Norethindrone enanthate (BioDeep_00000009927)
代谢物信息卡片
Norethindrone enanthate; Norethisterone enanthate; 17alpha-Ethynyl-17beta-heptanoyloxy-4-estren-3-one
化学式: C27H38O3 (410.2821)
中文名称: 炔诺酮庚酸酯
谱图信息:
最多检出来源 () 0%
分子结构信息
SMILES: C#CC1(OC(=O)CCCCCC)CCC2C3CCC4=CC(=O)CCC4C3CCC21C
InChI: InChI=1S/C27H38O3/c1-4-6-7-8-9-25(29)30-27(5-2)17-15-24-23-12-10-19-18-20(28)11-13-21(19)22(23)14-16-26(24,27)3/h2,18,21-24H,4,6-17H2,1,3H3/t21-,22+,23+,24-,26-,27-/m0/s1
描述信息
D012102 - Reproductive Control Agents > D003270 - Contraceptive Agents
Same as: D08285
同义名列表
数据库引用编号
12 个数据库交叉引用编号
- ChEBI: CHEBI:34894
- KEGG: C14486
- KEGGdrug: D08285
- PubChem: 229295
- Metlin: METLIN70097
- DrugBank: DB14678
- ChEMBL: CHEMBL3187229
- CAS: 3836-23-5
- PMhub: MS000023749
- PubChem: 17395486
- NIKKAJI: J59.376A
- KNApSAcK: 34894
分类词条
相关代谢途径
Reactome(0)
BioCyc(0)
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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)
0 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
- Smritee Dabee, Ramla F Tanko, Bryan P Brown, Rubina Bunjun, Christina Balle, Colin Feng, Iyaloo N Konstantinus, Shameem Z Jaumdally, Maricianah Onono, Gonasagrie Nair, Thesla Palanee-Phillips, Katherine Gill, Jared M Baeten, Linda-Gail Bekker, Jo-Ann S Passmore, Renee Heffron, Heather B Jaspan, Anna-Ursula Happel. Comparison of Female Genital Tract Cytokine and Microbiota Signatures Induced by Initiation of Intramuscular DMPA and NET-EN Hormonal Contraceptives - a Prospective Cohort Analysis.
Frontiers in immunology.
2021; 12(?):760504. doi:
10.3389/fimmu.2021.760504. [PMID: 34956191] - Jennifer E Balkus, Thesla Palanee-Phillips, Krishnaveni Reddy, Samantha Siva, Ishana Harkoo, Clemensia Nakabiito, Kenneth Kintu, Gonasangrie Nair, Catherine Chappell, Flavia Matovu Kiweewa, Samuel Kabwigu, Logashvari Naidoo, Nitesha Jeenarain, Mark Marzinke, Lydia Soto-Torres, Elizabeth R Brown, Jared M Baeten. Brief Report: Dapivirine Vaginal Ring Use Does Not Diminish the Effectiveness of Hormonal Contraception.
Journal of acquired immune deficiency syndromes (1999).
2017 10; 76(2):e47-e51. doi:
10.1097/qai.0000000000001455. [PMID: 28542081] - Joachim Wistuba, C Marc Luetjens, Jens Ehmcke, Klaus Redmann, Oliver S Damm, Antje Steinhoff, Reinhild Sandhowe-Klaverkamp, Eberhard Nieschlag, Manuela Simoni, Stefan Schlatt. Experimental endocrine manipulation by contraceptive regimen in the male marmoset (Callithrix jacchus).
Reproduction (Cambridge, England).
2013 Apr; 145(4):439-51. doi:
10.1530/rep-12-0373. [PMID: 23431271] - C Pelusi, A Costantino, S Cerpolini, G Pelusi, M C Meriggiola, R Pasquali. A placebo-controlled, randomized clinical trial using testosterone undecanoate with injectable norethisterone enanthate: effect on anthropometric, metabolic and biochemical parameters.
International journal of andrology.
