6α-メチルプレドニゾロン

6α-メチルプレドニゾロン · ナタスタープ · メチルプレドニゾロン · メチルプレドニソロン · 6α-メチル-11β,17,21-トリヒドロキシプレグナ-1,4-ジエン-3,20-ジオン · メドロン · ウルバゾン · ウルバソン

識別子と物理属性

CAS No.	83-43-2
分子式	C22H30O5
平均分子量	374.5 g/mol
単同位体質量	374.20932406 g/mol
SMILES	C[C@H]1C[C@@H]2[C@H]([C@@H](O)C[C@@]3(C)[C@H]2CC[C@]3(O)C(=O)CO)[C@@]2(C)C=CC(=O)C=C12
InChIKey	VHRSUDSXCMQTMA-PJHHCJLFSA-N
PubChem CID	6741
ChEMBL	CHEMBL650
ChEBI	CHEBI:6888
EC No.	201-476-4
DTXSID	DTXSID7023300
現地名	6α-メチルプレドニゾロン

化学・物理的性質

XLogP	1.9
極性表面積	94.8
水素結合供与体数	3
水素結合受容体数	5
回転可能結合数	2
重原子数	27
形式電荷	0
複雑度	754
医薬品	Pharmaceuticals -> Listed in ZINC15Pharmaceuticals -> Steroids
脂質	Lipids -> Sterol Lipids [ST] -> Steroids [ST02] -> C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives [ST0203]
SpringerMaterials Properties	Magnetic anisotropy
LogP（分配係数）	1.52.12
臭い	Odorless
Color/Form	CrystalsWhite to practically white crystalline powder
溶解度	MW 416.51, crystals, MP 205-208 °C, specific optical rotation: 101 deg at 20 °C (dioxane), uv max (95% ethanol): 243 nm (alpha m 14825), Sol in dioxanesparingly sol in acetone, alcohol, chloroform, methanolslightly sol in ether. Practically insol in water. /21-acetate/SOL IN WATER /METHYLPREDNISOLONE 21-SUCCINATE SODIUM SALT/Sparingly sol in alc, dioxane, methanolslightly sol in acetone, chloroformvery slightly sol in ether.In water, 1.20X10+2 mg/L at 25 °C1.09e-01 g/Lクロロホルム/メタノール (9:1): 50 mg/mL、透明、微黄色0.12g/L(25℃)
Human Drugs	Breast FeedingLactationMilk, HumanCorticosteroids, SystemicGlucocorticoidsAnti-Inflammatory AgentsFDA approved drugs -> Active ingredientHormones and antihormones
Animal Drugs	Active Ingredients (Methylprednisolone) -> FDA GreenbookPharmaceuticals -> Animal Drugs -> Approved in Taiwan
Endocrine Disruptors	Potential endocrine disrupting compound
融点	228-237 °C232.5 °C228-237°C (dec.)
Optical Rotation	Specific optical rotation: +83 deg at 20 °C/D (dioxane)max absorption (95% ethanol): 243 nm (alpha(m)= 14,875)
比旋光度	D20 +83° (dioxane)
沸点	423.47°C (rough estimate)
密度	1.0868 (rough estimate)
屈折率	82 ° (C=1, Dioxane)
貯蔵条件	0-6°C
pKa（酸解離定数）	12.46±0.70(Predicted)
外観・状態	Solid
色	ホワイトからオフホワイト
Merck	14,6111
BRN	2340300
ヘンリー定数	2.7×102 mol/(m3Pa) at 25℃, HSDB (2015)
BCS Class	2 or 4
主な用途	医薬品医薬品低分子化合物
InChIKey	VHRSUDSXCMQTMA-PJHHCJLFSA-N
SMILES	[H][C@@]12C[C@H](C)C3=CC(=O)C=C[C@]3(C)[C@@]1([H])[C@@H](O)C[C@@]4(C)[C@@]2([H])CC[C@]4(O)C(=O)CO
CAS データベース	83-43-2(CAS DataBase Reference)
NISTの化学物質情報	1,4-Pregnadiene-3,20-dione, 11beta,17alpha,21-trihydroxy-6alpha-methyl-(83-43-2)
EPAの化学物質情報	Pregna-1,4-diene-3,20-dione, 11,17,21-trihydroxy-6-methyl-, (6.alpha.,11.beta.)- (83-43-2)

