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    Chemistry

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    Also known as: Vitamin d2, Calciferol, 50-14-6, Viosterol, Ergorone, Ercalciol
    Molecular Formula
    C28H44O
    Molecular Weight
    396.6  g/mol
    InChI Key
    MECHNRXZTMCUDQ-RKHKHRCZSA-N
    FDA UNII
    VS041H42XC
    Vitamin D
    Derivatives of ERGOSTEROL formed by ULTRAVIOLET RAYS breaking of the C9-C10 bond. They differ from CHOLECALCIFEROL in having a double bond between C22 and C23 and a methyl group at C24.
    Ergocalciferol is a Provitamin D2 Compound.
    1 2D Structure

    Vitamin D

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (1S,3Z)-3-[(2E)-2-[(1R,3aS,7aR)-1-[(E,2R,5R)-5,6-dimethylhept-3-en-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidenecyclohexan-1-ol
    2.1.2 InChI
    InChI=1S/C28H44O/c1-19(2)20(3)9-10-22(5)26-15-16-27-23(8-7-17-28(26,27)6)12-13-24-18-25(29)14-11-21(24)4/h9-10,12-13,19-20,22,25-27,29H,4,7-8,11,14-18H2,1-3,5-6H3/b10-9+,23-12+,24-13-/t20-,22+,25-,26+,27-,28+/m0/s1
    2.1.3 InChI Key
    MECHNRXZTMCUDQ-RKHKHRCZSA-N
    2.1.4 Canonical SMILES
    CC(C)C(C)C=CC(C)C1CCC2C1(CCCC2=CC=C3CC(CCC3=C)O)C
    2.1.5 Isomeric SMILES
    C[C@H](/C=C/[C@H](C)C(C)C)[C@H]1CC[C@@H]\2[C@@]1(CCC/C2=C\C=C/3\C[C@H](CCC3=C)O)C
    2.2 Other Identifiers
    2.2.1 UNII
    VS041H42XC
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Calciferols

    2. D2, Vitamin

    3. Ergocalciferols

    4. Vitamin D 2

    5. Vitamin D2

    2.3.2 Depositor-Supplied Synonyms

    1. Vitamin D2

    2. Calciferol

    3. 50-14-6

    4. Viosterol

    5. Ergorone

    6. Ercalciol

    7. Deltalin

    8. Drisdol

    9. Ostelin

    10. Oleovitamin D2

    11. Sterogyl

    12. Detalup

    13. Condocaps

    14. Crystallina

    15. Fortodyl

    16. Mulsiferol

    17. Radsterin

    18. Condol

    19. Deratol

    20. Diactol

    21. Ertron

    22. Geltabs

    23. Daral

    24. Novovitamin-d

    25. Divit Urto

    26. D-tracetten

    27. Hi-deratol

    28. Calciferon 2

    29. Dee-ronal

    30. Vitavel-d

    31. D-arthin

    32. Dee-ron

    33. De-rat Concentrate

    34. Vio-d

    35. Rodine C

    36. Activated Ergosterol

    37. Calciferolum

    38. Hyperkil

    39. Rodinec

    40. Ergocalciferolum

    41. Mina D2

    42. Vitamind2

    43. Viosterol In Oil

    44. Radiostol

    45. Haliver

    46. Davitin

    47. Metadee

    48. Mykostin

    49. (+)-vitamin D2

    50. Decaps

    51. Infron

    52. Shock-ferol

    53. Davitamon D

    54. Dee-osterol

    55. Geltabs Vitamin D

    56. Dee-roual

    57. Buco-d

    58. Oleovitamin D, Synthetic

    59. Uvesterol D

    60. Oleovitamin D

    61. Chebi:28934

    62. Irradiated Ergosta-5,7,22-trien-3-beta-ol

    63. Synthetic Vitamin D

    64. Vitamin D (ergocalciferol)

    65. Condacaps

    66. Viostdrol

    67. Crtron

    68. 9,10-secoergosta-5,7,10(19),22-tetraen-3-beta-ol

    69. Vs041h42xc

    70. Uvesterol-d

    71. (3s,5z,7e,22e)-9,10-secoergosta-5,7,10,22-tetraen-3-ol

    72. (5z,7e,22e)-(3s)-9,10-seco-5,7,10(19),22-ergostatetraen-3-ol

    73. Ergosterol Activated

    74. Mfcd00166988

    75. Nsc-62792

    76. (1s,3z)-3-[(2e)-2-[(1r,3as,7ar)-1-[(e,2r,5r)-5,6-dimethylhept-3-en-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1h-inden-4-ylidene]ethylidene]-4-methylidenecyclohexan-1-ol

