ドキセルカルシフェロール

Doxercalciferol

HCID 5281107CAS 54573-75-0

基本情報

標準SMILES
C=C1/C(=C\C=C2/CCC[C@]3(C)[C@@H]([C@H](C)/C=C/[C@H](C)C(C)C)CC[C@@H]23)C[C@@H](O)C[C@@H]1O
InChIKey
HKXBNHCUPKIYDM-CGMHZMFXSA-N
分子式
C28H44O2
平均分子量
412.6 g/mol
単同位体質量
412.33413065

概要

Doxercalciferol is a hydroxy seco-steroid and synthetic vitamin D2 analogue that undergoes metabolic activation in vivo to form 1alpha,25-dihydroxyvitamin D2 (1alpha,25-(OH)2D2), a naturally occurring, biologically active form of vitamin D2. It is used to treat secondary hyperparathyroidism, a condition in which the body produces excess parathyroid hormone (PTH; a natural substance needed to control the amount of calcium in the blood) in certain people with chronic kidney disease. It has a role as a provitamin, a bone density conservation agent and a prohormone. It is a vitamin D and a hydroxy seco-steroid.

名称と識別子

優先名称
Doxercalciferol
IUPAC
trans-(1R,3S,5Z)-5-[(2E)-2-[(1R,3aS,7aR)-1-[(E,2R,5R)-5,6-dimethylhept-3-en-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidenecyclohexane-1,3-diol
現地名
ドキセルカルシフェロール
英語名
Doxercalciferol
分子式
C28H44O2
分子量
412.65

名称と別名

Doxercalciferol54573-75-0Hectorol1-Hydroxyergocalciferol1alpha-Hydroxyergocalciferol1alpha-hydroxyvitamin D21-alpha-Hydroxyvitamin D21-alpha-hydroxyergocalciferolDoxercalciferolum3DIZ9LF5Y9(1S,3R,5Z,7E,22E)-9,10-Secoergosta-5,7,10,22-tetraene-1,3-diol(1R,3S,5Z)-5-[(2E)-2-[(1R,3aS,7aR)-1-[(E,2R,5R)-5,6-dimethylhept-3-en-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidenecyclohexane-1,3-diol
名称をさらに表示
ドキセルカルシフェロールC08211TSA 8401α-OHD2ERCALCIDOLDocalcitol1ALPHA-OH-D2DoxecalciferolDoxercalcifero
TSA-840GZ427397CHEBI:4712doxacalciferol9,10-Secoergosta-5,7,10(19),22-tetraene-1,3-diol, (1alpha,3beta,5Z,7E,22E)-1alpha-OHD21alpha(OH)2D2H05BX03

データベース識別子

CAS
54573-75-0
PubChem CID
5281107
DTXSID
DTXSID1034214
ChEMBL
CHEMBL1200810
ChEBI
CHEBI:4712
UNII
3DIZ9LF5Y9
EC Number
643-005-9
Nikkaji
J527.612H

物性

構造計算による物性

XLogP
6.3
極性表面積
40.5 Ų
水素結合供与体数
2
水素結合受容体数
2
回転可能結合数
5
重原子数
30

実験および物理化学的性質

LipidsLipids -> Sterol Lipids [ST] -> Secosteroids [ST03] -> Vitamin D2 and derivatives [ST0301]
SolubilityRelatively insoluble
Human Drugs · 2 件

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

物理化学的性質

融点
138 · 138-140°C
沸点
538.7 · 538.7±50.0 °C(Predicted)
比重(密度)
1.01 · 1.01±0.1 g/cm3(Predicted)
貯蔵温度
-20 °C · Sealed in dry,Store in freezer, under -20°C
溶解性
10 mg/mL · DMSO:>10mg/mL
外見
白色結晶性固体

化学的性質

化学的特性Doxercalciferol is Crystalline Solid

安全と法規制

GHS分類

GHS Classification · 4 件

Danger

H300 (100%): Fatal if swallowed [Danger Acute toxicity, oral]

P264, P270, P301+P316, P321, P330, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 51 reports by companies from 2 notifications to the ECHA C&L Inventory.

