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Dienogest
|
Systematic (IUPAC) name |
[(17β)-17-Hydroxy-3-oxoestra-4,9-dien-17-yl]acetonitrile |
Clinical data |
Trade names |
Visanne |
AHFS/Drugs.com |
International Drug Names |
Pregnancy cat. |
B3 (AU) |
Legal status |
Prescription Only (S4) (AU) |
Routes |
Oral |
Pharmacokinetic data |
Bioavailability |
90%[1] |
Protein binding |
90%[2] |
Metabolism |
Hepatic (CYP3A4-mediated)[3] |
Half-life |
6-12 hours[4] |
Excretion |
Renal |
Identifiers |
CAS number |
65928-58-7 Y |
ATC code |
G03DB08
G03AB08 G03FA15 (combinations with estrogen) |
PubChem |
CID 68861 |
ChemSpider |
62093 N |
UNII |
46M3EV8HHE N |
KEGG |
D03799 Y |
ChEBI |
CHEBI:70708 N |
ChEMBL |
CHEMBL1201864 N |
Synonyms |
17-hydroxy-3-oxo-19-nor-17α-pregna-4,9-diene-21-nitrile
17α-cyanomethyl-17β-hydroxy-estra-4,9(10)-dien-3-one |
Chemical data |
Formula |
C20H25NO2 |
Mol. mass |
311.42 g/mol[1] |
Physical data |
Density |
1.2 g/cm³ |
Boiling point |
549 °C (1020 °F) |
N (what is this?) (verify) |
Dienogest is an orally-active semisynthetic, steroidal progestogen (or progestin).[5] It is available for use as an oral contraceptive in combination with ethinylestradiol. It has antiandrogenic activity and as a result can improve androgenic symptoms.[1][6] It is a non-ethinylated progestin which is structurally related to testosterone.[3] Dienogest given in isolation is available for the treatment of endometriosis under the trade name Visanne.
Contents
- 1 History
- 2 Indications
- 2.1 Contraception
- 2.2 Endometriosis
- 3 Pharmacodynamics
- 3.1 Progestational activity
- 3.2 Inhibition of ovulation
- 4 Adverse effects
- 5 References
History[edit]
Dienogest was synthesised in 1979 in Jena, Germany under the leadership of Prof. Kurt Ponsold, was initially referred to as STS 557.[7][8] It was found that its potency was 10 times that of levonorgestrel.[9] The first product on the market to contain dienogest as a contraceptive pill Valette in 1995 made by Jenapharm.[10] It has been little used outside of Germany.
Indications[edit]
Contraception[edit]
Dienogest is used primarily as a contraceptive in combination with ethinylestradiol. It is given as a tablet containing 2 mg of dienogest and 30 μg of ethinylestradiol.[12] Dienogest is also available in a quadriphasic oral contraceptive pill combined with estradiol valerate, marketed as Natazia in the United States and Qlaira in some European countries. This formulation is also approved for the treatment of heavy menstrual bleeding.
The minimum dose required to inhibit ovulation has been found to be approximately 1 mg.[13]
Endometriosis[edit]
Dienogest is also approved in the European Union for the treatment of endometriosis.[14][15] It has been shown to be equally effective as leuprorelin,[16] which is a second line medication against endometriosis.
Pharmacodynamics[edit]
Progestational activity[edit]
Dienogest has moderate affinity for the progesterone receptor in human uterus tissue, in vitro, about 10% that of progesterone.[17]
Inhibition of ovulation[edit]
The minimum effective dose of oral dienogest required to inhibit ovulation is 1 mg/day.[18] The inhibition of ovulation by dienogest occurs mainly via peripheral action as opposed to central action on gonadotrophin secretion.[1] Oral treatment of dienogest 2 mg/day in cyclical women reduced serum progesterone levels to anovulatory levels, however serum levels of lutenising hormone and follicle-stimulating hormone are not significantly altered.[18]
Adverse effects[edit]
Adverse effects associated with dienogest are the same as those expected of a progestogen.[1] These include weight gain, increased blood pressure, breast tenderness and nausea.[19] It produces no androgenic side effects and has little effect on metabolic and lipid haemostatic parameters.[20]
References[edit]
- ^ a b c d e Foster RH, Wilde MI (1998). "Dienogest". Drugs 56 (5): 825–33; discussion 834–5. doi:10.2165/00003495-199856050-00007. PMID 9829156.
- ^ de Lignieres B, Dennerstein L, Backstrom T (1995). "Influence of route of administration on progesterone metabolism". Maturitas 21 (3): 251–7. doi:10.1016/0378-5122(94)00882-8. PMID 7616875.
- ^ a b Stanczyk FZ (2003). "All progestins are not created equal". Steroids 68 (10–13): 879–90. doi:10.1016/j.steroids.2003.08.003. PMID 14667980.
