Grundinformationen
- Standard-SMILES
CC(=O)[C@@]1(O)CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3CC[C@@]21C- InChIKey
DBPWSSGDRRHUNT-CEGNMAFCSA-N- Summenformel
- C21H30O3
- Durchschnittliche Molmasse
- 330,5 g/mol
Überblick
17alpha-hydroxyprogesterone is a 17alpha-hydroxy steroid that is the 17alpha-hydroxy derivative of progesterone. It has a role as a metabolite, a progestin, a mouse metabolite and a human metabolite. It is a 17alpha-hydroxy-C21-steroid, a tertiary alpha-hydroxy ketone and a 17alpha-hydroxy steroid. It is functionally related to a progesterone.
Namen und Bezeichner
- Bevorzugter Name
- 17-Hydroxyprogesterone
- IUPAC
- (8R,9S,10R,13S,14S,17R)-17-acetyl-17-hydroxy-10,13-dimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-3-one
- Lokaler Name
- Hydroxyprogesteron
- Englischer Name
- 17α-Hydroxyprogesterone
- Summenformel
- C21H30O3
- Molmasse
- 330.46
Namen und Synonyme
Weitere Namen anzeigen
Datenbank-Bezeichner
- CAS
110850-01-6、68-96-2- PubChem CID
- 6238
- DTXSID
DTXSID00859075- ChEMBL
CHEMBL1062- ChEBI
CHEBI:17252- UNII
- 21807M87J2
- EC Number
- 200-699-4
- Nikkaji
- J4.862C
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 3,2
- Polarare Oberfläche (TPSA)
- 54,4 Ų
- H-Brücken-Donoren
- 1
- H-Brücken-Akzeptoren
- 3
- Frei drehbare Bindungen
- 1
- Schwere Atome
- 24
- Formalladung
- 0
- Komplexität
- 635
Experimentelle und physikochemische Eigenschaften
Melting Point
222-223 °C
219 - 220 °C
Collision Cross Section
184.4 Ų [M-H]- [CCS Type: DT; Buffer gas: N2; Ionization: ESI-; Dataset: TOXCAST; Source Identifier: DTXSID6040747]
183.4 Ų [M+H]+ [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]
187.57 Ų [M+H]+ [CCS Type: DT; Method: stepped-field]
179.9 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
202.46 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
187 Ų [M-H]-
Physikochemische Eigenschaften
- Schmelzpunkt
- 276 °C · 276°C
- Siedepunkt
- 407.89 °C · 407.89°C (rough estimate)
- Dichte
- 1.0998 · 1.0998 (rough estimate)
- Brechungsindex
- 90 ° · 90 ° (C=1, CHCl3)
- Flammpunkt
- 9 ℃ · 9℃
- storage temp.
- Sealed in dry,Room Temperature
- Löslichkeit
- soluble in Chloroform
- Aggregatzustand
- Solid
- pka
- 13.03 · 13.03±0.60(Predicted)
- Farbe
- White to Almost white
- Wasserlöslichkeit
- 5.056 mg/L · 5.056mg/L(20 ºC)
- Merck
- 14 · 14,4839
- BRN
- 3218109 · 3218109
- Major Application
- pharmaceutical small molecule
- CAS Datenbank
- 68 · 68-96-2(CAS DataBase Reference)
- NIST chemische Informationen
- -4 · Pregn-4-ene-3,20-dione, 17-hydroxy-(68-96-2)
Sicherheit und Regulatorisches
GHS-Klassifizierung
GHS Classification
Danger
H360 (95.1%): May damage fertility or the unborn child [Danger Reproductive toxicity]
P203, P280, P318, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 41 reports by companies from 4 notifications to the ECHA C&L Inventory.
Gefahrenhinweise
Regulatory Information
Status: Active Update: 28-07-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/20280
Hydroxyprogesterone: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
Toxikologische Informationen
Human Toxicity Excerpts
...MAY CAUSE EDEMA & LOCAL REACTIONS @ SITE OF INJECTION.
MOST COMMON EFFECTS ARE NAUSEA, EDEMA, & IRREGULAR VAGINAL BLEEDING. OTHER REPORTED EFFECTS INCL WT GAIN, DECR LIBIDO, DEPRESSION, JAUNDICE, & CONGESTIVE HEART FAILURE. /CAPROATE/
...HYDROXYPROGESTERONE CAPROATE OCCASIONALLY CAUSES HYPERSENSITIVITY, COUGHING, OR DYSPNEA. IN RARE INSTANCES IT MAY CAUSE VIRILIZATION OF FEMALE FETUS. /CAPROATE/
CONTINUOUS ADMIN OF PROGESTIN IN SUFFICIENT DOSE ABOLISHES CYCLE FOR AS LONG AS IT IS GIVEN & LEADS TO OVARIAN & ENDOMETRIAL ATROPHY. VERY SMALL DOSES MAY ALTER STRUCTURE OF ENDOMETRIUM & CONSISTENCY OF CERVICAL MUCUS WITHOUT DISRUPTING CYCLE OR INHIBITING OVULATION. /PROGESTINS/
For more Human Toxicity Excerpts (Complete) data for 17ALPHA-HYDROXYPROGESTERONE (10 total), please visit the HSDB record page.
