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Estradiol cypionate

Estradiol cypionate structure

CAS No:
313-06-4
Formula:
C26H36O3
Chemical Name:
Estradiol cypionate
Synonyms:
Estra-1,3,5(10)-triene-3,17-diol (17β)-,17-cyclopentanepropanoate;Estradiol,17-cyclopentanepropionate;Cyclopentanepropionic acid,3-hydroxyestra-1,3,5(10)-trien-17β-yl ester;Cyclopentanepropionic acid,17-ester with estradiol;Depoestradiol;Depo-estradiol cyclopentylpropionate;Depofemin;Estradiol 17β-cyclopentanepropionate;Estradiol 17β-cyclopentylpropionate;Estradiol cyclopentylpropionate;17β-Estradiol 17-cyclopentylpropionate;Estradiol 17β-cypionate;Depoestradiol cypionate;Estradiol 17-cypionate;ECP;Estradep;Depo-Estradiol;Estradiol 17-cyclopentylpropionate;Estradiol cypionate;Depgynogen;NSC 3354;Estradiolum valerianicum
Categories:
Biochemical Engineering > Inhibitors

Description

Estradiol cypionate is a 17 β-cyclopentylpropinate ester of estradiol, inhibits ET-1 synthesis via estrogen receptorIC50 value:Target: estrogen receptorEstradiol cypionate is a synthetic ester, is a estrogen. Compared to other commonly used estradiol esters, via the intramuscular route, Estradiol cypionate is found to have the longest duration of action with a duration of ~11 days,

Estradiol 17beta-cyclopentylpropionate is a steroid ester.|Estradiol Cypionate is a pro-drug ester of [DB00783], a naturally occurring hormone that circulates endogenously within the human body. Estradiol is the most potent form of all mammalian estrogenic steroids and acts as the major female sex hormone. As a pro-drug of estradiol, estradiol cypionate therefore has the same downstream effects within the body through binding to the Estrogen Receptor (ER) including ERα and ERβ subtypes, which are located in various tissues and organs such as the breasts, uterus, ovaries, skin, prostate, bone, fat, and brain. [DB00783] is commonly produced with an ester side-chain as endogenous estradiol has very low oral bioavailability on its own (2-10%). First-pass metabolism by the gut and the liver quickly degrades the estradiol molecule before it gets a chance to enter systemic circulation and exert its estrogenic effects. Esterification of estradiol aims to improve absorption and bioavailability after oral administration (such as with Estradiol Valerate) or to sustain release from depot intramuscular injections (such as with Estradiol Cypionate) through improved lipophilicity. Following absorption, the esters are cleaved, resulting in the release of endogenous estradiol, or 17β-estradiol. Ester pro-drugs of estradiol are therefore considered to be bioidentical forms of estrogen. Estradiol cypionate is commercially available as Depo-Estradiol, an intramuscular depot injection used for the treatment of moderate to severe vasomotor symptoms associated with menopause and for the treatment of hypoestrogenism due to hypogonadism. The primary source of estrogen in normally cycling adult women is the ovarian follicle, which secretes 70 to 500 mcg of estradiol daily, depending on the phase of the menstrual cycle. However, after menopause, most endogenous estrogen is produced by conversion of androstenedione, secreted by the adrenal cortex, to estrone by peripheral tissues. Thus, estrone and the sulfate conjugated form, estrone sulfate, are the most abundant circulating estrogens in postmenopausal women. Although circulating estrogens exist in a dynamic equilibrium of metabolic interconversions, estradiol is the principal intracellular human estrogen and is substantially more potent than its metabolites, estrone and estriol at the receptor level. Because of the difference in potency between estradiol and estrone, menopause (and a change in primary hormone from estradiol to estrone) is associated with a number of symptoms associated with this reduction in potency and in estrogenic effects. These include hot flashes, vaginal dryness, mood changes, irregular menses, chills, and sleeping problems. Administration of synthetic and bioidentical forms of estrogen, such as estradiol cypionate, has shown to improve these menopausal symptoms.|Estradiol Cypionate is the cypionate salt form of estradiol, the most potent, naturally produced estrogen. 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.

