(1S,2R,5S,10R,11S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadec-7-en-14-one

• ChemBase编号: 1482
• 分子式: C19H28O2
• 平均质量: 288.42442
• 单一同位素质量: 288.20893014
• SMILES: C1C[C@H](O)CC2=CC[C@@H]3[C@@H]([C@@]12C)CC[C@]1([C@H]3CCC1=O)C
• Canonical SMILES: O[C@H]1CC[C@]2(C(=CC[C@@H]3[C@@H]2CC[C@]2([C@H]3CCC2=O)C)C1)C
• InChI: InChI=1S/C19H28O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h3,13-16,20H,4-11H2,1-2H3/t13-,14-,15-,16-,18-,19-/m0/s1
• InChIKey: FMGSKLZLMKYGDP-USOAJAOKSA-N

名称和登记号

名称

• IUPAC标准名: (1S,2R,5S,10R,11S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-7-en-14-one; (1S,2R,5S,10R,11S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-one
• IUPAC传统名: dehydroepiandrosterone; 3-β-hydroxy-5-androsten-17-one
• 别名: 3β-羟基-5-雄烯-17-酮; 去氢表雄酮; 普拉睾酮; 脱氢异雄酮; 雄素-5-烯-3β-醇-17-酮; 反式-脱氢雄甾酮; DHEA; Dehydroepiandrosterone; trans-Dehydroandrosterone; Diandrone; GL 701; IM 28; Immunor; NSC 9896; Psicosterone; trans-Dehydroandrosterone; Dehydro Epiandrosterone; 3β-Hydroxyandrost-5-en-17-one; 5,6-Dehydroisoandrosterone; Androstenolone; Astenile; DHA; Deandros; Diandron; 3-Beta-Hydroxy-5-Androsten-17-One; 3β-Hydroxy-5-androsten-17-one; 5-Androsten-3β-ol-17-one; Dehydroepiandrosterone; Dehydroisoandrosterone; Prasterone; DEHYDROISOANDROSTERONE

登记号

• CAS号: 53-43-0; 53-43-0
• EC号: 200-175-5
• MDL号: MFCD00003613
• Beilstein号: 2058110
• PubChem SID: 160964941; 24278369; 46508824; 24858617
• PubChem CID: 5881

理论计算性质

JChem

• Acid pKa: 18.20429
• 质子受体: 2
• 质子供体: 1
• LogD (pH = 5.5): 3.361705
• LogD (pH = 7.4): 3.361705
• Log P: 3.361705
• 摩尔折射率: 84.6589 cm^3
• 极化性: 33.260063 Å^3
• 极化表面积: 37.3 Å^2
• 可自由旋转的化学键: 0
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 3.53
• LOG S: -3.82
• 溶解度: 4.38e-02 g/l

分子性质

理化性质

• 溶解度: 0.0635 mg/mL at 25 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]; Methanol
• 外观: White Solid
• 熔点: 146-147°C; 147-149 °C; 149-151 °C(lit.)
• 比旋光度: [α]20/D +12.5±1°, c = 3% in ethanol; [α]25/D +13.0°, c = 1 in ethanol
• 疏水性(logP): 3.23 [HANSCH,C ET AL. (1995)]

安全信息

• 保存条件: -20°C; Controlled Substance, -20°C Freezer
• RTECS编号: BV8396000
• 欧盟危险性物质标志: 刺激性(Irritant) (Xi)
• 德国WGK号: 2
• 危险公开号: 36/37/38
• 安全公开号: 26-36
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H315-H319-H335
• GHS警示性声明: P261-P305 + P351 + P338
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves
• 毒品管制信息: Home Office Schedule 4.2regulated under CDSA - not available from Sigma-Aldrich Canada; regulated under CDSA - not available from Sigma-Aldrich Canada

药理学性质

• 作用靶点: Androgen Receptor
• 相关基因信息: human ... GABRA1(2554), GABRA2(2555), GABRA3(2556), GABRA4(2557), GABRA5(2558), GABRA6(2559), GABRB1(2560), GABRB2(2561), GABRB3(2562), SERPINA6(866)rat ... Ar(24208); human ... SERPINA6(866)rat ... Ar(24208)

产品相关信息

• 纯度: ≥98.0% (GC); ≥99%; 97%
• 级别: purum
• 成盐信息: Free Base
• Empirical Formula (Hill Notation): C19H28O2

