxyprogesterone (OHP), also known as 17α-hydroxypregn-4-ene-3, 20-dione is used under the brand name Gestageno, and has been marketed for clinical use in Argentina. It was indicated for female infertility, hypertrichosis, menstrual disorders, premature labour, threatened or recurrent miscarriage. It is used to properly regulate the menstrual cycle and treat unusual stopping of the menstrual periods (amenorrhea). To help a pregnancy occur during egg donor or infertility procedures in women who do not produce enough progesterone. To prevent estrogen from thickening the lining of the uterus (endometrial hyperplasia) in women around menopause who are being treated with estrogen for ovarian hormone therapy (OHT). To treat a condition called endometriosis, to help prevent endometrial hyperplasia, or to treat unusual and heavy bleeding of the uterus (dysfunctional uterine bleeding) by starting or stopping the menstrual cycle. 17α-OHP is an agonist of the progesterone receptor (PR) similarly to progesterone. In addition, it is an antagonist of the mineralocorticoid receptor (MR) as well as a partial agonist of the glucocorticoid receptor (GR), albeit with very low potency (EC50 >100-fold less relative to cortisol) at the latter site, also similarly to progesterone.

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Gestageno
Primary
Gestageno
Preventing
Gestageno
Preventing
Gestageno

Cmax

ValueDoseCo-administeredAnalytePopulation
12.5 ng/mL
250 mg 1 times / week steady-state, intramuscular
HYDROXYPROGESTERONE CAPROATE plasma
Homo sapiens
5 ng/mL
250 mg 1 times / week multiple, intramuscular
HYDROXYPROGESTERONE CAPROATE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
1269.6 ng × h/mL
250 mg 1 times / week steady-state, intramuscular
HYDROXYPROGESTERONE CAPROATE plasma
Homo sapiens
571.4 ng × h/mL
250 mg 1 times / week multiple, intramuscular
HYDROXYPROGESTERONE CAPROATE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
16.4 day
250 mg 1 times / week multiple, intramuscular
HYDROXYPROGESTERONE CAPROATE plasma
Homo sapiens

Doses

PubMed

Sample Use Guides

In Vivo Use Guide
from 200 mg to 300 mg orally every 24 hours from the cycle day 15 to 28
Route of Administration: Other
In Vitro Use Guide
Linear regression analysis showed statistically significant linear inhibition of transactivation of the human mineralocorticoid receptor (hMR) by 10(-10) M aldosterone in the presence of increasing 17-hydroxyprogesterone (17OHP) [F(1,5) = 11.34, p = 0.019] and progesterone [F(1,5) = 11.08, p = 0.021] concentrations.
Substance Class Chemical
Record UNII
21807M87J2
Record Status Validated (UNII)
Record Version