Vitamin D3

Identification

Summary

Vitamin D3 is a form of Vitamin D used in the treatment of specific medical conditions such as refractory rickets, hypoparathyroidism, and familial hypophosphatemia, as well as osteoporosis and chronic kidney disease.

Brand Names

Adrovance, Animi-3 With Vitamin D, Citranatal B-calm Kit, Citranatal Harmony, Fosamax Plus D, Fosavance, Infuvite, Infuvite Pediatric, Mvc-fluoride, Natafort, Pregvit, Vidextra

Generic Name

Cholecalciferol
Commonly known or available as Vitamin D3

DrugBank Accession Number

DB00169

Background

Vitamin D, in general, is a secosteroid generated in the skin when 7-dehydrocholesterol located there interacts with ultraviolet irradiation - like that commonly found in sunlight ⁹. Both the endogenous form of vitamin D (that results from 7-dehydrocholesterol transformation), vitamin D3 (cholecalciferol), and the plant-derived form, vitamin D2 (ergocalciferol), are considered the main forms of vitamin d and are found in various types of food for daily intake ⁹. Structurally, ergocalciferol differs from cholecalciferol in that it possesses a double bond between C22 and C23 and has an additional methyl group at C24 ⁹. Finally, ergocalciferol is pharmacologically less potent than cholecalciferol, which makes vitamin D3 the preferred agent for medical use ⁹.

Appropriate levels of vitamin D must be upheld in the body in order to maintain calcium and phosphorus levels in a healthy physiologic range to sustain a variety of metabolic functions, transcription regulation, and bone metabolism ^{4,9,10,11,12,13,14}. However, studies are also ongoing to determine whether or not cholecalciferol may also play certain roles in cancer, autoimmune disorders, cardiovascular disease, and other medical conditions that may be associated with vitamin D deficiency ⁹.

Type

Small Molecule

Groups

Approved, Nutraceutical

Structure

3D

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MOLSDF3D-SDFPDBSMILESInChI

Similar Structures

Structure for Cholecalciferol (DB00169)

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Weight

Average: 384.6377
Monoisotopic: 384.33921603

Chemical Formula

C₂₇H₄₄O

Synonyms

• (+)-vitamin D3
• (3β,5Z,7E)-9,10-secocholesta-5,7,10(19)-trien-3-ol
• (5Z,7E)-(3S)-9,10-secocholesta-5,7,10(19)-trien-3-ol
• Activated 7-dehydrocholesterol
• Calciol
• CC
• Cholecalciferol
• Cholecalciferolum
• Colecalciferol
• Colecalciferolum
• Oleovitamin D3
• Vitamin D-3
• Vitamin D3

External IDs

• NSC-375571

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Pharmacology

Indication

Cholecalciferol use is indicated for the treatment of specific medical conditions like refractory rickets (or vitamin D resistant rickets), hypoparathyroidism, and familial hypophosphatemia ^12,13.

Concurrently, as one of the most commonly utilized forms of vitamin D, cholecalciferol is also very frequently used as a supplement in individuals to maintain sufficient vitamin d levels in the body or to treat vitamin D deficiency, as well as various medical conditions that can be associated directly or indirectly with vitamin d insufficiency like osteoporosis and chronic kidney disease, among others ^2,3,15.

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Associated Conditions

Indication Type	Indication	Combined Product Details	Approval Level	Age Group	Patient Characteristics	Dose Form
Used in combination to treat	Calcium and vitamin d deficiencies	Combination Product in combination with: Calcium carbonate (DB06724)	••••••••••••	•••••• •••••••
Used in combination to prevent	Deficiency, vitamin a	Combination Product in combination with: Vitamin A (DB00162)	••••••••••••			•••••••••• ••••••••
Used in combination to treat	Deficiency, vitamin a	Combination Product in combination with: Vitamin A (DB00162)	••••••••••••			•••••••••• ••••••••
Used in combination to treat	Deficiency, vitamin a	Combination Product in combination with: Vitamin A (DB00162)	••••••••••••			•••••••• • •••••
Used in combination to treat	Deficiency, vitamin d	Combination Product in combination with: Vitamin A (DB00162)	••••••••••••			•••••••• • •••••

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Associated Therapies

• Calcium supplementation
• Nutritional supplementation
• Vitamin D Supplementation
• Vitamin supplementation

Contraindications & Blackbox Warnings

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Pharmacodynamics

The in vivo synthesis of the predominant two biologically active metabolites of vitamin D occurs in two steps. The first hydroxylation of vitamin D3 cholecalciferol (or D2) occurs in the liver to yield 25-hydroxyvitamin D while the second hydroxylation happens in the kidneys to give 1, 25-dihydroxyvitamin D ^12,13,14. These vitamin D metabolites subsequently facilitate the active absorption of calcium and phosphorus in the small intestine, serving to increase serum calcium and phosphate levels sufficiently to allow bone mineralization ^12,13,14. Conversely, these vitamin D metabolites also assist in mobilizing calcium and phosphate from bone and likely increase the reabsorption of calcium and perhaps also of phosphate via the renal tubules ^12,13,14. There exists a period of 10 to 24 hours between the administration of cholecalciferol and the initiation of its action in the body due to the necessity of synthesis of the active vitamin D metabolites in the liver and kidneys ^12,13,14. It is parathyroid hormone that is responsible for the regulation of such metabolism at the level of the kidneys ^12,13,14.

Mechanism of action

Most individuals naturally generate adequate amounts of vitamin D through ordinary dietary intake of vitamin D (in some foods like eggs, fish, and cheese) and natural photochemical conversion of the vitamin D3 precursor 7-dehydrocholesterol in the skin via exposure to sunlight ^9,12,13,14.

Conversely, vitamin D deficiency can often occur from a combination of insufficient exposure to sunlight, inadequate dietary intake of vitamin D, genetic defects with endogenous vitamin D receptor, or even severe liver or kidney disease ¹. Such deficiency is known for resulting in conditions like rickets or osteomalacia, all of which reflect inadequate mineralization of bone, enhanced compensatory skeletal demineralization, resultant decreased calcium ion blood concentrations, and increases in the production and secretion of parathyroid hormone ⁴. Increases in parathyroid hormone stimulate the mobilization of skeletal calcium and the renal excretion of phosphorus ⁴. This enhanced mobilization of skeletal calcium leads towards porotic bone conditions ⁴.

