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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2014/07/26 19:44:31」(JST)

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Cortodoxone, also known as cortexolone or 11-deoxycortisol, is a steroid that can be oxygenated to cortisol (hydrocortisone). It was first synthesized by Tadeusz Reichstein.

On April 5, 1952, biochemist Durey Peterson and microbiologist Herbert Murray at Upjohn published the first report of a breakthrough fermentation process for the microbial 11α-oxygenation of steroids (e.g. progesterone) in a single step by common molds of the order Mucorales.^[1]

11α-oxygenation of cortodoxone produces 11α-hydrocortisone, which can be chemically oxidized to cortisone, or converted by further chemical steps to cortisol.

Subsequent fermentation processes for the microbial 11β-oxygenation of steroids in a single step were developed that could convert cortodoxone directly to cortisol.

Cortodoxone functions as a glucocorticoid, though is less potent than cortisol. It can be synthesized from 17-hydroxyprogesterone. In 11β-hydroxylase deficiency, cortodoxone levels increase dramatically, causing hypertension (as opposed to 21α-hydroxylase deficiency, in which patients have hypotension from a lack of mineralocorticoids).

Cortodoxone can also be converted to androstenedione.^[2] This could explain, at least in part, the marked increase in androstenedione levels in 11β-hydroxylase deficiency.^[2]

References

^ Peterson DH, Murray, HC (1952). "Microbiological oxygenation of steroids at carbon 11". J Am Chem Soc 74 (7): 1871–2. doi:10.1021/ja01127a531.
^ ^a ^b Auzéby A, Bogdan A, Touitou Y (January 1991). "Evidence for a new biologic pathway of androstenedione synthesis from 11-deoxycortisol". Steroids 56 (1): 33–6. doi:10.1016/0039-128X(91)90112-9. PMID 2028480.

UpToDate Contents

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1. メチラポン刺激試験 metyrapone stimulation tests
2. 下垂体機能低下症の診断 diagnosis of hypopituitarism
3. 血清および唾液中のコルチゾールの測定 measurement of cortisol in serum and saliva
4. 11βヒドロキシラーゼ欠損症による先天性副腎過形成 congenital adrenal hyperplasia due to 11 beta hydroxylase deficiency
5. 副腎ステロイド生合成 adrenal steroid biosynthesis

English Journal

Dried Blood Spot Testing for Seven Steroids Using Liquid Chromatography-Tandem Mass Spectrometry With Reference Interval Determination in the Korean Population.

Kim B1, Lee MN1, Park HD1, Kim JW1, Chang YS2, Park WS2, Lee SY3.
Annals of laboratory medicine.Ann Lab Med.2015 Nov;35(6):578-85. doi: 10.3343/alm.2015.35.6.578.
BACKGROUND: Conventional screening for congenital adrenal hyperplasia (CAH) using immunoassays generates a large number of false-positive results. A more specific liquid chromatography-tandem mass spectrometry (LC-MS/MS) method has been introduced to minimize unnecessary follow-ups. However, because
PMID 26354345

Concurrent Confirmation and Differential Diagnosis of Congenital Adrenal Hyperplasia from Dried Blood Spots: Application of a Second-Tier LC-MS/MS Assay in a Cross-Border Cooperation for Newborn Screening.

Monostori P1, Szabó P, Marginean O, Bereczki C, Karg E.
Hormone research in paediatrics.Horm Res Paediatr.2015 Sep 24. [Epub ahead of print]
BACKGROUND/AIMS: Newborn screening for congenital adrenal hyperplasia (CAH) is generally performed using 17- hydroxyprogesterone dissociation-enhanced, lanthanide fluorescence immunoassay (DELFIA®). The primary screening results must be confirmed due to high false-positive rates; however, the need
PMID 26397944

Steroid Profiling by LC-MS/MS in Nonsecreting and Subclinical Cortisol-Secreting Adrenocortical Adenomas.

Di Dalmazi G1, Fanelli F1, Mezzullo M1, Casadio E1, Rinaldi E1, Garelli S1, Giampalma E1, Mosconi C1, Golfieri R1, Vicennati V1, Pagotto U1, Pasquali R1.
The Journal of clinical endocrinology and metabolism.J Clin Endocrinol Metab.2015 Sep;100(9):3529-38. doi: 10.1210/JC.2015-1992. Epub 2015 Jul 10.
CONTEXT: Long-term follow-up studies revealed that patients with subclinical hypercortisolism (SH) due to adrenocortical adenomas have an increased incidence of cardiovascular diseases and mortality. No studies have yet investigated the steroid profile and its implications in patients with SH.OBJECT
PMID 26161451

Japanese Journal

Measurement of cortisol, cortisone, prednisolone, dexamethasone and 11-deoxycortisol with ultra high performance liquid chromatography-tandem mass spectrometry : Application for plasma, plasma ultrafiltrate, urine and saliva in a routine laboratory

MCWHINNEY Brett C.,BRISCOE Scott E.,UNGERER Jacobus P. J.,PRETORIUS Carel J.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 878(28), 2863-2869, 2010-10-15
NAID 10028042865

尿中テトラヒドロ-11-デオキシコルチゾール(THS) (広範囲血液・尿化学検査免疫学的検査(第7版・4)その数値をどう読むか) -- (内分泌学的検査副腎皮質関係)

水木一仁
日本臨床 68(-) (982), 401-403, 2010-07
NAID 40017200770

Related Pictures

★リンクテーブル★

リンク元	「副腎皮質ホルモン」「メチラポン」「11-デオキシコルチゾール」
拡張検索	「tetrahydro-11-deoxycortisol」
関連記事	「deoxycortisol」

