Ethisterone (BioDeep_00000009928)
Secondary id: BioDeep_00000399099
human metabolite Endogenous blood metabolite
代谢物信息卡片
化学式: C21H28O2 (312.2089)
中文名称: 炔孕酮
谱图信息:
最多检出来源 Homo sapiens(blood) 13.75%
分子结构信息
SMILES: C#CC1(O)CCC2C3CCC4=CC(=O)CCC4(C)C3CCC21C
InChI: InChI=1S/C21H28O2/c1-4-21(23)12-9-18-16-6-5-14-13-15(22)7-10-19(14,2)17(16)8-11-20(18,21)3/h1,13,16-18,23H,5-12H2,2-3H3/t16-,17+,18+,19+,20+,21+/m1/s1
描述信息
Ethisterone is a metabolite of danazol. Ethisterone is a progestogen hormone. The first orally active progestin, ethisterone (pregneninolone, 17α-ethynyltestosterone or 19–norandrostane), the 17α-ethynyl analog of testosterone, was synthesized in 1938 by Hans Herloff Inhoffen, Willy Logemann, Walter Hohlweg, and Arthur Serini at Schering AG in Berlin and marketed in Germany in 1939 as Proluton C and by Schering in the U.S. in 1945 as Pranone. Ethisterone was also marketed in the U.S. (Wikipedia)
G - Genito urinary system and sex hormones > G03 - Sex hormones and modulators of the genital system > G03D - Progestogens > G03DC - Estren derivatives
C147908 - Hormone Therapy Agent > C548 - Therapeutic Hormone > C1636 - Therapeutic Steroid Hormone
ATC code: G03DC04
同义名列表
45 个代谢物同义名
(1S,2R,10R,11S,14R,15S)-14-ethynyl-14-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one; 17-beta-Hydroxy-17-alpha-ethynyl-4-androsten-3-one; 17alpha-Ethynyl-17beta-hydroxyandrost-4-en-3-one; 17-b-Hydroxy-17-a-ethynyl-4-androsten-3-one; 17-Ethynyl-17beta-hydroxyandrost-4-en-3-one; 17-Β-hydroxy-17-α-ethynyl-4-androsten-3-one; 17a-Ethynyl-17b-hydroxyandrost-4-en-3-one; 17Α-ethynyl-17β-hydroxyandrost-4-en-3-one; 17-Hydroxy-17alpha-pregn-4-en-20-yn-3-one; 17-Ethynyl-17b-hydroxyandrost-4-en-3-one; 17-Ethynyl-17β-hydroxyandrost-4-en-3-one; 17-Hydroxy-17α-pregn-4-en-20-yn-3-one; 17-Hydroxy-17a-pregn-4-en-20-yn-3-one; 17alpha-Ethinyl testosterone; 17 alpha Ethynyltestosterone; 17 alpha-Ethynyltestosterone; 17alpha-Ethinyltestosterone; 17alpha-Ethynyltestosterone; Anhydrohydroxyprogesterone; 17Α-ethinyl testosterone; 17a-Ethinyl testosterone; 17Α-ethynyltestosterone; 17a-Ethynyltestosterone; 17Α-ethinyltestosterone; 17a-Ethinyltestosterone; Anhydroxyprogesterone; Ethynyltestosterone; Pregneninolone; Syngestrotabs; Aethisteronum; Ethisteronum; Progestolets; Progestoral; Ethisterone; Aethisteron; Etisterona; Nugestoral; Prodroxan; Progestab; Trosinone; Lutocylol; Ora-lutin; Produxan; Pranone; Ethisterone
数据库引用编号
13 个数据库交叉引用编号
- ChEBI: CHEBI:34749
- KEGG: C14487
- PubChem: 5284557
- HMDB: HMDB0060580
- Metlin: METLIN1923
- ChEMBL: CHEMBL241694
- Wikipedia: Ethisterone
- MeSH: Ethisterone
- CAS: 434-03-7
- PMhub: MS000023750
- PubChem: 17395487
- NIKKAJI: J5.729K
- KNApSAcK: 34749
分类词条
相关代谢途径
Reactome(0)
BioCyc(0)
PlantCyc(0)
代谢反应
0 个相关的代谢反应过程信息。
Reactome(0)
BioCyc(0)
WikiPathways(0)
Plant Reactome(0)
INOH(0)
PlantCyc(0)
COVID-19 Disease Map(0)
PathBank(0)
PharmGKB(0)
1 个相关的物种来源信息
在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：
- PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
- NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
- Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
- Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。
点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。
文献列表
- Jiameng Sun, Yunwei Ou, Xiaoyan Liu, Haidan Sun, Zhengguang Guo, Feng Qi, Ying Lan, Weiming Liu, Wei Sun. LC-MS-based urine metabolomics analysis of chronic subdural hematoma for biomarker discovery.
