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

General Information of Drug (ID: DR0260)
Drug Name
Calcitriol
Synonyms
Calcijex; Calcitriolum; Calcitriolum [INN-Latin]; DN 101; DN-101; Dihydroxyvitamin D3; Ro 21-5535; Rocaltrol; Silkis; Soltriol; Topitriol; Vectical; calcitriol; 1,25-DHCC; 1,25-DIHYDROXYCHOLECALCIFEROL; 1,25-Dihydroxycholecaliferol; 1,25-Dihydroxyvitamin D; 1,25-Dihydroxyvitamin D3; 1-alpha,25-Dihydroxycholecalciferol; 1-alpha,25-Dihydroxyvitamin D3; 1alpha,25(OH)2D3; 1alpha,25-Dihydroxycholecalciferol; 1alpha,25-Dihydroxyvitamin D; 1alpha,25-Dihydroxyvitamin D3; 32222-06-3; CCRIS 5522; EINECS 250-963-8; HSDB 3482; UNII-FXC9231JVH
Indication Congenital alopecia [ICD11: LC30] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 416.6 Topological Polar Surface Area 60.7
Heavy Atom Count 30 Rotatable Bond Count 6
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 3
Cross-matching ID
PubChem CID
5280453
PubChem SID
4817 ; 596357 ; 628349 ; 646010 ; 3225659 ; 7847197 ; 7850823 ; 7978847 ; 8143990 ; 8616278 ; 11528639 ; 12012574 ; 14758022 ; 14855739 ; 24850808 ; 24893473 ; 26719902 ; 26754891 ; 26759742 ; 39289574 ; 46386784 ; 46391717 ; 46508162 ; 47588739 ; 47662005 ; 47959455 ; 48334202 ; 48415682 ; 49681438 ; 49681793 ; 50110818 ; 53789169 ; 53789350 ; 56311224 ; 56311227 ; 56311279 ; 56311508 ; 56311775 ; 56312928 ; 56313898 ; 56314589 ; 56365636 ; 57288572 ; 57357744 ; 57647688 ; 71824963 ; 80321599 ; 89088644 ; 92308336 ; 92308939
ChEBI ID
CHEBI:17823
CAS Number
32222-06-3
TTD Drug ID
D0T2PL
Formula
C27H44O3
Canonical SMILES
CC(CCCC(C)(C)O)C1CCC2C1(CCCC2=CC=C3CC(CC(C3=C)O)O)C
InChI
1S/C27H44O3/c1-18(8-6-14-26(3,4)30)23-12-13-24-20(9-7-15-27(23,24)5)10-11-21-16-22(28)17-25(29)19(21)2/h10-11,18,22-25,28-30H,2,6-9,12-17H2,1,3-5H3/b20-10+,21-11-/t18-,22-,23-,24+,25+,27-/m1/s1
InChIKey
GMRQFYUYWCNGIN-NKMMMXOESA-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 D3-26,23-lactone DM000529
6438368
Oxidation - Hydroxylation 1 [2] , [5]
Calcitriol 25-O-glucuronide DM000534 N. A. Conjugation - Glucuronidation 1 [3]
Calcitroic acid DM000528
9547273
Oxidation - 24-Hydroxylation 1 [2]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR002815 Calcitriol Calcitroic acid Oxidation - 24-Hydroxylation CYP24A1 [2]
MR002816 Calcitriol 1a,25R(OH)2-26,23S-lactone D3 Oxidation - Hydroxylation CYP3A4 ... [2], [5]
MR002817 Calcitriol Calcitriol 25-O-glucuronide Conjugation - Glucuronidation UGT1A4 [3]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[2]
UDP-glucuronosyltransferase 1A4 (UGT1A4) DME0048 Homo sapiens
UD14_HUMAN
2.4.1.17
[3]
Vitamin D(3) 24-hydroxylase (CYP24A1) DME0038 Homo sapiens
CP24A_HUMAN
1.14.15.16
[4]
Experimental Enzyme Kinetic Data of This Drug
DME Name DME Info Kinetic Data Uniprot ID REF
UDP-glucuronosyltransferase 1A4 (UGT1A4) DME0048 Km = 0.0073 microM
UD14_HUMAN
[3]
References
1 Calcitriol was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Intestinal and hepatic CYP3A4 catalyze hydroxylation of 1alpha,25-dihydroxyvitamin D(3): implications for drug-induced osteomalacia. Mol Pharmacol. 2006 Jan;69(1):56-65.
3 Identification of human UDP-glucuronosyltransferases catalyzing hepatic 1alpha,25-dihydroxyvitamin D3 conjugation. Biochem Pharmacol. 2008 Mar 1;75(5):1240-50.
4 The role of vitamin D in reducing cancer risk and progression. Nat Rev Cancer. 2014 May;14(5):342-57.
5 Cytochromes P450 are essential players in the vitamin D signaling system. Biochim Biophys Acta. 2011 Jan;1814(1):186-99.

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