Progesteron Chemische Eigenschaften,Einsatz,Produktion Methoden
R-Sätze Betriebsanweisung:
R40:Verdacht auf krebserzeugende Wirkung.
R45:Kann Krebs erzeugen.
S-Sätze Betriebsanweisung:
S36/37:Bei der Arbeit geeignete Schutzhandschuhe und Schutzkleidung tragen.
S45:Bei Unfall oder Unwohlsein sofort Arzt zuziehen (wenn möglich, dieses Etikett vorzeigen).
S53:Exposition vermeiden - vor Gebrauch besondere Anweisungen einholen.
Beschreibung
Progesterone, along with pregnenolone, is the biosynthetic precursor of all other steroid hormones. Progesterone is synthesized from cholesterol by the sequential action of desmolase in the mitochondria, which produces pregnenolone, followed by Δ
4,5-
isomerase in the outer mitochondrial membrane and smooth endoplasmic reticulum of steroid-
secreting cells. Progesterone activates the human progesterone receptor with an EC
50 value of 0.5 nM.
Chemische Eigenschaften
White powder. Melting point 121°C. Stable in air. Insoluble in water. A female sex hormone. Low toxicity.
Occurrence
Colchicum luteum also yields this alkaloid.
Definition
ChEBI: Progesterone is a C21-steroid hormone in which a pregnane skeleton carries oxo substituents at positions 3 and 20 and is unsaturated at C(4)-C(5). As a hormone, it is involved in the female menstrual cycle, pregnancy and embryogenesis of humans and other species. It has a role as a contraceptive drug, a progestin, a progesterone receptor agonist, a human metabolite and a mouse metabolite. It is a 20-oxo steroid, a 3-oxo-Delta(4) steroid and a C21-steroid hormone. It derives from a hydride of a pregnane.
Allgemeine Beschreibung
Progesterone, pregn-4-en-3,20-dione, is so rapidly metabolized that it is not particularlyeffective orally, being only one twelfth as active as intramuscularly.An oral formulation of micronized progesterone(Prometrium) is available. Progesterone given intramuscularlycan be very irritating. A vaginal gel containing 4% or8% progesterone offers an alternative dosage form.Progesterone was originally obtained from animal ovariesbut is now prepared synthetically from plant sterol precursors.The discovery of 19-nortestosterones with progesteroneactivity made synthetically modified progestins of tremendoustherapeutic importance.
Progesterone (and all other steroid 4-ene-3-ones) is lightsensitive and should be protected from light.
Air & Water Reaktionen
Insoluble in water.
Reaktivität anzeigen
Progesterone is sensitive to light .
Hazard
A carcinogen (OSHA).
Health Hazard
ACUTE/CHRONIC HAZARDS: Progesterone may be absorbed through the skin.
Brandgefahr
Flash point data for Progesterone are not available; however, Progesterone is probably combustible.
Biologische Aktivität
Endogenous progesterone receptor (PR) agonist (EC 50 = 0.5 nM).
Nebenwirkungen
Common side effects of oral Progesterone include: chest pain, chills, cold or flu-like symptoms; cough or hoarseness; fever, and problems with urination. Rare side effects include: clear or bloody discharge; dimpling of the breast skin, lumps in the breast or armpit; persistent crusting or flaking; redness or swelling of the breast; and sores on the breast skin that do not heal. Other side effects that may occur are: abdominal or stomach pain; constipation, difficulty breathing, dizziness, fast, strong, or irregular heartbeat or pulse; headache, measles, indigestion, itching, joint pain, stiffness, or swelling; rash.
Sicherheitsprofil
NTP 10th Report
on Carcinogens. IARC Cancer Review:
Animal Lirmted Evidence IMEMDT 21,491,79; Animal Sufficient Evidence
IMEMDT 6,135,74. EPA Genetic
Toxicology Program. Reported in EPA
TSCA Inventory.
SAFETY PROFILE: Confirmed carcinogen
with experimental carcinogenic,
neoplastigenic, tumorigenic, and teratogenic
data. Poison by intravenous and
intraperitoneal routes. Human teratogenic
effects by ingestion and parenteral routes:
developmental abnormalities of the
urogenital system. Human male
reproductive effects by intramuscular route:
changes in spermatogenesis, the prostate,
seminal vesicle, Cowper's gland and
accessory glands, impotence, and breast
development. Human female reproductive
effects by ingestion, parenteral, and
intravaginal routes: ferthty changes;
menstrual cycle changes and disorders;
uterus, cervix, and vagina changes.
Experimental reproductive effects. Human
mutation data reported. When heated to
decomposition it emits acrid smoke and
irritating fumes.
Carcinogenicity
Progesterone is reasonably anticipated to be a human carcinogen based on sufficient evidence of carcinogenicity from studies in experimental animals.
läuterung methode
The form crystallises from EtOH with m 127-131o. The -form crystallises from pet ether or aqueous pet ether/aqueous Et2O with m 119-120o or 121o. It also crystallises from Et2O, Me2CO/EtOAc, MeOH, aqueous Et2O, aqueous MeOH, wet pet ether, Et2O/pet ether, pet ether/*C6H6, Et2O/pentane and isopropyl ether. The is at 240nm with log 4.25 (EtOH). [Wintersteiner & Allen J Biol Chem 107 max 321 1934, Beilstein 7 III 3648, 7 IV 2395.]
Progesteron Upstream-Materialien And Downstream Produkte
Upstream-Materialien
Downstream Produkte
17-Hydroxy-16-methylpregna-5,9(11)-diene-3,20-dione 3,20-diethyleneketal
Desoxycortonacetat
16,17-Epoxypregna-5,9(11)-diene-3,20-dione cyclic bis(1,2-ethanediyl acetal)
9-Bromo-11,17,21-trihydroxy-16-methylpregna-1,4-diene-3,20-dione-21-acetate
Pregna-4,16-dien-3,20-dion
17,21-Dihydroxy-16β-methylpregna-1,4,9(11)-trien-3,20-dion-21-acetat
11-α-Hydroxypregn-4-en-3,20-dion
Dexamethason-21-acetat
PREGNANEDIONE
9β,11β-Epoxy-17,21-dihydroxy-16β-methylpregna-1,4-dien-3,20-dion-21-acetat
METHYL 4-AZA-5ALPHA-ANDROSTA-3-ONE-17BETA-CARBOXYLATE
Pregna-4,14-diene-3,20-dione
5-α-Pregnan-3,20-dion
4-Aza-5a-androstan-1-ene-3-one-17b-carboxylic acid
