Cyproterone (BioDeep_00000018425)
human metabolite blood metabolite
代谢物信息卡片
(1S,2S,3S,5R,11R,12S,15R,16S)-15-acetyl-9-chloro-15-hydroxy-2,16-dimethylpentacyclo[9.7.0.0²,⁸.0³,⁵.0¹²,¹⁶]octadeca-7,9-dien-6-one
化学式: C22H27ClO3 (374.1648622)
中文名称:
谱图信息:
最多检出来源 Homo sapiens(blood) 11.49%
分子结构信息
SMILES: CC(=O)C1(CCC2C1(CCC3C2C=C(C4=CC(=O)C5CC5C34C)Cl)C)O
InChI: InChI=1S/C22H27ClO3/c1-11(24)22(26)7-5-14-12-9-18(23)17-10-19(25)13-8-16(13)21(17,3)15(12)4-6-20(14,22)2/h9-10,12-16,26H,4-8H2,1-3H3/t12-,13+,14-,15-,16-,20-,21-,22-/m0/s1
描述信息
An anti-androgen that, in the form of its acetate (cyproterone acetate), also has progestational properties. It is used in the treatment of hypersexuality in males, as a palliative in prostatic carcinoma, and, in combination with estrogen, for the therapy of severe acne and hirsutism in females. [Pubchem]
G - Genito urinary system and sex hormones > G03 - Sex hormones and modulators of the genital system > G03H - Antiandrogens > G03HA - Antiandrogens, plain
D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006727 - Hormone Antagonists > D000726 - Androgen Antagonists
C274 - Antineoplastic Agent > C163758 - Targeted Therapy Agent > C146993 - Androgen Receptor Inhibitor
C147908 - Hormone Therapy Agent > C547 - Hormone Antagonist > C242 - Anti-Androgen
同义名列表
15 个代谢物同义名
(1S,2S,3S,5R,11R,12S,15R,16S)-15-acetyl-9-chloro-15-hydroxy-2,16-dimethylpentacyclo[9.7.0.0²,⁸.0³,⁵.0¹²,¹⁶]octadeca-7,9-dien-6-one; 6-Chlor-delta(6)-1,2-alpha-methylen-17-alpha-hydroxyprogesteron; 6-Chlor-delta(6)-1,2-a-methylen-17-a-hydroxyprogesteron; 6-Chlor-δ(6)-1,2-α-methylen-17-α-hydroxyprogesteron; 6-Chlor-δ(6)-1,2-a-methylen-17-a-hydroxyprogesteron; Cyproterone, 1alpha,2 alpha,9 beta,10 alpha-isomer; Cyproterone Acetate Impurity F; Ciproterona servycal; Cyproterone acetate; Novo-cyproterone; Apo-cyproterone; Cyproteronum; Ciproterone; Cyproterone; Ciproterona
数据库引用编号
8 个数据库交叉引用编号
- ChEBI: CHEBI:50742
- PubChem: 5284537
- HMDB: HMDB0015587
- ChEMBL: CHEMBL142130
- Wikipedia: Cyproterone
- MeSH: Cyproterone
- chemspider: 4447594
- PMhub: MS000007890
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
- Naomi Even Zohar, Yael Sofer, Iris Yaish, Merav Serebro, Karen Tordjman, Yona Greenman. Low-Dose Cyproterone Acetate Treatment for Transgender Women.
The journal of sexual medicine.
2021 07; 18(7):1292-1298. doi:
10.1016/j.jsxm.2021.04.008. [PMID: 34176757] - Supanat Burinkul, Krasean Panyakhamlerd, Ammarin Suwan, Punkavee Tuntiviriyapun, Sorawit Wainipitapong. Anti-Androgenic Effects Comparison Between Cyproterone Acetate and Spironolactone in Transgender Women: A Randomized Controlled Trial.