Ordinarily, while vitamin D3 is made naturally via photochemical processes in the skin, both itself and vitamin D2 can be found in various food and pharmaceutical sources as dietary supplements. The principal biological function of vitamin D is the maintenance of normal levels of serum calcium and phosphorus in the bloodstream by enhancing the efficacy of the small intestine to absorb these minerals from the diet ⁴. At the liver, vitamin D3 or D2 is hydroxylated to 25-hydroxyvitamin D and then finally to the primary active metabolite 1,25-dihydroxyvitamin D in the kidney via further hydroxylation ^4,1. This final metabolite binds to endogenous vitamin d receptors, which results in a variety of regulatory roles - including maintaining calcium balance, the regulation of parathyroid hormone, the promotion of the renal reabsorption of calcium, increased intestinal absorption of calcium and phosphorus, and increased calcium and phosphorus mobilization of calcium and phosphorus from bone to plasma to maintain balanced levels of each in bone and the plasma ^4,1.

In particular, calcitriol interacts with vitamin D receptors in the small intestine to enhance the efficiency of intestinal calcium and phosphorous absorption from about 10-15% to 30-40% and 60% increased to 80%, respectively ⁹. Furthermore, calcitriol binds with vitamin D receptors in osteoblasts to stimulate a receptor activator of nuclear factor kB ligand (or RANKL) which subsequently interacts with receptor activator of nuclear factor kB (NFkB) on immature preosteoclasts, causing them to become mature bone-resorbing osteoclasts ⁹. Such mature osteoclasts ultimately function in removing calcium and phosphorus from bone to maintain blood calcium and phosphorus levels ⁹. Moreover, calcitriol also stimulates calcium reabsorption from the glomerular filtrate in the kidneys ⁹.

Additionally, it is believed that when calcitriol binds with nuclear vitamin D receptors, that this bound complex itself binds to retinoic acid X receptor (RXR) to generate a heterodimeric complex that consequently binds to specific nucleotide sequences in the DNA called vitamin D response elements ⁹. When bound, various transcription factors attach to this complex, resulting in either up or down-regulation of the associated gene's activity. It is thought that there may be as much as 200 to 2000 genes that possess vitamin D response elements or that are influenced indirectly to control a multitude of genes across the genome ⁹. It is in this way that cholecalciferol is believed to function in regulating gene transcription associated with cancer risk, autoimmune disorders, and cardiovascular disease linked to vitamin D deficiency ⁹. In fact, there has been some research to suggest calcitriol may also be able to prevent malignancies by inducing cellular maturation and inducing apoptosis and inhibiting angiogenesis, exhibit anti-inflammatory effects by inhibiting foam cell formation and promoting angiogenesis in endothelial colony-forming cells in vitro, inhibit immune reactions by enhancing the transcription of endogenous antibiotics like cathelicidin and regulate the activity and differentiation of CD4+ T cells, amongst a variety of other proposed actions ⁹.

Target	Actions	Organism
AVitamin D3 receptor	agonist	Humans

Absorption

Cholecalciferol is readily absorbed from the small intestine if fat absorption is normal ^12,13,14. Moreover, bile is necessary for absorption as well ^12,13,14.

In particular, recent studies have determined aspects about the absorption of vitamin D, like the fact that a) the 25-hydroxyvitamin D metabolite of cholecalciferol is absorbed to a greater extent than the nonhydroxy form of cholecalciferol, b) the quantity of fat with which cholecalciferol is ingested does not appear to largely affect its bioavailability, and c) age does not apparently effect vitamin D cholecalciferol ⁷.

Volume of distribution

Studies have determined that the mean central volume of distribution of administered cholecalciferol supplementation in a group of 49 kidney transplant patients was approximately 237 L ⁵.

Protein binding

The protein binding documented for cholecalciferol is 50 to 80% ⁸. Specifically, in the plasma, vitamin D3 (from either diet or the skin) is bound to vitamin D-binding protein (DBP) produced in the liver, for transport to the liver. Ultimately, the form of vitamin D3 reaching the liver is 25-hydroxylated, and such 25-hydroxycholecalciferol is bound to DBP (α2-globulin) whilst circulating in the plasma ¹⁴.

Metabolism

Within the liver, cholecalciferol is hydroxylated to calcifediol (25-hydroxycholecalciferol) by the enzyme vitamin D-25-hydroxylase ^12,13,14. At the kidney, calcifediol subsequently serves as a substrate for 1-alpha-hydroxylase, yielding calcitriol (1,25-dihydroxycholecalciferol), the biologically active form of vitamin D3 ^12,13,14.

Hover over products below to view reaction partners

• Cholecalciferol
  • (23S)-23,25-dihdroxy-24-oxovitamine D3 23-(beta-glucuronide)
  • Calcifediol
    • Calcitriol

Route of elimination

It has been observed that administered cholecalciferol and its metabolites are excreted primarily in the bile and feces ⁸.

Half-life

At this time, there have been resources that document the half-life of cholecalciferol as being about 50 days ⁸ while other sources have noted that the half-life of calcitriol (1,25-dihydroxyvitamin D3) is approximately 15 hours while that of calcidiol (25-hydroxyvitamin D3) is about 15 days ¹⁰.

Moreover, it appears that the half-lives of any particular administration of vitamin d can vary due to variations in vitamin d binding protein concentrations and genotype in particular individuals ⁶.

Clearance

Studies have determined that the mean clearance value of administered cholecalciferol supplementation in a group of 49 kidney transplant patients was approximately 2.5 L/day ⁵.

