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Estradiol benzoate

Estradiol benzoate structure

CAS No:
50-50-0
Formula:
C25H28O3
Chemical Name:
Estradiol benzoate
Synonyms:
Estra-1,3,5(10)-triene-3,17-diol (17β)-,3-benzoate;Estradiol,3-benzoate;Benovocylin;Benzhormovarine;Benzoestrofol;Benzofoline;Benzo-Gynoestryl;De Graafina;Diffollisterol;Difolliculine;Dimenformon benzoate;Diogyn B;Eston B;1,3,5(10)-Estratriene-3,17β-diol 3-benzoate;Femestrone;Graafina;Gynecormone;Hidroestron;Hormogynon;Oestroform [BDH];Ovasterol B;Ovocyclin M;Ovocyclin Benzoate;Ovocyclin MB;Primogyn B;Progynon B;Progynon benzoate;Recthormone Oestradiol;Unistradiol;Solestro;17β-Estradiol 3-benzoate;β-Estradiol 3-benzoate;Estradiol benzoate;Estradiol monobenzoate;β-Estradiol benzoate;3-Benzoyloxy-17β-hydroxyestra-1,3,5(10)-triene;Gynformone;Ovahormon benzoate;Primogyn B oleosum;17β-Estradiol benzoate;Folone;Agofollin Depot;Agofollin;Benztrone;Pelanin benzoate;NSC 9566;Cidirol;Estrogin;Mesalin;Ric-BE;Gonadiol;SY Esrone;Difolliculin;Oestradiol benzoate;1713228-24-0
Categories:
Active Pharmaceutical Ingredients > Hormones and the Endocrine System

Description

Estradiol benzoate is a synthetic ester, is the first form of estrogen to be marketed.

17beta-estradiol 3-benzoate is a benzoate ester resulting from the formal condensation of benzoic acid with the phenolic hydroxy group of 17beta-estradiol. It has a role as a xenoestrogen and an estrogen receptor agonist. It is a benzoate ester and a 17beta-hydroxy steroid. It derives from a 17beta-estradiol.|Estradiol Benzoate 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 benzoate 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 including in 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 improves 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 benzoate is not currently available in Canada or the US.|Estradiol Benzoate is the synthetic benzoate ester of estradiol, a steroid sex hormone vital to the maintenance of fertility and secondary sexual characteristics in females. As the primary, most potent estrogen hormone produced by the ovaries, estradiol binds to and activates specific nuclear receptors. This agent exhibits mild anabolic and metabolic properties, and increases blood coagulability. (NCI04)

Estradiol benzoate Basic Attributes

Molecular Weight：

376.49

Exact Mass：

376.49

EC Number：

200-043-7

UNII：

1S4CJB5ZGN

NSC Number：

9566

DSSTox ID：

DTXSID9022998

NCI Thesaurus Code：

C29769

HScode：

29372319

Characteristics

PSA：

46.5

XLogP3：

4.5

Density：

1.2±0.1 g/cm3

Melting Point：

196 °C

Boiling Point：

531.2°C at 760 mmHg

Flash Point：

212.0±22.9 °C

Refractive Index：

1.604

Water Solubility：

0.4mg/L(25 ºC)

Specific rotation：

D25 +58 to +63° (c = 2 in dioxane)

Safety Information

Packing level：

Ⅲ

Transport codes：

2811

wgk germany：

hazard class code：

60-61-40

safety instructions：

53-22-36/37/39-45

RTECS Number：

KG4050000

Marks：

Precautionary statement(s)：

P201-P280-P308 + P313

Hazard Statements：

H351-H360

GHS Classification：

|Danger|H302 (28.33%): Harmful if swallowed [Warning Acute toxicity, oral]|P201, P202, P261, P264, P270, P271, P280, P281, P301+P312, P302+P352, P304+P312, P304+P340, P308+P313, P312, P322, P330, P363, P405, and P501|Aggregated GHS information provided by 60 companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Toxicity

Protein Binding：

Estrogens circulate in the blood largely (>95%) bound to sex hormone binding globulin (SHBG) and to albumin.

Drug Information

Drug Indication：

Estradiol benzoate is not currently available in any FDA or Health Canada approved products.

