Alfacalcidol

HCID 5282181

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

alfacalcidol41294-56-81-HydroxycholecalciferolAlphacalcidol1alpha-Hydroxyvitamin D3AlfarolEinsAlpha1-Hydroxyvitamin D31alpha-HydroxycholecalciferolAlsiodolOxydevitBondiol
Show more names
HYDROXYVITAMIN D3Alfacalcidiol1α-Hydroxyvitamin D3EtαUn Alfa
alpha-CalcidolOne-AlphaEtalphaAlfacalcidolumAlpha D3AlpharolTevabone1alpha-Hydroxy-vitamin D3

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

Experimental & physicochemical properties

DrugsPharmaceuticals -> Listed in ZINC15
LipidsLipids -> Sterol Lipids [ST] -> Secosteroids [ST03] -> Vitamin D3 and derivatives [ST0302]
Solubility · 2 items

<1 mg/mL

1.63e-03 g/L

Melting Point136 °C
Physical DescriptionSolid

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

Safety & regulation

GHS classification

GHS Classification · 4 items

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

Regulatory InformationAlfacalcidol: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
Hazard Classes and CategoriesAcute Tox. 2 (100%)

Toxicology

Drug Induced Liver Injury · 4 items

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

Chemistry & industry

Pharmacology

ATC Code · 3 items

A11CC03

A - Alimentary tract and metabolism

QA - Alimentary tract and metabolism

Protein BindingThe active metabolite of alfacalcidol, 1,25-dihydroxyvitamin D, is transported to tissues via globulin, a specific transport protein.
Pharmacodynamics · 1 item

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 · 1 item

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.

Biological Half-LifeThe half-life of alfacalcidol ranges from three to four hours.
Metabolism/Metabolites · 1 item

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 · 4 items

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.

Suppliers100 total

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]
Hong Kong Tiansheng New Material Trading Co., Ltd+8617320695765 · [email protected]
温州共赢化学有限公司+86-0086-577-64498589 +86-15355981851 · [email protected]
Additional notes · 1 item

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

5 records

Compound notes

Loading…