Adverse Effects

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Toxicity

Chronic or acute administration of excessive doses of cholecalciferol may lead to hypervitaminosis D, manifested by hypercalcemia and its sequelae ^12,13,14. Early symptoms of hypercalcemia may include weakness, fatigue, somnolence, headache, anorexia, dry mouth, metallic taste, nausea, vomiting, vertigo, tinnitus, ataxia, and hypotonia ^12,13,14. Later and possibly more serious manifestation include nephrocalcinosis, renal dysfunction, osteoporosis in adults, impaired growth in children, anemia, metastatic calcification, pancreatitis, generalized vascular calcification, and seizures ^12,13,14.

Safety of doses in excess of 400 IU (10mcg) of vitamin D3 daily during pregnancy has not been established ^12,13,14. Maternal hypercalcemia, possibly caused by excessive vitamin D intake during pregnancy, has been associated with hypercalcemia in neonates, which may lead to supravalvular aortic stenosis syndrome, the features of which may include retinopathy, mental or growth retardation, strabismus, and other effects ^12,13,14. Hypercalcemia during pregnancy may also lead to suppression of parathyroid hormone release in the neonate, resulting in hypocalcemia, tetany, and seizures ^12,13,14.

Vitamin D is deficient in maternal milk; therefore, breastfed infants may require supplementation. Use of excessive amounts of Vitamin D in nursing mothers may result in hypercalcemia in infants. Doses of Vitamin D3 in excess of 10 µg daily should not be administered daily to nursing women.

Pathways

Pathway	Category
Lovastatin Action Pathway	Drug action
Cerivastatin Action Pathway	Drug action
Hypercholesterolemia	Disease
Chondrodysplasia Punctata II, X-Linked Dominant (CDPX2)	Disease
Smith-Lemli-Opitz Syndrome (SLOS)	Disease
Mevalonic Aciduria	Disease
Simvastatin Action Pathway	Drug action
Pravastatin Action Pathway	Drug action
Rosuvastatin Action Pathway	Drug action
Zoledronate Action Pathway	Drug action
Pamidronate Action Pathway	Drug action
Fluvastatin Action Pathway	Drug action
Lysosomal Acid Lipase Deficiency (Wolman Disease)	Disease
Cholesteryl Ester Storage Disease	Disease
Steroid Biosynthesis	Metabolic
Ibandronate Action Pathway	Drug action
Alendronate Action Pathway	Drug action
Risedronate Action Pathway	Drug action
Atorvastatin Action Pathway	Drug action
Desmosterolosis	Disease
CHILD Syndrome	Disease
Hyper-IgD Syndrome	Disease
Wolman Disease	Disease

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Not Available

Interactions

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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.

• Approved
• Vet approved
• Nutraceutical
• Illicit
• Withdrawn
• Investigational
• Experimental
• All Drugs

Drug	Interaction
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Abametapir	The serum concentration of Cholecalciferol can be increased when it is combined with Abametapir.
Acebutolol	The metabolism of Acebutolol can be decreased when combined with Cholecalciferol.
Acetaminophen	The metabolism of Acetaminophen can be decreased when combined with Cholecalciferol.
Acetyldigitoxin	The risk or severity of ventricular arrhythmias and Cardiac Arrhythmia can be increased when Cholecalciferol is combined with Acetyldigitoxin.
Alfacalcidol	The risk or severity of adverse effects can be increased when Cholecalciferol is combined with Alfacalcidol.

Food Interactions

No interactions found.

Products

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Product Images

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International/Other Brands

Delta-D / Micro-D / Optimal-D (RV Nutritional, LLC) / Vigantol

Brand Name Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End	Region	Image
D-tabs	Tablet	10000 unit	Oral	Laboratoire Riva Inc.	1992-12-31	Not applicable
Luxa-D	Capsule	25000 unit	Oral	Orimed Pharma Corporation	2015-07-31	Not applicable
Luxa-D	Capsule	2000 unit	Oral	Orimed Pharma Corporation	2015-07-31	Not applicable
Luxa-D	Capsule	5000 unit	Oral	Orimed Pharma Corporation	2015-10-20	Not applicable
Luxa-D	Capsule	10000 unit	Oral	Orimed Pharma Corporation	2015-10-20	Not applicable

Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End	Region	Image
Ag-vitamin D	Capsule	10000 unit	Oral	Angita Pharma Inc.	Not applicable	Not applicable
Ag-vitamin D	Tablet	10000 unit	Oral	Angita Pharma Inc.	2020-12-21	Not applicable
Euro D 10 000	Capsule	10000 unit	Oral	Euro Pharm International Canada Inc	2017-08-16	Not applicable
Euro-D 10000 Iu	Capsule	10000 unit	Oral	Euro Pharm International Canada Inc	2011-08-29	Not applicable
Euro-D 5000 Iu	Capsule	5000 unit	Oral	Euro Pharm International Canada Inc	Not applicable	Not applicable

Over the Counter Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End	Region	Image
BLACKMORES VITAMIN D3 1000IU CAPSULES	Capsule	1000 IU	Oral	BLACKMORES (MALAYSIA) SDN. BHD.	2020-09-08	Not applicable
D Caps 400 Units	Capsule	400 unit	Oral	Twin Laboratories Inc.	1995-12-31	1999-11-10
D Vi Sol Infants Drops 400unit/0.6ml	Solution / drops	400 unit / .6 mL	Oral	Mead Johnson Nutritionals	1985-12-31	1998-09-28
Growth Supportpatch, Hautuki	Patch	0.2 mg/100g	Topical	CUSTICS	2023-05-01	Not applicable
Hautuki	Patch	0.2 mg/100g	Topical	CUSTICS	2023-05-01	Not applicable