    77. Ergocalciferols

    78. Dsstox_cid_233

    79. (3beta,5z,7e,22e)-9,10-secoergosta-5,7,10(19),22-tetraen-3-ol

    80. (5z,7e,22e)-(3s)-9,10-secoergosta-5,7,10(19),22-tetraen-3-ol

    81. 9,10-secoergosta-5,7,10(19),22-tetraen-3-ol, (3b,5z,7e,22e)-

    82. 9,10-secoergosta-5,7,10(19),22-tetraen-3-ol, (3.beta.,5z,7e,22e)-

    83. Dsstox_rid_75449

    84. Dsstox_gsid_20233

    85. Vitamin D2 (ergocalciferol)

    86. Ergocalciferolo

    87. Disdrol

    88. Radstein

    89. Vd2-d3

    90. Ergocalciferolo [dcit]

    91. Smr000857106

    92. Ergocalciferolum [inn-latin]

    93. Vitamin D 2

    94. Ergosterol Irradiated

    95. Irradiated Ergosterol

    96. Shock-ferol Sterogyl

    97. Hsdb 819

    98. Sorex C.r.

    99. Einecs 200-014-9

    100. Nsc 62792

    101. Doral [vitamin Derivative]

    102. Unii-vs041h42xc

    103. Osteil

    104. Delta-tracetten

    105. Lanes

    106. Delta-arthin

    107. Beta-ol

    108. D-forte

    109. Ergocalciferol Oil

    110. Eciferol D2

    111. Vitamina D2

    112. Calciferol (tn)

    113. Cas-50-14-6

    114. Ergoral D2

    115. Ncgc00166307-01

    116. Sterogyl-15

    117. Sterogyl 15h

    118. Cyclohexanol, 4-methylene-3-((2e)-2-((1r,3as,7ar)-octahydro-7a-methyl-1-((1r,2e,4r)-1,4,5-trimethyl-2-hexen-1-yl)-4h-inden-4-ylidene)ethylidene)-, (1s,3z)-

    119. Cyclohexanol, 4-methylene-3-[(2e)-2-[(1r,3as,7ar)-octahydro-7a-methyl-1-[(1r,2e,4r)-1,4,5-trimethyl-2-hexen-1-yl]-4h-inden-4-ylidene]ethylidene]-, (1s,3z)-