Proteomics. Clinical applications.
2023 Sep; ?(?):e2200107. doi:
10.1002/prca.202200107. [PMID: 37697649] - Xiaowei Wu, Linyi You, Deliang Zhang, Mengna Gao, Zijing Li, Duo Xu, Pu Zhang, Lumei Huang, Rongqiang Zhuang, Hua Wu, Xianzhong Zhang. Synthesis and preliminary evaluation of a 18 F-labeled ethisterone derivative [18 F]EAEF for progesterone receptor targeting.
Chemical biology & drug design.
2017 04; 89(4):559-565. doi:
10.1111/cbdd.12878. [PMID: 27696769] - Yu Wang, Dilani C Dehigaspitiya, Paul M Levine, Adam A Profit, Michael Haugbro, Keren Imberg-Kazdan, Susan K Logan, Kent Kirshenbaum, Michael J Garabedian. Multivalent Peptoid Conjugates Which Overcome Enzalutamide Resistance in Prostate Cancer Cells.
Cancer research.
2016 09; 76(17):5124-32. doi:
10.1158/0008-5472.can-16-0385. [PMID: 27488525] - Xiangling Ma, Qing Wang, Lili Wang, Yanmei Huang, Xiaoxiang Liao, Hui Li. Investigation on the Interaction of Norgestrel with Human Serum Albumin Using Spectroscopy and Molecular-Docking Method.
Journal of biochemical and molecular toxicology.
2016 Jun; 30(6):287-94. doi:
10.1002/jbt.21790. [PMID: 26778492] - Hui Zhang, Fan-Xiang Kong, Shi-He Wang, Yang Yu, Min Zhang. Vitellogenin induction by a mixture of steroidal estrogens in freshwater fishes and relevant risk assessment.
Environmental toxicology.
2009 Oct; 24(5):484-91. doi:
10.1002/tox.20453. [PMID: 19016308] - L McRobb, D J Handelsman, R Kazlauskas, S Wilkinson, M D McLeod, A K Heather. Structure-activity relationships of synthetic progestins in a yeast-based in vitro androgen bioassay.
The Journal of steroid biochemistry and molecular biology.
2008 May; 110(1-2):39-47. doi:
10.1016/j.jsbmb.2007.10.008. [PMID: 18395441] - Rodny Montes de Oca Porto, Ariana Rodríguez Fernández, Dayamín Martínez Brito, Teresa Correa Vidal, Ahiram Lopez Diaz. Gas chromatography/mass spectrometry characterization of urinary metabolites of danazol after oral administration in human.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.
2006 Jan; 830(1):178-83. doi:
10.1016/j.jchromb.2005.10.032. [PMID: 16288903] - Terry White, John K Jain, Frank Z Stanczyk. Effect of oral versus transdermal steroidal contraceptives on androgenic markers.
American journal of obstetrics and gynecology.
2005 Jun; 192(6):2055-9. doi:
10.1016/j.ajog.2005.02.067. [PMID: 15970897] - Agnieszka Bartmańska, Jadwiga Dmochowska-Gładysz, Ewa Huszcza. Steroids' transformations in Penicillium notatum culture.
Steroids.
2005 Mar; 70(3):193-8. doi:
10.1016/j.steroids.2004.11.011. [PMID: 15763598] - U Gaspard. [Medication of the month. Evra: first contraceptive transdermal patch].
Revue medicale de Liege.
