Stanozolol (BioDeep_00000001435)
Secondary id: BioDeep_00000406024
human metabolite Endogenous blood metabolite Chemicals and Drugs
代谢物信息卡片
化学式: C21H32N2O (328.2515)
中文名称: 康力龙
谱图信息:
最多检出来源 Homo sapiens(blood) 11.32%
分子结构信息
SMILES: CC12Cc3c[nH]nc3CC1CCC1C2CCC2(C)C1CCC2(C)O
InChI: InChI=1S/C21H32N2O/c1-19-11-13-12-22-23-18(13)10-14(19)4-5-15-16(19)6-8-20(2)17(15)7-9-21(20,3)24/h12,14-17,24H,4-11H2,1-3H3,(H,22,23)
描述信息
Stanozolol is only found in individuals that have used or taken this drug. Stanozolol has is a synthetic anabolic steroid with therapeutic uses in treating hereditary angioedema. Stanozolol was first synthesized by Clinton et al. in 1959, as a heterocyclic anabolic androgenic steroid. The structure of Stanozolol differs from endogenous steroid hormones and most commercially available anabolic steroids. It most closely resembles methyl testosterone. Instead of the 3-ketogroup in methyltestosterone, there is a pyrazole ring fused to the androstane ring system. This slightly different structure has the disadvantage of making extraction and isolation of the molecule from matrices more difficult. Like most other anabolic steroids, Stanozolol has poor gas chromatographic behavior and is difficult to detect in urine, because of renal clearance and low urinary excretion. This is due to the rapid metabolization, leading to low concentration levels of the parent compound found in urine. Therefore, most research studies had focused on the detection of urinary metabolites. Androgens are drugs, derived from the natural male sex hormone testosterone, with high anabolic potential and minimized androgenic activity. It has been abused by several high profile professional athletes. Stanozolol binds to androgen receptors, such as membrane bound receptor proteins LAGS and stanozolol-binding protein (STBP). Anabolic steroids stimulate protein synthesis, resulting in an acceleration of the food conversion rate and increasing muscle growth, body mass and enhanced performance. Androgens can be used as therapeutics, because they accelerate the recovery of protein deficiency and protein-wasting disorders (e.g. osteoporosis), but they are also widely abused in doping, as well in animals as in men. (PMID: 10404632, 10435307, 11175645, 11284331, 12064656, 12580506, 1448813, 14698206, 15013688, 15458725, 15631866, 15664350, 16040239, 16259046, 16288903, 1640693, 17066372, 17146762, 2306548, 2362445, 2625454, 2663904, 6539197, 9001957, 9300863, 9580049).
Stanozolol was first synthesized by Clinton et al. in 1959, as a heterocyclic anabolic androgenic steroid. The structure of Stan differs from endogenous steroid hormones and most commercially available anabolic steroids. It most closely resembles methyl testosterone. Instead of the 3-ketogroup in methyltestosterone, there is a pyrazole ring fused to the androstane ring system. This slightly different structure has the disadvantage of making extraction and isolation of the molecule from matrices more difficult. Like most other anabolic steroids, Stan has poor gas chromatographic behavior and is difficult to detect in urine, because of renal clearance and low urinary excretion. This is due to the rapid metabolization, leading to low concentration levels of the parent compound found in urine. Therefore, most research studies had focused on the detection of urinary metabolites.
A - Alimentary tract and metabolism > A14 - Anabolic agents for systemic use > A14A - Anabolic steroids > A14AA - Androstan derivatives
D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones > D045930 - Anabolic Agents
D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones > D000728 - Androgens
C147908 - Hormone Therapy Agent > C548 - Therapeutic Hormone > C1636 - Therapeutic Steroid Hormone
C147908 - Hormone Therapy Agent > C548 - Therapeutic Hormone > C2360 - Anabolic Steroid
同义名列表
32 个代谢物同义名
1,2,3,3a,3b,4,5,5a,6,7,10,10a,10b,11,12,12a-hexadecahydro-1,10a,12a-Trimethyl-cyclopenta[7,8]phenanthro[2,3-c]pyrazol-1-ol; (1S,2S,10S,13R,14S,17S,18S)-2,17,18-trimethyl-6,7-diazapentacyclo[11.7.0.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁸]icosa-4,7-dien-17-ol; Cyclopenta[7,8]phenanthro[2,3-c]pyrazole, 2H-androst-2-eno[3,2-c]pyrazol-17-ol deriv.; 2H-5a-Androst-2-eno[3,2-c]pyrazol-17b-ol, 17-methyl- (8ci); (5a,17b)-17-Methyl-2H-androst-2-eno[3,2-c]pyrazol-17-ol; 17b-Hydroxy-17a-methyl-5a-androstano[3,2-c]pyrazole; 17a-Methyl-17b-hydroxy-5a-androstano(3,2-c)pyrazole; 17b-Hydroxy-17-methyl-5a-androstano[3,2-c]pyrazole; 17-Methyl-pyrazolo[4,3:2,3]-5a-androstan-17b-ol; 17-Methyl-5a-androstano[3,2-c]pyrazol-17b-ol; Sanofi-synthelabo brand OF stanozolol; Sanofi winthrop brand OF stanozolol; Zambon brand OF stanozolol; Androstanazolestanazol; Androstanazole; Methylstanazol; Winstrol depot; Androstanazol; Stanozololum; Strombaject; Estanozolol; Winstrol V; Stanazolol; Stanozolol; Tevabolin; Winstroid; Win 14833; Winstrol; Estazol; Stromba; Anabol; Stanozolol
