Estradiol Cypionate

HCID 9403

Basic information

CAS
313-06-4
Standard SMILES
C[C@]12CC[C@@H]3c4ccc(O)cc4CC[C@H]3[C@@H]1CC[C@@H]2OC(=O)CCC1CCCC1
InChIKey
UOACKFBJUYNSLK-XRKIENNPSA-N
Molecular formula
C26H36O3
Average molar mass
396.6 g/mol
Monoisotopic mass
396.26644501

Overview

Estradiol 17beta-cyclopentylpropionate is a steroid ester.

Names & identifiers

Preferred name
Estradiol Cypionate
IUPAC
[(8R,9S,13S,14S,17S)-3-hydroxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl] 3-cyclopentylpropanoate
English name
Estradiol Cypionate
Molecular formula
C26H36O3
Molecular weight
396.57

Names & synonyms

estradiol cypionate313-06-4Depo-EstradiolEstradiol cipionateEstradiol, 17-cyclopentanepropionateDTXSID402299917beta-Estradiol 17-cyclopentylpropionateNSC-33547E1DV054LONSC3354Estradiol cypionate (USP)Estradiol cypionate [USP]
Show more names
EstrofemEstradial Cypionateβ-Estradiol 17-cypionateEstradiol cyclopentylpropionate(17b)-estra-1,3,5(10)-triene-3,17-diol17-cyclopentanepropanoate3-cyclopentylpropanoic acid [(13S)-3-hydroxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl] esterDepogenEstrapo
DTXCID302999Estra-1,3,5(10)-triene-3,17-diol (17beta)-, 17-cyclopentanepropanoateESTRADIOL 17beta-CYCLOPENTANEPROPANOATEEstra-1,3,5(10)-triene-3,17-diol, (17beta)-, 17-cyclopentanepropanoateRefChem:55136206-237-8DepofeminDepoestradiol

Database identifiers

CAS
313-06-4
PubChem CID
9403
DTXSID
DTXSID4022999
ChEMBL
CHEMBL1200973
ChEBI
CHEBI:34745
UNII
7E1DV054LO
EC Number
206-237-8
Nikkaji
J5.661H

Properties

Computed structural properties

XLogP
7.1
Topological polar surface area
46.5 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
3
Rotatable bonds
5
Heavy atoms
29

Experimental & physicochemical properties

DrugsPharmaceuticals -> Listed in ZINC15
Human Drugs · 4 items

Breast Feeding; Lactation; Milk, Human; Estrogens; Hormones

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

Pharmaceuticals

Endocrine DisruptorsPotential endocrine disrupting compound
Collision Cross Section220.4 Ų [M-H]- [CCS Type: DT; Buffer gas: N2; Ionization: ESI-; Dataset: TOXCAST; Source Identifier: DTXSID4022999]

Physicochemical properties

Melting point
151 · 151-152°
alpha
25 · D25 +45° (chloroform)
Boiling point
460.24 °C · 460.24°C (rough estimate)
Density
1.0828 · 1.0828 (rough estimate)
refractive index
1.47 · 1.4700 (estimate)
storage temp.
Refrigerator

Safety & regulation

GHS classification

GHS Classification · 4 items

Danger

H302 (95.1%): Harmful if swallowed [Warning Acute toxicity, oral]

P203, P261, P264, P270, P271, P280, P301+P317, P302+P352, P304+P340, P317, P318, P321, P330, P362+P364, 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. Each notification may be associated with multiple companies.

Hazard information

Regulatory Information · 1 item

Estra-1,3,5(10)-triene-3,17-diol (17.beta.)-, 17-cyclopentanepropanoate: 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 - Estra-1,3,5(10)-triene-3,17-diol, 17-cyclopentanepropanoate, (17.beta.)-: Environment tier I assessment
Hazard Classes and CategoriesAcute Tox. 4 (95.1%)

Toxicology

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation

Safety data

PPE
Eyeshields, Gloves, type P3 (EN 143) respirator cartridges
wgk
3
tsca
TSCA listed
rtecs
KG4600000
hs_code
29372390
risk_code
45-46-61-20/21/22-36/37/38

Chemistry & industry

Pharmacology

Protein BindingEstrogens circulate in the blood largely bound to sex hormone binding globulin (SHBG) and albumin.
Pharmacodynamics · 1 item

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.

Mechanism of Action · 1 item

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.

Metabolism/Metabolites · 1 item

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.

FDA Pharmacological Classification · 2 items

ESTRADIOL CYPIONATE

Estradiol Congeners [CS]; Estrogen [EPC]; Estrogen Receptor Agonists [MoA]

MeSH Pharmacological Classification · 2 items

Chemical substances or agents with contraceptive activity in females. Use for female contraceptive agents in general or for which there is no specific heading.

Contraceptive agents that act on the ENDOCRINE SYSTEM.

Uses & manufacturing

Use ClassificationPharmaceuticals
General Manufacturing InformationEstra-1,3,5(10)-triene-3,17-diol (17.beta.)-, 17-cyclopentanepropanoate: INACTIVE
Applications · 1 item

UsesEstradiol Cypionate is the cypionate salt form of estradiol, the most potent, naturally produced estrogen. Estradiol Cypionate is present in injectable contraceptive formulations. Used in hormone replacement therapy with potential for improving cognition in post-menopausal women.

Suppliers100 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
Shanghai Biolang Biotechnology Co., Ltd.+86-15970428662 +86-13397199602 · [email protected]
陕西帕尼尔生物科技有限公司029-84385017-8003 13259417953 · [email protected]

Additional notes

DefinitionChEBI: Estradiol 17beta-cyclopentylpropionate is a steroid ester. It inhibits ET-1 synthesis via estrogen receptor.

Related reactions

1 records

Compound notes

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