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2021 07; 18(7):1299-1307. doi:
10.1016/j.jsxm.2021.05.003. [PMID: 34274044] - Jun Zhang, Mi Su, Liangzhi Xu, Zhilan Yang, Weiyao Yin, Ying Nie, Xiaoyong Qiao, Ran Cheng, Yaxian Ma. [Efficacy and metabolic safety of long-term treatment with ethinyl oestradiol/cyproterone and desogestrel/ethinyl oestradiol tablets in women with polycystic ovary syndrome].
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10.1007/s00404-010-1790-9. [PMID: 21140159] - Yu-Chen Hsu, Dar-In Tai. Unusually high alanine aminotransferase to aspartate aminotransferase ratio in a patient with cyproterone-induced icteric hepatitis.
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1990 Apr; 42(4):669-76. doi:
10.1095/biolreprod42.4.669. [PMID: 2112030] - B Corenblum, B W Baylis. Medical therapy for the syndrome of familial virilization, insulin resistance, and acanthosis nigricans.
Fertility and sterility.
1990 Mar; 53(3):421-5. doi:
10.1016/s0015-0282(16)53334-2. [PMID: 2137793] - P Spritzer, L Billaud, J C Thalabard, P Birman, I Mowszowicz, M C Raux-Demay, F Clair, F Kuttenn, P Mauvais-Jarvis. Cyproterone acetate versus hydrocortisone treatment in late-onset adrenal hyperplasia.
The Journal of clinical endocrinology and metabolism.
1990 Mar; 70(3):642-6. doi:
10.1210/jcem-70-3-642. [PMID: 2137832] - Q G Li, M Hümpel. Serum protein binding characteristics of cyproterone acetate, gestodene, levonorgestrel and norethisterone in rat, rabbit, dog, monkey and man.
Journal of steroid biochemistry.
1990 Feb; 35(2):319-26. doi:
10.1016/0022-4731(90)90291-y. [PMID: 2137890] - F Di Silverio, M Serio, G D'Eramo, F Sciarra. Zoladex vs. Zoladex plus cyproterone acetate in the treatment of advanced prostatic cancer: a multicenter Italian study.
European urology.
1990; 18 Suppl 3(?):54-61. doi:
10.1159/000463982. [PMID: 2151278] - F Di Silverio, F Sciarra, G D'Eramo. Advanced prostatic cancer: clinical and hormonal response to flutamide in patients pretreated with LHRH analogue and cyproterone acetate.
European urology.
1990; 18(1):10-5. doi:
10.1159/000463858. [PMID: 2144819] - C Servadio, Z Braf, Y Siegel, Z Leib, R Saranga, A Lindner. Local thermotherapy of the benign prostate: a 1-year follow-up.
European urology.
1990; 18(3):169-73. doi:
10.1159/000463902. [PMID: 1702056] - F H Schröder. Pure antiandrogens as monotherapy in prospective studies of prostatic carcinoma.
Progress in clinical and biological research.
1990; 359(?):93-103; discussion 105. doi:
NULL. [PMID: 2149460] - F H Schröder. Antiandrogenic substances in the management of prostatic cancer.
Recent results in cancer research. Fortschritte der Krebsforschung. Progres dans les recherches sur le cancer.
1990; 118(?):163-73. doi:
10.1007/978-3-642-83816-3_16. [PMID: 2146723] - P Jungers, F Liote, V Dehaine, M Dougados, J Viriot, C Pelissier, F Kuttenn. [Hormonal contraception and lupus].
Annales de medecine interne.
1990; 141(3):253-6. doi:
NULL. [PMID: 1695073] - G M Molinatti, P Biffignandi. [Physiopathology and therapy of female idiopathic hirsutism. State of the art].
Annali italiani di medicina interna : organo ufficiale della Societa italiana di medicina interna.
1990 Jan; 5(1):39-47. doi:
NULL. [PMID: 2144992] - J A Marcondes, B L Wajchenberg, A C Abujamra, W W Luthold, E Samojlik, M A Kirschner. Monthly cyproterone acetate in the treatment of hirsute women: clinical and laboratory effects.
