[(1S,10R,11S,15S)-15-methyl-14-oxotetracyclo[8.7.0.02,7.011,15]heptadeca-2(7),3,5-trien-5-yl]oxidanesulfonic acid

• ChemBase编号: 4142
• 分子式: C18H22O5S
• 平均质量: 350.42928
• 单一同位素质量: 350.1187948
• SMILES: S(=O)(=O)(Oc1cc2c([C@@H]3[C@H]([C@H]4[C@](CC3)(C(=O)CC4)C)CC2)cc1)O
• Canonical SMILES: O=C1CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CCc2c1ccc(c2)OS(=O)(=O)O
• InChI: InChI=1S/C18H22O5S/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)/t14-,15-,16+,18+/m1/s1
• InChIKey: JKKFKPJIXZFSSB-CBZIJGRNSA-N

名称和登记号

名称

• IUPAC标准名: [(1S,10R,11S,15S)-15-methyl-14-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-2(7),3,5-trien-5-yl]oxidanesulfonic acid; [(1S,10R,11S,15S)-15-methyl-14-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-trien-5-yl]oxidanesulfonic acid
• IUPAC传统名: OGEN; estrone sulfate
• 商标名: Ogen; ORTHO-EST
• 别名: Estrone sulfate; Estropipate (usp); OGEN; Ogen (TN); Ogen 2.5; Estropipate

登记号

• CAS号: 7280-37-7; 438-67-5
• PubChem SID: 46508976; 160967574
• PubChem CID: 3001028; 5284555
• CHEBI ID: 17474
• CHEMBL: 494753
• Chemspider ID: 2272513
• DrugBank ID: DB04574
• 美国药典/FDA物质标识码: 6K6FDA543A
• 维基百科标题: Estrone_sulfate

理论计算性质

JChem

• Acid pKa: -1.7480068
• 质子受体: 4
• 质子供体: 1
• LogD (pH = 5.5): 1.4573227
• LogD (pH = 7.4): 1.457317
• Log P: 3.8337157
• 摩尔折射率: 89.0742 cm^3
• 极化性: 35.487312 Å^3
• 极化表面积: 80.67 Å^2
• 可自由旋转的化学键: 2
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 0.29
• LOG S: -4.77
• 溶解度: 5.90e-03 g/l

详细说明

DrugBank - DB04574

• Drug Groups: approved
• Description: Estropipate is a form of estrogen. It has several uses such as: Alleviate symptoms of menopause as hormone replacement therapy, treatment some types of infertility, treatment of some conditions leading to underdevelopment of female sexual characteristics,treatment of vaginal atrophy,treatment of some types of breast cancer (particularly in men and postmenopausal women), treatment of prostate cancer and prevention of osteoporosis.
• Indication: Estropipate is used for the treatment of moderate to severe vasomotor symptoms associated with the monopause, and moderate to severe symptoms of vulval and vaginal atrophy associated with the menopause. It is also used to treat hypoestrogenism due to hypogonadism, castration or primary ovarian failure, and prevent postmenopausal osteoporosis.
• Pharmacology: Estropipate is an estrogenic substance. It acts as naturally produced estrogen does. Estrogens act through binding to nuclear receptors in estrogen-responsive tissues. Circulating estrogens modulate the pituitary secretion of the gonadotropins, luteinizing hormone (LH) and follicle stimulating hormone (FSH), through a negative feedback mechanism. Estrogens act to reduce the elevated levels of these hormones seen in postmenopausal women.
• Affected Organisms: Humans and other mammals
• Biotransformation: Exogenous estrogens are metabolized in the same manner as endogenous estrogens. Circulating estrogens exist in a dynamic equilibrium of metabolic interconversions. These transformations take place mainly in the liver. Estradiol is converted reversibly to estrone, and both can be converted to estriol, which is the major urinary metabolite. Estrogens also undergo enterohepatic recirculation via sulfate and glucuronide conjugation in the liver, biliary secretion of conjugates into the intestine, and hydrolysis in the gut followed by reabsorption. In postmenopausal women, a significant proportion of the circulating estrogens exist as sulfate conjugates, especially estrone sulfate, which serves as a circulating reservoir for the formation of more active estrogens.
• Absorption: Estropipate is well absorbed through the skin and gastrointestinal tract. When applied for a local action, absorption is usually sufficient to cause systemic effects.
• Elimination: Estradiol, estrone and estriol are excreted in the urine along with glucuronide and sulfate conjugates
• External Links: Wikipedia; RxList; PDRhealth