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Identification
NameCholecalciferol
Accession NumberDB00169  (APRD00506, NUTR00008)
Typesmall molecule
Groupsapproved, nutraceutical
Description

Derivative of 7-dehydroxycholesterol formed by ultraviolet rays breaking of the C9-C10 bond. It differs from ergocalciferol in having a single bond between C22 and C23 and lacking a methyl group at C24. [PubChem]

Structure
Thumb
Synonyms
SynonymLanguageCode
(+)-vitamin D3Not AvailableNot Available
(1S,3Z)-3-[(2e)-2-[(1R,3AR,7as)-7a-methyl-1-[(2R)-6-methylheptan-2-yl]-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidene-cyclohexan-1-olNot AvailableNot Available
(3beta,5Z,7e)-9,10-Secocholesta-5,7,10(19)-trien-3-olNot AvailableNot Available
(5Z,7e)-(3S)-9,10-Secocholesta-5,7,10(19)-trien-3-olNot AvailableNot Available
Activated 7-dehydrocholesterolNot AvailableNot Available
calciolNot AvailableNot Available
CCNot AvailableNot Available
CholecalciferolNot AvailableNot Available
ColecalciferolNot AvailableNot Available
delta-DNot AvailableNot Available
Oleovitamin D3Not AvailableNot Available
Vitamin D3Not AvailableNot Available
SaltsNot Available
Brand names
NameCompany
Micro-DNot Available
Optimal-DRV Nutritional, LLC
VigantolNot Available
Brand mixtures
Brand NameIngredients
SpectrumBeta-Carotene (Provitamin a) + Biotin + Calcium + Copper + D-Pantothenic Acid + Folic Acid + Iodine + Iron + Magnesium + Nicotinamide + Phosphorus + Vitamin a (Vitamin a Acetate) + Vitamin B1 (Thiamine Mononitrate) + Vitamin B12 (Cyanocobalamin) + Vitamin B2 (Riboflavin) + Vitamin B6 (Pyridoxine Hydrochloride) + Vitamin C (Ascorbic Acid) + Vitamin D3 (Cholecalciferol) + Vitamin E (Dl-Alpha Tocopheryl Acetate)
Spectrum ForteBeta-Carotene (Provitamin a) + Biotin + Calcium + Chlorine (Potassium Chloride) + Chromium + Copper + D-Pantothenic Acid + Folic Acid + Iodine + Iron + Magnesium + Manganese + Molybdenum (Sodium Molybdate) + Nickel + Nicotinamide + Phosphorus + Potassium + Selenium + Silicon + Tin (Stannous Chloride) + Vanadium + Vitamin a (Vitamin a Acetate) + Vitamin B1 (Thiamine Mononitrate) + Vitamin B12 (Cyanocobalamin) + Vitamin B2 (Riboflavin) + Vitamin B6 (Pyridoxine Hydrochloride) + Vitamin C (Ascorbic Acid) + Vitamin D3 (Cholecalciferol) + Vitamin E (Dl-Alpha Tocopheryl Acetate) + Zinc
Spectrum GoldBeta-Carotene (Provitamin a) + Biotin + Calcium + Chlorine (Potassium Chloride) + Chromium + Copper + D-Pantothenic Acid + Folic Acid + Iodine + Iron + Magnesium + Manganese + Molybdenum (Sodium Molybdate) + Nickel + Nicotinamide + Phosphorus + Potassium + Selenium + Silicon + Tin (Stannous Chloride) + Vanadium + Vitamin a (Vitamin a Acetate) + Vitamin B1 (Thiamine Mononitrate) + Vitamin B12 (Cyanocobalamin) + Vitamin B2 (Riboflavin) + Vitamin B6 (Pyridoxine Hydrochloride) + Vitamin C (Ascorbic Acid) + Vitamin D3 (Cholecalciferol) + Vitamin E (Dl-Alpha Tocopheryl Acetate) + Zinc
Watkin's Super MultiBeta-Carotene (Provitamin a) + Biotin + Calcium (Calcium Phosphate (Dibasic), Calcium Citrate) + Chromium + Copper (Copper Gluconate) + D-Pantothenic Acid + Folic Acid + Magnesium + Manganese + Molybdenum (Sodium Molybdate) + Nicotinic Acid + Phosphorus + Selenium (Selenium Hvp Chelate) + Vanadium (Vanadium Hvp Chelate) + Vitamin B1 (Thiamine Hydrochloride) + Vitamin B12 + Vitamin B2 (Riboflavin, Riboflavin-5-Phosphate) + Vitamin B6 (Pyridoxine Hydrochloride) + Vitamin C + Vitamin D (Cholecalciferol) + Vitamin E (Dl-Alpha Tocopheryl Acetate) + Zinc
Watkins J.R.Beta-Carotene (Provitamin a) + Biotin + Chromium + Copper (Copper Sulfate) + D-Pantothenic Acid + Folic Acid + Iodine + Iron + Manganese + Molybdenum (Sodium Molybdate) + Nicotinamide + Selenium (Selenium Hvp Chelate) + Silicon (Silicon Dioxide) + Vitamin B1 (Thiamine Mononitrate) + Vitamin B12 (Cyanocobalamin) + Vitamin B2 + Vitamin B6 (Pyridoxine Hydrochloride) + Vitamin C + Vitamin D (Cholecalciferol) + Vitamin E (Dl-Alpha Tocopheryl Acetate, D-Alpha Tocopheryl Acid Succinate) + Zinc (Zinc Hvp Chelate, Zinc Citrate)