    120. Prestwick_554

    121. Drisdol (tn)

    122. Vio D

    123. Ergocalciferol [usp:inn:ban:jan]

    124. Vitamin D2 Solution

    125. Ergo-d2

    126. Osto-d2

    127. Calciferol In Arach Oil

    128. 9,10-seco(5z,7e,22e)-5,7,10(19),22-ergostatetraen-3-ol

    129. Prestwick3_000420

    130. Bmse000510

    131. Vitamin D2 [mi]

    132. (3-beta,5z,7e,22e)-9,10-secoergosta-5,7,10,(19),22-tetraen-3-ol

    133. Vitamin D2 [fcc]

    134. Schembl3420

    135. Chembl1536

    136. Ergocalciferol [inn]

    137. Ergocalciferol [jan]

    138. Ergocalciferol; 50-14-6

    139. Bspbio_000380

    140. Ergocalciferol (jp17/usp)

    141. Ergocalciferol [hsdb]

    142. Ergocalciferol [inci]

    143. Mls001332467

    144. Mls001332468

    145. Ergocalciferol [vandf]

    146. Vitamin D2 [who-ip]

    147. Ergocalciferol [mart.]

    148. Ergocalciferol, (+)-

    149. Bpbio1_000418

    150. Megxm0_000466

    151. Ergocalciferol [usp-rs]

    152. Ergocalciferol [who-dd]

    153. Ergocalciferol [who-ip]

    154. Dtxsid5020233

    155. Acon1_002187

    156. Hms2096c22

    157. Hms2230e20

    158. 1217448-46-8

    159. Act02622

    160. Cs-m1019

    161. Zinc4629876

    162. Ergocalciferol [ep Impurity]

    163. Ergocalciferol [orange Book]

    164. Tox21_112404

    165. Tox21_202348

    166. Tox21_302752

    167. Bdbm50247883

    168. Ergocalciferol [ep Monograph]

    169. Lmst03010001

    170. S4035

    171. Ergocalciferol [usp Monograph]

    172. Vitamin D2; Ergocalciferol; Deltalin

    173. 9,10-secoergosta-5,7,10(19),22-tetraen-3-ol, (3beta,5z,7e,22e)-

    174. Akos022185284

    175. Ccg-268614

    176. Db00153

    177. Ergocalciferolum [who-ip Latin]

    178. Ergocalciferol, Sigma Reference Standard

    179. Ncgc00166307-02

    180. Ncgc00166307-03

    181. Ncgc00256529-01

    182. Ncgc00259897-01

    183. As-11649

    184. Bp-31119

    185. Ergocalciferol (d2), Analytical Standard

    186. Hy-76542

    187. Irradiated Ergosta-5,7,22-trien-3beta-ol

    188. Vitamin D2 Ergocalciferol 400,000 Iu/g

    189. Ergocalciferol, 40,000,000 Usp Units/g

    190. C05441

    191. D00187

    192. 166v988

    193. Q139200

    194. Q-201930

    195. 9,10-secoergosta-5,7,10(19),22-tetraen-3b-ol

    196. Ergocalciferol, >=98.0% (sum Of Enantiomers, Hplc)

    197. 22-tetraen 3beta 9,10,secoergosta-5,7,10(19)-ol

    198. 7e677dc1-e1c4-4fc5-8f4a-bce1857f7e87

    199. Vitamin D2 Solution, 100 Mug/ml In Ethanol, 98% (cp)

    200. (5e,7e,22e)-9,10-secoergosta-5,7,10,22-tetraen-3-ol

    201. Ergocalciferol, British Pharmacopoeia (bp) Reference Standard

    202. Ergocalciferol, European Pharmacopoeia (ep) Reference Standard

    203. Ergocalciferol, United States Pharmacopeia (usp) Reference Standard

    204. (3s,5z,7e,22e)-9,10-secoergosta-5,7,10(19),22-tetraen-3-ol

    205. Vitamin D2. Short Expiry Date Due To Chemical Nature Of Component(s)

    206. (3.beta.,5z,7e,22e)-9,10-secoergosta-5,7,10(19),22-tetraen-3-ol

    207. 24-methyl-9,10-secocholesta-5,7,10( 19),22-tetraene-3.beta.-ol [who-ip]

    208. Ergocalciferol (vitamin D2), Pharmaceutical Secondary Standard; Certified Reference Material

    209. Ergocalciferol For System Suitability, Europepharmacopoeia (ep) Reference Standard

    210. Vitamin D2 Solution, 1 Mg/ml In Ethanol, Ampule Of 1 Ml, Certified Reference Material

    211. (1s,3z)-3-[(2e)-2-[(1r,3as,7ar)-7a-methyl-1-[(e,1r,4r)-1,4,5-trimethylhex-2-enyl]-2,3,3a,5,6,7-hexahydro-1h-inden-4-ylidene]ethylidene]-4-methylene-cyclohexanol

    212. 4-methylene-3-[2-[tetrahydro-7a-methyl-1-(1,4,5-trimethyl-2-hexenyl)-4(3ah)-indanylidene]ethylidene]-cyclohexanol

    2.4 Create Date
    2005-06-24
    3 Chemical and Physical Properties
    Molecular Weight 396.6 g/mol
    Molecular Formula C28H44O
    XLogP37.4
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count1
    Rotatable Bond Count5
    Exact Mass396.339216023 g/mol
    Monoisotopic Mass396.339216023 g/mol
    Topological Polar Surface Area20.2 Ų
    Heavy Atom Count29
    Formal Charge0
    Complexity678
    Isotope Atom Count0
    Defined Atom Stereocenter Count6
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count3
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Therapeutic Uses

    MEDICATION (VET): ... Recommended for prophylaxis of milk fever in cows. ... Prevent atrophic rhinitis in pigs. ... Aid fracture healing in cats and dogs.