Non-Human Toxicity Excerpts
NO VIRILIZING EFFECTS WERE OBSERVED IN DBA MICE GIVEN DAILY SC INJECTIONS OF 0.25 MG 17ALPHA-HYDROXYPROGESTERONE CAPROATE ON DAYS 16-19 OF GESTATION OR IN SPRAGUE-DAWLEY RATS GIVEN 5 MG DAILY FROM DAY 14-19 OF GESTATION. /CAPROATE/
OF 19 YOUNG, RANDOM-BRED FEMALE RABBITS INJECTED IM WITH 13 MG...IN SESAME OIL ON ALTERNATE WK FOR UP TO 109 WK, 14 DEVELOPED...CYSTS OF ENDOMETRIUM DURING 1ST 267 DAYS. IN 7/8 ANIMALS...ALIVE @ 109 WK, CYSTS WERE UNILOCULAR... IN CONTROL...FEW CYSTS...LESS THAN 0.3 MM IN DIAM...SMALL NON-NEOPLASTIC POLYPS... /CAPROATE/
Sicherheitsdaten
- wgk
- 3
- ridadr
- UN1230 - class 3 - PG 2 - Methanol, solution
- hs_code
- 38220090
- RTECS-Nr.
- TU5060000
- risk_code
- 61-39/23/24/25-23/24/25-11
- hazard_code
- T,F
- safety_code
- 53-22-36/37/39-45-36/37-16
- Giftige Stoffe Daten
- 68-96-2(Hazardous Substances Data)
Chemie und Industrie
Pharmakologische Informationen
ATC Code
G - Genito urinary system and sex hormones
QG - Genito urinary system and sex hormones
Mechanism of Action
ADMIN OF ESTROGEN & PROGESTIN, AS CONTAINED IN COMBINATION OR SEQUENTIAL PREPN, COULD INTERFERE WITH FERTILITY IN ANY ONE OF SEVERAL WAYS. HOWEVER, IT IS CLEAR THAT, AS CURRENTLY USED, MIXTURE INHIBITS OVULATION. ...CONTINUED ACTION OF PROGESTERONE SERVES TO INHIBIT RELEASE OF LH. /PROGESTINS/
IT ACTS AS ANTIGONADOTROPHIC AGENT ON ANTERIOR PITUITARY INHIBITING FSH RELEASE &, THUS, FOLLICULAR GROWTH, ESTROGEN PRODUCTION, & ESTRUS. IT ALSO INHIBITS LH RELEASE, THUS PREVENTING OVULATION, CORPORA LUTEA FORMATION, & FURTHER PROGESTERONE SECRETION. BY INHIBITING LH...HOLDS PROGESTERONE LEVELS IN CHECK.
FDA Pharmacological Classification
21807M87J2
HYDROXYPROGESTERONE
Chemical Structure [CS] - Progesterone Congeners
Established Pharmacologic Class [EPC] - Progestin
Hydroxyprogesterone is a Progestin.
Absorption, Distribution and Excretion
...DURATION OF ACTION IS LONGER /THAN PROGESTERONE/, BUT ITS ONSET OF ACTION IS SLOWER. SINGLE INJECTION OF SOLN OF HYDROXYPROGESTERONE CAPROATE IN OIL WILL EXERT PROGESTATIONAL EFFECTS FOR 1-2 WK. /CAPROATE/
ABOUT 50-60% OF ADMIN RADIOACTIVE PROGESTERONE APPEARS IN URINE & ABOUT 10% IN FECES. ... WHEN PROGESTERONE IS GIVEN FOR PROLONGED PERIOD, DURING LUTEAL PHASE OF CYCLE, OR DURING PREGNANCY, LARGER PROPORTION (25-30%) APPEARS IN URINE AS PREGUANEDIOL. /PROGESTERONE/
RATE OF TURNOVER OF ENDOGENOUS PROGESTERONE IS UNUSUALLY RAPID, T/2 IN BLOOD BEING FEW MIN, & DOUBTLESS EXOGENOUS MATERIAL IS HANDLED IN SAME WAY. SMALL AMT...IS STORED IN BODY FAT... PRESUMABLY, ABSORPTION FROM INTESTINAL TRACT IS PROMPT, BUT COMPD IS RAPIDLY TRANSFORMED DURING PASSAGE THROUGH LIVER... /PROGESTERONE/
Verwendung und Herstellung
Uses
MEDICATION (VET)
MEDICATION
Use (kg; approx.) in Germany (2009): >25
This is an endogenously produced metabolite found in the human body. It is used in metabolic reactions, catabolic reactions or waste generation.
Methods of Manufacturing
HYDROXYPROGESTERONE IS ESTERIFIED BY HEATING WITH CAPROIC ANHYDRIDE IN PRESENCE OF P-TOLUENE-SULFONIC ACID UNDER ATMOSPHERE OF NITROGEN. US PATENT 2,753,360. /CAPROATE/
JULIAN ET AL, US PATENT 2,648,662 (1953 TO GLIDDEN)...STORK ET AL, US PATENTS 2,802,839 & 2,805,203 (BOTH 1957 TO SYNTEX)...DULANEY, MCALEER; US PATENTS 2,777,843; 2,786,856/7; 2,813,060 (ALL 1957 TO MERCK & CO)...PEDERSON, US PATENT 3,000,883 (1961 TO UPJOHN).
General Manufacturing Information
PROGESTINS CANNOT BE EQUATED AS GROUP WITH PROGESTERONE BECAUSE SOME ARE INHERENTLY ESTROGENIC, SOME SLIGHTLY ANDROGENIC, & SOME PURELY PROGESTATIONAL; CORRESPONDINGLY, THEIR OVULATION-INHIBITING POTENTIALITIES MAY BE MEDIATED IN SOMEWHAT DIFFERENT WAYS. /PROGESTINS/
Anwendungen
VerwendenProgesteron. It was isolated from adrenal glands.
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Ergänzende Hinweise
DefinitionChEBI: A 17alpha-hydroxy steroid that is the 17alpha-hydroxy derivative of progesterone.
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