详细说明

MP Biomedicals - 05206121

MP Biomedicals Rare Chemical collection

DrugBank - DB01708

• Drug Groups: experimental
• Description: Dehydroepiandrosterone (DHEA) is a major C19 steroid produced by the adrenal cortex. It is also produced in small quantities in the testis and the ovary. Dehydroepiandrosterone (DHEA) can be converted to testosterone; androstenedione; estradiol; and estrone. Most of DHEA is sulfated (dehydroepiandrosterone sulfate) before secretion.; ; In the United States, DHEA or DHEAS have been advertised with claims that they may be beneficial for a wide variety of ailments. DHEA and DHEAS are readily available in the United States, where they are marketed as over-the-counter dietary supplements.; ; In Canada, a prescription is required to buy DHEA.
• Indication: DHEA is taken as a supplement for a variety of unsubstantiated indications. The following indications have shown promise and are backed up by some scientific evidence: schizophrenia (DHEA may be more effective in women than men); improving the appearance of older people’s skin (taking DHEA by mouth seems to increase skin thickness and moisture, and decrease facial “age spots” in elderly men and women); improving ability to achieve an erection in men with sexual dysfunction. Additionally, DHEA has shown promise in improving symptoms of lupus (SLE). Taking DHEA by mouth along with conventional treatment may help reduce the number of times symptoms flare up and may allow a reduction in the dose of prescription drugs needed. DHEA may also help SLE symptoms such as muscle ache and mouth ulcers. DHEA also seems to strengthen bones in SLE patients being treated with high-dose steroids (corticosteroids).; DHEA also shows promise in the treatment of osteoporosis. Taking DHEA by mouth daily seems to improve bone mineral density (BMD) in older women and men with osteoporosis or osteopenia (pre-osteoporosis). DHEA may also increase BMD in young women with the eating disorder called anorexia nervosa. DHEA is often prescribed in India for the induction of ovulation to improve chances of pregnancy.
• Pharmacology: DHEA is naturally produced from cholesterol through two cytochrome P450 enzymes. Cholesterol is converted to pregnenolone by the enzyme P450 scc (side chain cleavage); then another enzyme, CYP17A1, converts pregnenolone to 17α-Hydroxypregnenolone and then to DHEA. Regular exercise is known to increase DHEA production in the body. Calorie restriction has also been shown to increase DHEA in primates. Some theorize that the increase in endogenous DHEA brought about by calorie restriction is partially responsible for the longer life expectancy known to be associated with calorie restriction.
• Toxicity: Acute oral toxicity (LD50): >10000 mg/kg [Rat]. Lowest Published Toxic Dose (TDL) [Man] - Route: Oral; Dose: 10 mg/kg/2W intermittent.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic. As shown by their high conversion ratios (in a study involving cynomolgus monkeys), the major circulating metabolites of DHEA are DHEA-S, androsterone glucuronide, and androstane-3 alpha,17 beta-diol-glucuronide. [PMID: 12970301]
• Absorption: Following a 50-mg DHEA PO dose in cynomolgus monkeys, systemic availability was only 3.1 +/- 0.4%. [PMID: 12970301]
• Half Life: 12 hours
• References: "The NIH National Library of Medicine":http://www.nlm.nih.gov/medlineplus/druginfo/natural/patient-dhea.html; Baker WL, Karan S, Kenny AM: Effect of dehydroepiandrosterone on muscle strength and physical function in older adults: a systematic review. J Am Geriatr Soc. 2011 Jun;59(6):997-1002. doi: 10.1111/j.1532-5415.2011.03410.x. Epub 2011 Jun 7. [Pubmed] ; Alkatib AA, Cosma M, Elamin MB, Erickson D, Swiglo BA, Erwin PJ, Montori VM: A systematic review and meta-analysis of randomized placebo-controlled trials of DHEA treatment effects on quality of life in women with adrenal insufficiency. J Clin Endocrinol Metab. 2009 Oct;94(10):3676-81. Epub 2009 Sep 22. [Pubmed] ; Arlt W: Dehydroepiandrosterone and ageing. Best Pract Res Clin Endocrinol Metab. 2004 Sep;18(3):363-80. [Pubmed] ; Wallace MB, Lim J, Cutler A, Bucci L: Effects of dehydroepiandrosterone vs androstenedione supplementation in men. Med Sci Sports Exerc. 1999 Dec;31(12):1788-92. [Pubmed] ; Grimley Evans J, Malouf R, Huppert F, van Niekerk JK: Dehydroepiandrosterone (DHEA) supplementation for cognitive function in healthy elderly people. Cochrane Database Syst Rev. 2006 Oct 18;(4):CD006221. [Pubmed] ; Fuller SJ, Tan RS, Martins RN: Androgens in the etiology of Alzheimer's disease in aging men and possible therapeutic interventions. J Alzheimers Dis. 2007 Sep;12(2):129-42. [Pubmed] ; Casson PR, et al. Dehydroepiandrosterone supplementation augments ovarian stimulation in poor responders: a case series. Hum Reprod, 2000;15:2129-2132.; Thijs L, Fagard R, Forette F, Nawrot T, Staessen JA: Are low dehydroepiandrosterone sulphate levels predictive for cardiovascular diseases? A review of prospective and retrospective studies. Acta Cardiol. 2003 Oct;58(5):403-10. [Pubmed] ; Barrett-Connor E, Khaw KT, Yen SS: A prospective study of dehydroepiandrosterone sulfate, mortality, and cardiovascular disease. N Engl J Med. 1986 Dec 11;315(24):1519-24. [Pubmed] ; Arnlov J, Pencina MJ, Amin S, Nam BH, Benjamin EJ, Murabito JM, Wang TJ, Knapp PE, D'Agostino RB Sr, Bhasin S, Vasan RS: Endogenous sex hormones and cardiovascular disease incidence in men. Ann Intern Med. 2006 Aug 1;145(3):176-84. [Pubmed] ; Crosbie D, Black C, McIntyre L, Royle PL, Thomas S: Dehydroepiandrosterone for systemic lupus erythematosus. Cochrane Database Syst Rev. 2007 Oct 17;(4):CD005114. [Pubmed] ; Chang DM, Lan JL, Lin HY, Luo SF. Dehydroepiandrosterone treatment of women with mild-to-moderate systemic lupus erythematosus: a multicenter randomized, double-blind, placebo-controlled trial. Arthritis Rheum. 2002 Nov;46(11):2924-7.; Mattison JA, Lane MA, Roth GS, Ingram DK: Calorie restriction in rhesus monkeys. Exp Gerontol. 2003 Jan-Feb;38(1-2):35-46. [Pubmed] ; Roberts E: The importance of being dehydroepiandrosterone sulfate (in the blood of primates): a longer and healthier life? Biochem Pharmacol. 1999 Feb 15;57(4):329-46. [Pubmed] ; Leblanc M, Labrie C, Belanger A, Candas B, Labrie F: Bioavailability and pharmacokinetics of dehydroepiandrosterone in the cynomolgus monkey. J Clin Endocrinol Metab. 2003 Sep;88(9):4293-302. [Pubmed]
• External Links: Wikipedia

