Doxercalciferol

HCID 5281107CAS 54573-75-0

Grundinformationen

Standard-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
Summenformel
C28H44O2
Durchschnittliche Molmasse
412,6 g/mol
Monoisotopische Masse
412,33413065

Überblick

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.

Namen und Bezeichner

Bevorzugter Name
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
Englischer Name
Doxercalciferol
Summenformel
C28H44O2
Molmasse
412.65

Namen und Synonyme

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
Weitere Namen anzeigen
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

Datenbank-Bezeichner

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

Eigenschaften

Berechnete Struktureigenschaften

XLogP
6,3
Polarare Oberfläche (TPSA)
40,5 Ų
H-Brücken-Donoren
2
H-Brücken-Akzeptoren
2
Frei drehbare Bindungen
5
Schwere Atome
30

Experimentelle und physikochemische Eigenschaften

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

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

Physikochemische Eigenschaften

Schmelzpunkt
138 · 138-140°C
Siedepunkt
538.7 · 538.7±50.0 °C(Predicted)
Dichte
1.01 · 1.01±0.1 g/cm3(Predicted)
storage temp.
-20 °C · Sealed in dry,Store in freezer, under -20°C
Löslichkeit
10 mg/mL · DMSO: >10mg/mL
Aggregatzustand
White crystalline solid

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 4 Einträge

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.

Gefahrenhinweise

Hazard Classes and CategoriesAcute Tox. 1 (100%)

Toxikologische Informationen

Drug Induced Liver Injury · 6 Einträge

Drug Induced Liver Injury Rank (DILIrank 2.0)

Doxercalciferol

Ambiguous-DILI-concern

3

Adverse reactions

DOI:10.1016/j.drudis.2016.02.015

Sicherheitsdaten

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

Chemie und Industrie

Pharmakologische Informationen

ATC Code · 2 Einträge

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

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

Mechanism of Action · 1 Eintrag

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 Eintrag

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 Einträge

3DIZ9LF5Y9

DOXERCALCIFEROL

Chemical Structure [CS] - Ergocalciferols

Established Pharmacologic Class [EPC] - Vitamin D2 Analog

Doxercalciferol is a Vitamin D2 Analog.

DOXERCALCIFEROL

MeSH Pharmacological Classification · 2 Einträge

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.

Anwendungen · 2 Einträge

BeschreibungDoxercalciferol 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.

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

Anbieter50 Anbieter

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]

Zugehörige Reaktionen

5

Verknüpfte Notizen

Wird geladen…