Calcipotriene is a synthetic analog of vitamin D. In humans, the natural supply of vitamin D depends mainly on exposure to the ultraviolet rays of the sun for conversion of 7-dehydrocholesterol to vitamin D3 (cholecalciferol) in the skin.

Mechanism of action

The precise mechanism of calcipotriol in remitting psoriasis is not well-understood, however, it has been shown to have comparable affinity with calcitriol for the Vitamin D receptor while being less than 1% the activity in regulating calcium metabolism. The Vitamin D receptor (VDR) belongs to the steroid/thyroid receptor superfamily, and is found on the cells of many different tissues including the thyroid, bone, kindney, and T cells of the immune system. T cells are known to play a role in psoriasis and are believed to undergo modulation of gene expression with binding of calcipotriol to the VDR. This modulation is thought to affect gene products related to cell differentiation and proliferation.

Target	Actions	Organism
UVitamin D3 receptor	antagonist	Humans

Absorption

Clinical studies with radiolabeled ointment indicate that approximately 6% (+3%, SD) of the applied dose of calcipotriene is absorbed systemically when the ointment is applied topically to psoriasis plaques or 5% (+2.6%, SO) when applied to normal skin.

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism

Hepatic. Calcipotriene metabolism following systemic uptake is rapid, and occurs via a similar pathway to the natural hormone. The primary metabolites are much less potent than the parent compound.

Route of elimination

The active form of the vitamin, 1,25-dihydroxy vitamin D3 (calcitriol), is known to be recycled via the liver and excreted in the bile. There is evidence that maternal 1,25-dihydroxy vitamin D3 (calcitriol) may enter the fetal circulation, but it is not known whether it is excreted in human milk.

Half-life

Not Available

Clearance

Not Available

Adverse Effects

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Toxicity

Topically applied calcipotriene can be absorbed in sufficient amounts to produce systemic effects. Elevated serum calcium has been observed with excessive use of calcipotriene.

Pathways

Not Available

Pharmacogenomic Effects/ADRs

Not Available

Interactions

Drug Interactions

This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.

Drug	Interaction
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Calcium acetate	The risk or severity of adverse effects can be increased when Calcium acetate is combined with Calcipotriol.
Calcium carbonate	The risk or severity of adverse effects can be increased when Calcium carbonate is combined with Calcipotriol.
Calcium chloride	The risk or severity of adverse effects can be increased when Calcium chloride is combined with Calcipotriol.
Calcium citrate	The risk or severity of adverse effects can be increased when Calcium citrate is combined with Calcipotriol.
Calcium glubionate anhydrous	The risk or severity of adverse effects can be increased when Calcium glubionate anhydrous is combined with Calcipotriol.
Calcium glucoheptonate	The risk or severity of adverse effects can be increased when Calcium glucoheptonate is combined with Calcipotriol.
Calcium gluconate	The risk or severity of adverse effects can be increased when Calcium gluconate is combined with Calcipotriol.
Calcium lactate	The risk or severity of adverse effects can be increased when Calcium lactate is combined with Calcipotriol.
Calcium levulinate	The risk or severity of adverse effects can be increased when Calcium levulinate is combined with Calcipotriol.
Calcium Phosphate	The risk or severity of adverse effects can be increased when Calcium Phosphate is combined with Calcipotriol.

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Food Interactions

No interactions found.

Products

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Product Ingredients

Ingredient	UNII	CAS	InChI Key
Calcipotriol hydrate	S7499TYY6G	147657-22-5	XBKHACNRWFKJNC-MANNPBRJSA-N