Mixture Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End	Region	Image
24 Multivitamins + Minerals	Cholecalciferol (400 unit) + Ascorbic acid (150 mg) + Beta carotene (10000 unit) + Biotin (25 mcg) + Calcium (130 mg) + Choline bitartrate (25 mg) + Chromium (20 mcg) + Copper (1 mg) + Cyanocobalamin (25 mcg) + Ferrous fumarate (15 mg) + Folic acid (.8 mg) + Inositol (25 mg) + Magnesium (65 mg) + Manganese (2 mg) + Molybdenum (20 mcg) + Niacin (25 mg) + Calcium pantothenate (25 mg) + Potassium (15 mg) + Potassium Iodide (.1 mg) + Pyridoxine hydrochloride (25 mg) + Racemethionine (25 mg) + Riboflavin (25 mg) + Selenium (20 mcg) + Thiamine hydrochloride (25 mg) + Vanadium (20 mcg) + Vitamin A palmitate (5000 unit) + Vitamin E (50 unit) + Zinc (10 mg)	Tablet	Oral	Stanley Pharmaceuticals, A Division Of Vita Health Products Inc.	1997-04-30	2002-07-31
50 Plus Multiple Vitamins & Minerals	Cholecalciferol (400 unit) + Ascorbic acid (90 mg) + Biotin (45 mcg) + Calcium (200 mg) + Chromium (10 mcg) + Copper (2 mg) + Cyanocobalamin (25 mcg) + Folic acid (0.4 mg) + Magnesium (100 mg) + Manganese (5 mg) + Molybdenum (25 mcg) + Nicotinamide (40 mg) + Pantothenic acid (10 mg) + Potassium Iodide (0.15 mg) + Pyridoxine hydrochloride (3 mg) + Riboflavin (3.2 mg) + Selenium (25 mcg) + Thiamine mononitrate (2.25 mg) + Vanadium (10 mcg) + Vitamin A palmitate (6000 unit) + Zinc (15 mg)	Tablet	Oral	Gfr Pharma Ltd.	2002-10-20	2004-06-15
A + D Ointment	Cholecalciferol (500 unit / g) + Vitamin A palmitate (2000 unit / g)	Ointment	Topical	National Care Products Ltd.	1993-12-31	2002-10-10
A.R.T.H. Away Formula	Cholecalciferol (45 unit) + Calcium (24 mg) + Copper (0.232 mg) + Folic acid (0.025 mg) + Manganese (0.58 mg) + Pyridoxine hydrochloride (0.5 mg) + Selenium (1.54 mcg) + Zinc (0.63 mg)	Capsule	Oral	Abundance Naturally Ltd	1999-02-01	2006-06-16
Aces Tab	Cholecalciferol (200 unit) + Calcium ascorbate (350 mg) + Chromium (25 mcg) + Selenium (100 mcg) + Vitamin A (5000 unit) + Vitamin E (200 unit) + Zinc (25 mg)	Tablet	Oral	Nu Life Nutrition Ltd.	1987-12-31	2005-03-15

Unapproved/Other Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End	Region	Image
Abavite	Cholecalciferol (0.025 mg/1) + Ascorbic acid (60 mg/1) + DL-alpha tocopheryl acetate (13.5 mg/1) + Ferrous sulfate (30 mg/1) + Folic acid (1 mg/1) + Magnesium oxide (25 mg/1) + Mecobalamin (0.5 mg/1) + Niacin (15 mg/1) + Calcium pantothenate (5 mg/1) + Potassium Iodide (0.25 mg/1) + Riboflavin (1.8 mg/1) + Thiamine mononitrate (1.6 mg/1) + Vitamin A palmitate (0.33 mg/1) + Zinc oxide (15 mg/1)	Tablet	Oral	ABACOS HEALTH	2021-03-31	Not applicable
Active FE	Cholecalciferol (400 [iU]/1) + Ascorbic acid (160 mg/1) + Beta carotene (2100 [iU]/1) + Cupric oxide (1 mg/1) + Cyanocobalamin (30 ug/1) + DL-alpha tocopheryl acetate (40 [iU]/1) + Folic acid (1250 ug/1) + Iron (75 mg/1) + Magnesium oxide (30 mg/1) + Nicotinamide (20 mg/1) + Pyridoxine hydrochloride (20 mg/1) + Riboflavin (4 mg/1) + Thiamine hydrochloride (4 mg/1) + Zinc oxide (20 mg/1)	Tablet	Oral	Gm Pharmaceuticals	2013-11-11	Not applicable
Active OB	Cholecalciferol (400 [iU]/1) + Ascorbic acid (100 mg/1) + Cupric sulfate pentahydrate (2 mg/1) + Cyanocobalamin (30 ug/1) + D-alpha-Tocopherol acetate (30 [iU]/1) + Doconexent (320 mg/1) + Folic acid (1 mg/1) + Iron (20 mg/1) + Pyridoxine hydrochloride (20 mg/1) + Riboflavin (4 mg/1) + Thiamine mononitrate (2 mg/1) + Zinc oxide (30 mg/1)	Capsule, liquid filled	Oral	Gm Pharmaceuticals	2013-10-28	2017-03-31
Animi-3	Cholecalciferol (1000 [iU]/1) + Cyanocobalamin (500 ug/1) + Doconexent (250 mg/1) + Folic acid (1 mg/1) + Icosapent (35 mg/1) + Omega-3 fatty acids (500 mg/1) + Pyridoxine hydrochloride (12.5 mg/1) + Soy sterol (200 mg/1)	Capsule	Oral	Pbm Pharmaceuticals Inc.	2011-06-01	Not applicable
Animi-3 with Vitamin D	Cholecalciferol (1000 [iU]/1) + Cyanocobalamin (500 ug/1) + Doconexent (250 mg/1) + Folic acid (1 mg/1) + Icosapent (35 mg/1) + Omega-3 fatty acids (500 mg/1) + Pyridoxine hydrochloride (12.5 mg/1) + Soy sterol (200 mg/1)	Capsule	Oral	Pbm Pharmaceuticals Inc.	2011-06-01	Not applicable

Categories

ATC Codes

M05BB09 — Ibandronic acid and colecalciferol

• M05BB — Bisphosphonates, combinations
• M05B — DRUGS AFFECTING BONE STRUCTURE AND MINERALIZATION
• M05 — DRUGS FOR TREATMENT OF BONE DISEASES
• M — MUSCULO-SKELETAL SYSTEM

M05BX53 — Strontium ranelate and colecalciferol

• M05BX — Other drugs affecting bone structure and mineralization
• M05B — DRUGS AFFECTING BONE STRUCTURE AND MINERALIZATION
• M05 — DRUGS FOR TREATMENT OF BONE DISEASES
• M — MUSCULO-SKELETAL SYSTEM