    Rossoff, I.S. Handbook of Veterinary Drugs. New York: Springer Publishing Company, 1974., p. 653

    MEDICATION (VET): To be effective ... supplementation with Ca & PO4. ... Fish meals & irradiated yeast may be used as supplemental ... source. ... Diets are routinely supplemented ... 1400-1600 IU/kg. Therapy for rickets ... Level 10-20 times daily requirement, alternate days for 1 wk. /Vitamin D/

    Jones, L.M., et al. Veterinary Pharmacology & Therapeutics. 4th ed. Ames: Iowa State University Press, 1977., p. 773

    In adults and children with nutritional rickets or osteomalacia and normal GI absorption, oral administration of ... ergocalciferol daily results in normal serum calcium and phosphate concentrations in about 10 days, radiographic evidence of healing of bone within 2-4 wk, and complete healing in about 6 months. ... Diet should be corrected and, after healing has occurred, supplemental doses of ergocalciferol may be discontinued in patients with normal GI absorption. In adults with severe malabsorption and vitamin D deficiency, /daily/ dosages ... have been given to correct osteomalacia. In children with malabsorption, oral ergocalciferol dosages ... have been recommended. In vitamin D-deficient infants with tetany and rickets, calcium should be administered orally or iv to control tetany. Vitamin D deficiency is then treated orally with /a daily dose/ of ergocalciferol ... until the bones have healed, ... .

    McEvoy, G.K. (ed.). American Hospital Formulary Service- Drug Information 2004. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2004 (Plus Supplements)., p. 3519

    In adults with Fanconi syndrome, oral ergocalciferol .. have been given along with treatment of acidosis. In children with Fanconi syndrome oral ergocalciferol ... have been used.

    McEvoy, G.K. (ed.). American Hospital Formulary Service- Drug Information 2004. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2004 (Plus Supplements)., p. 3519

    For more Therapeutic Uses (Complete) data for VITAMIN D2 (11 total), please visit the HSDB record page.

    4.2 Drug Warning

    ... Ergocalciferol should be administered with extreme caution, if at all, to patients with impaired renal function and with extreme caution in patient with heart disease, renal stones, or arterioscleroses.

    McEvoy, G.K. (ed.). American Hospital Formulary Service- Drug Information 2004. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2004 (Plus Supplements)., p. 3513

    Initial signs and symptoms ... consists of weakness, fatigue, lassitude, headache, nausea, vomiting, and diarrhea. Obtundation and coma may develop. Early impairment of renal function from hypercalcemia is manifest by polyuria, polydipsia, nocturia, decreased urinary concentration ability, and proteinuria.

    Gilman, A.G., T.W. Rall, A.S. Nies and P. Taylor (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 8th ed. New York, NY. Pergamon Press, 1990., p. 1514

    4.3 Drug Indication

    Ergocalciferol is indicated for the treatment of hypoparathyroidism, refractory rickets, and familial hypophosphatemia. Hypoparathyroidism is the result of inadequate parathyroid hormone production that occurs due to the presence of damage or removal of the parathyroid glands. This condition produces decreased calcium and increased phosphorus levels. Rickets is a condition produced due to a deficiency in vitamin D, calcium or phosphorus. However, this condition can also be related to renal diseases. It is characterized to present weak or soft bones. Familial hypophosphatemia is characterized by the impaired transport of phosphate and an altered vitamin D metabolism in the kidneys. The presence of this condition can derive in the presence of osteomalacia, bone softening and rickets.

