Completing data — usually done within a minute
Basic information
- CAS
474-86-2- Standard SMILES
C[C@]12CC[C@H]3C(=CCc4cc(O)ccc43)[C@@H]1CCC2=O- InChIKey
WKRLQDKEXYKHJB-HFTRVMKXSA-N- Molecular formula
- C18H20O2
- Average molar mass
- 268.3 g/mol
- Monoisotopic mass
- 268.14632988
Names & identifiers
- Preferred name
- Equilin
- IUPAC
- (9S,13S,14S)-3-hydroxy-13-methyl-9,11,12,14,15,16-hexahydro-6H-cyclopenta[a]phenanthren-17-one
Names & synonyms
Show more names
Database identifiers
- CAS
474-86-2- PubChem CID
- 223368
- DTXSID
DTXSID7047433- ChEMBL
CHEMBL323533- ChEBI
CHEBI:42309- UNII
- 08O86EX0J4
- EC Number
- 207-488-6
- Nikkaji
- J5.967F
Properties
Computed structural propertiesFilling in
- XLogP
- 2.9
- Topological polar surface area
- 37.3 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 0
- Heavy atoms
- 20
- Formal charge
- 0
- Complexity
- 466
Experimental & physicochemical properties
Collision Cross Section
172.2 Ų [M-H]- [CCS Type: DT; Buffer gas: N2; Ionization: ESI-; Dataset: TOXCAST; Source Identifier: DTXSID7047433]
157.92 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards];153.17 Ų [M+H-H2O]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards];160.72 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Safety & regulation
GHS classification
GHS Classification
Danger
H302 (20.5%): Harmful if swallowed [Warning Acute toxicity, oral];H312 (20.5%): Harmful in contact with skin [Warning Acute toxicity, dermal];H332 (20.5%): Harmful if inhaled [Warning Acute toxicity, inhalation];H351 (98.8%): Suspected of causing cancer [Warning Carcinogenicity];H360 (32.5%): May damage fertility or the unborn child [Danger Reproductive toxicity];H361 (66.3%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity];H362 (32.5%): May cause harm to breast-fed children [Reproductive toxicity, effects on or via lactation]
P203, P260, P261, P263, 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 83 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.;Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.
Hazard information
Toxicology
Toxicity Summary
Estrogens enter the cells of responsive tissues (e.g., female organs, breasts, hypothalamus, pituitary) where they interact with a protein receptor, subsequently increasing the rate of synthesis of DNA, RNA, and some proteins. Estrogens decrease the secretion of gonadotropin-releasing hormone by the hypothalamus, reducing the secretion of follicle-stimulating hormone (FSH) and luteinizing hormone (LH) from the pituitary.
USGS Health-Based Screening Levels for Evaluating Water-Quality
Equilin
Hormone
Smith, C.D. and Nowell, L.H., 2024. Health-Based Screening Levels for evaluating water-quality data (3rd ed.). DOI:10.5066/F71C1TWP
Chemistry & industry
Pharmacology
Pharmacodynamics
Equilin is a component of Premarin (conjugated estrogens), a mixture of the water soluble salts of sulfate esters from estrone, equilin, 17 alpha-dihydroequilin, and other related steroids, may be derived from pregnant equine urine or yam and soy plants. Estrogens are important in the development and maintenance of the female reproductive system and secondary sex characteristics. They promote growth and development of the vagina, uterus, and fallopian tubes, and enlargement of the breasts. Indirectly, they contribute to the shaping of the skeleton, maintenance of tone and elasticity of urogenital structures, changes in the epiphyses of the long bones that allow for the pubertal growth spurt and its termination, growth of axillary and pubic hair, and pigmentation of the nipples and genitals. Decline of estrogenic activity at the end of the menstrual cycle can bring on menstruation, although the cessation of progesterone secretion is the most important factor in the mature ovulatory cycle. However, in the preovulatory or nonovulatory cycle, estrogen is the primary determinant in the onset of menstruation. Estrogens also affect the release of pituitary gonadotropins. The pharmacologic effects of conjugated estrogens are similar to those of endogenous estrogens.
Mechanism of Action
Estrogens enter the cells of responsive tissues (e.g., female organs, breasts, hypothalamus, pituitary) where they interact with a protein receptor, subsequently increasing the rate of synthesis of DNA, RNA, and some proteins. Estrogens decrease the secretion of gonadotropin-releasing hormone by the hypothalamus, reducing the secretion of follicle-stimulating hormone (FSH) and luteinizing hormone (LH) from the pituitary.
Metabolism/Metabolites
Hepatic
Hepatic.
Uses & manufacturing
Uses
For the treatment of moderate to severe vasomotor symptoms associated with the menopause, atrophic vaginitis, osteoporosis, hypoestrogenism due to hypogonadism, castration, primary ovarian failure, breast cancer (for palliation only), and Advanced androgen-dependent carcinoma of the prostate (for palliation only)
Suppliers18 total
Related reactions
Compound notes
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