2003 Nov; 58(11):709-12. doi:
". [PMID: 14748201] - M Fanta. [A transdermal form of combined hormonal contraceptives (EVRA)].
Ceska gynekologie.
2003 Oct; 68(5):341-5. doi:
NULL. [PMID: 14692356] - George W Creasy, Alan C Fisher, Nancy Hall, Gary A Shangold. Transdermal contraceptive patch delivering norelgestromin and ethinyl estradiol. Effects on the lipid profile.
The Journal of reproductive medicine.
2003 Mar; 48(3):179-86. doi:
NULL. [PMID: 12698776] - Geoffrey L Hammond, Larry S Abrams, George W Creasy, Jaya Natarajan, J Glyn Allen, Pentti K Siiteri. Serum distribution of the major metabolites of norgestimate in relation to its pharmacological properties.
Contraception.
2003 Feb; 67(2):93-9. doi:
10.1016/s0010-7824(02)00473-0. [PMID: 12586319] - Ronald T Burkman. The transdermal contraceptive patch: a new approach to hormonal contraception.
International journal of fertility and women's medicine.
2002 Mar; 47(2):69-76. doi:
". [PMID: 11991433] - Larry S Abrams, Donna M Skee, Jaya Natarajan, Frankie A Wong, Gary D Anderson. Pharmacokinetics of a contraceptive patch (Evra/Ortho Evra) containing norelgestromin and ethinyloestradiol at four application sites.
British journal of clinical pharmacology.
2002 Feb; 53(2):141-6. doi:
10.1046/j.0306-5251.2001.01532.x. [PMID: 11851637] - Larry S Abrams, Donna Skee, Jaya Natarajan, Frankie A Wong. Pharmacokinetic overview of Ortho Evra/Evra.
Fertility and sterility.
2002 Feb; 77(2 Suppl 2):S3-12. doi:
10.1016/s0015-0282(01)03261-7. [PMID: 11849630] - L S Abrams, D M Skee, J Natarajan, F A Wong, P T Leese, G W Creasy, M M Shangold. Pharmacokinetics of norelgestromin and ethinyl estradiol delivered by a contraceptive patch (Ortho Evra/Evra) under conditions of heat, humidity, and exercise.
Journal of clinical pharmacology.
2001 Dec; 41(12):1301-9. doi:
10.1177/00912700122012887. [PMID: 11762557] - L S Abrams, D M Skee, F A Wong, N J Anderson, P T Leese. Pharmacokinetics of norelgestromin and ethinyl estradiol from two consecutive contraceptive patches.
Journal of clinical pharmacology.
2001 Nov; 41(11):1232-7. doi:
10.1177/00912700122012788. [PMID: 11697756] - J Y Kim, M H Choi, S J Kim, J B Kyong, B C Chung. GC-MS characterization of urinary metabolites and changes of ethisterone and testosterone profile after oral administration of danazol in equine.
Journal of veterinary pharmacology and therapeutics.
2001 Apr; 24(2):147-53. doi:
10.1046/j.1365-2885.2001.00317.x. [PMID: 11442791] - A E Lemus, J Enríquez, G A García, I Grillasca, G Pérez-Palacios. 5alpha-reduction of norethisterone enhances its binding affinity for androgen receptors but diminishes its androgenic potency.
The Journal of steroid biochemistry and molecular biology.
1997 Jan; 60(1-2):121-9. doi:
10.1016/s0960-0760(96)00172-0. [PMID: 9182866] - K Murakami, T Nakagawa, G Yamashiro, K Araki, K Akasofu. Adrenal steroids in serum during danazol therapy, taking into account cross-reactions between danazol metabolites and serum androgens.
Endocrine journal.
1993 Dec; 40(6):659-64. doi:
10.1507/endocrj.40.659. [PMID: 7951534] - A Plemenitas, H Lenasi, T Hudnik-Plevnik. Identification of progesterone binding sites in the plasma membrane of the filamentous fungus Cochliobolus lunatus.
The Journal of steroid biochemistry and molecular biology.