M05BB07 — Risedronic acid and colecalciferol

• M05BB — Bisphosphonates, combinations
• M05B — DRUGS AFFECTING BONE STRUCTURE AND MINERALIZATION
• M05 — DRUGS FOR TREATMENT OF BONE DISEASES
• M — MUSCULO-SKELETAL SYSTEM

M05BB08 — Zoledronic acid, calcium and colecalciferol, sequential

• M05BB — Bisphosphonates, combinations
• M05B — DRUGS AFFECTING BONE STRUCTURE AND MINERALIZATION
• M05 — DRUGS FOR TREATMENT OF BONE DISEASES
• M — MUSCULO-SKELETAL SYSTEM

A11CC55 — Colecalciferol, combinations

• A11CC — Vitamin D and analogues
• A11C — VITAMIN A AND D, INCL. COMBINATIONS OF THE TWO
• A11 — VITAMINS
• A — ALIMENTARY TRACT AND METABOLISM

M05BB05 — Alendronic acid, calcium and colecalciferol, sequential

• M05BB — Bisphosphonates, combinations
• M05B — DRUGS AFFECTING BONE STRUCTURE AND MINERALIZATION
• M05 — DRUGS FOR TREATMENT OF BONE DISEASES
• M — MUSCULO-SKELETAL SYSTEM

A11CC05 — Colecalciferol

• A11CC — Vitamin D and analogues
• A11C — VITAMIN A AND D, INCL. COMBINATIONS OF THE TWO
• A11 — VITAMINS
• A — ALIMENTARY TRACT AND METABOLISM

M05BB03 — Alendronic acid and colecalciferol

• M05BB — Bisphosphonates, combinations
• M05B — DRUGS AFFECTING BONE STRUCTURE AND MINERALIZATION
• M05 — DRUGS FOR TREATMENT OF BONE DISEASES
• M — MUSCULO-SKELETAL SYSTEM

M05BB04 — Risedronic acid, calcium and colecalciferol, sequential

• M05BB — Bisphosphonates, combinations
• M05B — DRUGS AFFECTING BONE STRUCTURE AND MINERALIZATION
• M05 — DRUGS FOR TREATMENT OF BONE DISEASES
• M — MUSCULO-SKELETAL SYSTEM

Drug Categories

• Alimentary Tract and Metabolism
• Bone Density Conservation Agents
• Calcium-Regulating Hormones and Agents
• Cholecalciferol, antagonists & inhibitors
• Cholestanes
• Cholestenes
• Cytochrome P-450 CYP2C8 Inhibitors
• Cytochrome P-450 CYP2C8 Inhibitors (strength unknown)
• Cytochrome P-450 CYP2D6 Inhibitors
• Cytochrome P-450 CYP2D6 Inhibitors (moderate)
• Cytochrome P-450 CYP3A Substrates
• Cytochrome P-450 CYP3A4 Substrates
• Cytochrome P-450 Enzyme Inhibitors
• Cytochrome P-450 Substrates
• Diet, Food, and Nutrition
• Drugs Affecting Bone Structure and Mineralization
• Drugs for Treatment of Bone Diseases
• Food
• Fused-Ring Compounds
• Growth Substances
• Lipids
• Membrane Lipids
• Micronutrients
• Musculo-Skeletal System
• Physiological Phenomena
• Secosteroids
• Steroids
• Sterols
• Vitamin D and Analogues
• Vitamins
• Vitamins (Fat Soluble)

Chemical TaxonomyProvided by Classyfire

Description

This compound belongs to the class of organic compounds known as vitamin d and derivatives. These are compounds containing a secosteroid backbone, usually secoergostane or secocholestane.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Vitamin D and derivatives

Direct Parent

Vitamin D and derivatives

Alternative Parents

Triterpenoids / Secondary alcohols / Cyclic alcohols and derivatives / Hydrocarbon derivatives

Substituents

Alcohol / Aliphatic homopolycyclic compound / Cyclic alcohol / Hydrocarbon derivative / Organic oxygen compound / Organooxygen compound / Secondary alcohol / Triterpenoid

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

secondary alcohol, steroid hormone, seco-cholestane, hydroxy seco-steroid, D3 vitamins (CHEBI:28940) / Vitamin D3 and derivatives, Fat-soluble vitamins (C05443) / Vitamin D3 and derivatives (LMST03020000)

Affected organisms

• Humans and other mammals

Chemical Identifiers

UNII

1C6V77QF41

CAS number

67-97-0

InChI Key

QYSXJUFSXHHAJI-YRZJJWOYSA-N

InChI

InChI=1S/C27H44O/c1-19(2)8-6-9-21(4)25-15-16-26-22(10-7-17-27(25,26)5)12-13-23-18-24(28)14-11-20(23)3/h12-13,19,21,24-26,28H,3,6-11,14-18H2,1-2,4-5H3/b22-12+,23-13-/t21-,24+,25-,26+,27-/m1/s1

IUPAC Name

(1S,3Z)-3-{2-[(1R,3aS,4E,7aR)-7a-methyl-1-[(2R)-6-methylheptan-2-yl]-octahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexan-1-ol

SMILES

CC(C)CCC[C@@H](C)[C@@]1([H])CC[C@@]2([H])\C(CCC[C@]12C)=C\C=C1\C[C@@H](O)CCC1=C

References

Synthesis Reference

Jean Jolly, Primo Rizzi, Jean Taillardat, "1.alpha.,25.alpha.-Dihydroxy-cholecalciferol and methods for the production thereof." U.S. Patent US4435325, issued May, 1977.