危険有害性情報

Hazard Classes and CategoriesAcute Tox. 1 (100%)

毒性情報

Drug Induced Liver Injury · 6 件

Drug Induced Liver Injury Rank (DILIrank 2.0)

Doxercalciferol

Ambiguous-DILI-concern

3

Adverse reactions

DOI:10.1016/j.drudis.2016.02.015

安全データ

wgk
3
rtecs
VS2950000
ridadr
UN 2811 6.1 / PGIII
毒性
LD50 orally in rats: 3.5-6.5 mg/kg (Sjden)
hs_code
2936299055
risk_code
28

化学と産業

薬理情報

ATC Code · 2 件

H - Systemic hormonal preparations, excl. sex hormones and insulins

QH - Systemic hormonal preparations, excl. sex hormones and insulin

Mechanism of Action · 1 件

Calcitriol (1α,25-(OH)2D3) and 1α,25-(OH)2D2 regulate blood calcium at levels required for essential body functions. Specifically, the biologically active vitamin D metabolites control the intestinal absorption of dietary calcium, the tubular reabsorption of calcium by the kidney and, in conjunction with parathyroid hormone (PTH), the mobilization of calcium from the skeleton. They act directly on bone cells (osteoblasts) to stimulate skeletal growth, and on the parathyroid glands to suppress PTH (parathyroid hormone) synthesis and secretion. These functions are mediated by the interaction of these biologically active metabolites with specific receptor proteins in the various target tissues. In patients with chronic kidney disease (CKD), deficient production of biologically active vitamin D metabolites (due to lack of or insufficient 25-hydroxyvitamin D-1-alpha-hydroxylase activity) leads to secondary hyperparathyroidism, which contributes to the development of metabolic bone disease.

Biological Half-Life32 to 37 hours.
Metabolism/Metabolites · 1 件

Doxercalciferol is absorbed from the gastrointestinal tract and activated by CYP 27 in the liver to form 1α,25-(OH)2D2 (major metabolite) and 1α,24-dihydroxyvitamin D2 (minor metabolite). Activation of doxercalciferol does not require the involvement of the kidneys.

FDA Pharmacological Classification · 6 件

3DIZ9LF5Y9

DOXERCALCIFEROL

Chemical Structure [CS] - Ergocalciferols

Established Pharmacologic Class [EPC] - Vitamin D2 Analog

Doxercalciferol is a Vitamin D2 Analog.

DOXERCALCIFEROL

MeSH Pharmacological Classification · 2 件

Organic substances that are required in small amounts for maintenance and growth, but which cannot be manufactured by the human body.

Agents that inhibit BONE RESORPTION and/or favor BONE MINERALIZATION and BONE REGENERATION. They are used to heal BONE FRACTURES and to treat METABOLIC BONE DISEASES such as OSTEOPOROSIS.

応用分野 · 2 件

説明Doxercalciferol is a synthetic vitamin D2 analog introduced in the US as Hectorol for the treatment of secondary hyperparathyroidism (SHPT) in patients with end-stage renal failure. It is actually 1-alpha-hydroxyvitamin D2 (one-alpha- D2) and can be synthesized by direct hydroxylation of vitamin D2 tosylate or in 5 steps from ergosterol. Doxercalciferol itself is inactive until metabolized by the liver into active 1,24-dihydroxyvitamin D2, showing a pharmacokinetic profile similar to calcitriol. During placebo-controlled clinical trials, patients with moderate to severe SHPT were treated with 1-alpha-D2 (10 μg doses) for 16 to 24 weeks; in 9 patients out of 10, blood levels of parathyroid hormone were considerably reduced, so maintaining a good control of the parathyroid hyperplasia. Moreover, only a moderate tendency to raise calcium and phosphate was observed. Doxercalciferol is orally-active and less toxic than other vitamin D analogs like alfacalcidol; it shows differentially controlled effects and has an improved safety profile compared to calcitriol.

使用Synthetic vitamin D prohormone. A new active Vitamin D analog which inhibits growth of human neuroblastoma. Antihyperparathyroid

サプライヤー50 社

北京华美互利生物化工010-56205725 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
上海策嵘生物科技有限公司[email protected]
济南百隆化学有限公司[email protected] · [email protected]
成都彼样生物科技有限公司18108052721 · [email protected]

関連反応

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