Categories
CAS number67-97-0
WeightAverage: 384.6377
Monoisotopic: 384.33921603
Chemical FormulaC27H44O
InChI KeyQYSXJUFSXHHAJI-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
Mass Specshow(11.1 KB)
Taxonomy
KingdomOrganic Compounds
SuperclassLipids
ClassSteroids and Steroid Derivatives
SubclassVitamin D and Derivatives
Direct parentVitamin D and Derivatives
Alternative parentsSesterterpenes; Cyclohexanols; Cyclic Alcohols and Derivatives; Polyamines
Substituentscyclohexanol; cyclic alcohol; secondary alcohol; polyamine; alcohol
Classification descriptionThis compound belongs to the vitamin d and derivatives. These are compounds containing a secosteroid backbone, usually secoergostane or secocholestane.
Pharmacology
IndicationFor the treatment of vitamin D deficiency or insufficiency, refractory rickets (vitamin D resistant rickets), familial hypophosphatemia and hypoparathyroidism, and in the management of hypocalcemia and renal osteodystrophy in patients with chronic renal failure undergoing dialysis. Also used in conjunction with calcium in the management and prevention of primary or corticosteroid-induced osteoporosis.
PharmacodynamicsCholecalciferol (vitamin D3) is a steroid hormone that has long been known for its important role in regulating body levels of calcium and phosphorus, in mineralization of bone, and for the assimilation of Vitamin A. The classical manifestations of vitamin D deficiency is rickets, which is seen in children and results in bony deformaties including bowed long bones. Deficiency in adults leads to the disease osteomalacia. Both rickets and osteomalacia reflect impaired mineralization of newly synthesized bone matrix, and usually result from a combination of inadequate exposure to sunlight and decreased dietary intake of vitamin D. Common causes of vitamin D deficiency include genetic defects in the vitamin D receptor, severe liver or kidney disease, and insufficient exposure to sunlight. Vitamin D plays an important role in maintaining calcium balance and in the regulation of parathyroid hormone (PTH). It promotes renal reabsorption of calcium, increases intestinal absorption of calcium and phosphorus, and increases calcium and phosphorus mobilization from bone to plasma.
Mechanism of actionThe first step involved in the activation of vitamin D3 is a 25-hydroxylation which is catalysed by the 25-hydroxylase in the liver and then by other enzymes. The mitochondrial sterol 27-hydroxylase catalyses the first reaction in the oxidation of the side chain of sterol intermediates. The active form of vitamin D3 (calcitriol) binds to intracellular receptors that then function as transcription factors to modulate gene expression. Like the receptors for other steroid hormones and thyroid hormones, the vitamin D receptor has hormone-binding and DNA-binding domains. The vitamin D receptor forms a complex with another intracellular receptor, the retinoid-X receptor, and that heterodimer is what binds to DNA. In most cases studied, the effect is to activate transcription, but situations are also known in which vitamin D suppresses transcription. Calcitriol increases the serum calcium concentrations by: increasing GI absorption of phosphorus and calcium, increasing osteoclastic resorption, and increasing distal renal tubular reabsorption of calcium. Calcitriol appears to promote intestinal absorption of calcium through binding to the vitamin D receptor in the mucosal cytoplasm of the intestine. Subsequently, calcium is absorbed through formation of a calcium-binding protein.
AbsorptionReadily absorbed
Volume of distributionNot Available
Protein binding50% to 80%
Metabolism