2011 Dec; 34(6 Pt 1):548-55. doi:
10.1111/j.1365-2605.2010.01122.x. [PMID: 21087288] - Binod Kumar Yadav, Rajesh Kumar Gupta, Prajwal Gyawali, Rojeet Shrestha, Bibek Poudel, Manoj Sigdel, Bharat Jha. Effects of long-term use of depo-medroxyprogesterone acetate on lipid metabolism in Nepalese women.
The Korean journal of laboratory medicine.
2011 Apr; 31(2):95-7. doi:
10.3343/kjlm.2011.31.2.95. [PMID: 21474983] - Ammar Qoubaitary, Cristina Meriggiola, Chiu Ming Ng, Leslie Lumbreras, Silvia Cerpolini, G Pelusi, Peter D Christensen, Laura Hull, Ronald S Swerdloff, Christina Wang. Pharmacokinetics of testosterone undecanoate injected alone or in combination with norethisterone enanthate in healthy men.
Journal of andrology.
2006 Nov; 27(6):853-67. doi:
10.2164/jandrol.106.000281. [PMID: 16837736] - Aris Junaidi, C Marc Luetjens, Joachim Wistuba, Axel Kamischke, Ching-Hei Yeung, Manuela Simoni, Eberhard Nieschlag. Norethisterone enanthate has neither a direct effect on the testis nor on the epididymis: a study in adult male cynomolgus monkeys (Macaca fascicularis).
European journal of endocrinology.
2005 Apr; 152(4):655-61. doi:
10.1530/eje.1.01878. [PMID: 15817923] - Thelma E Canto de Cetina, Manuel Ordoñez Luna, José Antonio Cetina Canto, Susana Bassol. Menstrual pattern and lipid profiles during use of medroxyprogesterone acetate and estradiol cypionate and NET-EN (200 mg) as contraceptive injections.
Contraception.
2004 Feb; 69(2):115-9. doi:
10.1016/j.contraception.2003.09.015. [PMID: 14759615] - Mags E Beksinska, Jenni A Smit, Immo Kleinschmidt, Helen V Rees, Tim M M Farley, Franco Guidozzi. Detection of raised FSH levels among older women using depomedroxyprogesterone acetate and norethisterone enanthate.
Contraception.
2003 Nov; 68(5):339-43. doi:
10.1016/j.contraception.2003.08.003. [PMID: 14636937] - . Comparative study of the effects of two once-a-month injectable contraceptives (Cyclofem and Mesigyna) and one oral contraceptive (Ortho-Novum 1/35) on coagulation and fibrinolysis.
Contraception.
2003 Sep; 68(3):159-76. doi:
10.1016/s0010-7824(03)00164-1. [PMID: 14561536] - Michael Zitzmann, Ralf Junker, Axel Kamischke, Eberhard Nieschlag. Contraceptive steroids influence the hemostatic activation state in healthy men.
Journal of andrology.
2002 Jul; 23(4):503-11. doi:
. [PMID: 12065457] - C Rolf, U Knie, G Lemmnitz, E Nieschlag. Interpersonal testosterone transfer after topical application of a newly developed testosterone gel preparation.
Clinical endocrinology.
2002 May; 56(5):637-41. doi:
10.1046/j.1365-2265.2002.01529.x. [PMID: 12030915] - C Rolf, S Kemper, G Lemmnitz, U Eickenberg, E Nieschlag. Pharmacokinetics of a new transdermal testosterone gel in gonadotrophin-suppressed normal men.
European journal of endocrinology.
2002 May; 146(5):673-9. doi:
10.1530/eje.0.1460673. [PMID: 11980623] - M Bulent Tiras, V Noyan, N Fener, H Guner, M Yildirim, P D Darney. Effects of a monthly injectable steroidal contraceptive, Mesigyna, on menstrual pattern, lipoproteins, and coagulation parameters.
Contraception.
2001 Mar; 63(3):151-3. doi:
10.1016/s0010-7824(01)00190-1. [PMID: 11368988] - A Kamischke, S Venherm, D Plöger, S von Eckardstein, E Nieschlag. Intramuscular testosterone undecanoate and norethisterone enanthate in a clinical trial for male contraception.
The Journal of clinical endocrinology and metabolism.