International/Other Brands

Daivonex

Brand Name Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Calcipotriene	Aerosol, foam	50 ug/1g	Topical	Mayne Pharma	2021-02-15	Not applicable
Calcipotriene 0.005% 60 gram Foam	Aerosol, foam	50 ug/1g	Topical	Trifluent Pharma LLC	2020-08-24	Not applicable
Calcipotriene Foam	Aerosol, foam	50 ug/1g	Topical	Ayurax	2020-01-08	2020-05-07
Dovonex	Solution	0.05 mg/1mL	Topical	Leo Pharma	1997-06-01	2013-04-01
Dovonex	Ointment	50 ug/1g	Topical	Bristol Myers Squibb Pharma Company	2009-06-01	2012-10-15
Dovonex	Solution	0.05 mg/1mL	Topical	Physicians Total Care, Inc.	2009-08-12	Not applicable
Dovonex	Solution	0.05 mg/1mL	Topical	Allergan	2006-01-01	2012-03-31
Dovonex	Ointment	50 ug/1g	Topical	Physicians Total Care, Inc.	2004-06-30	2010-12-29
Dovonex	Cream	50 ug/1g	Topical	LEO Pharma Inc.	1996-10-01	Not applicable
Dovonex	Cream	50 ug/1g	Topical	Allergan	2006-01-01	2012-03-31

Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Calcipotriene	Cream	50 ug/1g	Topical	Glenmark Pharmaceuticals Inc.,Usa	2015-06-10	Not applicable
Calcipotriene	Ointment	50 ug/1g	Topical	Prasco Laboratories	2013-07-01	Not applicable
Calcipotriene	Ointment	0.05 mg/1g	Topical	Taro Pharmaceuticals U.S.A., Inc.	2010-03-24	Not applicable
Calcipotriene	Ointment	50 ug/1g	Topical	Glenmark Pharmaceuticals Inc., USA	2010-03-24	Not applicable
Calcipotriene	Solution	0.05 mg/1mL	Topical	Sandoz	2009-11-20	2013-10-31
Calcipotriene	Solution	0.05 mg/1mL	Topical	Hi-Tech Pharmacal Co., Inc.	2014-10-06	Not applicable
Calcipotriene	Cream	0.05 mg/1g	Topical	Sandoz Inc.	2012-07-27	Not applicable
Calcipotriene	Solution	0.05 mg/1mL	Topical	Fougera Pharmaceuticals Inc.	2008-05-06	Not applicable
Calcipotriene	Cream	50 ug/1g	Topical	Prasco Laboratories	1996-10-01	Not applicable
Calcipotriene	Solution	0.05 mg/1mL	Topical	Amneal Pharmaceuticals of New York Llc	2009-11-20	Not applicable

Mixture Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End
Calcipotriene and Betamethasone Dipropionate	Calcipotriol (50 ug/1g) + Betamethasone dipropionate (.643 mg/1g)	Ointment	Topical	bryant ranch prepack	2020-01-30	Not applicable
Calcipotriene and Betamethasone Dipropionate	Calcipotriol hydrate (50 ug/1g) + Betamethasone dipropionate (0.5 mg/1g)	Ointment	Topical	Perrigo New York Inc	2008-06-01	Not applicable
Calcipotriene and Betamethasone Dipropionate	Calcipotriol (50 ug/1g) + Betamethasone dipropionate (0.5 mg/1g)	Ointment	Topical	Sandoz Inc.	2014-03-31	Not applicable
Calcipotriene and Betamethasone Dipropionate	Calcipotriol hydrate (50 ug/1g) + Betamethasone dipropionate (.5 mg/1g)	Suspension	Topical	Perrigo New York Inc	2020-10-09	Not applicable
Calcipotriene and Betamethasone Dipropionate	Calcipotriol (50 ug/1g) + Betamethasone dipropionate (.643 mg/1g)	Ointment	Topical	Perrigo New York Inc	2020-01-30	Not applicable
Calcipotriene and Betamethasone Dipropionate	Calcipotriol (50 ug/1g) + Betamethasone dipropionate (50 mg/1g)	Suspension	Topical	Taro Pharmaceuticals U.S.A., Inc.	2020-09-02	Not applicable
Calcipotriene and Betamethasone Dipropionate	Calcipotriol (50 ug/1g) + Betamethasone dipropionate (0.5 mg/1g)	Suspension	Topical	TOLMAR Inc.	2020-05-11	Not applicable
Calcipotriene and Betamethasone Dipropionate	Calcipotriol hydrate (50 ug/1g) + Betamethasone dipropionate (0.5 mg/1g)	Suspension	Topical	Prasco Laboratories	2020-01-07	Not applicable
Calcipotriene and Betamethasone Dipropionate	Calcipotriol hydrate (50 ug/1g) + Betamethasone dipropionate (0.5 mg/1g)	Ointment	Topical	Prasco Laboratories	2020-01-28	Not applicable
DAIVOBET	Calcipotriol (50 MCG/1G) + Betamethasone dipropionate (0.5 MG/1G)	Ointment	Topical	บริษัท ดีเคเอสเอช (ประเทศไทย) จำกัด	2010-03-11	Not applicable

