Compound Detail

CHEMBL846

CALCITRIOL

💊 Approved Drug

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💊 Approved Drug

C=C1/C(=C\C=C2/CCC[C@]3(C)[C@@H]([C@H](C)CCCC(C)(C)O)CC[C@@H]23)C[C@@H](O)C[C@@H]1O

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL846
Name	CALCITRIOL
Phase	Approved
Structure Type	MOL
InChI Key	GMRQFYUYWCNGIN-NKMMMXOESA-N
Therapeutic	✓ Yes

Known Names

1,25-dihydroxy vitamin d3 1,25-dihydroxyvitamin d3 1,25-hydroxylated vitamin d 1alpha,25-dihydroxycholecalciferol 1alpha,25-dihydroxyvitamin d3 Calcijex Calcitriol Dihydroxyvitamin d 3 RO 21-5535 RO-21-5535 RO-215535 Rocaltrol +2 more

Targets

145

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Mechanisms

Molecular Properties

416.6

MW (Da)

5.70

ALogP

HBA

HBD

60.7

PSA (Å²)

0.52

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
First Approval	1978
Availability	Prescription
Chirality	Single Enantiomer

Routes of Administration

Oral Parenteral Topical

Flags

Natural Product

USAN Stem	calci-
USAN Year	1978

Extended Properties

Molecular Formula	C27H44O3
MW	416.65
Aromatic Rings	0
Heavy Atoms	30
NP-Likeness	2.65

Mechanism of Action

Mechanism	Action Type	Target	Direct	Efficacy
Vitamin D receptor agonist	AGONIST	Vitamin D3 receptor	✓	✓

Indications

Hypocalcemia Hypoparathyroidism Kidney Failure, Chronic Psoriasis Psoriasis Adenomatous Polyposis Coli Diabetic Nephropathies Fibroma Osteopetrosis Osteoporosis Prostatic Neoplasms, Castration-Resistant Acute Kidney Injury Breast Neoplasms Breast Neoplasms Carcinoma, Basal Cell Cholangiocarcinoma Chronic Kidney Disease-Mineral and Bone Disorder Diabetes Mellitus, Type 1 Hyperparathyroidism, Secondary Hypertension