- ^ Sitruk-Ware R (2004). "Pharmacological profile of progestins". Maturitas 47 (4): 277–83. doi:10.1016/j.maturitas.2004.01.001. PMID 15063480.
- ^ Nakamura M, Katsuki Y, Shibutani Y, Oikawa T (1999). "Dienogest, a synthetic steroid, suppresses both embryonic and tumor-cell-induced angiogenesis". European Journal of Pharmacology 386 (1): 33–40. doi:10.1016/S0014-2999(99)00765-7. PMID 10611461.
- ^ Raudrant D, Rabe T (2003). "Progestogens with antiandrogenic properties". Drugs 63 (5): 463–92. doi:10.2165/00003495-200363050-00003. PMID 12600226.
- ^ Menzenbach B, Hübner M, K. Ponsold (1984). "Untersuchungen zur Bromierung/Dehydrobromierung von 17-Cyanmethyl-17-hydroxy-östr-5(10)-en-3-on". Journal für Praktische Chemie 326 (6): 893–898. doi:10.1002/prac.19843260606.
- ^ Kaufmann G, Dautzenberg H, Henkel H, et al. (August 1999). "Nitrile hydratase from Rhodococcus erythropolis: metabolization of steroidal compounds with a nitrile group". Steroids 64 (8): 535–40. doi:10.1016/S0039-128X(99)00028-8. PMID 10493599.
- ^ Oettel M, Kurischko A (1980). "STS 557, a new orally active progestin with antiprogestational and contragestational properties in rabbits". Contraception 21 (1): 61–9. doi:10.1016/0010-7824(80)90140-7. PMID 7357870.
- ^ http://www.jenapharm.de/unternehmen/ueber-uns/geschichte/1965-1995/
- ^ Wiegratz I, Mittmann K, Dietrich H, Zimmermann T, Kuhl H (2006). "Fertility after discontinuation of treatment with an oral contraceptive containing 30 microg of ethinyl estradiol and 2 mg of dienogest". Fertil. Steril. 85 (6): 1812–9. doi:10.1016/j.fertnstert.2005.11.052. PMID 16759929.
- ^ Moore C, Carol W, Gräser T, Mellinger U, Walter F (1999). "Influence of Dienogest on Ovulation in Young Fertile Women". Clinical Drug Investigation 18 (4): 271–278.
- ^ "Dienogest for the treatment of endometriosis" (PDF). London New Drugs Group. Retrieved 2010-12-07.
- ^ "Visanne" (in German). Netdoctor.de.
- ^ Strowitzki, T; Marr, J; Gerlinger, C; Faustmann, T; Seitz, C (2010). "Dienogest is as effective as leuprolide acetate in treating the painful symptoms of endometriosis: a 24-week, randomized, multicentre, open-label trial". Human reproduction (Oxford, England) 25 (3): 633–41. doi:10.1093/humrep/dep469. PMID 20089522.
- ^ Oettel M, Bervoas-Martin S, Elger W, Golbs S, Hobe G, Kaufmann G, Mathieu M, Moore C, Schneider B, Puri C, Ritter P, Reddersen G, Schon R, Strauch G, Zimmermann H (1995). "A 19-norprogestin without 17α-ethinyl group II: Dienogest from a pharmacokinetic point of view". Drugs of Today 31 (7): 499–516.
- ^ a b Oettel M, Carol W, Elger W, Kaufmann G, Moore C, Romer W, Klinger G, Schneider B, Schroder J, Sobek L, Walter F, Zimmermann H (1995). "A 19-norprogestin without 17α-ethinyl group II: Dienogest from a pharmacodynamic point of view". Drugs of Today 31 (7): 517–536.
- ^ Galbraith, Alan; Shane Bullock, Elizabeth Manias, Barry Hunt, Ann Richards (2007). Fundamentals of Pharmacology: An Applied Approach for Nursing and Health. United Kingdom: Pearson Education LTD. p. 632. ISBN 978-0-13-186901-1.
- ^ Wiegratz I, Lee JH, Kutschera E, Bauer HH, von Hayn C, Moore C, Mellinger U, Winkler UH, Gross W, Kuhl H (2002). "Effect of dienogest-containing oral contraceptives on lipid metabolism". Contraception 65 (3): 223–9. doi:10.1016/S0010-7824(01)00310-9. PMID 11929644.