Fertility and sterility.
1990 Jan; 53(1):40-4. doi:
10.1016/s0015-0282(16)53213-0. [PMID: 2136835] - S Nishimura. [Role of testosterone propionate and insulin in the regeneration and growth of bone].
Meikai Daigaku shigaku zasshi = The Journal of Meikai University School of Dentistry.
1990; 19(3):291-309. doi:
NULL. [PMID: 2152002] - G M Prelević, M I Würzburger, L Balint-Perić, Z Puzigaća. Effects of a low-dose estrogen-antiandrogen combination (Diane-35) on clinical signs of androgenization, hormone profile and ovarian size in patients with polycystic ovary syndrome.
Gynecological endocrinology : the official journal of the International Society of Gynecological Endocrinology.
1989 Dec; 3(4):269-80. doi:
10.3109/09513598909152466. [PMID: 2516704] - L Stárka, M Bicíková, R Hampl. Epitestosterone--an endogenous antiandrogen?.
Journal of steroid biochemistry.
1989 Nov; 33(5):1019-21. doi:
10.1016/0022-4731(89)90255-0. [PMID: 2532272] - L F Fanjul, F Estévez, A Déniz Cáceres, I Marrero, L Benitez, I Centol, J Quintana, J González, L Llanes, C M Ruiz de Galarreta. The androgen receptor does not mediate progestin regulation of progesterone biosynthesis in cultured rat granulosa cells.
Biochemistry international.
1989 Nov; 19(5):977-84. doi:
NULL. [PMID: 2534567] - A Nanbu, Y Kumamoto, H Tachiki, N Itoh, N Mikuma, T Tsunekawa, Y Takagi, H Maruta. [A clinical study of congenital adrenal hyperplasia].
Hinyokika kiyo. Acta urologica Japonica.
1989 Nov; 35(11):1831-7. doi:
NULL. [PMID: 2559616] - E Ernst, C Schmölzl, A Matrai, W Schramm. Hemorheological effects of oral contraceptives.
Contraception.
1989 Nov; 40(5):571-80. doi:
10.1016/0010-7824(89)90129-7. [PMID: 2692965] - W J Pichler, R Lehner, P J Späth. Recurrent angioedema associated with hypogonadism or anti-androgen therapy.
Annals of allergy.
1989 Oct; 63(4):301-5. doi:
NULL. [PMID: 2529797] - M Vincens, C Mercier-Bodard, I Mowszowicz, F Kuttenn, P Mauvais-Jarvis. Testosterone-estradiol binding globulin (TeBG) in hirsute patients treated with cyproterone acetate (CPA) and percutaneous estradiol.
Journal of steroid biochemistry.
1989 Oct; 33(4A):531-4. doi:
10.1016/0022-4731(89)90037-x. [PMID: 2530403] - N van der Vange, H van der Berg, H J Kloosterboer, A A Haspels. Effects of seven low-dose combined contraceptives on vitamin B6 status.
Contraception.
1989 Sep; 40(3):377-84. doi:
10.1016/0010-7824(89)90100-5. [PMID: 2527729] - U Ganten, G Schröder, M Witt, F Zimmermann, D Ganten, G Stock. Sexual dimorphism of blood pressure in spontaneously hypertensive rats: effects of anti-androgen treatment.
Journal of hypertension.
1989 Sep; 7(9):721-6. doi:
NULL. [PMID: 2529310] - R C Winneker, M M Wagner, C J Shaw, B W Snyder. Antiandrogens do not reverse androgen-induced inhibition of sex hormone-binding globulin levels in adult female rhesus monkeys.
Endocrinology.
1989 Aug; 125(2):715-20. doi:
10.1210/endo-125-2-715. [PMID: 2526727] - M Fujimoto. [Effect of cyproterone acetate on aromatase activity in cultured human genital skin fibroblasts: intracellular control of aromatase activity].