Selleck Chemicals - S2604

Research Area: Cancer
Biological Activity:
Dehydroepiandrosterone(DHEA) is a 19-carbon endogenous natural steroid hormone. It is the major secretory steroidal product of the adrenal glands and is also produced by the gonads and the brain. DHEA is the most abundant circulating steroid in humans. It acts on the androgen receptor both directly and through its metabolites, which include androstenediol and androstenedione, which can undergo further conversion to produce the androgen testosterone and the estrogens estrone and estradiol. DHEA is also a potent sigma-1 agonist. It is considered a neurosteroid. [1][2]References on Dehydroepiandrosterone(DHEA)[1] http://en.wikipedia.org/wiki/Dehydroepiandrosterone, , [2] J Steroid Biochem Mol Biol., 2006 Apr, 99(1):50-8.

Sigma Aldrich - D4000

Biochem/physiol Actions
Dehydroandrosterone (DHEA) is a negative modulator of GABAA receptors. It is a steroid secreted by the adrenal gland with both estrogenic and androgenic properties. DHEAs conversion to 5-androstenediol, a potent estrogen, enhances the growth and survival of estrogen-sensitive breast tumors.
Negative modulator of GABAA receptors. Steroid secreted by the adrenal gland with both estrogenic and androgenic properties. Its conversion to 5-androstenediol, a potent estrogen, enhances the growth and survival of estrogen-sensitive breast tumors. At high but physiologically valid concentrations, DHEA inhibits proliferation of chromaffin progenitor cells and induces dopaminergic differentiation.

Sigma Aldrich - 125784

Biochem/physiol Actions
Negative modulator of GABAA receptors. Steroid secreted by the adrenal gland with both estrogenic and androgenic properties. Its conversion to 5-androstenediol, a potent estrogen, enhances the growth and survival of estrogen-sensitive breast tumors. At high but physiologically valid concentrations, DHEA inhibits proliferation of chromaffin progenitor cells and induces dopaminergic differentiation.1

Sigma Aldrich - 30770

Other Notes
Sales restrictions may apply
Biochem/physiol Actions
Negative modulator of GABAA receptors. Steroid secreted by the adrenal gland with both estrogenic and androgenic properties. Its conversion to 5-androstenediol, a potent estrogen, enhances the growth and survival of estrogen-sensitive breast tumors. At high but physiologically valid concentrations, DHEA inhibits proliferation of chromaffin progenitor cells and induces dopaminergic differentiation.1

