Details of the Drug

General Information of Drug (ID: DMN4CV5)

Drug Name

Calcidiol

Synonyms

Calcifediolum; Calcifidiol; Delakmin; VDY; Calcifediol anhydrous; BML2-E02; Calcifediolum [INN-Latin]; Ro 8-8892; U-32070E; (1R,3Z)-3-[(2E)-2-[(1R,7aR)-1-[(2R)-6-hydroxy-6-methylheptan-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidenecyclohexan-1-ol; (1S,3Z)-3-[(2E)-2-[(1R,3aS,7aR)-1-[(2R)-6-hydroxy-6-methylheptan-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidenecyclohexan-1-ol; (3S,5Z,7E)-9,10-secocholesta-5,7,10(19)-triene-3,25-diol; (3S,5Z,7E)-9,10-secocholesta-5,7,10-triene-3,25-diol; (3beta,5Z,7E)-9,10-secocholesta-5,7,10(19)-triene-3,25-diol; (5Z,7E)-(3S)-9,10-secocholesta-5,7,10(19)-triene-3,25-diol; (5Z,7E)-9,10-Seco-5,7,10(19)-cholestatrien-3beta,25-diol; 25(OH)D3; 25-(OH)Vitamin D3; 25-Hydroxycholecalciferol; 25-Hydroxycholecalciferol (Calcifediol); 25-Hydroxycholescalciferol; 25-Hydroxyvitamin D; 25-Hydroxyvitamin D3 monohydrate; 25-hydroxyvitamin D3; 3-{2-[1-(5-HYDROXY-1,5-DIMETHYL-HEXYL)-7A-METHYL-OCTAHYDRO-INDEN-4-YLIDENE]-ETHYLIDENE}-4-METHYLENE-CYCLOHEXANOL; 5,6-cis-25-Hydroxyvitamin D3; 5,6-trans-25-Hydroxycholescalciferol; 5,6-trans-9,10-Seco-5,7,10(19)-cholestatrien-3beta,25-diol; 9,10-Secocholesta-5,7,10(19)-triene-3beta,25-diol

Indication

Disease Entry	ICD 11	Status	REF
Hypophosphatemia	N.A.	Approved	[1]
Renal osteodystrophy	N.A.	Approved	[2]
Rickets	5B57	Approved	[3]
Vitamin D deficiency	5B57	Approved	[4]
Autosomal dominant hypocalcemia	5A50.0Y	Investigative	[5]
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Therapeutic Class

Vitamins

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 1

Molecular Weight (mw)

400.6

Logarithm of the Partition Coefficient (xlogp)

6.2

Rotatable Bond Count (rotbonds)

6

Hydrogen Bond Donor Count (hbonddonor)

2

Hydrogen Bond Acceptor Count (hbondacc)

2

Chemical Identifiers

Formula: C27H44O2
IUPAC Name: (1S,3Z)-3-[(2E)-2-[(1R,3aS,7aR)-1-[(2R)-6-hydroxy-6-methylheptan-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidenecyclohexan-1-ol
Canonical SMILES: C[C@H](CCCC(C)(C)O)[C@H]1CC[C@@H]\\2[C@@]1(CCC/C2=C\\C=C/3\\C[C@H](CCC3=C)O)C
InChI: InChI=1S/C27H44O2/c1-19-10-13-23(28)18-22(19)12-11-21-9-7-17-27(5)24(14-15-25(21)27)20(2)8-6-16-26(3,4)29/h11-12,20,23-25,28-29H,1,6-10,13-18H2,2-5H3/b21-11+,22-12-/t20-,23+,24-,25+,27-/m1/s1
InChIKey: JWUBBDSIWDLEOM-DTOXIADCSA-N

Cross-matching ID

PubChem CID: 5283731
ChEBI ID: CHEBI:17933
CAS Number: 19356-17-3
DrugBank ID: DB00146
TTD ID: D02VPX
INTEDE ID: DR0259
ACDINA ID: D00089

Repurposed Drugs (RPD)

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Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Vitamin D3 receptor (VDR)	TTK59TV	VDR_HUMAN	Antagonist	[6]

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Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
Vitamin D(3) 24-hydroxylase (CYP24A1)	DEFI12S	CP24A_HUMAN	Substrate	[7]
Calcidiol 1-monooxygenase (CYP27B1)	DE3FYEM	CP27B_HUMAN	Substrate	[8]