2001 Jan; 86(1):303-9. doi:
10.1210/jcem.86.1.7057. [PMID: 11232016] - A Kamischke, J Diebäcker, E Nieschlag. Potential of norethisterone enanthate for male contraception: pharmacokinetics and suppression of pituitary and gonadal function.
Clinical endocrinology.
2000 Sep; 53(3):351-8. doi:
10.1046/j.1365-2265.2000.01097.x. [PMID: 10971453] - T A Lawrie, G J Hofmeyr, M De Jager, M Berk, J Paiker, E Viljoen. A double-blind randomised placebo controlled trial of postnatal norethisterone enanthate: the effect on postnatal depression and serum hormones.
British journal of obstetrics and gynaecology.
1998 Oct; 105(10):1082-90. doi:
10.1111/j.1471-0528.1998.tb09940.x. [PMID: 9800931] - O F Giwa-Osagie. Metabolic effects of once-a-month combined injectable contraceptives. The World Health Organization Task Force on Long-Acting Systemic Agents for Fertility Regulation, Geneva, Switzerland.
Contraception.
1994 May; 49(5):421-33. doi:
10.1016/0010-7824(94)90001-9. [PMID: 8045129] - J A McEwan, M Griffin, K Fotherby, I Trayner. Long-term use of depot-norethisterone enanthate: effect on blood lipid fractions.
Contraception.
1992 Jul; 46(1):49-60. doi:
10.1016/0010-7824(92)90131-c. [PMID: 1424623] - L Enk, B M Landgren, U B Lindberg, G Silfverstolpe, N Crona. A prospective, one-year study on the effects of two long acting injectable contraceptives (depot-medroxyprogesterone acetate and norethisterone oenanthate) on serum and lipoprotein lipids.
Hormone and metabolic research = Hormon- und Stoffwechselforschung = Hormones et metabolisme.
1992 Feb; 24(2):85-9. doi:
10.1055/s-2007-1003262. [PMID: 1533383] - K Fahmy, M Abdel-Razik, M Shaaraway, G al-Kholy, S Saad, A Wagdi, M al-Azzony. Effect of long-acting progestagen-only injectable contraceptives on carbohydrate metabolism and its hormonal profile.
Contraception.
1991 Oct; 44(4):419-30. doi:
10.1016/0010-7824(91)90032-b. [PMID: 1836754] - E Kesserü, H Albornoz, M Díaz, R Socolsky. Serum lipid variations in women on copper intrauterine devices, triphasic oral contraceptives and monthly injectable contraceptives.
Contraception.
1991 Sep; 44(3):235-44. doi:
10.1016/0010-7824(91)90015-8. [PMID: 1662595] - M M Shaaban. Contraception with progestogens and progesterone during lactation.
The Journal of steroid biochemistry and molecular biology.
1991; 40(4-6):705-10. doi:
10.1016/0960-0760(91)90294-f. [PMID: 1835650] - S Chalaby, S Abdel-Al, A el-Seginy, H Gamal-Eldin, M Nor-Eldin. The toxic pathophysiology of retinol hypervitaminosis and norethisterone enantate in rats.
Journal of the Egyptian Society of Parasitology.
1990 Jun; 20(1):257-64. doi:
. [PMID: 2332653] - A R Genazzani, F Petraglia, M Silferi, A M Lattesa, G Coukos, A D Genazzani, P Artini, C Nappi, A Volpe. Progestins modulate the action of estrogen on gonadotropin-releasing hormone, luteinizing hormone and prolactin in the rat.
Gynecologic and obstetric investigation.
1990; 29(3):197-202. doi:
10.1159/000293378. [PMID: 2141585] - J V Joshi, K T Hazari, R S Shah, U C Chadha, S Chitlange, J S Gokral, S G Arolkar. Serum progesterone and norethisterone levels following injection of norethisterone enanthate in different sites and doses.
Steroids.
1989 Jun; 53(6):751-61. doi:
10.1016/0039-128x(89)90065-2. [PMID: 2815152] - J Garza-Flores, V M Alba, M C Cravioto, L Hernandez, G Perez-Palacios, G Alvarado, R Rivera, R Recio, S Bassol. Estrogen-progestogen once-a-month injectable contraceptives and serum prolactin.