    FDA Label

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    After the activation of the vitamin D receptor, some of the biological changes produced by ergocalciferol include mobilization and accretion of calcium and phosphorus in the bone, absorption of calcium and phosphorus in the intestine, and reabsorption of calcium and phosphorus in the kidney. Some other effects known to be produced due to the presence of vitamin D are osteoblast formation, fetus development, induction of pancreatic function, induction of neural function, improvement of immune function, cellular growth and cellular differentiation. When compared to its vitamin D counterpart [cholecalciferol], ergocalciferol has been shown to present a reduced induction of calcidiol and hence, it is less potent. Ergocalciferol supplementation in patients with end-stage renal disease has been shown to generate a significant benefit in lab parameters of bone and mineral metabolism as well as improvement in glycemic control, serum albumin levels and reduced levels of inflammatory markers.

    5.2 MeSH Pharmacological Classification

    Bone Density Conservation Agents

    Agents that inhibit BONE RESORPTION and/or favor BONE MINERALIZATION and BONE REGENERATION. They are used to heal BONE FRACTURES and to treat METABOLIC BONE DISEASES such as OSTEOPOROSIS. (See all compounds classified as Bone Density Conservation Agents.)

    Calcium-Regulating Hormones and Agents

    Hormones and molecules with calcium-regulating hormone-like actions that modulate OSTEOLYSIS and other extra-skeletal activities to maintain calcium homeostasis. (See all compounds classified as Calcium-Regulating Hormones and Agents.)

    Vitamins

    Organic substances that are required in small amounts for maintenance and growth, but which cannot be manufactured by the human body. (See all compounds classified as Vitamins.)

    5.3 FDA Pharmacological Classification
    5.3.1 Active Moiety
    ERGOCALCIFEROL
    5.3.2 FDA UNII
    VS041H42XC
    5.3.3 Pharmacological Classes
    Provitamin D2 Compound [EPC]; Ergocalciferols [CS]
    5.4 ATC Code

    A - Alimentary tract and metabolism

    A11 - Vitamins

    A11C - Vitamin a and d, incl. combinations of the two

    A11CC - Vitamin d and analogues

    A11CC01 - Ergocalciferol

    5.5 Absorption, Distribution and Excretion

    Absorption

    Ergocalciferol is absorbed in the intestine and carried to the liver in chylomicrons. Its intestinal absorption does not present limitations unless the presence of conditions related to fat malabsorption. However, for absorption to take place, the presence of bile is required.

    Route of Elimination

    The active form of ergocalciferol, calcitrol, cannot be maintained for long periods in storage tissue mainly in periods of dietary or UVB deprivation. Therefore, ergocalciferol and its metabolites are excreted via the bile with a minor contribution of renal elimination. This major fecal elimination is explained due to the cubilin-megalin receptor system-mediated renal reuptake of vitamin D metabolites bound to vitamin D binding protein.

    Volume of Distribution

    The amount of circulating ergocalciferol is very limited as this compound is rapidly stored in fat tissue such as adipose tissue, liver and muscle. This is very obvious in reports that indicate that circulating ergocalciferol is significantly reduced in obese patients.

    Clearance

    There are no formal reports regarding the clearance rate of ergocalciferol. Due to the structural similarity, it is recommended to consult this parameter with [cholecalciferol]. On the other hand, the proposed renal clearance of calcitriol is of 31 ml/min.

    Both vitamin D2 & vitamin D3 are absorbed from the small intestine, although vitamin D3 may be absorbed more efficiently. The exact portion of the gut that is most effective in vitamin D absorption reflects the vehicle in which the vitamin is dissolved. Most of the vitamin appears first within chylomicrons in lymph.

    Hardman, J.G., L.E. Limbird, P.B., A.G. Gilman. Goodman and Gilman's The Pharmacological Basis of Therapeutics. 10th ed. New York, NY: McGraw-Hill, 2001., p. 1729

    The presence of bile is required for absorption of ergocalciferol and the extent of GI absorption may be decreased in patients with hepatic, biliary, or GI disease (e.g., Crohn's disease, Whipple's disease, sprue).

