アリルエストレノール
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出典(authority):フリー百科事典『ウィキペディア(Wikipedia)』「2014/04/15 15:09:22」(JST)
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Allylestrenol
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Systematic (IUPAC) name |
(17β)-17-(prop-2-en-1-yl)estr-4-en-17-ol |
Clinical data |
Pregnancy cat. |
Used in threatened miscarriage and RPL |
Legal status |
? |
Identifiers |
CAS number |
432-60-0 Y |
ATC code |
G03DC01 |
PubChem |
CID 235905 |
DrugBank |
DB01431 |
ChemSpider |
205855 Y |
UNII |
I47VB5DZ8O Y |
KEGG |
D01374 Y |
ChEMBL |
CHEMBL1445549 N |
Synonyms |
17α-Allylestr-4-en-17β-ol |
Chemical data |
Formula |
C21H32O |
Mol. mass |
300.48 g/mol |
SMILES
- O[C@]2(CC[C@H]1[C@H]4[C@H](CC[C@@]12C)[C@@H]3\C(=C/CCC3)CC4)C\C=C
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InChI
-
InChI=1S/C21H32O/c1-3-12-21(22)14-11-19-18-9-8-15-6-4-5-7-16(15)17(18)10-13-20(19,21)2/h3,6,16-19,22H,1,4-5,7-14H2,2H3/t16-,17+,18+,19-,20-,21-/m0/s1 Y
Key:ATXHVCQZZJYMCF-XUDSTZEESA-N Y
|
N (what is this?) (verify) |
Allylestrenol (BAN/INN), also known as allyloestrenol and allyl estrenol, is a synthetic progestogen used to prevent threatened miscarriage, recurrent pregnancy loss and premature labor.[1][2] In men, it has also been studied as a treatment for benign prostatic hyperplasia, with encouraging results.[3][4]
Allylestrenol is sold under several trade names, including Gestin, Turinal,Gestrenol, Gestanin, Gestanol or Gestanon, Maintaine, Orageston, and Profar. It is currently not marketed in the United States, United Kingdom, or Canada, but as of 2011[update], is extensively used in Bangladesh,Japan, Russia, India, and much of Southeast Asia.[1]
References
- ^ a b Sweetman, Sean C., ed. (2009). "Sex hormones and their modulators". Martindale: the complete drug reference (36th ed.). London: Pharmaceutical Press. p. 2082. ISBN 978-0-85369-840-1.
- ^ Cortés-Prieto J, Bosch AO, Rocha JA (1980). "Allylestrenol: three years of experience with Gestanon in threatened abortion and premature labor". Clinical Therapeutics 3 (3): 200–8. PMID 7459930.
- ^ Fukuoka H, Ishibashi Y, Shiba T, Tuchiya F, Sakanishi S (July 1993). "[Clinical study of allylestrenol (Perselin) on patients with prostatic hypertrophy]". Hinyokika Kiyo. Acta Urologica Japonica (in Japanese) 39 (7): 679–83. PMID 7689782.
- ^ Noguchi K, Takeda M, Hosaka M, Kubota Y (May 2002). "[Clinical effects of allylestrenol on patients with benign prostatic hyperplasia (BPH) evaluated with criteria for treatment efficacy in BPH]". Hinyokika Kiyo. Acta Urologica Japonica (in Japanese) 48 (5): 269–73. PMID 12094708.
External links
- "AUA 2007 - Prostate Cancer Basic Research (II)" - Uro Today
Progestogenics
|
|
Receptor |
|
|
Enzyme
(inhibitors) |
20,22-Desmolase
|
- 22-ABC
- 3,3′-Dimethoxybenzidine
- 3-Methoxybenzidine
- Aminoglutethimide
- Cyanoketone
- Danazol
- Etomidate
- Mitotane
- Trilostane
|
|
17α-Hydroxylase,
17,20-Lyase
|
- 22-ABC
- 22-Oxime
- Abiraterone
- Bifonazole
- Clotrimazole
- Cyanoketone
- Cyproterone acetate
- Danazol
- Econazole
- Galeterone
- Gestrinone
- Isoconazole
- Ketoconazole
- L-39
- Levonorgestrel
- Liarozole
- LY-207,320
- MDL-27,302
- Miconazole
- Mifepristone
- Orteronel
- Pioglitazone
- Rosiglitazone
- Spironolactone
- Stanozolol
- SU-10,603
- TGF-β
- Tioconazole
- Troglitazone
- VN/87-1
- YM116
|
|
3β-HSD
|
- 4-MA
- Azastene
- Cyanoketone
- Danazol
- Epostane
- Genistein
- Gestrinone
- Metyrapone
- Norethisterone
- Oxymetholone
- Pioglitazone
- Rosiglitazone
- Trilostane
- Troglitazone
|
|
21-Hydroxylase
|
- Aminoglutethimide
- Amphenone B
- Bifonazole
- Clotrimazole
- Diazepam
- Econazole
- Genistein
- Isoconazole
- Ketoconazole
- Metyrapone
- Miconazole
- Midazolam
- Tioconazole
|
|
|
Other |
Endogenous
|
- Progestogens: Deoxycorticosterone
- 17-Hydroxyprogesterone
- Progesterone
- Precursors: Cholesterol
- 22R-Hydroxycholesterol
- 20α,22R-Dihydroxycholesterol
- Pregnenolone
- 17-Hydroxypregnenolone
|
|
Indirect
|
- Androgens/Antiandrogens (see here)
- Estrogens/Antiestrogens (see here)
- GnRH agonists/antagonists (see here)
- Gonadotropins/Antigonadotropins (see here)
- Plasma proteins (Transcortin, Albumin)
|
|
Procedures
|
- Adrenalectomy
- Hypophysectomy
- Oophorectomy
- Orchiectomy
|
|
|
English Journal
- Using indirect covariance processing for structure elucidation of small molecules in cases of spectral crowding.
