Hydroxyprogesteron
17-Hydroxyprogesterone
Grundinformationen
- CAS
110850-01-6- 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
hydroxyprogesterone68-96-217ALPHA-HYDROXYPROGESTERONE17-HydroxyprogesteroneProdixProdoxGestageno gador17-alpha-Hydroxyprogesterone17-Hydroxypregn-4-ene-3,20-dioneGestagenoHidroxiprogesteronaHydroxyprogesteronum
Weitere Namen anzeigen
17A-HYDROXYPROGESTERONE17α-Hydroxyprogesterone17-OHPHYDROXYPROGESTERONE, 17A-U 3096
17alpha-Hydroxy-4-pregnene-3,20-dione17-OH Progesteronedelta(4)-Pregnene-17alpha-ol-3,20-dione17alpha-Hydroxy-progesteronePregn-4-ene-3,20-dione-17-olIdrossiprogesteronealpha Hydroxy progesteroneDTXSID6040747
Datenbank-Bezeichner
- CAS
110850-01-6、68-96-2- PubChem CID
- 6238
- DTXSID
DTXSID00859075- ChEMBL
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
LipidsLipids -> Sterol Lipids [ST] -> Steroids [ST02] -> C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives [ST0203]
SpringerMaterials PropertiesChemical shift
LogP3.17
Color/FormRHOMBIC OR HEXAGONAL LEAFLETS FROM ACETONE OR ALCOHOL
Solubility0.00648 mg/mL
Animal DrugsPharmaceuticals -> Animal Drugs -> Approved in Taiwan
Endocrine DisruptorsPotential endocrine disrupting compound
Melting Point
222-223 °C
219 - 220 °C
Optical RotationSPECIFIC OPTICAL ROTATION (CHLOROFORM, 1.0417%): +105.6 DEG @ 17 °C/D
Physical DescriptionSolid
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
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.
Other Safety InformationIMAP assessments - Pregn-4-ene-3,20-dione, 17-hydroxy-: Environment tier I assessment
Hazard Classes and CategoriesRepr. 1B (95.1%)
Toxikologische Informationen
Interactions...ESTROGEN ENHANCED SUPPRESSIVE EFFECT OF PROGESTIN & LED TO GENERAL USE OF MIXTURE OF TWO. /PROGESTINS/
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/
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.
Metabolism/Metabolites17alpha-hydroxy-progesterone has known human metabolites that include 17Beta-21-dihydroxyprogesterone.
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/
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