Grundinformationen
- Standard-SMILES
C=C1/C(=C\C=C2/CCC[C@]3(C)[C@@H]([C@H](C)CCCC(C)C)CC[C@@H]23)C[C@@H](O)C[C@@H]1O- InChIKey
OFHCOWSQAMBJIW-AVJTYSNKSA-N- Summenformel
- C27H44O2
- Durchschnittliche Molmasse
- 400,6 g/mol
- Monoisotopische Masse
- 400,33413065
Überblick
Alfacalcidol is a member of the class of D3 vitamins that is calciol in which the hydrogen at the 1alpha position is replaced by a hydroxy group. It is an active metabolite of cholecalciferol, which performs important functions in regulation of the calcium balance and the bone metabolism. It has a role as a bone density conservation agent. It is a diol, a seco-cholestane, a hydroxycalciol and a member of D3 vitamins. It is functionally related to a calciol.
Namen und Bezeichner
- Bevorzugter Name
- Alfacalcidol
- IUPAC
- trans-(1R,3S,5Z)-5-[(2E)-2-[(1R,3aS,7aR)-7a-methyl-1-[(2R)-6-methylheptan-2-yl]-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidenecyclohexane-1,3-diol
- Lokaler Name
- Alfacalcidol
- Englischer Name
- Alfacalcidol
- Summenformel
- C27H44O2
- Molmasse
- 400.64
Namen und Synonyme
Weitere Namen anzeigen
Datenbank-Bezeichner
- CAS
41294-56-8- PubChem CID
- 5282181
- DTXSID
DTXSID0022569- ChEMBL
CHEMBL1601669- ChEBI
CHEBI:31186- UNII
- URQ2517572
- EC Number
- 255-297-1
- Nikkaji
- J9.282G
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 6,8
- Polarare Oberfläche (TPSA)
- 40,5 Ų
- H-Brücken-Donoren
- 2
- H-Brücken-Akzeptoren
- 2
- Frei drehbare Bindungen
- 6
- Schwere Atome
- 29
- Formalladung
- 0
- Komplexität
- 643
Experimentelle und physikochemische Eigenschaften
Solubility
<1 mg/mL
1.63e-03 g/L
Physikochemische Eigenschaften
- Schmelzpunkt
- 134 · 134-136°C
- Siedepunkt
- 531.5 · 531.5±50.0 °C(Predicted)
- Dichte
- 1.01 · 1.01±0.1 g/cm3(Predicted)
- storage temp.
- 20 °C · −20°C
- Löslichkeit
- Practically insoluble in water, freely soluble in ethanol (96 per cent), soluble in fatty oils.
- Aggregatzustand
- White crystalline solid
- pka
- 14.43 · 14.43±0.40(Predicted)
- Farbe
- White to Almost white
- Biologische Quelle
- synthetic
- Merck
- 14 · 14,4819
- Stabilität
- Light Sensitive
- InChIKey
- OFHCOWSQAMBJIW-GITLSTMWSA-N
- SMILES
- [C@@H]1(O)CC(=C/C=C2\CCC[C@@]3(C)[C@@]\2([H])CC[C@@H]3[C@H](C)CCCC(C)C)C(=C)[C@H](O)C1
- CAS Datenbank
- 41294 · 41294-56-8(CAS DataBase Reference)
- EPA chemische Informationen
- Alphacalcidol (41294-56-8)
Sicherheit und Regulatorisches
GHS-Klassifizierung
GHS Classification
Danger
H300 (100%): Fatal if swallowed [Danger Acute toxicity, oral]
P260, P262, P264, P270, P271, P280, P284, P301+P316, P302+P352, P304+P340, P316, P320, P321, P330, P361+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 48 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Gefahrenhinweise
Toxikologische Informationen
Drug Induced Liver Injury
Drug-Induced Liver Injury Severity and Toxicity (DILIst)
Alfacalcidol
DILI Positive
DOI:10.1016/j.drudis.2019.09.022
Sicherheitsdaten
- F
- 8-10
- wgk
- 3
- ridadr
- UN 2811 6.1/PG 1
- hs_code
- 29361000
- RTECS-Nr.
- VS2851000
- risk_code
- 26/27/28-36/37/38
- hazard_code
- T+,Xi
- safety_code
- 28-36/37-45-36-26
- hazard_class
- 6.1(a)
- packing_group
- I
- Speicherklasse
- 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
- Hazard Classifications
- Acute Tox. 1 Oral
Chemie und Industrie
Pharmakologische Informationen
ATC Code
A11CC03
A - Alimentary tract and metabolism
QA - Alimentary tract and metabolism
Pharmacodynamics
Alfacalcidol works to increase serum levels of calcium by stimulating intestinal calcium absorption, reabsorption of calcium from bone, and possibly the renal reabsorption of calcium. It also modestly promotes intestinal phosphorus absorption. In patients with renal failure, alfacalcidol increased intestinal calcium and phosphorus absorption in a dose-related manner. This increase in calcium and phosphorus levels occurs within three days following drug administration: this effect was reversed within three days of drug discontinuation. In patients with chronic renal failure, serum calcium levels were elevated while parathyroid hormone and alkaline phosphatase levels returned to normal levels within five days following alfacalcidol administration. Since alfacalcidol suppresses parathyroid hormone, a reduction in parathyroid hormone levels is achieved more rapidly in patients on intermittent intravenous therapy, with significant reductions occurring within three months of therapy. In patients receiving daily oral therapy of alfacalcidol, the time it takes alfacalcidol to normalize plasma calcium levels may be up to several months, possibly reflecting calcium being utilized for bone mineralization. In patients with nutritional osteomalacia, alfacalcidol increased calcium absorption with six hours of oral administration and the effects peaked at 24 hours.
Mechanism of Action
In conditions like chronic renal failure, renal bone disease, hypoparathyroidism, and vitamin D dependent rickets, the kidneys' capacity for 1α-hydroxylation is impaired, leading to reduced production of endogenous 1,25-dihydroxyvitamin D and aberrated mineral metabolism. As an active and potent analog of vitamin D, alfacalcidol works to restore the functions and activities of endogenous 1,25-dihydroxyvitamin D.
Metabolism/Metabolites
Alfacalcidol is rapidly converted in the liver to 1,25-dihydroxyvitamin D, which is essentially the metabolite of vitamin D that regulates calcium and phosphate metabolism. Alfacalcidol is further metabolized to other polar inactive metabolites, excreted primarily through the bile.
Anwendungen
VerwendenA synthetic analog of Calcitiol (the hormonal form of vitamin D3), which shows identical potency with respect to stimulation of intestinal calcium absorption and bone mineral mobilization. Vitamin D source
Vor- und nachgelagerte Produkte
Vorgelagerte Rohstoffe
Anbieter50 Anbieter
Ergänzende Hinweise
DefinitionChEBI: A member of the class of D3 vitamins that is calciol in which the hydrogen at the 1alpha position is replaced by a hydroxy group. It is an active metabolite of cholecalciferol, which performs important functions in reg lation of the calcium balance and the bone metabolism.
Zugehörige Reaktionen
Verknüpfte Notizen
Wird geladen…