US4435325

General References

1. Armas LA, Hollis BW, Heaney RP: Vitamin D2 is much less effective than vitamin D3 in humans. J Clin Endocrinol Metab. 2004 Nov;89(11):5387-91. [Article]
2. Jean G, Souberbielle JC, Chazot C: Vitamin D in Chronic Kidney Disease and Dialysis Patients. Nutrients. 2017 Mar 25;9(4). pii: nu9040328. doi: 10.3390/nu9040328. [Article]
3. Heaney RP: Alendronate plus cholecalciferol for the treatment of osteoporosis. Womens Health (Lond). 2006 Jan;2(1):23-7. doi: 10.2217/17455057.2.1.23. [Article]
4. DeLuca HF: Overview of general physiologic features and functions of vitamin D. Am J Clin Nutr. 2004 Dec;80(6 Suppl):1689S-96S. [Article]
5. Benaboud S, Urien S, Thervet E, Prie D, Legendre C, Souberbielle JC, Hirt D, Friedlander G, Treluyer JM, Courbebaisse M: Determination of optimal cholecalciferol treatment in renal transplant recipients using a population pharmacokinetic approach. Eur J Clin Pharmacol. 2013 Mar;69(3):499-506. doi: 10.1007/s00228-012-1378-3. Epub 2012 Aug 31. [Article]
6. Jones KS, Assar S, Harnpanich D, Bouillon R, Lambrechts D, Prentice A, Schoenmakers I: 25(OH)D2 half-life is shorter than 25(OH)D3 half-life and is influenced by DBP concentration and genotype. J Clin Endocrinol Metab. 2014 Sep;99(9):3373-81. doi: 10.1210/jc.2014-1714. Epub 2014 Jun 2. [Article]
7. Borel P, Caillaud D, Cano NJ: Vitamin D bioavailability: state of the art. Crit Rev Food Sci Nutr. 2015;55(9):1193-205. doi: 10.1080/10408398.2012.688897. [Article]
8. Caroline Ashley, Aileen Dunleavy (2018). The Renal Drug Handbook: The Ultimate Prescribing Guide for Renal Practitioners, 5th Edition (5th ed.). CRC Press. [ISBN:0429863632]
9. Cholecalciferol (Vitamin D3) – Pharmacological Properties, Therapeutic Utility and Potential New Fields of Clinical Application by Yulian Voynikov, Georgi Momekov, Plamen Peikov [Link]
10. Vitamin D Supplementation: An Update [Link]
11. NIH Vitamin D Fact Sheet for Health Professionals [Link]
12. Cholecalciferol Canadian Prescribing Information [File]
13. Decalcitrol (coated cholecalciferol tablet) US FDA Monograph [File]
14. CLH Report for Cholecalciferol [File]
15. Alendronate sodium and cholecalciferol Canadian Product Monograph [File]

External Links

Human Metabolome Database

HMDB0000876

KEGG Drug

D00188

KEGG Compound

C05443

PubChem Compound

5280795

PubChem Substance

46506365

ChemSpider

4444353

BindingDB

50030475

RxNav

1244014

ChEBI

28940

ChEMBL

CHEMBL1042

ZINC

ZINC000004474460

Therapeutic Targets Database

DAP001273

PharmGKB

PA164748138

PDBe Ligand

VD3

Drugs.com

Drugs.com Drug Page

PDRhealth

PDRhealth Drug Page

Wikipedia

Cholecalciferol

MSDS

Download (123 KB)

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">

Phase	Status	Purpose	Conditions	Count
4	Active Not Recruiting	Prevention	Coronavirus Disease 2019 (COVID‑19) / Deficiency, Vitamin D / Viral Respiratory Tract Infection	1
4	Active Not Recruiting	Prevention	Food Allergy	1
4	Completed	Basic Science	25-Hydroxyvitamin D Concentration / Deficiency, Vitamin D	1
4	Completed	Basic Science	Deficiency, Vitamin D	2
4	Completed	Basic Science	Premature Births	1

Pharmacoeconomics

Manufacturers

Not Available

Packagers

• Chain Drug
• CVS Pharmacy
• Freeda Vitamins
• Major Pharmaceuticals
• Mason Distributors
• Merck & Co.
• MSD Frosst Iberica SA
• Pharmavite
• Physicians Total Care Inc.
• Professional Co.
• Spectrum Pharmaceuticals