化学的特性

White to Off-White Crystalline Powder

安全性と法規制

GHS 分類	This chemical does not meet GHS hazard criteria for 0.9% (1 of 110) of reports.DangerH302 (16.4%): Harmful if swallowed [Warning Acute toxicity, oral]P203, P260, P264, P270, P280, P301+P317, P302+P352, P317, P318, P319, P321, P330, P362+P364, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 110 reports by companies from 15 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
規制情報	Status: Active Update: 22-11-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/16624Methylprednisolone: Does not have an individual approval but may be used under an appropriate group standard
その他の安全情報	IMAP assessments - Pregna-1,4-diene-3,20-dione, 11,17,21-trihydroxy-6-methyl-,(6.alpha.,11.beta.)-: Environment tier I assessment
FDA 要件	The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl methylprednisolone approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act.The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl methylprednisolone acetate approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act. /Methylprednisolone acetate/The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl methylprednisolone sodium succinate approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act. /Methylprednisolone sodium succinate/The Generic Animal Drug and Patent Restoration act requires that each sponsor of an approved animal drug must submit to the FDA certain information regarding patents held for the animal drug or its method of use. The Act requires that this information, as well as a list of all animal drug products approved for safety and effectiveness, be made available to the public. Methylprednisolone is included on this list.For more FDA Requirements (Complete) data for METHYLPREDNISOLONE (7 total), please visit the HSDB record page.
Hazard Classes and Categories	Acute Tox. 4 (16.4%)

用途

解説

メチルプレドニゾロン，11β,17α,21-trihydroxy-6α-methylpregna-1,4-diene-3,20-dione．C22H30O5(374.46)．プレドニゾロンの6α-メチル誘導体．1956年，G.B. Speroらにより11α-アセトオキシプロゲステロンより数工程を経て合成された．白色の結晶．分解点232～240 ℃．[α]20D＋79～＋86°(ジオキサン)．メタノール，ジオキサンに微溶，エタノール，アセトンに難溶，水，エーテルに不溶．副じん皮質ホルモン作用，とくに糖質コルチコイド作用が強い．リウマチ性関節炎，アレルギー性および炎症性眼疾患などの治療に用いられる．LD50 4000 mg/kg(ラット，経口)．

用途

糖質コルチコイド受容体（GR）アゴニストです。抗炎症及び抗酸化作用を示します。

用途

メチルプレドニゾロン (methylprednisolone) はステロイド糖質コルチコイド系薬剤の1つである。電解質コルチコイド作用をほぼ完全に抑え、かつ、糖質コルチコイド作用はヒドロコルチゾン（コルチゾール）に比べ5倍に増強されている。また肺への移行性はプレドニゾロンに比べ良好とされており、気管支喘息治療においても用いられる。糖質コルチコイドは広い適用範囲を持ち、これには代謝や免疫反応への影響も含まれる。一般的な用途は上記のほかに関節リウマチの治療、さまざまな呼吸器系の疾患によって起こる細気管支炎の短期治療などがある。急性および慢性の自己免疫疾患、特に全身性エリテマトーデスの制御にも用いられる。

一般的な説明

Methylprednisolone, 11β,17,21-trihydroxy-6α-methyl-1,4-pregnadiene-3,20-dione, isavailable unmodified or as ester derivatives.Methylprednisolone acetate, USPMethylprednisolone sodium succinate, USP.

製法・合成法

純化方法

Recrystallise medrol from EtOAc. The UV has max at in 95% EtOH 243nm ( 14,875). The 21-acetoxy derivative has m 205-208o (from EtOAc), and [] D +95o ( c 1, CHCl3). [Spero et al. J Am Chem Soc 78 6213 1956; Fried et al. J Am Chem Soc 81 1235 1959; 1H NMR: Slomp & McGarvey J Am Chem Soc 81 2200 1959, Beilstein 8 IV 3498.]