- Aspers RL, Geutjes PE, Honing M, Jaeger M.SourceMSD, Merck Research Laboratories, Medicinal Chemistry Oss, Molenstraat 110, 5342 CC Oss, The Netherlands.
- Magnetic resonance in chemistry : MRC.Magn Reson Chem.2011 Jul;49(7):425-36. doi: 10.1002/mrc.2766. Epub 2011 May 17.
- Indirect and unsymmetrical indirect covariance NMR provide powerful tools to compute and visualize correlation information by transforming component spectra into combined spectral data matrices. Sensitive component spectra such as TOCSY, HSQC and NOESY can be quickly converted into experimentally in
- PMID 21590729
- Application of a sensitive liquid chromatographic/tandem mass spectrometric method to a pharmacokinetic study of allylestrenol in healthy Chinese female volunteers.
- Shi X, Wu Y, Hang T, Xu X, Ding L, Tian Y, Wen A.SourceDepartment of Pharmacy, Xijing Hospital, The Fourth Military Medical University, Xi'an, Shaanxi, China.
- Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.J Chromatogr B Analyt Technol Biomed Life Sci.2008 Aug 1;871(1):90-4. doi: 10.1016/j.jchromb.2008.06.054. Epub 2008 Jul 6.
- A sensitive, specific and rapid liquid chromatographic/tandem mass spectrometric (LC/MS/MS) assay for the determination of allylestrenol in human plasma was established. Plasma samples were extracted by tert-butyl ether and separated by LC/MS/MS using a Phenomenex Curosil-PFP column (250 mm x 4.6 mm
- PMID 18639502
- Effects of steroidal and non-steroidal antiandrogens on wild-type and mutant androgen receptors.
- Urushibara M, Ishioka J, Hyochi N, Kihara K, Hara S, Singh P, Isaacs JT, Kageyama Y.SourceDepartment of Urology, Graduate School, Tokyo Medical and Dental University, Tokyo, Japan.
- The Prostate.Prostate.2007 Jun 1;67(8):799-807.
- BACKGROUND: Molecular basis for secondary antiandrogen therapy in prostate cancer with mutant androgen receptors (ARs) is not fully elucidated.MATERIALS AND METHODS: Effects of steroidal and non-steroidal antiandrogens on transcriptional activities of wild-type and mutant (W741C, T877A, and W741C+T8
- PMID 17373727
Japanese Journal
- 難水溶性製剤の溶出試験に界面活性剤として使用されるポリソルベート80の品質に関する研究
- 梶村 計志,川口 正美,四方田 千佳子
- 医薬品医療機器レギュラトリーサイエンス 43(7), 650-655, 2012-00-00
- NAID 40019383655
- Application of a sensitive liquid chromatographic/tandem mass spectrometric method to a pharmacokinetic study of allylestrenol in healthy Chinese female volunteers
- SHI Xiaopeng,WU Yin,HANG Taijun,XU Xiaofeng,DING Likun,TIAN Yun,WEN Aidong
- Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 871(1), 90-94, 2008-08-01
- NAID 10028003763
- アリルエストレノールによる前立腺肥大症の治療中断後,PSA値の回復に必要な期間についての検討
- 野口 和美,鈴木 康太郎,寺西 淳一 [他],Kondo Keiichi,Kishida Takeshi,Saito Kazuo,Uemura Hiroji,Kubota Yoshinobu
- 泌尿器科紀要 52(7), 527-530, 2006-07-00
- … With informed consent, 12 patients (72.8 +/- 12.2* years old) with BPH were treated with allylestrenol 50 mg/day for 4 months. … After treatment with allylestrenol for 4 months, mean serum testosterone and PSA levels were significantly decreased from 408 +/- 136* to 87.9 +/- 76.2* ng/dl, and from 2.81 +/- 0.87* to 2.04 +/- 0.82* ng/ml, respectively. …
- NAID 120001159918
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