Within the liver, cholecalciferal is hydroxylated to calcidiol (25-hydroxycholecalciferol) by the enzyme 25-hydroxylase. Within the kidney, calcidiol serves as a substrate for 1-alpha-hydroxylase, yielding calcitriol (1,25-dihydroxycholecalciferol), the biologically active form of vitamin D3.

SubstrateEnzymesProduct
Cholecalciferol
Not Available
(23S)-23,25-dihdroxy-24-oxovitamine D3 23-(beta-glucuronide)Details
Route of eliminationNot Available
Half lifeSeveral weeks
ClearanceNot Available
ToxicityHypercalcemia - Early symptoms of hypercalcemia, include nausea and vomiting, weakness, headache, somnolence, dry mouth, constipation, metallic taste, muscle pain and bone pain. Late symptoms and signs of hypercalcemia, include polyuria, polydipsia, anorexia, weight loss, nocturia, conjunctivitis, pancreatitis, photophobia, rhinorrhea, pruritis, hyperthermia, decreased libido, elevated BUN, albuminuria, hypercholesterolemia, elevated ALT (SGPT) and AST (SGOT), ectopic calcification, nephrocalcinosis, hypertension and cardiac arrhythmias.
Affected organisms
  • Humans and other mammals
Pathways
PathwayCategorySMPDB ID
Lysosomal Acid Lipase Deficiency (Wolman Disease)DiseaseSMP00319
Mevalonic aciduriaDiseaseSMP00510
Atorvastatin Action PathwayDrug actionSMP00131
Pravastatin Action PathwayDrug actionSMP00089
Simvastatin Action PathwayDrug actionSMP00082
Alendronate Action PathwayDrug actionSMP00095
Zoledronate Action PathwayDrug actionSMP00107
Risedronate Action PathwayDrug actionSMP00112
Rosuvastatin Action PathwayDrug actionSMP00092
Lovastatin Action PathwayDrug actionSMP00099
Pamidronate Action PathwayDrug actionSMP00117
Ibandronate Action PathwayDrug actionSMP00079
Fluvastatin Action PathwayDrug actionSMP00119
Cerivastatin Action PathwayDrug actionSMP00111
Steroid BiosynthesisMetabolicSMP00023
Chondrodysplasia Punctata II, X Linked Dominant (CDPX2)DiseaseSMP00388
CHILD SyndromeDiseaseSMP00387
Cholesteryl ester storage diseaseDiseaseSMP00508
DesmosterolosisDiseaseSMP00386
Wolman diseaseDiseaseSMP00511
Hyper-IgD syndromeDiseaseSMP00509
HypercholesterolemiaDiseaseSMP00209
Smith-Lemli-Opitz Syndrome (SLOS)DiseaseSMP00389
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 substrate Non-inhibitor 0.9071
CYP450 2D6 substrate Non-inhibitor 0.9551
CYP450 2C19 substrate Non-inhibitor 0.9026
CYP450 3A4 substrate 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
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
CapsuleOral
TabletOral
Prices
Unit descriptionCostUnit
Cholecalciferol crystals104.3USDg
Vitamin d3 2400 unit/ml liquid0.8USDml
Vitamin d3 2000 unit spray0.44USDml
Vitamin d3 3000 unit tablet0.11USDtablet
Vitamin d-3 2000 unit tablet0.07USDtablet
CVS Pharmacy vitamin d 1000 unit tablet0.04USDtablet
Delta d3 400 unit tablet0.04USDeach
Vitamin d 1000 unit tablet0.03USDtablet
Pv vitamin d 2000 unit tablet0.02USDtablet
Pv vitamin d 5000 unit tablet0.02USDtablet
Vitamin d 400 unit tablet0.02USDtablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point84.5 °CPhysProp
water solubilityInsolubleNot Available
logP7.5Not Available
Predicted Properties
PropertyValueSource
water solubility3.80e-04 g/lALOGPS
logP7.98ALOGPS
logP7.13ChemAxon
logS-6ALOGPS
pKa (strongest acidic)18.38ChemAxon
pKa (strongest basic)-1.3ChemAxon
physiological charge0ChemAxon
hydrogen acceptor count1ChemAxon
hydrogen donor count1ChemAxon
polar surface area20.23ChemAxon
rotatable bond count6ChemAxon
refractivity123.22ChemAxon
polarizability49.6ChemAxon
number of rings3ChemAxon
bioavailability1ChemAxon
rule of fiveNoChemAxon
Ghose filterNoChemAxon
Veber's ruleYesChemAxon
MDDR-like ruleYesChemAxon
Spectra
SpectraNot Available
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 Reference
  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. Pubmed
External Links
ResourceLink