数据库引用编号
23 个数据库交叉引用编号
- ChEBI: CHEBI:181111
- ChEBI: CHEBI:9249
- KEGG: C07311
- KEGGdrug: D00444
- PubChem: 25249
- PubChem: 5277
- HMDB: HMDB0003116
- Metlin: METLIN2487
- DrugBank: DB06718
- ChEMBL: CHEMBL2079587
- Wikipedia: Stanozolol
- MeSH: Stanozolol
- foodb: FDB023109
- chemspider: 23582
- CAS: 875293-72-4
- CAS: 22957-48-8
- CAS: 10418-03-8
- CAS: 302-96-5
- PMhub: MS000000512
- PubChem: 9519
- NIKKAJI: J3.432K
- RefMet: Stanozolol
- KNApSAcK: 181111
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
- Mohammad Derakhshandeh, Farzaneh Taghian, Khosro Jalali Dehkordi, Seyed Ali Hosseini. Synchronized resistance training and bioactive herbal compounds of Tribulus Terrestris reverse the disruptive influence of Stanozolol.
Steroids.
2022 06; 182(?):109000. doi:
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Journal of agricultural and food chemistry.
2022 Apr; 70(15):4749-4754. doi:
10.1021/acs.jafc.1c08055
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Drug testing and analysis.
2021 Nov; 13(11-12):1921-1928. doi:
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. [PMID: 34505743] - Lorenz Göschl, Günter Gmeiner, Peter Gärtner, Georg Stadler, Valentin Enev, Mario Thevis, Wilhelm Schänzer, Sven Guddat, Guro Forsdahl. Stanozolol-N-glucuronide metabolites in human urine samples as suitable targets in terms of routine anti-doping analysis.
Drug testing and analysis.
2021 Sep; 13(9):1668-1677. doi:
10.1002/dta.3109
. [PMID: 34089570] - Wei-Ying Qu, Lin Zhao, Xv-Cheng Tan, Yi-Han Zhao. Stanozolol for the treatment of anemic lower-risk myelodysplastic syndromes without del(5q) after failure of epoetin alfa: findings from a retrospective study.
Annals of hematology.
2021 Jun; 100(6):1451-1457. doi:
10.1007/s00277-021-04508-w
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2021 Feb; 195(?):113886. doi:
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Drug testing and analysis.
2021 Feb; 13(2):283-298. doi:
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2020 Dec; 44(8):834-839. doi:
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Drug testing and analysis.
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2020 03; 155(?):108550. doi:
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2019 Oct; 303(?):109925. doi:
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2019 Apr; 124(4):360-369. doi:
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2018 Jan; 38(1):101-103. doi:
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2017 11; 174(?):265-275. doi:
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Drug testing and analysis.
2017 Nov; 9(11-12):1685-1694. doi:
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Drug testing and analysis.
2017 Jul; 9(7):1001-1010. doi:
10.1002/dta.2107
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Molecules (Basel, Switzerland).
2017 Jun; 22(6):. doi:
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Andrologia.
2017 Mar; 49(2):. doi:
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. [PMID: 27272124] - Zhe Wang, Xinmiao Zhou, Xin Liu, Ying Dong, Jinlan Zhang. A novel HPLC-MRM strategy to discover unknown and long-term metabolites of stanozolol for expanding analytical possibilities in doping-control.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.
2017 Jan; 1040(?):250-259. doi:
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. [PMID: 27842983] - E Nebot, V A Aparicio, D Camiletti-Moirón, R Martinez, R G Erben, G Kapravelou, C Sánchez-González, C De Teresa, J M Porres, M López-Jurado, P Aranda, P Pietschmann. Stanozolol Decreases Bone Turnover Markers, Increases Mineralization, and Alters Femoral Geometry in Male Rats.
Calcified tissue international.
2016 06; 98(6):609-18. doi:
10.1007/s00223-016-0108-8
. [PMID: 26801156] - Ahmed M Alkhunaizi, Mohamed A ElTigani, Rola S Rabah, Samih H Nasr. Acute bile nephropathy secondary to anabolic steroids.
Clinical nephrology.
2016 Feb; 85(2):121-6. doi:
10.5414/cn108696
. [PMID: 26587777] - Mario Thevis, Josef Dib, Andreas Thomas, Sebastian Höppner, Andreas Lagojda, Dirk Kuehne, Mark Sander, Georg Opfermann, Wilhelm Schänzer. Complementing the characterization of in vivo generated N-glucuronic acid conjugates of stanozolol by collision cross section computation and analysis.
