sodium (1S,10R,11S,15S)-15-methyl-14-oxotetracyclo[8.7.0.02,7.011,15]heptadeca-2,4,6-trien-5-yl sulfate

• ChemBase ID: 171
• Molecular Formular: C18H21NaO5S
• Molecular Mass: 372.41111
• Monoisotopic Mass: 372.10073905
• 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

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium (1S,10R,11S,15S)-15-methyl-14-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-2,4,6-trien-5-yl sulfate; 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
• IUPAC Traditional name: sodium estrone 3-sulfate(1-); potassium estrone 3-sulfate(1-)
• Brand Name: Conestoral; Evex; Hyhorin; Morestin; Par Estro; Premarin; Prempro/Premphase; Premarin tabs; Premarin Vaginal; Prempro
• Synonyms: 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; 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

Database IDs

• CAS Number: 438-67-5
• PubChem SID: 46505680; 160963634
• PubChem CID: 23667301

CALCULATED PROPERTIES

JChem

• Acid pKa: -1.7480068
• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 1.4573227
• LogD (pH = 7.4): 1.457317
• Log P: 3.8337157
• Molar Refractivity: 87.9525 cm^3
• Polarizability: 35.38073 Å^3
• Polar Surface Area: 83.5 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.75
• LOG S: -4.92
• Solubility (Water): 4.50e-03 g/l

PROPERTIES

Physical Property

• Solubility: 0.0036 mg/ml; Methanol
• Apperance: Off-White Solid; White Solid
• Melting Point: 230-233°C; 258-260°C

Safety Information

• Storage Condition: -20°C Freezer; Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

DrugBank - DB00286

• 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

Estrogen used in hormone replacement therapy.

Toronto Research Chemicals - E889065

Estrogen used in hormone replacement therapy.

REFERENCES

• 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)
• 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)