Pharmacology：

Estradiol, the principal intracellular human estrogen, is substantially more active than its metabolites, estrone and estriol, at the cellular level.

MeSH：

Contraceptive agents that act on the ENDOCRINE SYSTEM. (See all compounds classified as Contraceptive Agents, Hormonal.)

Metabolism/Metabolites：

Exogenous estrogens are metabolized using the same mechanism as endogenous estrogens. Estrogens are partially metabolized by cytochrome P450.

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.

MeSH Entry Terms：

17beta-estradiol-3-benzoate

Estradiol benzoate Use and Manufacturing

Uses

Estradiol is the major estrogen secreted by the premenopausal ovary. Estradiol benzoate is an estradiol analog which contains a benzyl ester at the C-3 position. Estradiol benzoate is useful in the treatment of lesions produced by diminution of bodily production of estrogens.

Use Classification：

Pharmaceuticals -> Animal Drugs -> Approved in Taiwan

Computed Properties

Molecular Weight:376.5
XLogP3:4.5
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:3
Exact Mass:376.20384475
Monoisotopic Mass:376.20384475
Topological Polar Surface Area:46.5
Heavy Atom Count:28
Complexity:582
Defined Atom Stereocenter Count:5
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Drug Function and Efficacy

The benzoate of natural estradiol contained in this product has the pharmacological effects of estradiol. It promotes and regulates the normal development of female reproductive organs and secondary sexual characteristics. Estradiol is the estrogen with the highest receptor activity level secreted by the ovaries in women of childbearing age. After menopause, the ovaries fail and the production of estradiol almost stops, causing vascular dysfunction and unstable body temperature regulation. Clinical manifestations include hot flashes, sweating, sleep disorders, atrophy of the urogenital system and osteoporosis.

This ingredient has been used in drugs with the following functions (note: it does not mean that the ingredient itself has the following health functions)

Related Drugs

Estradiol benzoate ointment
Ingredients	3-Hydroxyestr-1,3,5(10)-triene-17b-ol-3-benzoate. Structural formula: Molecular formula: C25H28O3 Molecular weight: 376.50
Indication	1. When used with anticoagulants, estrogen can reduce the anticoagulant effect. If it must be used together, the dosage of the anticoagulant should be adjusted. 2. When used with carbamazepine, phenobarbital, phenytoin sodium, primidone, rifampicin, etc., the effect of estrogen can be reduced. This is due to the induction of liver microsomal enzymes and the acceleration of estrogen metabolism. 3. When used with tricyclic antidepressants, large amounts of estrogen can enhance the adverse reactions of antidepressants and reduce their proper effects. 4. When used with antihypertensive drugs, the antihypertensive effect can be reduced. 5. Reduce the therapeutic effect of tamoxifen. 6. Increase the absorption of calcium.
Specifications	1.5g:1.35mg
Manufacturer	Medisea Pharmaceutical Co., Ltd.

Estradiol Benzoate Injection
Ingredients	The main ingredient of this product is estradiol benzoate. Its chemical name is: 3-hydroxyestrone-1,3,5 (10)-triene-17beta;-ol-3-benzoate. Its structural formula is: Molecular formula: C25H28O3 Molecular weight: 376.50
Indication	When used in combination with hypoglycemic drugs, their hypoglycemic effect may be weakened and the dosage should be adjusted.
Specifications	1ml:1mg
Manufacturer	Guangzhou Baiyunshan Mingxing Pharmaceutical Co., Ltd.

Estradiol Benzoate Injection
Ingredients	The main ingredient of this product is estradiol benzoate. Its chemical name is: 3-hydroxyestrone-1,3,5 (10)-triene-17beta;-ol-3-benzoate. Its structural formula is: Molecular formula: C25H28O3 Molecular weight: 376.50
Indication	When used in combination with hypoglycemic drugs, their hypoglycemic effect may be weakened and the dosage should be adjusted.
Specifications	1ml:5mg
Manufacturer	Tianjin Pharmaceutical Heping (Tianjin) Pharmaceutical Co., Ltd.

See More Related Drugs

Registered Holders

VALDEPHARM

France
Active
Zhejiang Xianju Pharmaceutical Co., Ltd.

China
Active
VALDEPHARM Val De

European Union
Active

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