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an androgenic compound contained in drugs that are used to treat testosterone deficiency and female breast cancer and to stimulate growth and weight gain

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2017/05/12 10:14:51」(JST)

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Methyltestosterone (brand names Android, Androral, Metandren, Oraviron, Testred, Virilon),^[1] also known as 17α-methyltestosterone or as 17α-methylandrost-4-en-17β-ol-3-one, is a synthetic, orally active androgenic-anabolic steroid (AAS) and 17α-methylated derivative of testosterone that is used to treat males with androgen deficiency.^[2] It bears close structural similarity to testosterone, but has a methyl group at the C17α position in order to increase oral bioavailability. Due to efficient aromatization into the potent estrogen methylestradiol, methyltestosterone has relatively high estrogenicity and hence potential side effects such as gynecomastia.^[3]^[4]

Confiscated methyltestosterone.

History

Methyltestosterone was first synthesized in 1935, and was the first 17α-alkylated AAS to be synthesized.^[5]

References

^ "Methyltestosterone Oral : Uses, Side Effects, Interactions, Pictures, Warnings & Dosing". WebMD. Retrieved 2012-02-13.
^ "Truestar health".
^ Detlef Thieme; Peter Hemmersbach (18 December 2009). Doping in Sports. Springer Science & Business Media. pp. 470–. ISBN 978-3-540-79088-4.
^ Andrea R. Genazzani (17 January 2006). Postmenopausal Osteoporosis: Hormones & Other Therapies. Taylor & Francis US. pp. 243–. ISBN 978-1-84214-311-7.
^ Shahidi NT (2001). "A review of the chemistry, biological action, and clinical applications of anabolic-androgenic steroids". Clin Ther. 23 (9): 1355–90. doi:10.1016/s0149-2918(01)80114-4. PMID 11589254.

UpToDate Contents

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1. 女性における性機能障害：管理 sexual dysfunction in women management
2. 性腺機能低下を呈する男性に対するテストステロン治療 testosterone treatment of male hypogonadism
3. 遺伝性血管浮腫：一般診療および長期予防 hereditary angioedema general care and long term prophylaxis
4. 遺伝性血管浮腫：処置前の予防（短期予防） hereditary angioedema prophylaxis prior to procedures short term prophylaxis
5. 女性におけるアンドロゲン欠乏症および治療の概要 overview of androgen deficiency and therapy in women

English Journal

Two cyp17 genes perform different functions in the sex hormone biosynthesis and gonadal differentiation in Japanese flounder (Paralichthys olivaceus).

Meng L, Yu H, Qu J, Niu J, Ni F, Han P, Yu H, Wang X.
Gene. 2019 Jun;702()17-26.
P450c17, a key enzyme in the steroid generation pathway, plays an important role in the production of sex steroid and cortisol. In this study, two cyp17 gene isoforms, Pocyp17-I and Pocyp17-II were isolated from Paralichthys olivaceus gonads. Domain architecture analysis of Pocyp17-I and Pocyp17-II
PMID 30898704

Roles of piwil1 gene in gonad development and gametogenesis in Japanese flounder, Paralichthys olivaceus.

Ni F, Yu H, Liu Y, Meng L, Yan W, Zhang Q, Yu H, Wang X.
Gene. 2019 Jun;701()104-112.
PIWI family member piwil1, which associates with Piwi-interacting RNA (piRNA), is responsible in regulation of germ cell differentiation and maintenance of reproductive stem cells. In this study, we analyzed the piwil1 gene in Paralichthys olivaceus. Bioinformatics analysis and structure prediction
PMID 30905810

Persistence of androgens, progestogens, and glucocorticoids during commercial animal manure composting process.

