313-06-4 Usage
Description
Depofemin, also known as Estradiol Cypionate, is a steroid ester that is the cypionate salt form of estradiol, the most potent naturally produced estrogen. It is characterized by its white to off-white solid appearance and solubility in organic solvents such as ethanol, DMSO, and dimethyl formamide (DMF). Depofemin inhibits ET-1 synthesis via estrogen receptor and is used in various medical applications due to its estrogenic properties.
Uses
Used in Contraceptive Applications:
Depofemin is used as an injectable contraceptive agent, providing a long-lasting and effective method of birth control for women.
Used in Hormone Replacement Therapy (HRT):
Depofemin is used as a hormone replacement agent in post-menopausal women, helping to alleviate symptoms associated with menopause and potentially improving cognition.
Used in Pharmaceutical Industry:
Depofemin is used as an active pharmaceutical ingredient in the development of various medications, primarily focused on hormone-related treatments.
Brand Names:
Depofemin is marketed under the brand names depGynogen (Forest) and Depo (Pharmacia & Upjohn).
Originator
Depo-Estradiol,Upjohn,US,1952
Manufacturing Process
A solution of 80.0 grams (0.294 mol) of estradiol-17β in 860 ml of pyridine
was cooled in an ice-bath and 130.0 grams (0.81 mol) of
cyclopentanepropionyl chloride was added dropwise with stirring during a
period of about 20 minutes. The ice-bath was removed, stirring was continued
for 1 hour and the reaction mixture was allowed to stand at room temperature
overnight. The mixture was warmed on a steam bath and stirred for about 45
minutes, cooled and poured slowly onto about 1,000 grams of ice to which
had been added 330 ml of concentrated sulfuric acid. The precipitated product
was extracted with 400 to 500 mi of ether, and the extract was washed
successively with two 100-ml portions of cold 1 N sulfuric acid, two 100-ml
portions of saturated sodium carbonate solution and water until the pH was 7
and dried over anhydrous sodium sulfate. After removal of the drying agent,
the solution was concentrated to a volume of about 250 ml and an equal
volume of methanol was added.After chilling overnight a total of 120.0 grams (78.5%) of estradiol 3,17β-
dicyclopentanepropionate was obtained which melted at 87° to 90°C. A
sample recrystallized from ether methanol for analysis melted at 90.5° to
91.5°C.To a solution of 2.5 grams (18.1 mmol) of potassium carbonate in 25 ml of
water was added 225 ml of methanol followed by 5.0 grams (9.6 mmol) of
estradiol 3,17β-dicyclopentanepropionate. The mixture was stirred for 2?
hours at 202°C during which time some precipitation occurred. The mixture was poured into 700 ml of water with efficient stirring and the precipitated
solid was removed by filtration, washed with water and dried.Recrystallization of the crude product from 80% methanol gave 3.16 grams
(83%) of estradiol 17β-cyclopentanepropionate melting at 148° to 151°C.
Recrystallization from benzenepetroleum ether raised the MP to 151° to
152°C.
Therapeutic Function
Estrogen
Biological Activity
estradiol cypionate is the 17 β-cyclopentylpropinate ester of estradiol, which inhibits et-1 synthesis via estrogen receptor.
Safety Profile
An experimental
teratogen. Other experimental reproductive
effects. A steroid. When heated to
decomposition it emits acrid smoke and
fumes.
Mode of action
Estradiol cypionate diffuses through the cell membrane and binds to and subsequently activates the nuclear estrogen receptor found in the reproductive tract, breast, pituitary, hypothalamus, liver, and bone. The activated complex binds to the estrogen response element on the DNA and activates the transcription of genes involved in the functioning of the female reproductive system and secondary sex characteristics.
Check Digit Verification of cas no
The CAS Registry Mumber 313-06-4 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 3,1 and 3 respectively; the second part has 2 digits, 0 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 313-06:
(5*3)+(4*1)+(3*3)+(2*0)+(1*6)=34
34 % 10 = 4
So 313-06-4 is a valid CAS Registry Number.
InChI:InChI=1/C26H36O3/c1-26-15-14-21-20-10-8-19(27)16-18(20)7-9-22(21)23(26)11-12-24(26)29-25(28)13-6-17-4-2-3-5-17/h8,10,16-17,21-24,27H,2-7,9,11-15H2,1H3/t21?,22?,23?,24-,26-/m0/s1