Basic information
- CAS
41294-56-8- 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- Molecular formula
- C27H44O2
- Average molar mass
- 400.6 g/mol
- Monoisotopic mass
- 400.33413065
Overview
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.
Names & identifiers
- Preferred 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
- English name
- Alfacalcidol
- Molecular formula
- C27H44O2
- Molecular weight
- 400.64
Names & synonyms
Show more names
Database identifiers
- CAS
41294-56-8- PubChem CID
- 5282181
- DTXSID
DTXSID0022569- ChEMBL
CHEMBL1601669- ChEBI
CHEBI:31186- UNII
- URQ2517572
- EC Number
- 255-297-1
- Nikkaji
- J9.282G
Properties
Computed structural properties
- XLogP
- 6.8
- Topological polar surface area
- 40.5 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 6
- Heavy atoms
- 29
- Formal charge
- 0
- Complexity
- 643
Experimental & physicochemical properties
Solubility
<1 mg/mL
1.63e-03 g/L
Physicochemical properties
- Melting point
- 134 · 134-136°C
- Boiling point
- 531.5 · 531.5±50.0 °C(Predicted)
- Density
- 1.01 · 1.01±0.1 g/cm3(Predicted)
- storage temp.
- 20 °C · −20°C
- solubility
- Practically insoluble in water, freely soluble in ethanol (96 per cent), soluble in fatty oils.
- form
- White crystalline solid
- pka
- 14.43 · 14.43±0.40(Predicted)
- color
- White to Almost white
- biological source
- synthetic
- λmax
- 264 nm · 264nm(Diethyl ether)(lit.)
- Merck
- 14 · 14,4819
- Stability
- 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 DataBase Reference
- 41294 · 41294-56-8(CAS DataBase Reference)
- FDA UNII
- 2517572 · URQ2517572
- ATC code
- 11 CC03 · A11CC03
- EPA Substance Registry System
- Alphacalcidol (41294-56-8)
- UNSPSC Code
- 41116107 · 41116107
- NACRES
- 79 · NA.79
- Protein binding
- Extensive plasma protein binding
- Excreted unchanged in urine
- 13 % · 13%
- Biological half-life
- 3 · <3 / -
- Symbol(GHS)
- 6 · GHS06
- Signal word
- Danger
- Hazard statements
- 300 · H300
- Precautionary statements
- 301 · P301+P310+P330
- PPE
- 3 · Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges
- Hazard Codes
- T+,Xi
- Risk Statements
- 26 · 26/27/28-36/37/38
- Safety Statements
- 28 · 28-36/37-45-36-26
- RIDADR
- 2811 · UN 2811 6.1/PG 1
- WGK Germany
- 3 · 3
- RTECS
- 2851000 · VS2851000
- F
- 8 · 8-10
- HazardClass
- 6.1 · 6.1(a)
- PackingGroup
- I
- HS Code
- 29361000 · 29361000
- Storage Class
- 6.1 A · 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
- Hazard Classifications
- 1 Oral · Acute Tox. 1 Oral
Safety & regulation
GHS classification
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.
Hazard information
Toxicology
Drug Induced Liver Injury
Drug-Induced Liver Injury Severity and Toxicity (DILIst)
Alfacalcidol
DILI Positive
DOI:10.1016/j.drudis.2019.09.022
Safety data
- F
- 8-10
- PPE
- Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges
- wgk
- 3
- rtecs
- VS2851000
- ridadr
- UN 2811 6.1/PG 1
- hs_code
- 29361000
- risk_code
- 26/27/28-36/37/38
- Signal word
- Danger
- Symbol(GHS)
- GHS06
- hazard_code
- T+,Xi
- safety_code
- 28-36/37-45-36-26
- hazard_class
- 6.1(a)
- Storage Class
- 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
- packing_group
- I
- Hazard statements
- H300
- Hazard Classifications
- Acute Tox. 1 Oral
- Precautionary statements
- P301+P310+P330
Chemistry & industry
Pharmacology
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.
Applications
DescriptionAlfacalcidol(41294-56-8) is a vitamin D analog. It is important for the regulation of the bone metabolism. Alfacaldidol is a regulator of calcium and phosphorus metabolism, which helps calcium and phosphorus to be absorbed more effectively in the intestines. Thus, alfacalcidol is used to treat renal (kidney) bone diseases, rickets, osteoporosis, and patients with high or low activity of the parathyroid gland. Also, it is used to maintain normal calcium levels within the body. Alfacalcidol has significant effects on the immune system, including regulatory T cells. Alfacalcidol is furthermore used as a poultry feed additive to prevent tibial dyschondroplasia and increases phytate bioavailability.
UsesFor the treatment of osteoporosis, vitamin D-dependent rickets and osteomalacia
UsesA 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
General DescriptionHas biological properties similar to 1α-Hydroxyvitamin D2 (Cat. No. 679100). Converted to active Calcitriol (1α,25-Dihydroxyvitamin D3; Cat. No. 679101) in vivo. Inhibits the formation of nephrocalcinosis in streptozotocin-induced diabetic rats fed on low zinc diets.
Upstream & downstream products
Upstream raw materials
Suppliers100 total
Additional notes
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.
Related reactions
Compound notes
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