KEGG DrugD00188
KEGG CompoundC05443
ChEBI28940
ChEMBLCHEMBL1042
Therapeutic Targets DatabaseDAP001273
PharmGKBPA164748138
Drug Product Database2242651
Drugs.comhttp://www.drugs.com/mtm/cholecalciferol.html
PDRhealthhttp://www.pdrhealth.com/drug_info/nmdrugprofiles/nutsupdrugs/vit_0265.shtml
WikipediaCholecalciferol
ATC CodesA11CC05
AHFS Codes
  • 88:16.00
PDB EntriesNot Available
FDA labelNot Available
MSDSshow(123 KB)
Interactions
Drug Interactions
Drug
AlfacalcidolVitamin D analogs may enhance the adverse/toxic effect of other Vitamin D analogs. Avoid combined use of multiple vitamin D analogs (at pharmacologic doses). Prescribing information for calcitriol, doxercalciferol, paricalcitol, and alfacalcidol each specifically cautions against such combined use. Though not specified in the prescribing information for calcipotriene, cholecalciferol, and ergocalciferol, each contains warnings regarding the potential for vitamin D toxicity.
Aluminum hydroxideVitamin D analogs such as cholecalciferol may increase the serum concentration of aluminum hydroxide. Specifically, the absorption of aluminum may be increased, leading to increased serum aluminum concentrations. Avoid chronic and/or excessive use of aluminum and aluminum-containing products in patients who are also taking vitamin D analogs. Any patients consuming such a combination should be monitored closely for aluminum status and signs/symptoms of aluminum-related toxicities.
CalcipotriolVitamin D Analogs may enhance the adverse/toxic effect of other Vitamin D Analogs. Avoid combined use of multiple vitamin D analogs (at pharmacologic doses). hough not specified in the prescribing information for calcipotriene, cholecalciferol, and ergocalciferol, each contains warnings regarding the potential for vitamin D toxicity.
CalcitriolVitamin D analogs may enhance the adverse/toxic effect of other Vitamin D analogs. Avoid combined use of multiple vitamin D analogs (at pharmacologic doses). Prescribing information for calcitriol, doxercalciferol, paricalcitol, and alfacalcidol each specifically cautions against such combined use. Though not specified in the prescribing information for calcipotriene, cholecalciferol, and ergocalciferol, each contains warnings regarding the potential for vitamin D toxicity.
CholestyramineBile acid sequestrants such as cholestyramine may decrease the serum concentration of Vitamin D analogs such as cholecalciferol. More specifically, bile acid sequestrants may impair absorption of Vitamin D analogs. Avoid concomitant administration of vitamin D analogs and bile acid sequestrants. Monitor plasma calcium concentrations in patients receiving combined therapy with these agents. This is particularly important in patients receiving higher doses of a bile acid sequestant (i.e., 30 g/day or more of cholestyramine or equivalent) or in patients experiencing bile acid sequestrant-induced steatorrhea. Specific recommendations regarding the separation of administration of these agents are not defined; however, it would seem prudent to separate the administration of these agents by several hours to minimize the potential risk of interaction. Similar precautions do not apply to parenterally administered vitamin D analogs.
ColesevelamBile acid sequestrants such as colesevelam may decrease the serum concentration of Vitamin D analogs such as cholecalciferol. More specifically, bile acid sequestrants may impair absorption of Vitamin D analogs. Avoid concomitant administration of vitamin D analogs and bile acid sequestrants. Monitor plasma calcium concentrations in patients receiving combined therapy with these agents. This is particularly important in patients receiving higher doses of a bile acid sequestant (i.e., 30 g/day or more of cholestyramine or equivalent) or in patients experiencing bile acid sequestrant-induced steatorrhea. Specific recommendations regarding the separation of administration of these agents are not defined; however, it would seem prudent to separate the administration of these agents by several hours to minimize the potential risk of interaction. Similar precautions do not apply to parenterally administered vitamin D analogs.
