Dydrogesteron

Dydrogesteron · (9beta,10alpha)-pregna-4,6-diene-3,20-dione · isopregnenone · gynorest · duphaston · hydrogesterone · DH 33 · prodel

https://huagongshe.com/de/chemical/9051

Identifikatoren & physikalische Daten

CAS No.	152-62-5
Summenformel	C21H28O2
Durchschnittliche Molmasse	312,4 g/mol
Monoisotopische Masse	312,20893013 g/mol
SMILES	CC(=O)[C@H]1CC[C@H]2[C@@H]3C=CC4=CC(=O)CC[C@@]4(C)[C@@H]3CC[C@]12C
InChIKey	JGMOKGBVKVMRFX-HQZYFCCVSA-N
PubChem CID	9051
ChEMBL	CHEMBL1200853
ChEBI	CHEBI:31527
EC No.	205-806-8
DTXSID	DTXSID1022974
Lokaler Name	Dydrogesteron

Chemische & physikalische Eigenschaften

XLogP	3,8
Polarare Oberfläche (TPSA)	34,1
H-Brücken-Donoren	0
H-Brücken-Akzeptoren	2
Frei drehbare Bindungen	1
Schwere Atome	23
Formalladung	0
Komplexität	628
LogP (Verteilungskoeffizient)	3.4
Geruch	Odorless
Color/Form	Crystals from acetone + hexaneWhite to off-white...crystalline powder.
Löslichkeit	Soluble in acetone, chloroform (1 in 2), ethanol (1 in 40) and diethyl ether (1 in 200)slightly soluble in fixed oilssparingly soluble in methanol.4.86e-03 g/LPractically insoluble in water, soluble in acetone, sparingly soluble in ethanol (96 per cent).
Schmelzpunkt	168-169170 °C169.5 °C168-173°C
Optical Rotation	Specific optical rotation: -484.5 deg at 25 °C/D (chloroform)
Physical Description	Solid
Siedepunkt	392.36°C (rough estimate)
Dichte	1.0697 (rough estimate)
Brechungsindex	1.4900 (estimate)
Lagerbedingungen	2-8°C
Aggregatzustand	Solid
Farbe	White to Light Yellow
Hauptanwendungen	pharmaceuticalpharmaceutical small molecule
InChI	InChI=1/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+/s3
InChIKey	JGMOKGBVKVMRFX-HQZYFCCVSA-N
SMILES	C[C@@]12CCC(=O)C=C1C=C[C@@]1([H])[C@]3([H])CC[C@H](C(=O)C)[C@@]3(C)CC[C@@]21[H] \|&1:1,10,12,16,20,24,r\|
CAS Datenbank	152-62-5(CAS DataBase Reference)

Sicherheit & Vorschriften

GHS-Einstufung	DangerH372 (97.8%): Causes damage to organs through prolonged or repeated exposure [Danger Specific target organ toxicity, repeated exposure]H410 (91.3%): Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard]P260, P264, P270, P273, P319, P391, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 46 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.
FDA-Anforderungen	The Approved Drug Products with Therapeutic Equivalence Evaluations identifies discontinued drug products. Dydrogesterone is included on this list.
Hazard Classes and Categories	STOT RE 1 (97.8%)Aquatic Chronic 1 (91.3%)
Lagerbedingungen	Do not store above 30 °C.
Entsorgungsverfahren	SRP: At the time of review, regulatory criteria for small quantity disposal are subject to significant revision, however, household quantities of waste pharmaceuticals may be managed as follows: Mix with wet cat litter or coffee grounds, double bag in plastic, discard in trash.SRP: Expired or waste pharmaceuticals shall carefully take into consideration applicable DEA, EPA, and FDA regulations. It is not appropriate to dispose by flushing the pharmaceutical down the toilet or discarding to trash. If possible return the pharmaceutical to the manufacturer for proper disposal being careful to properly label and securely package the material. Alternatively, the waste pharmaceutical shall be labeled, securely packaged and transported by a state licensed medical waste contractor to dispose by burial in a licensed hazardous or toxic waste landfill or incinerator.
Human Toxicity Excerpts	/HUMAN EXPOSURE STUDIES/ The aim of this study was to evaluate the impact of a three-month continuous administration of oral E2, alone, or combined with 2 different dosages of dydrogesterone, on the glucose tolerance and insulin sensitivity in postmenopausal women. In a prospective placebo-controlled study, 43 normal weight and normoinsulinemic women were randomized to receive either 2 mg of oral 17beta E2 daily (group A), or 2 mg E2 daily plus 5 mg daily oral dydrogesterone, from day 14 to 28, in a sequentially combined regimen (group B), or 2 mg of E2 and 10 mg dydrogesterone in the same sequentially combined regimen (group C) or placebo for 12 weeks. An OGTT and a euglycemic hyperinsulinemic clamp were performed before and after treatment. Serum glucose and insulin concentrations were measured both in fasting conditions and after OGTT. C-peptide pancreatic secretion was tested only in fasting conditions. Total body glucose utilization (M), for insulin sensitivity evaluation, was determined in each subject. Postmenopausal women treated with unopposed 17beta E2 (group A) showed a slight but statistically significant decrease of insulin sensitivity (p<0.05). A more marked deterioration of the same parameter was observed in the 2 groups treated with E2 plus dydrogesterone (group B and group C: p<0.01). Post hoc testing for the percent change from baseline indicated that group A significantly differed from group C (p<0.05) and all treated groups significantly differed from the placebo group (p<0.01). Finally, after treatment in group C, a significant reduction of insulin and an increase of glucose responses to OGTT (p<0.01) were observed. These results indicate that, in a short-term period, the use of 17beta E2 and overall 17beta E2 plus dydrogesterone, even with the reduction of insulin plasma levels, might cause a decrease in insulin sensitivity in normal weight and normoinsulinemic post-menopausal women.

Anwendungen & Verwendung

Beschreibung

Dydrogesterone is a synthetic progestogen that has no estrogenic, androgenic, glucocorticoid, or anabolic effects, although it is an agonist of progesterone receptors (EC50 = 12.3 nM) and an antagonist of androgen, mineralocorticoid, and glucocorticoid receptors (IC50s = 28.6, 82.7, and 363 nM, respectively). Dydrogesterone protects against sound stress-induced abortion in mice when administered at a dose of 1.25 mg per animal prior to the stressor on day five of pregnancy. Formulations containing dydrogesterone have been used in hormone replacement therapy, in the treatment of menstrual disorders, and to prevent miscarriage.

Verwenden

Dydrogesterone is a synthetic progestin largely used in hormone therapy, on the central nervous system by studying two markers of the neuroendocrine function: the neurosteroid allopregnanolone and the opioid .beta.-endorphin. Progestogen.