Drug testing and analysis.
2015 Nov; 7(11-12):1050-6. doi:
10.1002/dta.1907
. [PMID: 26514814] - Seyed Morteza Tabatabaee, Reza Elahi, Shokoufeh Savaj. Bile cast nephropathy due to cholestatic jaundice after using stanozolol in 2 amateur bodybuilders.
Iranian journal of kidney diseases.
2015 Jul; 9(4):331-4. doi:
. [PMID: 26174462]
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Annals of allergy, asthma & immunology : official publication of the American College of Allergy, Asthma, & Immunology.
2015 Apr; 114(4):281-288.e7. doi:
10.1016/j.anai.2015.01.003
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The international journal of lower extremity wounds.
2015 Mar; 14(1):11-8. doi:
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Journal of forensic sciences.
2014 Jul; 59(4):1025-8. doi:
10.1111/1556-4029.12424
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Journal of pharmaceutical and biomedical analysis.
2014 Jan; 88(?):45-52. doi:
10.1016/j.jpba.2013.08.019
. [PMID: 24021270] - Wilhelm Schänzer, Sven Guddat, Andreas Thomas, Georg Opfermann, Hans Geyer, Mario Thevis. Expanding analytical possibilities concerning the detection of stanozolol misuse by means of high resolution/high accuracy mass spectrometric detection of stanozolol glucuronides in human sports drug testing.
Drug testing and analysis.
2013 Nov; 5(11-12):810-8. doi:
10.1002/dta.1516
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Acta pharmacologica Sinica.
2013 Jul; 34(7):969-75. doi:
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2013 May; 1292(?):195-200. doi:
10.1016/j.chroma.2013.01.001
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Current allergy and asthma reports.
2012 Aug; 12(4):273-80. doi:
10.1007/s11882-012-0273-4
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Analytical and bioanalytical chemistry.
2012 May; 403(5):1361-71. doi:
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The Journal of steroid biochemistry and molecular biology.
2012 Apr; 129(3-5):172-8. doi:
10.1016/j.jsbmb.2011.11.008
. [PMID: 22133647] - Amin Kanani, Robert Schellenberg, Richard Warrington. Urticaria and angioedema.
Allergy, asthma, and clinical immunology : official journal of the Canadian Society of Allergy and Clinical Immunology.
2011 Nov; 7 Suppl 1(?):S9. doi:
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Journal of medical case reports.
2011 Apr; 5(?):138. doi:
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Analytica chimica acta.
2011 Jan; 684(1-2):98-111. doi:
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. [PMID: 21167991] - Benjamin Davis, Jonathan A Bernstein. Conestat alfa for the treatment of angioedema attacks.
Therapeutics and clinical risk management.
2011; 7(?):265-73. doi:
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Clinical, cosmetic and investigational dermatology.
2011; 4(?):61-8. doi:
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. [PMID: 21760740] - Sylvi Wolf, Felicitas Rataj, Oliver Zierau, Kai Ostermann, Patrick Diel, Maria Kristina Parr, Günter Vollmer, Gerhard Rödel. A novel combined approach to detect androgenic activities with yeast based assays in Schizosaccharomyces pombe and Saccharomyces cerevisiae.
Toxicology letters.
2010 Dec; 199(3):410-5. doi:
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Bioanalysis.
2010 Dec; 2(12):1971-88. doi:
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2010 Sep; 52(5):727-33. doi:
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Neuropharmacology.
2010 Jun; 58(7):1078-84. doi:
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Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.
2010 Jan; 878(2):243-52. doi:
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Steroids.
2010 Jan; 75(1):57-69. doi:
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. [PMID: 19854209] - Sven Guddat, Mario Thevis, James Kapron, Andreas Thomas, Wilhelm Schänzer. Application of FAIMS to anabolic androgenic steroids in sport drug testing.
Drug testing and analysis.
2009 Nov; 1(11-12):545-53. doi:
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. [PMID: 20355171] - Rhiannon T Stewart, Andrew R McKinney, Carmel M Kerwick, E Bruce Young, Andrew Vadasz, Ian A Cade, Anthony C Willis, Malcolm D McLeod. Metabolism of stanozolol: chemical synthesis and identification of a major canine urinary metabolite by liquid chromatography-electrospray ionisation ion trap mass spectrometry.
The Journal of steroid biochemistry and molecular biology.
2009 Nov; 117(4-5):152-8. doi:
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. [PMID: 19748583] - Oscar J Pozo, Peter Van Eenoo, Koen Deventer, Leen Lootens, Susana Grimalt, Juan V Sancho, Felix Hernández, Philip Meuleman, Geert Leroux-Roels, Frans T Delbeke. Detection and structural investigation of metabolites of stanozolol in human urine by liquid chromatography tandem mass spectrometry.
Steroids.
2009 Oct; 74(10-11):837-52. doi:
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. [PMID: 19464304] - George Kaklamanos, Georgios Theodoridis, Themistoklis Dabalis. Determination of anabolic steroids in bovine urine by liquid chromatography-tandem mass spectrometry.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.
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