Unapproved/Other Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End
Calcipotriene 0.005% / Clobetasol Propionate 0.05%	Calcipotriol (0.005 g/100g) + Clobetasol propionate (0.05 g/100g)	Solution	Topical	Sincerus Florida, LLC	2019-05-20	Not applicable
Calcipotriene 0.005% / Diclofenac Sodium 3% / Hyaluronic Acid Sodium Salt 2% / Niacinamide 2%	Calcipotriol (0.005 g/100g) + Diclofenac sodium (3 g/100g) + Sodium hyaluronate (2 g/100g) + Nicotinamide (2 g/100g)	Cream	Topical	Sincerus Florida, LLC	2019-05-07	Not applicable
Calcipotriene 0.005% / Niacinamide 4%	Calcipotriol (0.005 g/100g) + Nicotinamide (4 g/100g)	Cream	Topical	Sincerus Florida, LLC	2019-05-14	Not applicable
Calcipotriene 0.005% / Triamcinolone Acetonide 0.1%	Calcipotriol (0.005 g/100g) + Triamcinolone acetonide (0.1 g/100g)	Ointment	Topical	Sincerus Florida, LLC	2019-05-11	Not applicable

Chemical Identifiers

UNII: 143NQ3779B
CAS number: 112965-21-6
InChI Key: LWQQLNNNIPYSNX-UROSTWAQSA-N
InChI: InChI=1S/C27H40O3/c1-17(6-13-25(29)20-8-9-20)23-11-12-24-19(5-4-14-27(23,24)3)7-10-21-15-22(28)16-26(30)18(21)2/h6-7,10,13,17,20,22-26,28-30H,2,4-5,8-9,11-12,14-16H2,1,3H3/b13-6+,19-7+,21-10-/t17-,22-,23-,24+,25-,26+,27-/m1/s1
IUPAC Name: (1R,3S,5Z)-5-{2-[(1R,3aS,4E,7aR)-1-[(2R,3E,5S)-5-cyclopropyl-5-hydroxypent-3-en-2-yl]-7a-methyl-octahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexane-1,3-diol
SMILES: O[C@H](\C=C\[C@@H](C)[C@@]1([H])CC[C@@]2([H])\C(CCC[C@]12C)=C\C=C1\C[C@@H](O)C[C@H](O)C1=C)C1CC1

References

Synthesis Reference

Andrzej Kutner, Michal Chodynski, Teresa Ryznar, Hanna Fitak, Jerzy Winiarski, Bartlomiej Gorecki, Agnieszka Burzynska, Wieslaw Szelejewski, "Process for Preparation of Pharmaceutically Pure Anhydrous Calcipotriol." U.S. Patent US20080214876, issued September 04, 2008.

US20080214876

General References

Not Available

External Links

Human Metabolome Database: HMDB0015567
KEGG Drug: D01125
PubChem Compound: 5288783
PubChem Substance: 46507122
ChemSpider: 4450880
BindingDB: 50369964
RxNav: 29365
ChEBI: 50749
ChEMBL: CHEMBL1200666
ZINC: ZINC000003921872
Therapeutic Targets Database: DAP000292
PharmGKB: PA448714
Guide to Pharmacology: GtP Drug Page
PDBe Ligand: MC9
RxList: RxList Drug Page
Wikipedia: Calcipotriol

