WordNet
- the most powerful female hormone that occurs naturally; synthesized and used to treat estrogen deficiency and breast cancer (同)oestradiol
Wikipedia preview
出典(authority):フリー百科事典『ウィキペディア(Wikipedia)』「2012/12/08 09:53:25」(JST)
[Wiki en表示]
See also: estradiol and estrogen
Estradiol valerate
|
Systematic (IUPAC) name |
(17β)-3-hydroxyestra-1,3,5(10)-trien-17-yl valerate |
Clinical data |
Pregnancy cat. |
? |
Legal status |
℞ Prescription only |
Routes |
Oral, IM[1] |
Identifiers |
CAS number |
979-32-8 |
ATC code |
None |
PubChem |
CID 13791 |
ChemSpider |
13194 |
Synonyms |
17β-Estradiol-17-valerate
pentanoate d'estra-1,3,5(10)-triène-3-ol-17β-yle
|
Chemical data |
Formula |
C23H32O3 |
Mol. mass |
356.498 g/mol |
SMILES
- O=C(O[C@H]3CC[C@H]4[C@H]2[C@@H](c1ccc(O)cc1CC2)CC[C@]34C)CCCC
|
InChI
-
InChI=1S/C23H32O3/c1-3-4-5-22(25)26-21-11-10-20-19-8-6-15-14-16(24)7-9-17(15)18(19)12-13-23(20,21)2/h7,9,14,18-21,24H,3-6,8,10-13H2,1-2H3/t18-,19-,20+,21+,23+/m1/s1
Key:RSEPBGGWRJCQGY-RBRWEJTLSA-N
|
Estradiol valerate (INN, USAN; brand names Altadiol, Deladiol, Delestrogen, Estraval, Progynova, Valergen, many others), or oestradiol valerate (BAN), is a synthetic ester, specifically the 17-pentanoyl ester, of the natural estrogen, 17β-estradiol.[2][3] It was introduced in the 1950s, and along with estradiol benzoate and estradiol cypionate, has since become one of the most widely used esters of estradiol.[4] Upon ingestion, regardless of the route of administration, estradiol valerate behaves as a prodrug, being cleaved by esterases in blood plasma and the liver into 17β-estradiol and valeric acid.[5][6] However, compared to estradiol itself, estradiol valerate is absorbed more slowly and possesses a longer duration, especially when given in an oil solution via intramuscular injection (in which it acts as a depot), and as a result, can be administered less frequently.[7][8]
See also
- Estrogen ester
- Estradiol and estrogen
References
- ^ Christoph Zink (1 January 1988). Dictionary of Obstetrics and Gynecology. Walter de Gruyter. p. 86. ISBN 978-3-11-085727-6. http://books.google.com/books?id=EQlvzV9V7xIC&pg=PA86. Retrieved 20 May 2012.
- ^ A. D. Roberts (1991). Dictionary of Steroids: Chemical Data, Structures, and Bibliographies. CRC Press. p. 415. ISBN 978-0-412-27060-4. http://books.google.com/books?id=qw5X0NK1A90C&pg=PA415. Retrieved 20 May 2012.
- ^ Index Nominum 2000: International Drug Directory. Taylor & Francis US. 2000. p. 405. ISBN 978-3-88763-075-1. http://books.google.com/books?id=5GpcTQD_L2oC&pg=PA405. Retrieved 20 May 2012.
- ^ Samuel S. C. Yen (1991). Reproductive endocrinology: physiology, pathophysiology, and clinical management. Saunders. ISBN 978-0-7216-3206-3. http://books.google.com/books?id=RN1qAAAAMAAJ. Retrieved 20 May 2012.
- ^ Düsterberg B, Nishino Y (December 1982). "Pharmacokinetic and pharmacological features of oestradiol valerate". Maturitas 4 (4): 315–24. PMID 7169965. http://linkinghub.elsevier.com/retrieve/pii/0378-5122(82)90064-0.
- ^ "Progynova 1mg (SPC) | Drugs.com" (HTML). http://www.drugs.com/uk/progynova-1mg-spc-3430.html. Retrieved 2012-09-06.
- ^ Sriram. Medicinal Chemistry. Pearson Education India. p. 427. ISBN 978-81-317-0031-0. http://books.google.com/books?id=9HSoZrcBRl0C&pg=PA427. Retrieved 20 May 2012.
- ^ Oriowo MA, Landgren BM, Stenström B, Diczfalusy E (April 1980). "A comparison of the pharmacokinetic properties of three estradiol esters". Contraception 21 (4): 415–24. PMID 7389356.