Toronto Research Chemicals - D229585

Major secretory steroidal product of the adrenal gland; secretion progresively declines with aging. May have estrogen-or androgen-like effects depending on the hormonal milieu. Intracellularly converted to androstenedione. It is used in treatment of menop

参考文献

• "The NIH National Library of Medicine":http://www.nlm.nih.gov/medlineplus/druginfo/natural/patient-dhea.html
• Casson PR, et al. Dehydroepiandrosterone supplementation augments ovarian stimulation in poor responders: a case series. Hum Reprod, 2000;15:2129-2132.
• Baker WL, Karan S, Kenny AM: Effect of dehydroepiandrosterone on muscle strength and physical function in older adults: a systematic review. J Am Geriatr Soc. 2011 Jun;59(6):997-1002. doi: 10.1111/j.1532-5415.2011.03410.x. Epub 2011 Jun 7. Pubmed
• Alkatib AA, Cosma M, Elamin MB, Erickson D, Swiglo BA, Erwin PJ, Montori VM: A systematic review and meta-analysis of randomized placebo-controlled trials of DHEA treatment effects on quality of life in women with adrenal insufficiency. J Clin Endocrinol Metab. 2009 Oct;94(10):3676-81. Epub 2009 Sep 22. Pubmed
• Arlt W: Dehydroepiandrosterone and ageing. Best Pract Res Clin Endocrinol Metab. 2004 Sep;18(3):363-80. Pubmed
• Wallace MB, Lim J, Cutler A, Bucci L: Effects of dehydroepiandrosterone vs androstenedione supplementation in men. Med Sci Sports Exerc. 1999 Dec;31(12):1788-92. Pubmed
• Grimley Evans J, Malouf R, Huppert F, van Niekerk JK: Dehydroepiandrosterone (DHEA) supplementation for cognitive function in healthy elderly people. Cochrane Database Syst Rev. 2006 Oct 18;(4):CD006221. Pubmed
• Fuller SJ, Tan RS, Martins RN: Androgens in the etiology of Alzheimer's disease in aging men and possible therapeutic interventions. J Alzheimers Dis. 2007 Sep;12(2):129-42. Pubmed
• Thijs L, Fagard R, Forette F, Nawrot T, Staessen JA: Are low dehydroepiandrosterone sulphate levels predictive for cardiovascular diseases? A review of prospective and retrospective studies. Acta Cardiol. 2003 Oct;58(5):403-10. Pubmed
• Barrett-Connor E, Khaw KT, Yen SS: A prospective study of dehydroepiandrosterone sulfate, mortality, and cardiovascular disease. N Engl J Med. 1986 Dec 11;315(24):1519-24. Pubmed
• Arnlov J, Pencina MJ, Amin S, Nam BH, Benjamin EJ, Murabito JM, Wang TJ, Knapp PE, D'Agostino RB Sr, Bhasin S, Vasan RS: Endogenous sex hormones and cardiovascular disease incidence in men. Ann Intern Med. 2006 Aug 1;145(3):176-84. Pubmed
• Crosbie D, Black C, McIntyre L, Royle PL, Thomas S: Dehydroepiandrosterone for systemic lupus erythematosus. Cochrane Database Syst Rev. 2007 Oct 17;(4):CD005114. Pubmed
• Chang DM, Lan JL, Lin HY, Luo SF. Dehydroepiandrosterone treatment of women with mild-to-moderate systemic lupus erythematosus: a multicenter randomized, double-blind, placebo-controlled trial. Arthritis Rheum. 2002 Nov;46(11):2924-7.
• Mattison JA, Lane MA, Roth GS, Ingram DK: Calorie restriction in rhesus monkeys. Exp Gerontol. 2003 Jan-Feb;38(1-2):35-46. Pubmed
• Roberts E: The importance of being dehydroepiandrosterone sulfate (in the blood of primates): a longer and healthier life? Biochem Pharmacol. 1999 Feb 15;57(4):329-46. Pubmed
• Leblanc M, Labrie C, Belanger A, Candas B, Labrie F: Bioavailability and pharmacokinetics of dehydroepiandrosterone in the cynomolgus monkey. J Clin Endocrinol Metab. 2003 Sep;88(9):4293-302. Pubmed
• Mo Q et al. J Steroid Biochem Mol Biol. 2006 Apr
• Yahara, M., et al.: J. Toxicol. Sci., 2, 161 (1977)
• Morales, A.J., et al.: J. Clin. Endocrinol. Metab., 78, 1360 (1977)
• Ebeling, P., et al.: Lancet, 343, 1479 (1977)