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
Show more names
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
- Formal charge
- 0
- Complexity
- 597
Experimental & physicochemical properties
Human Drugs
Breast Feeding; Lactation; Milk, Human; Estrogens; Hormones
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Pharmaceuticals
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
- solubility
- Chloroform (Slightly), Methanol (Slightly)
- pka
- 10.25 · 10.25±0.60(Predicted)
- form
- Solid
- color
- White to Off-White
- biological source
- synthetic (organic)
- InChIKey
- UOACKFBJUYNSLK-JCRQLOERNA-N
- SMILES
- C[C@]12CC[C@]3([H])C4C=CC(O)=CC=4CC[C@@]3([H])[C@]1([H])CC[C@@H]2OC(=O)CCC1CCCC1 |&1:1,4,15,17,21,r|
- CAS DataBase Reference
- 313 · 313-06-4(CAS DataBase Reference)
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 7 E1DV054LO · 7E1DV054LO
- NIST Chemistry Reference
- Estradiol cypionate(313-06-4)
- EPA Substance Registry System
- -1 · Estra-1,3,5(10)-triene-3,17-diol (17.beta.)-, 17-cyclopentanepropanoate (313-06-4)
- UNSPSC Code
- 12352200 · 12352200
- NACRES
- 77 · NA.77
- Symbol(GHS)
- 7 · GHS07,GHS08
- Signal word
- Danger
- Hazard statements
- 302 · H302+H312+H332-H350-H360
- Precautionary statements
- 201 · P201-P280-P301+P312-P302+P352+P312-P304+P340+P312-P308+P313
- PPE
- 3 · Eyeshields, Gloves, type P3 (EN 143) respirator cartridges
- Hazard Codes
- T,Xi
- Risk Statements
- 45 · 45-46-61-20/21/22-36/37/38
- Safety Statements
- 53 · 53-22-36/37/39-45-26
- WGK Germany
- 3 · 3
- RTECS
- 4600000 · KG4600000
- TSCA
- TSCA listed
- HS Code
- 29372390 · 29372390
- Storage Class
- 6.1 C · 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- Hazard Classifications
- 4 DermalAcute · Acute Tox. 4 DermalAcute Tox. 4 InhalationAcute Tox. 4 OralCarc. 1BRepr. 1B
Safety & regulation
GHS classification
GHS Classification
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
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.
Toxicology
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
- Signal word
- Danger
- Symbol(GHS)
- GHS07,GHS08
- hazard_code
- T,Xi
- safety_code
- 53-22-36/37/39-45-26
- Storage Class
- 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- Hazard statements
- H302+H312+H332-H350-H360
- Hazard Classifications
- Acute Tox. 4 DermalAcute Tox. 4 InhalationAcute Tox. 4 OralCarc. 1BRepr. 1B
- Precautionary statements
- P201-P280-P301+P312-P302+P352+P312-P304+P340+P312-P308+P313
Chemistry & industry
Pharmacology
Pharmacodynamics
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
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
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
ESTRADIOL CYPIONATE
Estradiol Congeners [CS]; Estrogen [EPC]; Estrogen Receptor Agonists [MoA]
MeSH Pharmacological Classification
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.
Absorption, Distribution and Excretion
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.
Uses & manufacturing
Applications
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.
Upstream & downstream products
Upstream raw materials
Suppliers100 total
Additional notes
DefinitionChEBI: Estradiol 17beta-cyclopentylpropionate is a steroid ester. It inhibits ET-1 synthesis via estrogen receptor.
Related reactions
Compound notes
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