Basic information
- CAS
979-32-8- Standard SMILES
CCCCC(=O)O[C@H]1CC[C@H]2[C@@H]3CCc4cc(O)ccc4[C@H]3CC[C@]12C- InChIKey
RSEPBGGWRJCQGY-RBRWEJTLSA-N- Molecular formula
- C23H32O3
- Average molar mass
- 356.5 g/mol
- Monoisotopic mass
- 356.23514488
Overview
Estradiol valerate is a steroid ester.
Names & identifiers
- Preferred name
- Estradiol Valerate
- 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] pentanoate
- English name
- Estradiol valerate
- Molecular formula
- C23H32O3
- Molecular weight
- 356.5
Names & synonyms
estradiol valerate979-32-8Estradiol 17-valerateDelestrogenClimavalOestradiol valerateDeladumoneNSC-17590DTXSID8023004OKG364O896[(8R,9S,13S,14S,17S)-3-hydroxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl] pentanoateDTXCID903004
Show more names
β-Estradiol 17-valerateprogynova(8R,9S,13S,14S,17S)-3-hydroxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-17-yl pentanoateNuvellefemogexpharlonestravalValergen
beta-Estradiol 17-valerateNSC1759017-pentanoyl-estra-1,3,5(10)-triene-3,17beta-diolEstra-1,3,5(10)-triene-3,17-diol(17beta)-, 17-pentanoateFemtabProgynon-depot-10((8R,9S,13S,14S,17S)-3-hydroxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta(a)phenanthren-17-yl) pentanoateRefChem:55138
Database identifiers
- CAS
Properties
Computed structural properties
- XLogP
- 6
- Topological polar surface area
- 46.5 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 5
- Heavy atoms
- 26
- Formal charge
- 0
- Complexity
- 518
Experimental & physicochemical properties
LipidsLipids -> Sterol Lipids [ST] -> Steroids [ST02] -> C18 steroids (estrogens) and derivatives [ST0201]
SpringerMaterials PropertiesFusion temperature
Human Drugs
Breast Feeding; Lactation; Milk, Human; Estrogens; Hormones
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Pharmaceuticals
Animal DrugsFDA approved animal drugs -> Active ingredient
Endocrine DisruptorsPotential endocrine disrupting compound
Collision Cross Section171 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physicochemical properties
- Melting point
- 144 °C · 144°C
- Boiling point
- 438.83 °C · 438.83°C (rough estimate)
- Density
- 1.1024 · 1.1024 (rough estimate)
Safety & regulation
GHS classification
GHS Classification
Danger
H302 (29.7%): 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 64 reports by companies from 11 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory InformationOestradiol valerate: 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.
Hazard Classes and CategoriesAcute Tox. 4 (29.7%)
Toxicology
Drug Induced Liver Injury
Drug Induced Liver Injury Rank (DILIrank 2.0)
Estradiol valerate
vLess-DILI-concern
2
Adverse reactions
DOI:10.1016/j.drudis.2016.02.015
Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
Safety data
- PPE
- Eyeshields, Gloves, type P3 (EN 143) respirator cartridges
- wgk
- 3
- rtecs
- KG5793000
- hs_code
- 29372390
- risk_code
- 60-61
- Signal word
- Warning
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, which are primarily caused by a loss of estrogenic activity.
Metabolism/MetabolitesExogenous estrogens are metabolized using the same mechanism as endogenous estrogens. Estrogens are partially metabolized by cytochrome P450.
FDA Pharmacological Classification
ESTRADIOL VALERATE
Estrogen Receptor Agonists [MoA]; Estrogen [EPC]; Estradiol Congeners [CS]
MeSH Pharmacological Classification
Compounds that interact with ESTROGEN RECEPTORS in target tissues to bring about the effects similar to those of ESTRADIOL. Estrogens stimulate the female reproductive organs, and the development of secondary female SEX CHARACTERISTICS. Estrogenic chemicals include natural, synthetic, steroidal, or non-steroidal compounds.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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