AHFS Codes

84:92.00 — Misc. Skin and Mucous Membrane Agents

PDB Entries

1s19

Clinical Trials

Clinical Trials

Phase	Status	Purpose	Conditions	Count
4	Active Not Recruiting	Treatment	Psoriasis Vulgaris (Plaque Psoriasis)	1
4	Completed	Other	Psoriasis Vulgaris (Plaque Psoriasis)	1
4	Completed	Supportive Care	Adherence	1
4	Completed	Treatment	Psoriasis	5
4	Completed	Treatment	Psoriasis Vulgaris (Plaque Psoriasis)	7
4	Completed	Treatment	Psoriasis / Psoriasis Vulgaris (Plaque Psoriasis)	1
4	Not Yet Recruiting	Treatment	Nail Psoriasis	1
4	Not Yet Recruiting	Treatment	Psoriasis Vulgaris (Plaque Psoriasis)	1
4	Recruiting	Treatment	Psoriasis	3
4	Terminated	Treatment	Psoriasis Vulgaris (Plaque Psoriasis)	2

Pharmacoeconomics

Manufacturers

Not Available

Packagers

Contract Pharm
Dispensing Solutions
E. Fougera and Co.
Glenmark Generics Ltd.
Hi Tech Pharmacal Co. Inc.
LEO Pharma Inc.
Nycomed Inc.
Physicians Total Care Inc.
Sandoz
Warner Chilcott Co. Inc.
WC Pharmaceuticals

Dosage Forms

Form	Route	Strength
Gel	Topical
Cream	Topical	0.05 mg/1g
Solution	Topical	.05 mg/1mL
Solution	Topical
Cream	Topical
Ointment	Cutaneous
Solution	Cutaneous; Topical
Ointment	Topical	0.05 mg/1g
Gel
Ointment
Ointment
Solution	Cutaneous
Solution	Topical
Cream	Topical	5 mg
Lotion	Topical	5 mg
Ointment	Topical	0.005 g
Gel	Cutaneous
Ointment	Cutaneous
Cream	Topical	50 ug/1g
Ointment	Topical	50 ug/1g
Solution	Topical	0.05 mg/1mL
Cream	Topical	50 mcg / g
Ointment	Topical	50 mcg / g
Solution	Topical	50 mcg / mL
Aerosol, foam	Cutaneous
Aerosol, foam	Topical
Kit	Topical
Cream	Topical
Ointment	Topical
Aerosol, foam	Topical	50 ug/1g
Ointment	Topical
Spray, metered	Topical
Suspension	Topical

Prices

Unit description	Cost	Unit
Dovonex 0.005% Cream 120 gm Tube	607.03USD	tube
Dovonex 0.005% Solution 60ml Bottle	323.98USD	bottle
Dovonex 0.005% Cream 60 gm Tube	303.51USD	tube
Dovonex 0.005% cream	4.23USD	g
Dovonex 50 mcg/ml Solution	0.84USD	ml
Dovonex 50 mcg/g Cream	0.83USD	g
Dovonex 50 mcg/g Ointment	0.81USD	g

DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.

Patents

Patent Number	Pediatric Extension	Approved	Expires (estimated)
US5763426	No	1998-06-09	2015-06-09
US6753013	No	2004-06-22	2020-01-27
US6787529	No	2004-09-07	2020-01-27
US8263580	No	2012-09-11	2028-09-27
US8629128	No	2014-01-14	2026-05-26
US9119781	Yes	2015-09-01	2031-12-10
US10130640	Yes	2018-11-20	2031-12-10
US9566286	No	2017-02-14	2031-06-10
US10617698	No	2011-06-10	2031-06-10
US10660908	No	2011-06-10	2031-06-10
US10688108	No	2011-06-10	2031-06-10
US10682364	No	2011-06-10	2031-06-10
US10716799	No	2011-06-10	2031-06-10
US10265265	No	2007-09-27	2027-09-27

Properties

State

Solid

Experimental Properties

Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.0135 mg/mL	ALOGPS
logP	4.63	ALOGPS
logP	3.84	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	14.39	ChemAxon
pKa (Strongest Basic)	-1.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	60.69 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	125.45 m³·mol^-1	ChemAxon
Polarizability	49.59 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted ADMET Features