ColestipolBile acid sequestrants such as colestipol may decrease the serum concentration of Vitamin D analogs such as cholecalciferol. More specifically, bile acid sequestrants may impair absorption of Vitamin D analogs. Avoid concomitant administration of vitamin D analogs and bile acid sequestrants. Monitor plasma calcium concentrations in patients receiving combined therapy with these agents. This is particularly important in patients receiving higher doses of a bile acid sequestant (i.e., 30 g/day or more of cholestyramine or equivalent) or in patients experiencing bile acid sequestrant-induced steatorrhea. Specific recommendations regarding the separation of administration of these agents are not defined; however, it would seem prudent to separate the administration of these agents by several hours to minimize the potential risk of interaction. Similar precautions do not apply to parenterally administered vitamin D analogs.
DoxercalciferolVitamin D analogs may enhance the adverse/toxic effect of other Vitamin D analogs. Avoid combined use of multiple vitamin D analogs (at pharmacologic doses). Prescribing information for calcitriol, doxercalciferol, paricalcitol, and alfacalcidol each specifically cautions against such combined use. Though not specified in the prescribing information for calcipotriene, cholecalciferol, and ergocalciferol, each contains warnings regarding the potential for vitamin D toxicity.
ErgocalciferolVitamin D analogs may enhance the adverse/toxic effect of other Vitamin D analogs. Avoid combined use of multiple vitamin D analogs (at pharmacologic doses). Prescribing information for calcitriol, doxercalciferol, paricalcitol, and alfacalcidol each specifically cautions against such combined use. Though not specified in the prescribing information for calcipotriene, cholecalciferol, and ergocalciferol, each contains warnings regarding the potential for vitamin D toxicity.
OrlistatOrlistat may decrease the serum concentration of Vitamin D analogs. More specifically, orlistat may impair absorption of Vitamin D analogs such as cholecalciferol. Monitor clinical response (plasma calcium concentrations) to orally administered vitamin D analogs closely if used with orlistat. When this combination must be used, consider administering the vitamin D analog at least 2 hours before or after the administration of orlistat.
ParicalcitolVitamin D analogs may enhance the adverse/toxic effect of other Vitamin D analogs. Avoid combined use of multiple vitamin D analogs (at pharmacologic doses). Prescribing information for calcitriol, doxercalciferol, paricalcitol, and alfacalcidol each specifically cautions against such combined use. Though not specified in the prescribing information for calcipotriene, cholecalciferol, and ergocalciferol, each contains warnings regarding the potential for vitamin D toxicity.
SucralfateVitamin D analogs such as cholecalciferol may increase the serum concentration of sucralfate. Specifically, the absorption of aluminum from sucralfate may be increased, leading to an increase in the serum aluminum concentration. Avoid chronic and/or excessive use of aluminum and aluminum-containing products (such as sucralfate) in patients who are also taking vitamin D analogs. Any patients consuming such a combination should be monitored closely for aluminum status and signs/symptoms of aluminum-related toxicities.
Food InteractionsNot Available