    McEvoy, G.K. (ed.). American Hospital Formulary Service- Drug Information 2004. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2004 (Plus Supplements)., p. 3515

    A longitudinal, randomized, double blind, placebo controlled study was conducted for 6 months to monitor ultraviolet B light exposure in human milk-fed infants both with and without supplemental vitamin D2, and to measure longitudinally the bone mineral content, growth, and serum concentrations of calcium, phosphorus, 25-hydroxyvitamin D3, 25-hydroxyvitamin D2, 1,25-dihydroxyvitamin D, and parathyroid hormone. Sequential sampling was performed of 46 human milk-fed white infants; 24 received 400 IU/day of vitamin D2, and 22 received placebo. An additional 12 patients were followed who received standard infant formula. 83% of patients completed a full 6 months of the study. Ultraviolet B light exposure and measurements of growth did not differ between groups. At 6 months, the human milk groups did not differ significantly in bone mineral content or serum concentrations of parathyroid hormone or 1,25-dihydroxyvitamin D, although total 25-hydroxyvitamin D values were significantly less in the unsupplemented human milk group (23.53 + or - 9.94 vs 36.96 + or - 11.86 ng/ml; p< 0.01). However, 25-hydroxyvitamin D3 serum concentrations were significantly higher in the unsupplemented human milk-fed group compared with the supplemented group (21.77 + or - 9.73 vs 11.74 + or - 10.27 ng/ml, p< 0.01) by 6 months of age. It was concluded that unsupplemented, human milk-fed infants had no evidence of vitamin D deficiency during the first 6 months of life.

    PMID:2783734 Greer FR, Marshall S; J Pediatr 114 (2): 204-12 (1989)

    A comparison was made of the ability of ergocalciferol and cholecalciferol to elevate plasma concentrations of vitamin D and 25-hydroxyvitamin D in cats. Cholecalciferol, given as an oral bolus in oil, resulted in a rapid elevation of plasma concentration of cholecalciferol followed by a rapid decline. In contrast, 25-hydroxyvitamin D concentration in plasma increased until day 3 after administration and remained elevated for a further 5 days. When 337 microg of both cholecalciferol and ergocalciferol in oil were given as an oral bolus to 10 cats, the peak plasma concentrations of cholecalciferol and ergocalciferol occurred at 8 or 12 h after administration. Peak concentrations of cholecalciferol were over twice those of ergocalciferol (570 +/- 80 vs. 264 +/- 42 nmol/l). The area under the curve 0-169 h for cholecalciferol was also more than twice that for ergocalciferol. When ergocalciferol and cholecalciferol were administered in a parenteral oil-based emulsion, higher concentrations of 25-hydroxyvitamin D3 than 25-hydroxyvitamin D2 were maintained in plasma. When both vitamins were included in the diet in the nutritional range, plasma concentrations of 25-hydroxyvitamin D2 were 0.68 of those of 25-hydroxyvitamin D3. Discrimination against ergocalciferol by cats appears to result from differences in affinity of the binding protein for the metabolites of the two forms of vitamin D. These results indicate that cats discriminate against ergocalciferol, and use it with an efficiency of 0.7 of that of cholecalciferol to maintain plasma 25-hydroxyvitamin D concentration.

    PMID:15379909 Morris JG; J Anim Physiol Anim Nutr (Berl) 86 (7-8): 229-38 (2002)

    Osteoporosis diminishes the quality of life in adults with cystic fibrosis (CF). Vitamin D deficiency resulting from malabsorption may be a factor in the etiology of low bone mineral density (BMD) in patients with CF. OBJECTIVE: Absorption of oral ergocalciferol (vitamin D2) and the consequent response of 25-hydroxyvitamin D in 10 adults with CF and exocrine pancreatic insufficiency was compared with that of 10 healthy control subjects. DESIGN: In this pharmacokinetic study, CF patients and control subjects were pair-matched on age, sex, and race. Each subject consumed 2500 microg oral vitamin D2 with a meal. The CF group also took pancreatic enzymes that provided > or = 80000 U lipase. Blood samples were obtained at baseline and at 5, 10, 24, 30, and 36 h after vitamin D2 consumption to measure serum vitamin D2 and 25-hydroxyvitamin D concentrations. RESULTS: Vitamin D2 concentrations in all subjects were near zero at baseline. CF patients absorbed less than one-half the amount of oral vitamin D2 that was absorbed by control subjects (P < 0.001). Absorption by the CF patients varied greatly; 2 patients absorbed virtually no vitamin D2. The rise in 25-hydroxyvitamin D in response to vitamin D2 absorption was significantly lower over time in the CF group than in the control group (P = 0.0012). CONCLUSIONS: Vitamin D2 absorption was significantly lower in CF patients than in control subjects. These results may help explain the etiology of vitamin D deficiency in CF patients, which may contribute to their low BMD.