Zhang JN, Yang L, Zhang M, Liu YS, Zhao JL, He LY, Zhang QQ, Ying GG.
The Science of the total environment. 2019 May;665()91-99.
Animal manure contains various organic contaminants such as steroids. The fate of these steroids during composting is still unknown. Here we investigated the fate of androgens, progestogens, and glucocorticoids during animal manure composting and evaluated their residues in compost-applied soils. Th
PMID 30772582

Japanese Journal

根治的前立腺摘除術後にアンドロゲン補充療法を施行したLOH症候群の1例

中野剛佑,木内寛,宮川康,辻村晃,野々村祝夫
泌尿器科紀要 = Acta urologica Japonica 60(8), 397-400, 2014-08
… After confirming that the prostate specific antigen value was under 0.01 ng/ml for three years after prostatectomy, the patient received 125 mg methyltestosterone monthly. …
NAID 120005468364

Occurrence of 17 alpha-methyltestosterone in masculinization process of Nile tilapia fry

LIMPIYAKORN Tawan,LEEPIPATPAIBOON Natchanun,ONG Say Kee [他]
旭硝子財団助成研究成果報告, 18p, 2013
NAID 40019978790

ホシガレイ仔稚魚の雄化誘導におけるメチルテストステロン投与の効果

築山陽介,征矢野清
水産増殖 61(2), 137-144, 2013
ホシガレイの仔稚魚を用いて，メチルテストステロン（MT）の雄化誘導に及ぼす影響を調べた。40日齢から MT を0.001，0.01，0.1，1，10μg/g･diet の濃度で経口投与した結果，0.1および 1μg/g･diet では雄への性比の偏りが認められた。また，10μg/g･diet では性比に偏りはみられず，GSI が減少していることから，過剰投与であると考えられた。46～110，130 …
NAID 130005062503

「メチルテストステロン」

Methyltestosterone
Clinical data
Trade names	Android, Androral, Metandren, Oraviron, Testred, Virilon
AHFS/Drugs.com	Monograph
Routes of; administration	Oral
ATC code	G03BA02 (WHO);
Legal status
Legal status	CA: Schedule IV; US: Schedule III; In general: ℞ (Prescription only);
Pharmacokinetic data
Metabolism	Liver
Biological half-life	6-8 hours
Excretion	90% urine / 10% feces
Identifiers
	IUPAC name 17α-Methylandrost-4-en-17β-ol-3-one;
CAS Number	58-18-4 ;
PubChem CID	6010;
IUPHAR/BPS	6945;
DrugBank	DB06710 ;
ChemSpider	5788 ;
UNII	V9EFU16ZIF;
ChEBI	CHEBI:27436 ;
ChEMBL	CHEMBL1395 ;
ECHA InfoCard	100.000.333
Chemical and physical data
Formula	C20H30O2
Molar mass	302.451
3D model (Jmol)	Interactive image;
	SMILES O=C4\C=C3/[C@]([C@H]2CC[C@]1([C@@H](CC[C@@]1(O)C)[C@@H]2CC3)C)(C)CC4 ;
	InChI InChI=1S/C20H30O2/c1-18-9-6-14(21)12-13(18)4-5-15-16(18)7-10-19(2)17(15)8-11-20(19,3)22/h12,15-17,22H,4-11H2,1-3H3/t15-,16+,17+,18+,19+,20+/m1/s1 ; Key:GCKMFJBGXUYNAG-HLXURNFRSA-N ;
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　　[★]

英: methyltestosterone
ラ: methyltestosteronum
商: エナルモン、エネルファ

[1] "Methyltestosterone Oral : Uses, Side Effects, Interactions, Pictures, Warnings & Dosing". WebMD. Retrieved 2012-02-13.

[2] "Truestar health".

[ThiemeHemmersbach2009-3] Detlef Thieme; Peter Hemmersbach (18 December 2009). Doping in Sports. Springer Science & Business Media. pp. 470–. ISBN 978-3-540-79088-4.

[Genazzani2006-4] Andrea R. Genazzani (17 January 2006). Postmenopausal Osteoporosis: Hormones & Other Therapies. Taylor & Francis US. pp. 243–. ISBN 978-1-84214-311-7.

[pmid11589254-5] Shahidi NT (2001). "A review of the chemistry, biological action, and clinical applications of anabolic-androgenic steroids". Clin Ther. 23 (9): 1355–90. doi:10.1016/s0149-2918(01)80114-4. PMID 11589254.

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methyltestosterone