Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR0060)
Drug Name
Alfacalcidol
Synonyms
Alfacalcidol [INN:BAN:JAN]; Alfacalcidolum; Alfacalcidolum [INN-Latin]; Alfarol; Alpha D 3; Alphacalcidol; Alsiodol; Bondiol; EinsAlpha; One-Alpha; Oxydevit; Sinovul; URQ2517572; Un-Alpha; Vitamin D3, 1alpha-Hydroxy-; alfacalcidol; alpha-Calcidol; (5Z,7E)-9,10-Seco-5,7,10(19)-cholestatrien-1alpha,3beta-diol; 1-Hydroxycholecalciferol; 1-Hydroxyvitamin D3; 1alpha-Hydroxy-vitamin D3; 1alpha-Hydroxycholecalciferol; 1alpha-Hydroxyvitamin D3; 1alpha-OH-D3; 41294-56-8; CCRIS 3341; CHEBI:31186; UNII-URQ2517572
Indication Diabetes mellitus [ICD11: 5A10] Phase 4 [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 400.6 Topological Polar Surface Area 40.5
Heavy Atom Count 29 Rotatable Bond Count 6
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 2
Cross-matching ID
PubChem CID
5282181
ChEBI ID
CHEBI:31186
CAS Number
41294-56-8
Formula
C27H44O2
Canonical SMILES
CC(C)CCCC(C)C1CCC2C1(CCCC2=CC=C3CC(CC(C3=C)O)O)C
InChI
1S/C27H44O2/c1-18(2)8-6-9-19(3)24-13-14-25-21(10-7-15-27(24,25)5)11-12-22-16-23(28)17-26(29)20(22)4/h11-12,18-19,23-26,28-29H,4,6-10,13-17H2,1-3,5H3/b21-11+,22-12-/t19-,23-,24-,25+,26+,27-/m1/s1
InChIKey
OFHCOWSQAMBJIW-AVJTYSNKSA-N
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
1,25-dihydroxyvitamin D3 DM001542
5280453
Unclear 1 [4]
1,24,25-trihydroxyvitamin D3 DM001546
9910685
Unclear 2 [5]
1,25,26-trihydroxyvitamin D3 DM001544
5283758
Unclear 2 [5]
1,25-dihydroxyvitamin D3-26,23-lactone DM000529
6438368
Unclear 2 [4]
24-oxo-1,25-dihydroxyvitamin D3 DM001545 N. A. Unclear 2 [5]
Calcitroic acid DM000528
9547273
Unclear 2 [5]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR000118 Alfacalcidol 1,25-dihydroxyvitamin D3 Unclear Unclear [4]
MR000113 1,25-dihydroxyvitamin D3 Calcitroic Acid Unclear Unclear [5]
MR000114 1,25-dihydroxyvitamin D3 1,25-dihydroxyvitamin D3-26,23-lactone Unclear Unclear [4]
MR000115 1,25-dihydroxyvitamin D3 1,25,26-trihydroxyvitamin D3 Unclear Unclear [5]
MR000116 1,25-dihydroxyvitamin D3 24-oxo-1,25-dihydroxyvitamin D3 Unclear Unclear [5]
MR000117 1,25-dihydroxyvitamin D3 1,24,25-trihydroxyvitamin D3 Unclear Unclear [5]
⏷ Show the Full List of 6 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 2J2 (CYP2J2) DME0031 Homo sapiens
CP2J2_HUMAN
1.14.14.24
[2]
Vitamin D(3) 25-hydroxylase (CYP27A1) DME0026 Homo sapiens
CP27A_HUMAN
1.14.15.15
[3]
Experimental Enzyme Kinetic Data of This Drug
DME Name DME Info Kinetic Data Uniprot ID REF
Cytochrome P450 2J2 (CYP2J2) DME0031 Km = 0.0044 microM
CP2J2_HUMAN
[2]
References
1 ClinicalTrials.gov (NCT03147677) Clinical Study of Treating Type 2 Diabetic Nephropathy With Alfacalcidol and Irbesartan.
2 Characterization of rat and human CYP2J enzymes as Vitamin D 25-hydroxylases. Steroids. 2006 Oct;71(10):849-56.
3 Kidney microsomal 25- and 1alpha-hydroxylase in vitamin D metabolism: catalytic properties, molecular cloning, cellular localization and expression during development. Biochim Biophys Acta. 2002 Feb 28;1580(2-3):133-44.
4 A new look at the most successful prodrugs for active vitamin D (D hormone): alfacalcidol and doxercalciferol Molecules. 2009 Sep 29;14(10):3869-80. doi: 10.3390/molecules14103869.
5 Metabolism of 1,25-dihydroxyvitamin D3 Physiol Rev. 1984 Apr;64(2):478-504. doi: 10.1152/physrev.1984.64.2.478.

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