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Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
1,25-dihydroxyvitamin D(3) 24-hydroxylase, mitochondrial (CYP24A1)	OTG2T749	CP24A_HUMAN	Gene/Protein Processing	[9]
25-hydroxyvitamin D-1 alpha hydroxylase, mitochondrial (CYP27B1)	OTTK98BH	CP27B_HUMAN	Biotransformations	[10]
Alkaline phosphatase, tissue-nonspecific isozyme (ALPL)	OTG7J4BP	PPBT_HUMAN	Gene/Protein Processing	[10]
Apoptosis regulator BAX (BAX)	OTAW0V4V	BAX_HUMAN	Gene/Protein Processing	[10]
Apoptosis regulator Bcl-2 (BCL2)	OT9DVHC0	BCL2_HUMAN	Gene/Protein Processing	[10]
Cyclin-dependent kinase inhibitor 1 (CDKN1A)	OTQWHCZE	CDN1A_HUMAN	Gene/Protein Processing	[10]
G1/S-specific cyclin-D1 (CCND1)	OT8HPTKJ	CCND1_HUMAN	Gene/Protein Processing	[10]
Insulin (INS)	OTZ85PDU	INS_HUMAN	Protein Interaction/Cellular Processes	[11]
Integrin-binding sialoprotein (IBSP)	OT29944Y	SIAL_HUMAN	Gene/Protein Processing	[10]
Proliferating cell nuclear antigen (PCNA)	OTHZ1RIA	PCNA_HUMAN	Gene/Protein Processing	[10]

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Molecular Interaction Atlas (MIA)

MIA Detail

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Molecular Expression Atlas of This Drug

The Studied Disease

Hypophosphatemia

ICD Disease Classification

Molecule Name	Molecule Type	Gene Name	p-value	Fold-Change	Z-score
Vitamin D3 receptor (VDR)	DTT	VDR	1.69E-02	-0.23	-0.66
Vitamin D(3) 24-hydroxylase (CYP24A1)	DME	CYP24A1	7.29E-01	1.85E-01	9.48E-02
Calcidiol 1-monooxygenase (CYP27B1)	DME	CYP27B1	8.48E-02	-6.84E-01	-9.36E-01

Molecular Expression Atlas (MEA)

MEA Detail

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Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Disease Different from Calcidiol (Comorbidity)

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Comorbidity	REF
Magnesium Sulfate	DMVEK07	Moderate	Increased risk of hypermagnesemia by the combination of Calcidiol and Magnesium Sulfate.	Acute pain [MG31]	[12]
Butalbital	DM9J04X	Moderate	Increased metabolism of Calcidiol caused by Butalbital mediated induction of CYP450 enzyme.	Anxiety disorder [6B00-6B0Z]	[12]
Methylphenobarbital	DMDSWAG	Moderate	Increased metabolism of Calcidiol caused by Methylphenobarbital mediated induction of CYP450 enzyme.	Anxiety disorder [6B00-6B0Z]	[12]
Secobarbital	DM14RF5	Moderate	Increased metabolism of Calcidiol caused by Secobarbital mediated induction of CYP450 enzyme.	Chronic insomnia [7A00]	[12]
Primidone	DM0WX6I	Moderate	Increased metabolism of Calcidiol caused by Primidone mediated induction of CYP450 enzyme.	Epilepsy/seizure [8A61-8A6Z]	[12]
Felbamate	DM1V5ZS	Moderate	Increased metabolism of Calcidiol caused by Felbamate mediated induction of CYP450 enzyme.	Epilepsy/seizure [8A61-8A6Z]	[12]
Oxcarbazepine	DM5PU6O	Moderate	Increased metabolism of Calcidiol caused by Oxcarbazepine mediated induction of CYP450 enzyme.	Epilepsy/seizure [8A61-8A6Z]	[12]
Phenytoin	DMNOKBV	Moderate	Increased metabolism of Calcidiol caused by Phenytoin mediated induction of CYP450 enzyme.	Epilepsy/seizure [8A61-8A6Z]	[12]
Fosphenytoin	DMOX3LB	Moderate	Increased metabolism of Calcidiol caused by Fosphenytoin mediated induction of CYP450 enzyme.	Epilepsy/seizure [8A61-8A6Z]	[12]
Rufinamide	DMWE60C	Moderate	Increased metabolism of Calcidiol caused by Rufinamide mediated induction of CYP450 enzyme.	Epilepsy/seizure [8A61-8A6Z]	[12]
Phenobarbital	DMXZOCG	Moderate	Increased metabolism of Calcidiol caused by Phenobarbital mediated induction of CYP450 enzyme.	Epilepsy/seizure [8A61-8A6Z]	[12]
Carbamazepine	DMZOLBI	Moderate	Increased metabolism of Calcidiol caused by Carbamazepine mediated induction of CYP450 enzyme.	Epilepsy/seizure [8A61-8A6Z]	[12]
Isoniazid	DM5JVS3	Moderate	Increased metabolism of Calcidiol caused by Isoniazid mediated induction of CYP450 enzyme.	HIV-infected patients with tuberculosis [1B10-1B14]	[12]
Rifampin	DMA8J1G	Moderate	Increased metabolism of Calcidiol caused by Rifampin mediated induction of CYP450 enzyme.	HIV-infected patients with tuberculosis [1B10-1B14]	[12]
Rifapentine	DMCHV4I	Moderate	Increased metabolism of Calcidiol caused by Rifapentine mediated induction of CYP450 enzyme.	HIV-infected patients with tuberculosis [1B10-1B14]	[12]
Amobarbital	DM0GQ8N	Moderate	Increased metabolism of Calcidiol caused by Amobarbital mediated induction of CYP450 enzyme.	Insomnia [7A00-7A0Z]	[12]
Butabarbital	DMC5AST	Moderate	Increased metabolism of Calcidiol caused by Butabarbital mediated induction of CYP450 enzyme.	Insomnia [7A00-7A0Z]	[12]
Pentobarbital	DMFNH7L	Moderate	Increased metabolism of Calcidiol caused by Pentobarbital mediated induction of CYP450 enzyme.	Insomnia [7A00-7A0Z]	[12]
Rifabutin	DM1YBHK	Moderate	Increased metabolism of Calcidiol caused by Rifabutin mediated induction of CYP450 enzyme.	Mycobacterium infection [1B10-1B21]	[12]
Orlistat	DMRJSP8	Minor	Decreased absorption of Calcidiol caused by Orlistat.	Obesity [5B80-5B81]	[13]
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Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG

DIG Name	DIG ID	PubChem CID	Functional Classification
Butylated hydroxytoluene	E00336	31404	Antioxidant
FD&C blue no. 1	E00263	19700	Colorant
Isopropyl alcohol	E00070	3776	Antimicrobial preservative; Solvent
Hexahydric alcohol	E00083	5780	Diluent; Flavoring agent; Humectant; Plasticizing agent
Medium-chain triglyceride	E00640	Not Available	Emollient; Lubricant; Surfactant
Propylene glycol	E00040	1030	Antimicrobial preservative; Humectant; Plasticizing agent; Solvent
Titanium dioxide	E00322	26042	Coating agent; Colorant; Opacifying agent
Water	E00035	962	Solvent
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Pharmaceutical Formulation

Formulation Name	Drug Dosage	Dosage Form	Route
Calcifediol 0.03 mg capsule	0.03 mg	24 HR Extended Release Oral Capsule	Oral

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References

1	Tertiary 'hyperphosphatoninism' accentuates hypophosphatemia and suppresses calcitriol levels in renal transplant recipients. Am J Transplant. 2007 May;7(5):1193-200.
2	Patterns of renal osteodystrophy 1?year after kidney transplantation. Nephrol Dial Transplant. 2021 Nov 9;36(11):2130-2139.
3	Correction of vitamin D status by calcidiol: pharmacokinetic profile, safety, and biochemical effects on bone and mineral metabolism of daily and weekly dosage regimens. Osteoporos Int. 2017 Nov;28(11):3239-3249.
4	URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 6921).
5	A standard database for drug repositioning. Sci Data. 2017 Mar 14;4:170029.
6	Vitamin D in health and disease. Clin J Am Soc Nephrol. 2008 Sep;3(5):1535-41.
7	Asthma families show transmission disequilibrium of gene variants in the vitamin D metabolism and signalling pathway. Respir Res. 2006 Apr 6;7:60.
8	Cytochromes P450 are essential players in the vitamin D signaling system. Biochim Biophys Acta. 2011 Jan;1814(1):186-99.
9	Retinoic acid via RARalpha inhibits the expression of 24-hydroxylase in human prostate stromal cells. Biochem Biophys Res Commun. 2005 Dec 30;338(4):1973-81. doi: 10.1016/j.bbrc.2005.10.178. Epub 2005 Nov 7.
10	Effects of 25-hydroxyvitamin D(3) on proliferation and osteoblast differentiation of human marrow stromal cells require CYP27B1/1alpha-hydroxylase. J Bone Miner Res. 2011 May;26(5):1145-53.
11	Season of birth, neonatal vitamin D status, and cardiovascular disease risk at 35 y of age: a cohort study from Sweden. Am J Clin Nutr. 2014 Mar;99(3):472-8. doi: 10.3945/ajcn.113.072520. Epub 2014 Jan 8.
12	Product Information. Hectorol (doxercalciferol). Genzyme Corporation, Cambridge, MA.
13	Product Information. Xenical (orlistat). Roche Laboratories, Nutley, NJ.