Estrogens and progestogens (G03C-D, L02)
|
|
Progestogens |
Agonist |
1st |
- Norpregnene
- Norethisterone#/Norethisterone acetate
- Etynodiol diacetate
|
|
2nd |
- Norpregnene
- Levonorgestrel#/Norgestrel/Norelgestromin
|
|
3rd |
- 19-Nortestosterone
- Desogestrel/Etonogestrel
- Gestodene
- Norgestimate
|
|
4th |
- Androstene
- 19-Norprogesterone
- Nomegestrol acetate
- Promegestone
- Trimegestone
- 19-Nortestosterone
|
|
17-OH |
- Chlormadinone acetate
- Cyproterone acetate
- Medroxyprogesterone acetate#
- Megestrol acetate
|
|
Other/
ungrouped |
- Pregnenedione
- Pregnene
- Pregnadiene
- Norpregnane
- Lynestrenol
- Norethynodrel
- Tibolone
- Dydrogesterone
- Quingestanol
|
|
|
Antiprogestogens/
SPRMs |
- Antagonists
- Aglepristone
- Mifepristone
- Asoprisnil
- Telapristone
- Ulipristal acetate
|
|
|
Estrogens |
Agonists |
Steroidal |
- Diosgenin
- Estetrol
- Estradiol
- Estradiol acetate
- Estradiol benzoate
- Estradiol cypionate#
- Estradiol dipropionate
- Estradiol enanthate
- Estradiol hemihydrate
- Estradiol undecylate
- Estradiol valerate
- Polyestradiol phosphate
- Estriol
- Estrone
- Estriol
- Ethinylestradiol#
- Promestriene
- Equilenin
- Equilin
|
|
Nonsteroidal |
- Chlorotrianisene
- Dienestrol
- Fosfestrol
- Diethylstilbestrol
- Zeranol
|
|
|
Antiestrogens/
SERMs |
- Afimoxifene
- Arzoxifene
- Bazedoxifene
- Clomifene#
- Cyclofenil
- Epimestrol
- Lasofoxifene
- Mepitiostane
- Nafoxidine
- Ormeloxifene
- Raloxifene
- Tamoxifen
- Toremifene
- Pure antagonists: Fulvestrant
|
|
Aromatase inhibitors |
- Nonselective
- Aminoglutethimide
- Testolactone
- Selective
- Anastrozole
- Atamestane
- Exemestane
- Fadrozole
- Formestane
- Letrozole
- Minamestane
- Plomestane
- Vorozole
|
|
|
- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
|
|
noco/cong/npls, sysi/epon
|
proc/asst, drug (G1/G2B/G3CD)
|
|
|
|
Estrogenics
|
|
Receptor |
ER (α, β)
|
|
|
GPER
|
- Agonists: Estradiol
- Fulvestrant
- G-1
- Genistein
- Quercetin
- Tamoxifen
|
|
|
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
- Danazol
- Econazole
- Galeterone
- Gestrinone
- Isoconazole
- Ketoconazole
- L-39
- 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
- Oxymetholone
- Pioglitazone
- Rosiglitazone
- Trilostane
- Troglitazone
|
|
17β-HSD
|
|
|
Aromatase
|
- 1,4,6-Androstatriene-3,17-dione
- 4-Androstene-3,6,17-trione
- 4-Cyclohexylaniline
- 4-Hydroxytestosterone
- 5α-DHNET
- Abyssinone II
- Aminoglutethimide
- Anastrozole
- Ascorbic acid (Vitamin C)
- Atamestane
- Bifonazole
- CGP-45,688
- CGS-47,645
- Clotrimazole
- DHT
- Difeconazole
- Econazole
- Exemestane
- Fadrozole
- Fenarimol
- Finrozole
- Formestane
- Imazalil
- Isoconazole
- Ketoconazole
- Letrozole
- Liarozole
- MEN-11066
- Miconazole
- Minamestane
- Nimorazole
- NKS01
- ORG-33,201
- Penconazole
- Plomestane
- Prochloraz
- Propioconazole
- Pyridoglutethimide
- Rogletimide
- Rotenone
- Talarozole
- Testolactone
- Tioconazole
- Triadimefon
- Triadimenol
- Troglitazone
- Vorozole
- YM511
- Zinc
Note: 5α-reductase and 21-hydroxylase inhibitors may also affect estrogen levels as they prevent metabolism of estrogen steroid precursors.
|
|
|
Other |
Endogenous
|
- Estrogens: 5α-Androstane-3β,17β-diol
- DHEA
- Estetrol
- Estradiol
- Estriol
- Estrone
- Antiestrogens: 2-Hydroxyestrone
- 16-Hydroxyestrone
- Precursors: Cholesterol
- 22R-Hydroxycholesterol
- 20α,22R-Dihydroxycholesterol
- Pregnenolone
- 17-Hydroxypregnenolone
- Progesterone
- 17-Hydroxyprogesterone
- Cortodoxone/Deoxycortisol
- DHEA
- DHEA sulfate
- 16-Hydroxy-DHEA
- 16-Hydroxy-DHEA sulfate
- Androstenediol
- Androstenedione
- 16-Hydroxyandrostenedione
- Testosterone
|
|
Indirect
|
- Androgens/Antiandrogens (see here)
- Calcitriol (a form of Vitamin D)
- GnRH agonists/antagonists (see here)
- Gonadotropins//Antigonadotropins (see here)
- Plasma proteins (SHBG, ABP, Albumin)
- Progestogens/Antiprogestins (see here)
- Prolactin
|
|
Procedures
|
- Adrenalectomy
- Hypophysectomy
- Oophorectomy
- Orchiectomy
|
|
|
UpToDate Contents
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English Journal
- Comparison of the symptomatic response in Indian menopausal women with different estrogen preparations for the treatment of menopausal symptoms: a randomized controlled trial.