Dosage Forms

Form	Route	Strength
Ointment	Topical
Granule, effervescent; kit; tablet	Oral
Injection, solution	Intramuscular; Oral
Tablet, chewable	Oral	1000 [iU]/1
Capsule	Oral
Solution	Oral	50000 U.I./5ML
Solution / drops	Oral	10000 UI/1ML
Tablet, film coated	Oral	30000 U.I.
Cream	Topical
Injection, solution	Parenteral
Solution	Intravenous	1.914 mg
Bar, chewable	Oral
Solution	Oral	25000 UI
Solution	Oral	50000 UI
Powder, for solution	Oral
Capsule	Oral	1000 IU
Tablet, effervescent	Oral	2500 mg
Granule	Oral
Tablet, effervescent	Oral
Powder, for suspension	Oral
Tablet	Oral	600.000 mg
Tablet, coated	Oral	1500 mg
Injection, powder, for solution	Intramuscular; Intravenous
Injection, powder, for solution	Parenteral
Injection, solution	Intramuscular; Intravenous
Injection, powder, for solution	Intravenous
Kit; tablet; tablet, film coated	Oral
Capsule	Oral
Solution / drops	Oral
Capsule	Oral	20000 IE
Capsule	Oral	10000 UI
Capsule	Oral	100000 UI
Capsule	Oral	25000 UI
Capsule	Oral	50000 UI
Solution	Oral	25000 UI/2.5ML
Solution / drops	Oral	10000 U.I./ML
Solution	Oral	25000 IU/2.5ml
Capsule	Oral	10000 I.U.
Capsule	Oral	25000 I.U.
Solution / drops	Oral	10000 UI/ML
Solution	Oral	50000 UI/2.5ML
Capsule	Oral	1000 UI
Capsule	Oral	20000 UI
Capsule	Oral	400 unit
Tablet
Solution / drops	Oral	400 unit / .6 mL
Capsule	Oral	1.25 mg/1
Solution	Oral	300000 IU
Solution / drops	Oral	50000 IU/15ml
Capsule	Oral	2000 i.u.
Capsule	Oral	5000 i.u.
Capsule	Oral	50000 i.u.
Solution / drops	Oral	150000 i.u./10ml
Solution / drops	Oral	15000 i.u./ml
Tablet	Oral	10000 unit
Solution / drops	Oral	150000 iu/10ml
Solution	Oral	400 [iU]/1mL
Capsule, liquid filled	Oral	100000 IU
Tablet, coated	Oral	50000 [iU]/1
Capsule	Oral	10000 [iU]/1
Capsule	Oral	25000 [iU]/1
Capsule	Oral	50000 [iU]/1
Capsule, liquid filled	Oral	1000 IU
Capsule, liquid filled	Oral	7000 IU
Capsule, liquid filled	Oral	200000000 IU
Tablet	Oral	1000 IE
Tablet	Oral	400 IE
Tablet	Oral	500 IE
Tablet, film coated	Oral	2000 iu
Solution / drops	Oral	200000 i.u./10ml
Tablet	Oral	400 IU/1
Solution	Intramuscular	300000 IU/ml
Solution	Intramuscular
Syrup	Oral
Capsule	Oral	2000 U.I.
Capsule	Oral	6000 U.I.
Injection, solution		100000 U.I./ml
Injection, solution		300000 U.I./ml
Injection, solution	Intramuscular	100000 UI/ML
Injection, solution	Intramuscular	100000 U.I./ml
Injection, solution	Intramuscular	300000 UI/ML
Solution	Oral	100000 U.I.
Solution	Oral	25000 U.I./2.5ML
Solution	Oral	50000 U.I./2.5ML
Solution / drops	Oral	10000 UI
Film	Oral	50000 U.I.
Powder, for solution	Intravenous
Capsule	Oral	10000 unit
Capsule	Oral	5000 unit
Capsule	Oral	50000 unit
Capsule, liquid filled	Oral	1 mg
Capsule, liquid filled	Oral	5000 IU
Capsule, liquid filled; kit; tablet	Oral
Wafer	Oral	100 unit / waf
Tablet	Oral	70 mg
Gel	Oral
Solution / drops	Oral	14400 IE
Solution / drops	Oral	28800 IE
Capsule, delayed release	Oral
Patch	Topical	0.2 mg/100g
Tablet, chewable	Oral
Solution	Oral	25000 IU
Tablet, chewable	Oral	5000 IU
Tablet, coated	Oral
Powder	Oral
Capsule	Oral	2000 unit
Capsule	Oral	25000 unit
Granule, effervescent	Oral
Capsule, coated	Oral
Suspension	Oral
Tablet, film coated	Oral	0.125 MG
Tablet	Oral
Solution	Oral	50000 U.I.
Solution	Intramuscular; Oral
Solution	Intramuscular; Oral	7.5 mg
Solution	Oral	50000 IU/15ml
Solution	Intravenous
Solution	Oral
Tablet	Oral
Solution	Parenteral
Capsule	Oral	50 mg
Tablet, coated	Oral	1000 iu
Tablet, orally disintegrating	Oral
Capsule, gelatin coated; kit; tablet	Oral
Capsule	Oral	1000 U.I.
Capsule	Oral	10000 U.I.
Capsule	Oral	20000 U.I.
Capsule	Oral	50000 U.I.
Gum, chewing	Oral
Solution	Oral	5600 IU
Solution	Oral	0.00014 g
Solution	Oral	100000 IU
Tablet, coated	Oral	7000 IU
Capsule, liquid filled; kit; tablet, film coated	Oral
Tablet, film coated	Oral	1000 I.E.
Tablet, film coated	Oral	30000 I.E.
Tablet, film coated	Oral	7000 I.E.
Tablet, film coated	Oral	800 I.E.
Solution / drops	Oral	50000 i.u./15ml
Liquid	Oral	50000 [iU]/3mL
Capsule	Oral	125 MCG
Capsule	Oral	7 mg
Powder
Injection, solution; kit	Intravenous
Injection, solution	Intravenous
Suspension / drops	Oral
Solution / drops	Oral
Capsule, liquid filled; kit; tablet, coated	Oral
Capsule, liquid filled	Oral
Tablet, film coated	Oral
Capsule, gelatin coated	Oral
Pill	Oral
Tablet, chewable	Buccal
Tablet, film coated	Oral
Tablet, chewable	Oral
Wafer	Oral
Syrup
Capsule; kit; tablet, coated	Oral
Capsule	Oral	20000 i.u.
Kit; tablet; tablet, coated	Oral
Powder, for solution	Intramuscular; Intravenous
Tablet, film coated	Oral	10000 I.E.
Tablet, film coated	Oral	20000 I.E.
Tablet, film coated	Oral	5000 I.E.
Solution	Oral	25000 U.I.
Solution	Oral
Liquid	Oral
Capsule; kit; tablet, film coated	Oral
Capsule; kit; tablet	Oral
Injection, powder, lyophilized, for solution	Intramuscular; Intravenous
Capsule	Oral	125 mg/1
Tablet, chewable	Oral	1000 IU
Strip	Oral
Tablet	Oral	1000 unit
Tablet	Oral	1000 IU
Tablet	Oral	400 unit
Capsule	Oral	7000 iu
Tablet	Oral	400 unit / tab
Tablet	Oral	500 IU
Capsule	Oral	20000 unit
Capsule	Oral	40000 unit
Capsule, liquid filled	Oral	50 ug/1
Solution	Oral	25000 unit / amp
Solution	Oral	60000 [iU]/1
Capsule	Oral	100000 unit
Solution	Oral	2000 IU
Capsule, liquid filled	Oral	2000 IU
Kit	Oral
Solution	Oral	25000 I.E.
Solution	Oral	50000 I.E.
Capsule	Oral	25000 U.I.
Tablet, coated	Oral
Capsule	Oral	100000 U.I.
Injection, solution	Intramuscular	300000 U.I./ml
Solution	Oral	100000 U.I./2.5ml
Solution / drops	Oral	25 ug/0.04mL
Solution / drops	Oral	10 ug/0.04mL
Solution / drops	Oral	15 ug/0.04mL
Tablet, film coated	Oral	10 mg
Tablet, coated	Oral	2000 iu
Tablet, film coated	Oral	1000 iu
Tablet, film coated