ATC Classification

A11CC04

calcitriol

Level 1: ALIMENTARY TRACT AND METABOLISM

Level 2: VITAMINS

D05AX03

calcitriol

Level 1: DERMATOLOGICALS

Level 2: ANTIPSORIATICS

Activity Summary

IC50 67 meas. best 11.0

EC50 61 meas. best 10.97

Ki 13 meas. best 10.6

Kd 4 meas. best 10.19

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
HCT-116 CHEMBL394	IC50	11.0	11.0	0.0	1
NON-PROTEIN TARGET CHEMBL3879801	IC50	11.0	8.0392	0.0	12
Vitamin D3 receptor CHEMBL1977	EC50	10.97	8.5919	0.0	36
Vitamin D3 receptor CHEMBL2353	Ki	10.6	10.6	0.0	1
PBMC CHEMBL613107	IC50	10.54	8.89	0.0	4
Vitamin D3 receptor CHEMBL1977	IC50	10.4	9.0805	0.0	20
Vitamin D3 receptor CHEMBL3150	Ki	10.4	10.0364	0.0	11
Vitamin D3 receptor CHEMBL3452	IC50	10.32	10.32	0.0	1
T-cell CHEMBL614309	IC50	10.3	10.3	0.1	1
Vitamin D3 receptor CHEMBL3452	EC50	10.3	10.225	0.1	2
Vitamin D3 receptor CHEMBL3150	EC50	10.3	9.8029	0.1	7
Vitamin D3 receptor CHEMBL1977	Kd	10.19	10.19	0.1	1
Vitamin D3 receptor CHEMBL5304	Kd	10.15	10.15	0.1	1
NON-PROTEIN TARGET CHEMBL3879801	EC50	9.14	9.14	0.7	1
T47D CHEMBL614361	IC50	8.89	8.89	1.3	1
Retinoic acid receptor RXR-alpha/Vitamin D3 receptor CHEMBL3885632	EC50	8.8	8.8	1.6	1
HL-60 CHEMBL383	EC50	8.7	8.5086	2.0	7
HL-60 CHEMBL383	Ki	8.7	8.7	2.0	1
Bone marrow cell CHEMBL4296515	EC50	8.7	7.85	2.0	2
1,25-dihydroxyvitamin D(3) 24-hydroxylase, mitochondrial CHEMBL4521	EC50	8.52	8.52	3.0	1
Unchecked CHEMBL612545	IC50	8.51	6.8983	3.1	6
Vitamin D3 receptor A CHEMBL3217399	EC50	8.26	8.26	5.5	1
RWLeu4 CHEMBL614885	IC50	8.22	8.22	6.0	1
U-937 CHEMBL612794	IC50	8.0	7.885	10.0	2
Vitamin D-binding protein CHEMBL2259	Kd	7.62	7.62	24.0	1
Keratinocyte CHEMBL613995	IC50	7.56	7.56	27.3	1
HL-60 CHEMBL383	IC50	7.3	7.3	50.0	1
Homo sapiens CHEMBL372	IC50	7.3	7.3	50.0	1
MCF7 CHEMBL387	EC50	7.28	7.28	52.0	1
Vitamin D3 receptor CHEMBL5601	EC50	7.0	7.0	100.0	1
PE CHEMBL614846	IC50	7.0	7.0	100.0	1
ADMET CHEMBL612558	IC50	6.17	6.17	670.0	1
L02 CHEMBL4296457	IC50	6.17	5.245	670.0	2
Vitamin D3 receptor A CHEMBL3217399	Kd	5.92	5.92	1200.0	1
Caco-2 CHEMBL614058	IC50	5.35	5.35	4460.0	1
MCF7 CHEMBL387	IC50	5.25	5.06	5590.0	5
PC-3 CHEMBL390	IC50	5.02	4.89	9530.0	2
SW480 CHEMBL612544	IC50	4.78	4.78	16780.0	1
BXPC-3 CHEMBL614530	IC50	4.68	4.68	21070.0	1
Bile salt export pump CHEMBL6020	IC50	4.4	4.4	39700.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
AUC	40.0	ng.hr.mL-1	Mus musculus
AUC	40.0	ng.hr.mL-1	Mus musculus
AUC	0.8333	ng.hr.mL-1	Homo sapiens
Cmax	24.0	nM	Mus musculus
Cmax	24.0	nM	Mus musculus
Cmax	4500.0	nM	Homo sapiens
Cmax	18000.0	nM	Homo sapiens
F	61.0	%	Homo sapiens
F	30.83	%	Rattus norvegicus
T1/2	-	hr	Rattus norvegicus
T1/2	4.27	hr	Rattus norvegicus
T1/2	7.55	hr	Rattus norvegicus
T1/2	2.0	hr	Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
HCT-116	IC50	=	0.01	nM	11.0	Cytotoxicity against human HCT116 assessed as decrease in cell count after 120 h...	22926068
NON-PROTEIN TARGET	IC50	=	0.01	nM	11.0	Growth inhibition of human SK-MEL-188 cells measured after 48 hrs by MTS/PMS ass...	27070779
Vitamin D3 receptor	EC50	=	0.0106	nM	10.97	Effect on VDR transcriptional activity in human osteosarcoma cells	18054230
Vitamin D3 receptor	EC50	=	0.011	nM	10.96	Agonist activity at human VDR expressed in HOS cells co-expressing human RXR by ...	30446437
Vitamin D3 receptor	Ki	=	0.025	nM	10.6	Displacement from vitamin D receptor in chick intestine: 50% displacement	-
Vitamin D3 receptor	EC50	=	0.026	nM	10.59	Transactivation of VDR-mediated osteocalcin promoter in human HOS/SF cells after...	24900728
PBMC	IC50	=	0.029	nM	10.54	Inhibition of LPS-induced TNFalpha production in human PBMC after 24 hrs by ELIS...	19309155
NON-PROTEIN TARGET	IC50	=	0.03	nM	10.52	Antiproliferative activity against mouse LM05e cells assessed as decrease in cel...	24900339
Vitamin D3 receptor	Ki	=	0.04	nM	10.4	Displacement of [3H]1alpha,25-(OH)2D3 from full-length recombinant rat VDR by sc...	26630444
Vitamin D3 receptor	IC50	=	0.04	nM	10.4	Displacement of [3H]-1,25D3 from C-terminal GST-tagged human recombinant VDR LBD...	29936834
Vitamin D3 receptor	IC50	=	0.048	nM	10.32	Displacement of [3H]-1-alpha,25-(OH)2D3 from bovine thymus VDR incubated for 18 ...	33369416
Vitamin D3 receptor	IC50	=	0.05	nM	10.3	Transrepression of VP16-tagged VDR (unknown origin) expressed in HEK293 cells ha...	29989817
Vitamin D3 receptor	Ki	=	0.05	nM	10.3	Displacement of [3H]1-alpha,25-(OH)2D3 from rat recombinant full length VDR	18722130
Vitamin D3 receptor	EC50	=	0.05	nM	10.3	Displacement of 1-alpha,25-dihydroxyvitamin from rat recombinant VDR	17960924
Vitamin D3 receptor	EC50	=	0.05	nM	10.3	Displacement of [3H]1,25-(OH)2D3 from bovine thymus vitamin D receptor	19193059
T-cell	IC50	=	0.05	nM	10.3	Concentration to inhibit T-cell activation in Murine MLR	-
Vitamin D3 receptor	IC50	=	0.06	nM	10.22	Displacement of [3H]-1alpha,25-dihydroxyvitamin D3 from recombinant human VDR LB...	26515040
Vitamin D3 receptor	Kd	=	0.065	nM	10.19	Binding affinity to VDR receptor	11462969
Vitamin D3 receptor	EC50	=	0.071	nM	10.15	Displacement of [3H]1,25-(OH)2D3 from vitamin D receptor in bovine thymus	17298045
Vitamin D3 receptor	Kd	=	0.07	nM	10.15	Displacement of [3H]1-alpha,25-(OH)2D3 from VDR in pig intestinal mucosa	19739672