1993 Apr; 45(4):281-5. doi:
10.1016/0960-0760(93)90343-u. [PMID: 8499335] - M S Rizk, N A Zakhari, M I Walash, S S Toubar, C J Brooks, R Anderson. Gas chromatography and mass spectrometry of dimethylethylsilyl ether derivatives of norethisterone metabolites in plasma.
Acta pharmaceutica Nordica.
1991; 3(4):205-10. doi:
NULL. [PMID: 1781912] - G L Rose, M Dowsett, J E Mudge, J O White, S L Jeffcoate. The inhibitory effects of danazol, danazol metabolites, gestrinone, and testosterone on the growth of human endometrial cells in vitro.
Fertility and sterility.
1988 Feb; 49(2):224-8. doi:
10.1016/s0015-0282(16)59706-4. [PMID: 3338580] - H B He, S L Sun, D L Liu, H E Zheng. [Analysis of danazol and its metabolites in serum by RP-HPLC with maxplot UV detector].
Yao xue xue bao = Acta pharmaceutica Sinica.
1988; 23(9):698-702. doi:
NULL. [PMID: 3256205] - M Dowsett, K L Forbes, G L Rose, J E Mudge, S L Jeffcoate. A comparison of the effects of danazol and gestrinone on testosterone binding to sex hormone binding globulin in vitro and in vivo.
Clinical endocrinology.
1986 May; 24(5):555-63. doi:
10.1111/j.1365-2265.1986.tb03285.x. [PMID: 3641693] - D Rosi, H C Neumann, R G Christiansen, H P Schane, G O Potts. Isolation, synthesis, and biological activity of five metabolites of danazol.
Journal of medicinal chemistry.
1977 Mar; 20(3):349-52. doi:
10.1021/jm00213a007. [PMID: 403283] - J Barbosa, U S Seal, R P Doe. Effects of steroids on plasma proteins--progestational agents.
The Journal of clinical endocrinology and metabolism.
1971 Apr; 32(4):547-54. doi:
10.1210/jcem-32-4-547. [PMID: 4100683] - A Despopoulos. Hepatic and renal excretory metabolism of bile salts: a background for understanding steroid-induced cholestasis.
The Journal of pharmacology and experimental therapeutics.
1971 Feb; 176(2):273-83. doi:
NULL. [PMID: 4254976] - L Mazurek, L Jeromin, K Stapor, G Brauner, J Wiernicki. [Hormonal treatment of renal cancers with anhydrohydroxyprogesterone (Ethisterone)].
Polski przeglad chirurgiczny.
1970; 42(6):Suppl 6a:962+. doi:
NULL. [PMID: 5453131] - F J Thomas, A W Steinbeck. Semiquantitative estimation of urinary pregnanetriol, pregnanetriolone and tetrahydro S in the investigation of adrenocortical function.
Acta endocrinologica.
1969 Apr; 60(4):645-56. doi:
10.1530/acta.0.0600645. [PMID: 4306403] - G D Lubash, R H Bard, J A Kline. Serum 'Angiotensinase activity' and female steroidal hormones.
The American journal of the medical sciences.
1969 Mar; 257(3):155-63. doi:
10.1097/00000441-196903000-00001. [PMID: 4304725] - K Kinoshita. [Gas chromatographic estimation of urinary pregnanetriol, pregnanetriolone and pregnanetetrole before and during administration of ACTH, metopirone and corticosteroids in patients with congenital adrenal hyperplasia].
Nihon Hinyokika Gakkai zasshi. The japanese journal of urology.
1967 Dec; 58(12):1191-201. doi:
10.5980/jpnjurol1928.58.12_1191. [PMID: 4299750] - W J RAWLINGS. PREGNANEDIOL EXCRETION AND PLACENTAL INSUFFICIENCY.
Fertility and sterility.
1965 May; 16(?):323-36. doi:
10.1016/s0015-0282(16)35585-6. [PMID: 14285363] - S D SOULE, M YANOW. Recovery of pregnanediol from urine following administration of oral anhydrohydroxyprogesterone, buccal progesterone, and intramuscular progesterone.
Obstetrics and gynecology.
1953 Jul; 2(1):68-72. doi:
. [PMID: 13073082]