- Malik S1, Pannu D2, Prateek S1, Sinha R1, Gaikwad H1.
- Archives of gynecology and obstetrics.Arch Gynecol Obstet.2016 Jun;293(6):1325-33. doi: 10.1007/s00404-016-4034-9. Epub 2016 Feb 16.
- PURPOSE: To compare symptomatic response in Indian women using different estrogen preparations for treatment of menopausal symptoms.METHODOLOGY: A randomized, single blind, four arm, parallel assignment study was conducted in VMMC and SJH, New Delhi, India. 200 Indian menopausal women were recruited
- PMID 26884352
- Estrogen and progestogen inhibit NF-κB in atherosclerotic tissues of ovariectomized ApoE (-/-) mice.
- Chen Y1, Zhao H2, Ren X3.
- Climacteric : the journal of the International Menopause Society.Climacteric.2016 May 3:1-7. [Epub ahead of print]
- OBJECTIVES: To determine the effects of estrogen and progestogen treatment on atherosclerotic inflammation and vascular remodeling.METHODS: Atherosclerosis was induced by feeding ovariectomized ApoE (-/-) mice a cholesterol-rich diet. Estrogen and progestogen were supplied as estradiol valerate (E2V
- PMID 27138353
- Bleeding pattern and cycle control with estetrol-containing combined oral contraceptives: results from a phase II, randomised, dose-finding study (FIESTA).
- Apter D1, Zimmerman Y2, Beekman L2, Mawet M3, Maillard C4, Foidart JM5, Coelingh Bennink HJ2.
- Contraception.Contraception.2016 May 3. pii: S0010-7824(16)30050-6. doi: 10.1016/j.contraception.2016.04.015. [Epub ahead of print]
- OBJECTIVES: This study aims to assess vaginal bleeding patterns and cycle control of oral contraceptives containing estetrol (E4) combined with either drospirenone (DRSP) or levonorgestrel (LNG).STUDY DESIGN: An open-label, multicentre, randomised, dose-finding study lasting six cycles in healthy wo
- PMID 27153745
Japanese Journal
- Simultaneous Determination of Estradiol Valerate and Medroxyprogesterone Acetate in a Tablet Formulation by Gas Chromatography-Mass Spectrometry
- Yilmaz Bilal
- Analytical sciences : the international journal of the Japan Society for Analytical Chemistry 26(3), 391-393, 2010-03-10
- NAID 10026782665
- Simultaneous Determination of Estradiol Valerate and Medroxyprogesterone Acetate in a Tablet Formulation by Gas Chromatography-Mass Spectrometry
- Analytical Sciences 26(3), 391-393, 2010
- … A new and simple gas chromatography–mass spectrometry (GC-MS) method has been developed for simultaneous determination of estradiol valerate (EV) and medroxyprogesterone acetate (MPA) in a tablet formulation. …
- NAID 130004441965
- Effect of Estrogen on Pressor Responses to .ALPHA.1-Adrenoreceptor Agonist in Conscious Female Rats.
- , , , , ,
- Hypertension Research 25(4), 609-613, 2002
- … At the age of 15 weeks, ovariectomized (OVX) rats received intramuscular injection of estradiol valerate (EV) 5μg (OVX+EV 5μg group; …
- NAID 130004436999
Related Links
- Easy to read patient leaflet for estradiol valerate. Includes indications, proper use, special instructions, precautions, and possible side effects. ... How to use estradiol valerate: Use estradiol valerate as directed by your doctor. Check ...
- Consumer information about the medication ESTRADIOL VALERATE - INJECTION (Delestrogen), includes side effects, drug interactions, recommended dosages, and storage information. Read more about the prescription drug ...
★リンクテーブル★
[★]
- 英
- estradiol, E2, oestradiol
- 化
- 安息香酸エストラジオール, estradiol benzoate, EB、ジプロピオン酸エストラジオール, estradiol dipropionate、吉草酸エストラジオール estradiol valerate
- 商
- ペラニン、ル・エストロ、プロギノン、フェミエスト、ディビ、ジュリナ、オバホルモン、エストラーナ、エストラダームTTS、エストルモンデポー
- (ヒドロキシプロゲステロン、エストラジオール)E・P・ホルモン
- (レボノルゲストレル、エストラジオール)ウェールナラ
- (テストステロン、エストラジオール)プリモジアン、ダイホルモン、ボセルモン
- (ノルエチステロン、エストラジオール)メノエイドコンビパッチ
- (ヒドロキシプロゲステロン、エストラジオール)ルテス
- 関
- エストロゲン、17 beta-estradiol、estradiol-17beta
[★]
吉草酸、吉草酸エステル、吉草酸塩
- 関
- valeric acid
[★]
エストラジオール E2