「副腎皮質ホルモン」

Cortodoxone
	IUPAC name (8R,9S,10R,13S,14S,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-3-one
	Other names 11-Deoxycortisol; Cortoxelone; 17,21-Dihydroxypregn-4-ene-3,20-dione; 17,21-Dihydroxyprogesterone; 11-Desoxycortisol; 11-Deoxyhydrocortisone; 11-Desoxyhydrocortisone; Reichstein's Substance S; Compound S
Identifiers
CAS number	152-58-9
PubChem	440707
ChemSpider	389582
UNII	WDT5SLP0HQ
KEGG	D03595
ChEBI	CHEBI:28324
ChEMBL	CHEMBL253144
Jmol-3D images	Image 1
	SMILES O=C4\C=C2/[C@]([C@H]1CC[C@@]3([C@@](O)(C(=O)CO)CC[C@H]3[C@@H]1CC2)C)(C)CC4 ;
	InChI InChI=1S/C21H30O4/c1-19-8-5-14(23)11-13(19)3-4-15-16(19)6-9-20(2)17(15)7-10-21(20,25)18(24)12-22/h11,15-17,22,25H,3-10,12H2,1-2H3/t15-,16+,17+,19+,20+,21+/m1/s1 ; Key: WHBHBVVOGNECLV-OBQKJFGGSA-N InChI=1/C21H30O4/c1-19-8-5-14(23)11-13(19)3-4-15-16(19)6-9-20(2)17(15)7-10-21(20,25)18(24)12-22/h11,15-17,22,25H,3-10,12H2,1-2H3/t15-,16+,17+,19+,20+,21+/m1/s1; Key: WHBHBVVOGNECLV-OBQKJFGGBG ;
Properties
Molecular formula	C21H30O4
Molar mass	346.46 g mol−1
Melting point	215 °C
	Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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	Infobox references

　　[★]

英: adrenocortical hormone
同: 副腎皮質ステロイド adrenocorticoids
関: 副腎皮質刺激ホルモン放出ホルモン、副腎皮質刺激ホルモン; ステロイド
関: 副腎、副腎皮質、ステロイド、コルチコステロイド、ステロイドホルモン、コルチコイド。副腎皮質ホルモン剤

図：SP.891(組織),892(構造式)
副腎皮質の球状層、索状層、網状層で合成される

種類(主要なもののみ)

電解質コルチコイド

球状層から分泌される。アルドステロン

糖質コルチコイド

索状層から分泌される。コルチゾール

副腎アンドロジェン

網状層から分泌される。アンドロステンジオン

コレステロール cholesterol
↓CYP11A1
プレグネノロン pregnenolone	－－→ CYP17 17α-hydroxylase	17α-ヒドロキシプレグネノロン 17α-hydroxypregnenolone	－－→ CYP17 17α-hydroxylase	デヒドロエピアンドロステロン dehydroepiandrosterone DHEA
↓3β-HSD 3β-hydroxysteroid dehydrogenase		↓3β-HSD		↓3β-HSD
プロゲステロン progesterone	－－→ CYP17 17α-hydroxylase	17α-ヒドロキシプロゲステロン 17α-hydroxyprogesterone	－－→ CYP17 17α-hydroxylase	アンドロステンジオン androstenedione Δ⁴androstene-3,17-dion
↓CYP21 21-hydroxylase		↓CYP21 21-hydroxylase
デオキシコルチコステロン deoxycorticosterone		11-デオキシコルチゾール 11-deoxycortisol
↓CYP11B2　11β-hydroxylase		↓CYP11B1　11β-hydroxylase
コルチコステロン corticosterone		コルチゾール cortisol
↓CYP11B2 18-hydroxylase
18-ヒドロキシコルチコステロン 18-hydroxycorticosterone
↓CYP11B2 18-hydroxydehydrogenase
アルドステロン aldosterone

球状増 zona glomerulosa		索状層 zona fasciculata		網状層 zona reticularis

臨床関連

21-hydroxylaseが正常に機能しないことにより生じる (L.320)

薬理学

副腎皮質ホルモン製剤

副腎皮質から分泌されるホルモン (SP.895)

名称		血漿濃度 (ng/ml)	1日分泌量 (mg/day)
糖質コルチコイド	コルチゾール	40～180	15～20
糖質コルチコイド	コルチコステロン	2～6	2～5
鉱質コルチコイド	アルドステロン	0.05～0.20	0.05～0.15
鉱質コルチコイド	11-DOC	0.05～0.30	0.10～0.20
副腎アンドロジェン	DHEA	2～8	7～15
	DHEA-S	1～4
	アンドロステンジオン	1～2	2～3

「メチラポン」

　　[★]

英: metyrapone
商: メトロピン METOPIRONE
関: メチラポン負荷試験、糖質コルチコイド、副腎皮質

概念

下垂体機能検査薬。下垂体ACTH分泌予備能の検査薬。
副腎でのコルチゾール産生を阻害する。

薬理作用

11β-hydroxylase阻害作用

メチラポン負荷試験

11β-hydroxylase阻害作用によりコルチゾール産生減少　→　ネガティブフィードバック機構によりATCH産生亢進　→　コルチゾール前駆体 11-deoxycortisol産生↑　→　11-deoxycortisolの代謝産物である17-OHCSの尿中排泄↑
血中ATCHと尿17-OHCSを測定