Targets

1. Vitamin D3 receptor

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: agonist

Components

Name UniProt ID Details
Vitamin D3 receptor P11473 Details

References:

  1. Reinhart GA: Vitamin D analogs: novel therapeutic agents for cardiovascular disease? Curr Opin Investig Drugs. 2004 Sep;5(9):947-51. Pubmed
  2. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed
  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. Epub 2010 May 6. Pubmed

Enzymes

1. Vitamin D 25-hydroxylase

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Vitamin D 25-hydroxylase Q6VVX0 Details

References:

  1. Flanagan JN, Young MV, Persons KS, Wang L, Mathieu JS, Whitlatch LW, Holick MF, Chen TC: Vitamin D metabolism in human prostate cells: implications for prostate cancer chemoprevention by vitamin D. Anticancer Res. 2006 Jul-Aug;26(4A):2567-72. Pubmed
  2. Segura-Aguilar J: Peroxidase activity of liver microsomal vitamin D 25-hydroxylase and cytochrome P450 1A2 catalyzes 25-hydroxylation of vitamin D3 and oxidation of dopamine to aminochrome. Biochem Mol Med. 1996 Jun;58(1):122-9. Pubmed
  3. Schuster I: Cytochromes P450 are essential players in the vitamin D signaling system. Biochim Biophys Acta. 2010 Jul 7. Pubmed
  4. Ohyama Y, Yamasaki T: Eight cytochrome P450s catalyze vitamin D metabolism. Front Biosci. 2004 Sep 1;9:3007-18. Pubmed

2. Sterol 26-hydroxylase, mitochondrial

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Sterol 26-hydroxylase, mitochondrial Q02318 Details

References:

  1. Lehmann B, Tiebel O, Meurer M: Expression of vitamin D3 25-hydroxylase (CYP27) mRNA after induction by vitamin D3 or UVB radiation in keratinocytes of human skin equivalents—a preliminary study. Arch Dermatol Res. 1999 Sep;291(9):507-10. Pubmed
  2. Sawada N, Sakaki T, Yoneda S, Kusudo T, Shinkyo R, Ohta M, Inouye K: Conversion of vitamin D3 to 1alpha,25-dihydroxyvitamin D3 by Streptomyces griseolus cytochrome P450SU-1. Biochem Biophys Res Commun. 2004 Jul 16;320(1):156-64. Pubmed
  3. Uchida E, Kagawa N, Sakaki T, Urushino N, Sawada N, Kamakura M, Ohta M, Kato S, Inouye K: Purification and characterization of mouse CYP27B1 overproduced by an Escherichia coli system coexpressing molecular chaperonins GroEL/ES. Biochem Biophys Res Commun. 2004 Oct 15;323(2):505-11. Pubmed
  4. Sakaki T, Kagawa N, Yamamoto K, Inouye K: Metabolism of vitamin D3 by cytochromes P450. Front Biosci. 2005 Jan 1;10:119-34. Print 2005 Jan 1. Pubmed
  5. Tokar EJ, Webber MM: Cholecalciferol (vitamin D3) inhibits growth and invasion by up-regulating nuclear receptors and 25-hydroxylase (CYP27A1) in human prostate cancer cells. Clin Exp Metastasis. 2005;22(3):275-84. Pubmed
  6. Schuster I: Cytochromes P450 are essential players in the vitamin D signaling system. Biochim Biophys Acta. 2010 Jul 7. Pubmed
  7. Ohyama Y, Yamasaki T: Eight cytochrome P450s catalyze vitamin D metabolism. Front Biosci. 2004 Sep 1;9:3007-18. Pubmed

3. Cytochrome P450 2J2

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 2J2 P51589 Details

References:

  1. Aiba I, Yamasaki T, Shinki T, Izumi S, Yamamoto K, Yamada S, Terato H, Ide H, Ohyama Y: Characterization of rat and human CYP2J enzymes as Vitamin D 25-hydroxylases. Steroids. 2006 Oct;71(10):849-56. Epub 2006 Jul 13. Pubmed
  2. Schuster I: Cytochromes P450 are essential players in the vitamin D signaling system. Biochim Biophys Acta. 2010 Jul 7. Pubmed

4. Cytochrome P450 3A4

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 3A4 P08684 Details

References:

  1. Schuster I: Cytochromes P450 are essential players in the vitamin D signaling system. Biochim Biophys Acta. 2010 Jul 7. Pubmed
  2. Ohyama Y, Yamasaki T: Eight cytochrome P450s catalyze vitamin D metabolism. Front Biosci. 2004 Sep 1;9:3007-18. Pubmed

5. Cholesterol side-chain cleavage enzyme, mitochondrial

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cholesterol side-chain cleavage enzyme, mitochondrial P05108 Details

References:

  1. Tuckey RC, Janjetovic Z, Li W, Nguyen MN, Zmijewski MA, Zjawiony J, Slominski A: Metabolism of 1alpha-hydroxyvitamin D3 by cytochrome P450scc to biologically active 1alpha,20-dihydroxyvitamin D3. J Steroid Biochem Mol Biol. 2008 Dec;112(4-5):213-9. Epub 2008 Oct 21. Pubmed
  2. Tuckey RC, Nguyen MN, Slominski A: Kinetics of vitamin D3 metabolism by cytochrome P450scc (CYP11A1) in phospholipid vesicles and cyclodextrin. Int J Biochem Cell Biol. 2008;40(11):2619-26. Epub 2008 May 20. Pubmed
  3. Guryev O, Carvalho RA, Usanov S, Gilep A, Estabrook RW: A pathway for the metabolism of vitamin D3: unique hydroxylated metabolites formed during catalysis with cytochrome P450scc (CYP11A1). Proc Natl Acad Sci U S A. 2003 Dec 9;100(25):14754-9. Epub 2003 Dec 1. Pubmed

6. Cytochrome P450 1A1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Cytochrome P450 1A1 P04798 Details

References:

  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

7. Cytochrome P450 2B6

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Cytochrome P450 2B6 P20813 Details

References:

  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

8. Cytochrome P450 2C19

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Cytochrome P450 2C19 P33261 Details

References:

  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed
  2. Lexicomp.

9. Cytochrome P450 2C8

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Cytochrome P450 2C8 P10632 Details

References:

  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

10. Cytochrome P450 2C9

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Cytochrome P450 2C9 P11712 Details

References:

  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed
  2. Lexicomp.

11. Cytochrome P450 2D6

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Cytochrome P450 2D6 P10635 Details

References:

  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed
  2. Lexicomp

Carriers

1. Vitamin D-binding protein

Kind: protein

Organism: Human

Pharmacological action: no

Components

Name UniProt ID Details
Vitamin D-binding protein P02774 Details

References:

  1. Nykjaer A, Dragun D, Walther D, Vorum H, Jacobsen C, Herz J, Melsen F, Christensen EI, Willnow TE: An endocytic pathway essential for renal uptake and activation of the steroid 25-(OH) vitamin D3. Cell. 1999 Feb 19;96(4):507-15. Pubmed
  2. Verboven C, Rabijns A, De Maeyer M, Van Baelen H, Bouillon R, De Ranter C: A structural basis for the unique binding features of the human vitamin D-binding protein. Nat Struct Biol. 2002 Feb;9(2):131-6. Pubmed
  3. Houghton LA, Vieth R: The case against ergocalciferol (vitamin D2) as a vitamin supplement. Am J Clin Nutr. 2006 Oct;84(4):694-7. Pubmed
  4. Yamamoto N, Naraparaju VR: Vitamin D3-binding protein as a precursor for macrophage activating factor in the inflammation-primed macrophage activation cascade in rats. Cell Immunol. 1996 Jun 15;170(2):161-7. Pubmed
  5. Yamamoto N, Naraparaju VR: Role of vitamin D3-binding protein in activation of mouse macrophages. J Immunol. 1996 Aug 15;157(4):1744-9. Pubmed

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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:08