    PMID:11237938 Lark RK et al; Am J Clin Nutr 73 (3): 602-6 (2001)

    5.6 Metabolism/Metabolites

    Ergocalciferol is inactive and hence, the first step in the body is ruled by the conversion of this parent compound to 25-hydroxyvitamin D by the action of CYP2R1 followed by the generation of the major circulating metabolite, 1,25-dihydroxyvitamin D or calcitrol. The generation of this major metabolite is ruled by the activity of CYP27B1 which is a key 1-hydroxylase and CYP24A1 which is responsible for the 25-hydroxylation. As part of the minor metabolism, ergocalciferol is transformed into 25-hydroxyvitamin D in the liver by the activity of D-25-hydroxylase and CYP2R1. As well, the formation of 24(R),25dihydroxyvitamin D is performed mainly in the kidneys by the action of 25-(OH)D-1-hydroxylase and 25-(OH)D-24-hydroxylase. Additionally, there are reports indicating significant activity of 3-epimerase in the metabolism of ergocalciferol which modifies the hydroxy group in C3 from the alpha position to a beta. The epimers formed seemed to have a reduced affinity for the vitamin D plasma proteins and to the vitamin D receptor. An alternative activation metabolic pathway has been reported and this process is characterized by the activity of CYP11A1 and its hydroxylation in the C-20. This 20-hydroxylated vitamin D seems to have similar biological activity than calcitriol.

    Vitamin D ... is hydroxylated at the 25 position in liver to produce 25-hydroxy-vitamin D3 which is the major metabolite circulating in the plasma. The metabolite is further hydroxylated in the kidney to 1,25-dihydroxy-vitamin D3, the most active metabolite in initiating intestinal transport of calcium & phosphate & mobilization of mineral from bone.

    American Medical Association. AMA Drug Evaluations Annual 1991. Chicago, IL: American Medical Association, 1991., p. 1952

    A polar, biologically active metabolite of vitamin D2, 25-hydroxyergocalciferol, which is about 1.5 times more active in curing rickets in rats, has been isolated from pig plasma.

    O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition, Whitehouse Station, NJ: Merck and Co., Inc., 2001., p. 1786

    Dihydrotachysterol is a vitamin D analog that may be regaurded as a reduction product of vitamin D2 ... Dihydrotachysterol is about 1/450 as active as vitamin D in the antirachitic assay, but at high doses it is much more effective than vitamin D in mobilizing bone mineral.

    Hardman, J.G., L.E. Limbird, P.B., A.G. Gilman. Goodman and Gilman's The Pharmacological Basis of Therapeutics. 10th ed. New York, NY: McGraw-Hill, 2001., p. 1730

    Vitamin D2 has known human metabolites that include Vitamin D2 3-glucuronide.

    S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560

    5.7 Biological Half-Life

    Ergocalciferol can be found circulation for 1-2 days. This quick turnover is presented due to hepatic conversion and uptake by fat and muscle cells where it is transformed to the active form.

    19 to 48 hours (however, stored in fat deposits in body for prolonged periods).

    Thomson.Micromedex. Drug Information for the Health Care Professional. 24th ed. Volume 1. Plus Updates. Content Reviewed by the United States Pharmacopeial Convention, Inc. Greenwood Village, CO. 2004., p. 2850

    5.8 Mechanism of Action

    For its activity, ergocalciferol is required to be transformed to its major active circulating hydroxylated metabolite and transported to the target organs in order to bind to its target, the vitamin D receptor. The activation of the vitamin D receptor is part of the vitamin D endocrine system and it is described by the production of a change in the transcription rates of the vitamin D receptor target genes. The target genes in the DNA affected by the presence of ergocalciferol are called vitamin D response elements which are dependent on co-modulators. The vitamin D receptor is a transcription factor and member of the steroid hormone nuclear receptor family. It presents a DNA binding domain (VDRE) that, when activated, recruits coregulatory complexes to regulate the genomic activity. Additionally, ergocalciferol presents nongenomic effects such as the stimulation of intestinal calcium transport via transcaltachia.

