독세르칼시페롤

Doxercalciferol

HCID 5281107CAS 54573-75-0

기본 정보

표준 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
분자식
C28H44O2
평균 분자량
412.6 g/mol
단동위원소 질량
412.33413065

개요

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.

이름 및 식별자

우선 이름
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
현지명
독세르칼시페롤
영어명
Doxercalciferol
분자식
C28H44O2
분자량
412.65

이름 및 동의어

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
이름 더 보기
독세르칼시페롤C08211TSA 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

데이터베이스 식별자

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

물성

구조 계산 물성

XLogP
6.3
극성 표면적
40.5 Ų
수소 결합 공여자 수
2
수소 결합 수용자 수
2
회전 가능 결합 수
5
무거운 원자 수
30

실험 및 물리화학적 성질

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

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

물리화학적 성질

녹는점
138 · 138-140°C
끓는 점
538.7 · 538.7±50.0 °C(Predicted)
밀도
1.01 · 1.01±0.1 g/cm3(Predicted)
저장 조건
-20 °C · Sealed in dry,Store in freezer, under -20°C
용해도
10 mg/mL · DMSO: >10mg/mL
물리적 상태
백색 결정성 고체

화학적 성질

Doxercalciferol is Crystalline Solid

안전 및 규제

GHS 분류

GHS Classification · 4건

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.

유해성 정보

Hazard Classes and CategoriesAcute Tox. 1 (100%)

독성 정보

Drug Induced Liver Injury · 6건

Drug Induced Liver Injury Rank (DILIrank 2.0)

Doxercalciferol

Ambiguous-DILI-concern

3

Adverse reactions

DOI:10.1016/j.drudis.2016.02.015

안전 데이터

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

화학 및 산업

약리 정보

ATC Code · 2건

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

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

Mechanism of Action · 1건

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 · 1건

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 · 6건

3DIZ9LF5Y9

DOXERCALCIFEROL

Chemical Structure [CS] - Ergocalciferols

Established Pharmacologic Class [EPC] - Vitamin D2 Analog

Doxercalciferol is a Vitamin D2 Analog.

DOXERCALCIFEROL

MeSH Pharmacological Classification · 2건

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.

응용 분야 · 2건

개요Doxercalciferol 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.

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

공급사50 곳

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]

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5건

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