Nihon Naibunpi Gakkai zasshi.
1989 Jun; 65(6):585-602. doi:
10.1507/endocrine1927.65.6_585. [PMID: 2551746] - J Jensen, B J Riis, V Strøm, C Christiansen. Long-term and withdrawal effects of two different oestrogen-progestogen combinations on lipid and lipoprotein profiles in post-menopausal women.
Maturitas.
1989 Jun; 11(2):117-28. doi:
10.1016/0378-5122(89)90004-2. [PMID: 2547137] - R Miccoli, M C Orlandi, F Fruzzetti, O Giampietro, G Melis, C Ricci, A Bertolotto, P Fioretti, R Navalesi. Metabolic effects of three new low-dose pills: a six-month experience.
Contraception.
1989 Jun; 39(6):643-52. doi:
10.1016/0010-7824(89)90039-5. [PMID: 2526717] - S Kasayama, M Yoshimura, T Oka. The regulation by thyroid hormones and androgen of epidermal growth factor synthesis in the submandibular gland and its plasma concentrations in mice.
The Journal of endocrinology.
1989 May; 121(2):269-75. doi:
10.1677/joe.0.1210269. [PMID: 2526843] - A H Nielsen, A Johannessen, K Poulsen. Inactive plasma renin exhibits sex difference in mice.
Clinical science (London, England : 1979).
1989 Apr; 76(4):439-46. doi:
10.1042/cs0760439. [PMID: 2523771] - C H Kasperk, J E Wergedal, J R Farley, T A Linkhart, R T Turner, D J Baylink. Androgens directly stimulate proliferation of bone cells in vitro.
Endocrinology.
1989 Mar; 124(3):1576-8. doi:
10.1210/endo-124-3-1576. [PMID: 2521824] - U F Habenicht, M F el Etreby. Selective inhibition of androstenedione-induced prostate growth in intact beagle dogs by a combined treatment with the antiandrogen cyproterone acetate and the aromatase inhibitor 1-methyl-androsta-1,4-diene-3,17-dione (1-methyl-ADD).
The Prostate.
1989; 14(4):309-22. doi:
10.1002/pros.2990140404. [PMID: 2473459] - R J Bosch, D J Griffiths, J H Blom, F H Schroeder. Treatment of benign prostatic hyperplasia by androgen deprivation: effects on prostate size and urodynamic parameters.
The Journal of urology.
1989 Jan; 141(1):68-72. doi:
10.1016/s0022-5347(17)40591-x. [PMID: 2462067] - B L Neubauer, P Biser, C D Jones, A Mariotti, D M Hoover, T Thornton, M O Thornton, R L Goode. Antagonism of androgen and estrogen effects in guinea pig seminal vesicle epithelium and fibromuscular stroma by keoxifene (LY156758).
The Prostate.
1989; 15(3):273-86. doi:
10.1002/pros.2990150308. [PMID: 2531383] - W Parzefall, P Monschau, R Schulte-Hermann. Induction by cyproterone acetate of DNA synthesis and mitosis in primary cultures of adult rat hepatocytes in serum free medium.
Archives of toxicology.
1989; 63(6):456-61. doi:
10.1007/bf00316448. [PMID: 2533487] - V Amice, J P Bercovici, K Nahoul, M H Hatahet, J Amice. Increase in H-Y antigen-positive lymphocytes in hirsute women: effects of cyproterone acetate and estradiol treatment.
The Journal of clinical endocrinology and metabolism.
1989 Jan; 68(1):58-62. doi:
10.1210/jcem-68-1-58. [PMID: 2521223] - T F Davison, A R Ezzat, J Rea. Use of cyproterone acetate to lower circulating corticosterone and its effects on lymphocytes in domestic fowl.
Research in veterinary science.
1989 Jan; 46(1):105-9. doi:
10.1016/s0034-5288(18)31127-5. [PMID: 2537991]
