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438-67-5 molecular structure
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sodium (1S,10R,11S,15S)-15-methyl-14-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2,4,6-trien-5-yl sulfate

ChemBase ID: 171
Molecular Formular: C18H21NaO5S
Molecular Mass: 372.41111
Monoisotopic Mass: 372.10073905
SMILES and InChIs

SMILES:
c1c(cc2c(c1)[C@@H]1[C@@H](CC2)[C@H]2[C@@](CC1)(C)C(=O)CC2)OS(=O)(=O)[O-].[Na+]
Canonical SMILES:
O=C1CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CCc2c1ccc(c2)OS(=O)(=O)[O-].[Na+]
InChI:
InChI=1S/C18H22O5S.Na/c1-18-9-8-14-13-5-3-12(23-24(20,21)22)10-11(13)2-4-15(14)16(18)6-7-17(18)19;/h3,5,10,14-16H,2,4,6-9H2,1H3,(H,20,21,22);/q;+1/p-1/t14-,15-,16+,18+;/m1./s1
InChIKey:
VUCAHVBMSFIGAI-ZFINNJDLSA-M

Cite this record

CBID:171 http://www.chembase.cn/molecule-171.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
sodium (1S,10R,11S,15S)-15-methyl-14-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2,4,6-trien-5-yl sulfate
sodium (1S,10R,11S,15S)-15-methyl-14-oxotetracyclo[8.7.0.02,7.011,15]heptadeca-2,4,6-trien-5-yl sulfate
IUPAC Traditional name
potassium estrone 3-sulfate(1-)
sodium estrone 3-sulfate(1-)
Brand Name
Conestoral
Evex
Hyhorin
Morestin
Par Estro
Premarin
Prempro/Premphase
Premarin tabs
Premarin Vaginal
Prempro
Synonyms
Estrone Estrone Hydrogen Sulfate
Estrogens
Estrone-sulfate
Estrone Sulphate
Estrone Sulfate Sodium
Estrone Sulfate
Estrone Sodium Sulfate
Estrone Hydrogen Sulfate
Oestrone Sulphate
Sodium Estrone Sulfate
Conjugated Estrogens
Estra-1,3,5(10)-trien-17-one 3-(Sulfooxy) Sodium Salt
Estrone Sulfate Sodium Salt
Conestoral
Morestin
NSC 18313
Sodium Estrone-3-sulfate
Estrone 3-Sulfate Sodium Salt, Stabilized with TRISDISCONTINUED. See E889070
Estrone 3-Sulfate Sodium Salt
CAS Number
438-67-5
PubChem SID
160963634
46505680
PubChem CID
23667301

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa -1.7480068  H Acceptors
H Donor LogD (pH = 5.5) 1.4573227 
LogD (pH = 7.4) 1.457317  Log P 3.8337157 
Molar Refractivity 87.9525 cm3 Polarizability 35.38073 Å3
Polar Surface Area 83.5 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 2.75  LOG S -4.92 
Solubility (Water) 4.50e-03 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
0.0036 mg/ml expand Show data source
Methanol expand Show data source
Apperance
Off-White Solid expand Show data source
White Solid expand Show data source
Melting Point
230-233°C expand Show data source
258-260°C expand Show data source
Storage Condition
-20°C Freezer expand Show data source
Hygroscopic, -20°C Freezer, Under Inert Atmosphere expand Show data source
MSDS Link
Download expand Show data source
Certificate of Analysis
Download expand Show data source

DETAILS

DETAILS

DrugBank DrugBank TRC TRC
DrugBank - DB00286 external link
Item Information
Drug Groups approved
Description Conjugated estrogens, a mixture of the water-soluble salts of sulfate esters from estrone, equilin, 17 α-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.
Indication 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)
Pharmacology Conjugated estrogens, a mixture of the water soluble salts of sulfate esters from estrone, equilin, 17 α-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.
Toxicity Nausea and vomiting
Affected Organisms
Humans and other mammals
Biotransformation Hepatic
Absorption Well absorbed
Half Life 7.4 hours
Protein Binding 90% bound to plasma proteins
Elimination Estradiol, estrone, and estriol are excreted in the urine, along with glucuronide and sulfate conjugates. Exogenous estrogens are metabolized in the same manner as endogenous estrogens.
External Links
RxList
Drugs.com
Toronto Research Chemicals - E889070 external link
Estrogen used in hormone replacement therapy.
Toronto Research Chemicals - E889065 external link
Estrogen used in hormone replacement therapy.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Kannel, W., et al.: J. Clin. Epidemiol., 44, 183 (1991)
  • • Raisz, L., et al.: J. Clin. Endocrinol. Metab., 81, 37 (1991)
  • • Gelfand, M., et al.: Clin. Ther., 19, 383 (1991)
  • • Vermeulen, A., et al.: J. Endocrinol. Invest., 22, 110 (1991)
  • • Kannel, W., et al.: J. Clin. Epidemiol., 44, 183 (1991)
  • • Raisz, L., et al.: J. Clin. Endocrinol. Metab., 81, 37 (1991)
  • • Gelfand, M., et al.: Clin. Ther., 19, 383 (1991)
  • • Vermeulen, A., et al.: J. Endocrinol. Invest., 22, 110 (1991)
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PATENTS

PATENTS

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INTERNET

INTERNET

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