Equilin

HCID 223368

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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

equilin474-86-27-DehydroestroneDihydroequilenin3-HYDROXYESTRA-1,3,5(10),7-TETRAEN-17-ONE1,3,5,7-Estratetraen-3-ol-17-oneDTXSID7047433Estra-1,3,5(10),7-tetraen-17-one, 3-hydroxy-NSC-10971Equilin (USP)Equilin [USP]08O86EX0J4
Show more names
DTXCID5027433CHEBI:42309NSC10971DTXSID90859387RefChem:591016DTXCID90210237(1S,11S,15S)-5-hydroxy-15-methyltetracyclo(8.7.0.02,7.011,15)heptadeca-2(7),3,5,9-tetraen-14-one207-488-6

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

Experimental & physicochemical properties

Solubility1.41
Melting Point239
Kovats Retention Index2745.3;2765.4;2766.1
Collision Cross Section · 2 items

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 · 5 items

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

Hazard Classes and CategoriesAcute Tox. 4 (20.5%);Acute Tox. 4 (20.5%);Acute Tox. 4 (20.5%);Carc. 2 (98.8%);Repr. 1A (32.5%);Repr. 2 (66.3%);Lact. (32.5%)

Toxicology

Exposure RoutesWell absorbed.
Toxicity Summary · 1 item

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.

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
USGS Health-Based Screening Levels for Evaluating Water-Quality · 3 items

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

Protein Binding90% bound to plasma proteins
Pharmacodynamics · 1 item

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 · 1 item

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 · 2 items

Hepatic

Hepatic.

Absorption, Distribution and ExcretionWell absorbed.

Uses & manufacturing

Uses · 1 item

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

广州隽唐科技有限公司020-36607679 13502246435 · [email protected]
武汉易泰科技有限公司上海分公司18930552037 · [email protected]
梯希爱(上海)化工贸易有限公司021-61109150 · [email protected]
上海柯维化学技术有限公司021-64609169 18901607656 · [email protected]
斯百全化学(上海)有限公司021-021-021-67601398-809-809-809 15221380277 · [email protected]

Related reactions

27 records

Compound notes

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