Prices

Unit description	Cost	Unit
Cholecalciferol crystals	104.3USD	g
Vitamin d3 2400 unit/ml liquid	0.8USD	ml
Vitamin d3 2000 unit spray	0.44USD	ml
Vitamin d3 3000 unit tablet	0.11USD	tablet
Vitamin d-3 2000 unit tablet	0.07USD	tablet
CVS Pharmacy vitamin d 1000 unit tablet	0.04USD	tablet
Delta d3 400 unit tablet	0.04USD	each
Vitamin d 1000 unit tablet	0.03USD	tablet
Pv vitamin d 2000 unit tablet	0.02USD	tablet
Pv vitamin d 5000 unit tablet	0.02USD	tablet
Vitamin d 400 unit tablet	0.02USD	tablet

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

Patents

Patent Number	Pediatric Extension	Approved	Expires (estimated)	Region
US5994329	Yes	1999-11-30	2019-01-17

Properties

State

Solid

Experimental Properties

Property	Value	Source
melting point (°C)	84.5 °C	PhysProp
water solubility	Insoluble	Not Available
logP	7.5	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.00038 mg/mL	ALOGPS
logP	7.98	ALOGPS
logP	7.13	Chemaxon
logS	-6	ALOGPS
pKa (Strongest Acidic)	18.38	Chemaxon
pKa (Strongest Basic)	-1.3	Chemaxon
Physiological Charge	0	Chemaxon
Hydrogen Acceptor Count	1	Chemaxon
Hydrogen Donor Count	1	Chemaxon
Polar Surface Area	20.23 Å2	Chemaxon
Rotatable Bond Count	6	Chemaxon
Refractivity	123.22 m3·mol-1	Chemaxon
Polarizability	49.63 Å3	Chemaxon
Number of Rings	3	Chemaxon
Bioavailability	1	Chemaxon
Rule of Five	No	Chemaxon
Ghose Filter	No	Chemaxon
Veber's Rule	Yes	Chemaxon
MDDR-like Rule	Yes	Chemaxon

Predicted ADMET Features

Property	Value	Probability
Human Intestinal Absorption	+	1.0
Blood Brain Barrier	+	0.959
Caco-2 permeable	+	0.8342
P-glycoprotein substrate	Substrate	0.6706
P-glycoprotein inhibitor I	Inhibitor	0.7603
P-glycoprotein inhibitor II	Non-inhibitor	0.5346
Renal organic cation transporter	Non-inhibitor	0.7818
CYP450 2C9 substrate	Non-substrate	0.8384
CYP450 2D6 substrate	Non-substrate	0.9116
CYP450 3A4 substrate	Substrate	0.7302
CYP450 1A2 substrate	Non-inhibitor	0.9256
CYP450 2C9 inhibitor	Non-inhibitor	0.9071
CYP450 2D6 inhibitor	Non-inhibitor	0.9551
CYP450 2C19 inhibitor	Non-inhibitor	0.9026
CYP450 3A4 inhibitor	Non-inhibitor	0.7881
CYP450 inhibitory promiscuity	Low CYP Inhibitory Promiscuity	0.7093
Ames test	Non AMES toxic	0.9132
Carcinogenicity	Non-carcinogens	0.921
Biodegradation	Not ready biodegradable	0.9878
Rat acute toxicity	3.9310 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.773
hERG inhibition (predictor II)	Non-inhibitor	0.7589

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

Spectra

Mass Spec (NIST)

Download (11.1 KB)

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	splash10-0aou-3029000000-1950c74de34369a70400
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0fri-0149000000-7ae3301ba6364f84969d
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	splash10-001i-0009000000-1562a1d7477455ae97ca
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	splash10-001i-0009000000-23bc946044bc596f809b
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0a70-4529000000-06d2a00a83ad66a96bff
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	splash10-03fr-0319000000-071ea8bb1c8c6bd58dc2
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	splash10-01bi-4946000000-bd5ae21f84bf32da16b6
Predicted 1H NMR Spectrum	1D NMR	Not Applicable
Predicted 13C NMR Spectrum	1D NMR	Not Applicable

Chromatographic Properties

Collision Cross Sections (CCS)

Adduct	CCS Value (Å2)	Source type	Source
[M-H]-	209.0081397	predicted	DarkChem Lite v0.1.0
[M-H]-	212.5105397	predicted	DarkChem Lite v0.1.0
[M-H]-	212.8281397	predicted	DarkChem Lite v0.1.0
[M-H]-	208.23943	predicted	DeepCCS 1.0 (2019)
[M+H]+	208.3363397	predicted	DarkChem Lite v0.1.0
[M+H]+	212.3635397	predicted	DarkChem Lite v0.1.0
[M+H]+	213.6981397	predicted	DarkChem Lite v0.1.0
[M+H]+	210.21617	predicted	DeepCCS 1.0 (2019)
[M+Na]+	209.0911397	predicted	DarkChem Lite v0.1.0
[M+Na]+	212.6965397	predicted	DarkChem Lite v0.1.0
[M+Na]+	212.7794397	predicted	DarkChem Lite v0.1.0
[M+Na]+	216.12914	predicted	DeepCCS 1.0 (2019)

Targets

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Details1. Vitamin D3 receptor

Kind

Protein

Organism

Humans

Pharmacological action

Yes

Actions

Agonist

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

1. Reinhart GA: Vitamin D analogs: novel therapeutic agents for cardiovascular disease? Curr Opin Investig Drugs. 2004 Sep;5(9):947-51. [Article]
2. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
3. Fujishima T, Tsuji G, Tanaka C, Harayama H: Novel vitamin D receptor ligands having a carboxyl group as an anchor to arginine 274 in the ligand-binding domain. J Steroid Biochem Mol Biol. 2010 Jul;121(1-2):60-2. doi: 10.1016/j.jsbmb.2010.04.020. Epub 2010 May 6. [Article]

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Drug created at June 13, 2005 13:24 / Updated at February 20, 2024 23:55