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)
|
|
|
|
Androgenics
|
|
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 (I, II)
|
- 4-MA
- Azastene
- Cyanoketone
- Danazol
- Epostane
- Genistein
- Gestrinone
- Levonorgestrel
- Metyrapone
- Oxymetholone
- Pioglitazone
- Rosiglitazone
- Trilostane
- Troglitazone
|
|
17β-HSD (I-XIV)
|
|
|
5α-Reductase (I, II)
|
- 22-Oxime
- Alfatradiol
- Azelaic acid
- β-Sitosterol
- Bexlosteride
- Dutasteride
- Epitestosterone
- Epristeride
- Finasteride
- gamma-Linolenic acid
- Ganoderic acid
- Izonsteride
- L-39
- Lapisteride
- Polyunsaturated fatty acids (α-linolenic acid, linoleic acid, γ-linolenic acid, oleic acid)
- saw palmetto
- Turosteride
- Vitamin B6
- Zinc
|
|
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: 21-Hydroxylase inhibitors may also affect androgen levels as they prevent metabolism of androgen steroid precursors.
|
|
|
Other |
Endogenous
|
- Androgens: Dihydrotestosterone
- Testosterone
- Antiandrogens: Epitestosterone
- Precursors: Cholesterol
- 22R-Hydroxycholesterol
- 20α,22R-Dihydroxycholesterol
- Pregnenolone
- 17-Hydroxypregnenolone
- Progesterone
- 17-Hydroxyprogesterone
- Cortodoxone/Deoxycortisol
- DHEA
- DHEA sulfate
- Androstenediol
- Androstenedione
|
|
Indirect
|
- Estrogens/Antiestrogens (see here)
- GnRH agonists/antagonists (see here)
- Gonadotropins/Antigonadotropins (see here)
- Plasma proteins (SHBG, ABP, Albumin)
- Progestogens/Antiprogestins (see here)
- Prolactin
|
|
Procedures
|
- Adrenalectomy
- Hypophysectomy
- Oophorectomy
- Orchiectomy
|
|
|
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
|
|
|
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
|
|
|
UpToDate Contents
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English Journal
- Medical treatment of idiopathic heavy menstrual bleeding. What is new? An evidence based approach.
- Abu Hashim H.SourceDepartment of Obstetrics and Gynecology, Mansoura Faculty of Medicine, Mansoura University, Mansoura, Egypt, hatem_ah@hotmail.com.
- Archives of gynecology and obstetrics.Arch Gynecol Obstet.2013 Feb;287(2):251-60. doi: 10.1007/s00404-012-2605-y. Epub 2012 Nov 3.
- BACKGROUND: Heavy menstrual bleeding (HMB) is an important health problem affecting up to 30 % of reproductive age women, interfering with their quality of life. Medical therapy, with the avoidance of unnecessary surgery, is an attractive option.PURPOSE: To provide a comprehensive review of the cur
- PMID 23117248
- Pituitary, ovarian and additional contraceptive effects of an estradiol-based combined oral contraceptive: results of a randomized, open-label study.
- Endrikat J, Parke S, Trummer D, Serrani M, Duijkers I, Klipping C.SourceBayer HealthCare Pharmaceuticals, 13353 Berlin, Germany; Universitätskliniken des Saarlandes, Frauenklinik, 66421 Homburg/Saar, Germany. Electronic address: jan.endrikat@bayer.com.
- Contraception.Contraception.2013 Feb;87(2):227-34. doi: 10.1016/j.contraception.2012.07.008. Epub 2012 Sep 17.
- BACKGROUND: The estrogen step-down/progestogen step-up 28-day estradiol valerate/dienogest (E(2)V/DNG) oral contraceptive effectively inhibits ovulation; however, limited data are available regarding its effects on estradiol (E(2)), progesterone, luteinizing hormone (LH) and follicle-stimulating hor
- PMID 22995539
Japanese Journal
- 田坂 美恵,松原 圭一,金子 久恵
- 現代産婦人科 = Modern trends in obstetrics & gynecology 60(2), 439-442, 2012-03-30
- NAID 10030697783
- 腹腔鏡下子宮内膜症手術後に再発する骨盤痛にジエノゲストを長期投与した1例
- 熊谷 広治,奥田 喜代司,寺井 義人,安田 勝行,山下 能毅,大道 正英
- 産婦人科の進歩 64(1), 2012
- 腹腔鏡下子宮内膜症手術後に再発する骨盤痛に対してジエノゲストを長期投与した1例を経験したので報告する.症例は,初診時38歳(現在46歳)の2経妊,1経産の女性で,月経期および月経周辺期の骨盤痛を訴えて来院した.低用量ピル(low dose estrogen progestin,以下,LEPと略す)等の内服でも疼痛が持続し,また両側卵巣にチョコレート嚢胞を認めたので腹腔鏡下手術を行い子宮内膜症のre …
- NAID 130001890090
Related Links
- Dienogest is an orally-active semisynthetic, steroidal progestogen (or progestin). It is available for use as an oral contraceptive in combination with ethinylestradiol . It has antiandrogenic activity and as a result can improve androgenic ...
Related Pictures
★リンクテーブル★
[★]
- 英
- dienogest
- 商
- ディナゲスト Dinagest