Literature References

PubMed	DOI	Target Context	# Activities
-	10.6019/CHEMBL3885881	Rattus norvegicus	215
2153815	10.1021/jm00164a003	Rattus norvegicus	48
22301272	10.1124/dmd.111.041681	ADMET	36
7798955	10.1021/np50111a003	HL-60	25
30193216	10.1016/j.ejmech.2018.08.085	MCF7	20
16472241	10.2174/1570163043334794	Hepatotoxicity	18
22194678	10.1371/journal.pcbi.1002310	Hepatotoxicity	14
12139448	10.1021/jm020007m	Rattus norvegicus	14
22989379	10.1021/jm3008272	Vitamin D3 receptor	12
19402630	10.1021/jm9001583	Rattus norvegicus	12
29733645	10.1021/acs.jmedchem.8b00337	Vitamin D3 receptor	11
8893845	10.1021/jm950745t	Rattus norvegicus	10
-	10.6019/CHEMBL5303304	U2OS	10
20452225	10.1016/j.bmc.2010.03.078	Mus musculus	10
30471551	10.1016/j.ejmech.2018.11.028	Unchecked	9
30579121	10.1016/j.ejmech.2018.12.024	MCF7	9
-	10.6019/CHEMBL5303304	HEK-293T	9
21902235	10.1021/jm200743p	Rattus norvegicus	8
9804706	10.1021/jm9802618	Rattus norvegicus	8
22018918	10.1016/j.bmc.2011.09.048	Rattus norvegicus	8

Data from ChEMBL 36 via Core Engine