Estradiol cypionate Basic Attributes

Molecular Weight：

396.56

Exact Mass：

396.56

EC Number：

206-237-8

UNII：

7E1DV054LO

NSC Number：

3354

DSSTox ID：

DTXSID4022999

NCI Thesaurus Code：

C47991

HScode：

29372390

Characteristics

PSA：

46.53000

XLogP3：

7.59

Appearance：

White or off-white crystalline powder

Density：

1.2±0.1 g/cm3

Melting Point：

151-152 °C

Boiling Point：

532.8±50.0 °C at 760 mmHg

Flash Point：

207.7±22.9 °C

Refractive Index：

1.579

Specific rotation：

D25 +45° (chloroform)

Safety Information

Transport codes：

NONH for all modes of transport

wgk germany：

hazard class code：

45-46-61-20/21/22-36/37/38

safety instructions：

53-22-36/37/39-45-26

RTECS Number：

KG4600000

Marks：

T,Xi

Precautionary statement(s)：

P201-P280-P308 + P313

Hazard Statements：

H302-H312-H332-H350-H360

Toxicity

Protein Binding：

Estrogens circulate in the blood largely bound to sex hormone binding globulin (SHBG) and albumin.

Drug Information

Drug Indication：

Depo-Estradiol intramuscular depot injection is indicated for the treatment of moderate to severe vasomotor symptoms and hypoestrogenism due to hypogonadism.|FDA Label

Pharmacology：

Estrogen mediates its effects across the body through potent agonism of the Estrogen Receptor (ER), which is located in various tissues including in the breasts, uterus, ovaries, skin, prostate, bone, fat, and brain. Estradiol binds to both subtypes of the Estrogen Receptor: Estrogen Receptor Alpha (ERα) and Estrogen Receptor Beta (ERβ). Estradiol also acts as a potent agonist of G Protein-coupled Estrogen Receptor (GPER), which has recently been recognized as a major mediator of estradiol's rapid cellular effects.

MeSH：

Chemical substances or agents with contraceptive activity in females. Use for female contraceptive agents in general or for which there is no specific heading. (See all compounds classified as Contraceptive Agents, Female.)|Contraceptive agents that act on the ENDOCRINE SYSTEM. (See all compounds classified as Contraceptive Agents, Hormonal.)

Absorption：

When conjugated with aryl and alkyl groups for parenteral administration, the rate of absorption of oily preparations is slowed with a prolonged duration of action, such that a single intramuscular injection of estradiol valerate or estradiol cypionate is absorbed over several weeks.|Estradiol, estrone and estriol are excreted in the urine along with glucuronide and sulfate conjugates.|The distribution of exogenous estrogens is similar to that of endogenous estrogens. Estrogens are widely distributed in the body and are generally found in higher concentrations in the sex hormone target organs.

Metabolism/Metabolites：

Exogenous estrogens are metabolized in the same manner as endogenous estrogens. Circulating estrogens exist in a dynamic equilibrium of metabolic interconversions. These transformations take place mainly in the liver. Estradiol is converted reversibly to estrone, and both can be converted to estriol, which is the major urinary metabolite. Estrogens also undergo enterohepatic recirculation via sulfate and glucuronide conjugation in the liver, biliary secretion of conjugates into the intestine, and hydrolysis in the gut followed by reabsorption. In postmenopausal women, a significant proportion of the circulating estrogens exist as sulfate conjugates, especially estrone sulfate, which serves as a circulating reservoir for the formation of more active estrogens.

Mechanism of Action：

Estradiol enters target cells freely (e.g., female organs, breasts, hypothalamus, pituitary) and interacts with a target cell receptor. When the estrogen receptor has bound its ligand it can enter the nucleus of the target cell, and regulate gene transcription which leads to formation of messenger RNA. The mRNA interacts with ribosomes to produce specific proteins that express the effect of estradiol upon the target cell. Estrogens increase the hepatic synthesis of sex hormone binding globulin (SHBG), thyroid-binding globulin (TBG), and other serum proteins and suppress follicle-stimulating hormone (FSH) from the anterior pituitary. Increases in the down-stream effects of ER binding reverses some of the symptoms of menopause and of hypoestrogenism, which are primarily caused by a loss of estrogenic activity.

MeSH Entry Terms：

Depo-estradiol

Estradiol cypionate Use and Manufacturing

Uses

estrogen

Manufacturing Info：

Estra-1,3,5(10)-triene-3,17-diol (17.beta.)-, 17-cyclopentanepropanoate: INACTIVE

Use Classification：

Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients|Pharmaceuticals

Computed Properties

Molecular Weight:396.6
XLogP3:7.1
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:5
Exact Mass:396.26644501
Monoisotopic Mass:396.26644501
Topological Polar Surface Area:46.5
Heavy Atom Count:29
Complexity:597
Defined Atom Stereocenter Count:5
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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