Property	Value	Probability
Human Intestinal Absorption	+	0.9945
Blood Brain Barrier	+	0.8426
Caco-2 permeable	+	0.7643
P-glycoprotein substrate	Substrate	0.7718
P-glycoprotein inhibitor I	Non-inhibitor	0.7297
P-glycoprotein inhibitor II	Non-inhibitor	0.9687
Renal organic cation transporter	Non-inhibitor	0.813
CYP450 2C9 substrate	Non-substrate	0.8383
CYP450 2D6 substrate	Non-substrate	0.8975
CYP450 3A4 substrate	Substrate	0.7113
CYP450 1A2 substrate	Non-inhibitor	0.7455
CYP450 2C9 inhibitor	Non-inhibitor	0.7898
CYP450 2D6 inhibitor	Non-inhibitor	0.9336
CYP450 2C19 inhibitor	Non-inhibitor	0.7994
CYP450 3A4 inhibitor	Non-inhibitor	0.8014
CYP450 inhibitory promiscuity	Low CYP Inhibitory Promiscuity	0.7475
Ames test	Non AMES toxic	0.9132
Carcinogenicity	Non-carcinogens	0.9332
Biodegradation	Not ready biodegradable	0.9871
Rat acute toxicity	3.9699 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.9198
hERG inhibition (predictor II)	Non-inhibitor	0.8018

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	Not Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	Not Available

Targets

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Property	Measurement	pH	Temperature (°C)	References
Kd (nM)	0.31	N/A	N/A	A29890

Details1. Vitamin D3 receptor

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Antagonist

General Function: Zinc ion binding
Specific Function: Nuclear hormone receptor. Transcription factor that mediates the action of vitamin D3 by controlling the expression of hormone sensitive genes. Recruited to promoters via its interaction with BAZ1B...
Gene Name: VDR
Uniprot ID: P11473
Uniprot Name: Vitamin D3 receptor
Molecular Weight: 48288.64 Da

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]

Enzymes

Details1. Myeloperoxidase

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Inhibitor

General Function: Peroxidase activity
Specific Function: Part of the host defense system of polymorphonuclear leukocytes. It is responsible for microbicidal activity against a wide range of organisms. In the stimulated PMN, MPO catalyzes the production o...
Gene Name: MPO
Uniprot ID: P05164
Uniprot Name: Myeloperoxidase
Molecular Weight: 83867.71 Da

References

Sato H, Ogino Y, Takagi H, Hata J, Asano S, Ohta T, Komoriya K: Pharmacological profiles of high-concentration (20 microg/g) tacalcitol ointment: effects on cutaneous inflammation, epidermal proliferation, and differentiation in mice. J Dermatol. 2003 Jul;30(7):510-24. [Article]

Details2. 1,25-dihydroxyvitamin D(3) 24-hydroxylase, mitochondrial

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

General Function: Oxidoreductase activity
Specific Function: Has a role in maintaining calcium homeostasis. Catalyzes the NADPH-dependent 24-hydroxylation of calcidiol (25-hydroxyvitamin D(3)) and calcitriol (1-alpha,25-dihydroxyvitamin D(3)). The enzyme can...
Gene Name: CYP24A1
Uniprot ID: Q07973
Uniprot Name: 1,25-dihydroxyvitamin D(3) 24-hydroxylase, mitochondrial
Molecular Weight: 58874.695 Da

References

Jones G, Byford V, West S, Masuda S, Ibrahim G, Kaufmann M, Knutson JC, Strugnell S, Mehta R: Hepatic activation and inactivation of clinically-relevant vitamin D analogs and prodrugs. Anticancer Res. 2006 Jul-Aug;26(4A):2589-95. [Article]

Drug created on June 13, 2005 13:24 / Updated on June 23, 2021 06:08

Calcipotriol

Identification

Structure for Calcipotriol (DB02300)

Pharmacology

Interactions

Products

Categories

Chemical Identifiers

References

Clinical Trials

Pharmacoeconomics

Properties

Spectra

Targets

References

Enzymes

References

References