Contraception.
1989 May; 39(5):519-29. doi:
10.1016/0010-7824(89)90107-8. [PMID: 2524362] - K Amatayakul, W Petpoo, N Ratanawananukul, O Tanthayaphinant, S Tovanabutra, V Suriyanon. A study of adrenal corticol function and its reserve activity in long-acting injectable contraceptive users.
Contraception.
1988 May; 37(5):483-92. doi:
10.1016/0010-7824(88)90018-2. [PMID: 2970367] - H J Born, P Hörster-Poschmann, W Stoll, J Sandow, H D Taubert, H Kuhl. Investigations upon the mechanism of inhibition of spermatogenesis in the rat by a dimeric ethynodiol-testosterone ester.
Acta endocrinologica.
1988 Apr; 117(4):536-44. doi:
10.1530/acta.0.1170536. [PMID: 3133917] - M Griffin, D A Heaton, J A McEwan. Long-term use of an injectable contraceptive: effect of depot-norethisterone oenanthate on carbohydrate metabolism.
Contraception.
1988 Jan; 37(1):53-60. doi:
10.1016/0010-7824(88)90148-5. [PMID: 3284711] - T Rabe, B Runnebaum. [Parenteral contraceptive drugs: depot progestins].
Wiener medizinische Wochenschrift (1946).
1987 Nov; 137(20-21):474-9. doi:
NULL. [PMID: 2967589] - C Chaudhuri, T Bhowmik, M Mukherjea. Alterations in blood sugar, protein, and lipid levels in Indian women by norethisterone enanthate.
International journal of fertility.
1987 May; 32(3):240-4. doi:
. [PMID: 2885291] - P Virutamasen, S Dhanapas, S Leepipatpaiboon. Serum levels of norethisterone, estradiol and progesterone after administration of norethisterone oenanthate at different sites: a cross-over study.
Asia-Oceania journal of obstetrics and gynaecology.
1987 Mar; 13(1):49-53. doi:
10.1111/j.1447-0756.1987.tb00008.x. [PMID: 3593083] - T Bhowmik, M Mukherjea. Effect of Depo-Provera and Noristerat on some biochemical constituents of rat uterus.
Indian journal of experimental biology.
1986 Mar; 24(3):145-8. doi:
". [PMID: 2942471] - H Kuhl, H J Born, R Schneider, M Schneider, H D Taubert. Dose- and time-dependent effects of a dimeric ethynodiol-testosterone depot-preparation in female rat.
Endocrinologia experimentalis.
1985 Jun; 19(2):105-15. doi:
. [PMID: 3874766] - J Garza-Flores, S Cardenas, V Rodríguez, M C Cravioto, V Diaz-Sanchez, G Perez-Palacios. Return to ovulation following the use of long-acting injectable contraceptives: a comparative study.
Contraception.
1985 Apr; 31(4):361-6. doi:
10.1016/0010-7824(85)90004-6. [PMID: 3159544] - M G Elder. Injectable contraception.
Clinics in obstetrics and gynaecology.
1984 Dec; 11(3):723-41. doi:
10.1016/s0306-3356(21)00624-5. [PMID: 6239732] - S Zalányi, B M Landgren, E Johannisson. Pharmacokinetics, pharmacodynamic and endometrial effects of a single dose of 200 mg norethisterone enanthate.
Contraception.
1984 Sep; 30(3):225-37. doi:
10.1016/0010-7824(84)90086-6. [PMID: 6509978] - C Chaudhuri, M Mukherjea. Studies on some enzymes and sialic acid during progestational contraceptive therapy.
Contraception.
1984 Jun; 29(6):573-83. doi:
10.1016/s0010-7824(84)80019-0. [PMID: 6467944] - K Fotherby, S Yong-En, G Howard, M G Elder, J Muggeridge. Return of ovulation and fertility in women using norethisterone oenanthate.
Contraception.
1984 May; 29(5):447-55. doi:
10.1016/0010-7824(84)90018-0. [PMID: 6744861] - K M Kandeel, S A Nayel, M S Abaza. The effect of injectable contraceptive on lipid metabolism in women.
Biomedica biochimica acta.
1984; 43(1):111-5. doi:
NULL. [PMID: 6721873] - K Fotherby, O Towobola, J Muggeridge, M G Elder. Norethisterone levels in maternal serum and milk after intramuscular injection of norethisterone oenanthate as a contraceptive.
Contraception.
1983 Nov; 28(5):405-11. doi:
10.1016/0010-7824(83)90073-2. [PMID: 6673900] - G Etchegoyen, E Wolpert, E Galván, J Landeros, G Pérez-Palacios. Effects of synthetic steroid contraceptives on biliary lipid composition of normal Mexican women.
Contraception.
1983 Jun; 27(6):591-603. doi:
10.1016/0010-7824(83)90024-0. [PMID: 6617205] - P Lähteenmäki, J Toivonen, P L Lähteenmäki. Postabortal contraception with norethisterone enanthate injections.
Contraception.
1983 Jun; 27(6):553-62. doi:
10.1016/0010-7824(83)90020-3. [PMID: 6413130] - K Fotherby, S Koetsawang. Metabolism of injectable formulations of contraceptive steroids in obese and thin women.
Contraception.
1982 Jul; 26(1):51-8. doi:
10.1016/0010-7824(82)90171-8. [PMID: 7128134] - K Fotherby, I Trayner, G Howard, A Hamawi, M G Elder. Effect of injectable norethisterone oenanthate (Norigest) on blood lipid levels.
Contraception.
1982 Apr; 25(4):435-46. doi:
10.1016/0010-7824(82)90099-3. [PMID: 6955136] - G W Sang, K Fotherby, G Howard, M Elder, P G Bye. Pharmacokinetics of norethisterone oenanthate in humans.
Contraception.
1981 Jul; 24(1):15-27. doi:
10.1016/0010-7824(81)90065-2. [PMID: 7273765] - K V Prasad, K M Nair, B Sivakumar, K Prema, B S Rao. Plasma levels of norethidrone in Indian women receiving norethidrone enanthate (20 mg) injectable.
Contraception.
1981 May; 23(5):497-506. doi:
10.1016/0010-7824(81)90077-9. [PMID: 7285573] - D J Back, A M Breckenridge, C R Chapman, F E Crawford, K A Olsen, M L Orme, P H Rowe. Studies on the enzymatic cleavage of norethisterone oenanthate.
Contraception.
1981 Feb; 23(2):125-32. doi:
10.1016/0010-7824(81)90098-6. [PMID: 7238040] - N Andino. Phase I clinical trial of two contraceptive preparations. Norethisterone enanthate (NEN) and norethisterone acetate (NET).
Contraception.
1981 Feb; 23(2):141-55. doi:
10.1016/0010-7824(81)90100-1. [PMID: 6786825] - F S Khan, K Fotherby. In vitro hydrolysis of 19-norsteroid esters.
Journal of steroid biochemistry.
1980 Apr; 13(4):461-2. doi:
10.1016/0022-4731(80)90355-6. [PMID: 7392623] - K Prema, B A Ramalakshmi, S Babu. Serum copper and zinc in hormonal contraceptive users.
Fertility and sterility.
1980 Mar; 33(3):267-71. doi:
10.1016/s0015-0282(16)44591-7. [PMID: 6444895] - S Werawatgoompa, B Vaivanijkul, S Leepipatpaiboon, K Channiyom, P Virutamasen, N Dusitsin. The effect of injectable norethisterone oenanthate on ovarian hormones in Thai women.
Contraception.
1980 Mar; 21(3):299-309. doi:
10.1016/0010-7824(80)90008-6. [PMID: 7389353] - H J Gilfrich, E Nieschlag, J Dudeck, C Overzier. [Norethisterone enanthate. Studies during the use of a long-acting parenteral contraceptive].
Deutsche medizinische Wochenschrift (1946).
1969 Nov; 94(48):2473-7. doi:
10.1055/s-0028-1110466. [PMID: 5351331]