    The mechanism of action of calcitriol, the activated form of vitamin D, resembles that of the steroid and thyroid hormones. Thus, calcitriol binds to cytosolic receptors within target cells, and the receptor-hormone complex interacts with the DNA of certain genes to either enhance or inhibit their transcription. Structural analysis of the calcitriol receptor indicates that it belongs to the same supergene family as the steroid receptors. Calcitriol also appears to exert a few effects that occur too rapidly to be explained by genomic actions. /Calcitriol/

    Hardman, J.G., L.E. Limbird, P.B., A.G. Gilman. Goodman and Gilman's The Pharmacological Basis of Therapeutics. 10th ed. New York, NY: McGraw-Hill, 2001., p. 1728

    The mechanisms responsible for mobilization of bone salts have been only partially defined, and the interaction of multiple factors appears to be involved. Paradoxically, the cells responsible for bone resorption (osteoclasts) are not directly acted upon by calcitriol and do not appear to contain calcitriol receptors. Instead, calcitriol causes an increase in the number of osteoclasts available to resorb bone; this may result from an action upon myeloid hematopoietic precursor cells that are induced to differentiate toward functional osteoclasts. The cells responsible for bone formation (osteoblasts) do contain receptors, and calcitriol causes them to elaborate several proteins, including osteocalcin, a vitamin K-dependent protein that contains gamma-carboxyglutamic acid residues. The exact role of this protein is not known, but other unidentified substances are also elaborated that appear to stimulate the function of osteoclasts. In addition, calcitriol acts synergistically with gamma-interferon to increase the production of interleukin-1, a lymphokine that promotes bone resorption.

    Hardman, J.G., L.E. Limbird, P.B., A.G. Gilman. Goodman and Gilman's The Pharmacological Basis of Therapeutics. 10th ed. New York, NY: McGraw-Hill, 2001., p. 1728

    DRUG PRODUCT COMPOSITIONS

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    DOSAGE - FOR SOLUTION;INTRAVENOUS - 80MG/VIAL...DOSAGE - FOR SOLUTION;INTRAVENOUS - 80MG/VIAL;0.02MG/VIAL;0.001MG/VIAL;5MG/VIAL;0.01MG/VIAL;0.14MG/VIAL;17MG/VIAL;0.2MG/VIAL;1MG/VIAL;1.4MG/VIAL;EQ 1.2MG BASE/VIAL;0.7MG/VIAL;7MG/VIAL

    USFDA APPLICATION NUMBER - 18920

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    DOSAGE - INJECTABLE;INTRAVENOUS - 200MG/VIAL;...DOSAGE - INJECTABLE;INTRAVENOUS - 200MG/VIAL;0.06MG/VIAL;0.005MG/VIAL;15MG/VIAL;0.005MG/VIAL;0.6MG/VIAL;40MG/VIAL;6MG/VIAL;3.6MG/VIAL;6MG/VIAL;1MG/VIAL;10MG/VIAL;0.15MG/VIAL

    USFDA APPLICATION NUMBER - 21625

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    DOSAGE - CAPSULE;ORAL - 50,000 IU

    USFDA APPLICATION NUMBER - 3444

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    DOSAGE - INJECTABLE;INJECTION - 20MG/ML;0.006...DOSAGE - INJECTABLE;INJECTION - 20MG/ML;0.006MG/ML;0.05MCG/ML;1.5MG/ML;0.0005MG/ML;0.06MG/ML;4MG/ML;0.6MG/ML;0.36MG/ML;0.6MG/ML;0.1MG/ML;1MG/ML

    USFDA APPLICATION NUMBER - 8809

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    ABOUT THIS PAGE

    Looking for 50-14-6 / Vitamin D API manufacturers, exporters & distributors?

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    PharmaCompass offers a list of Vitamin D API manufacturers, exporters & distributors, which can be sorted by GMP, USDMF, JDMF, KDMF, CEP (COS), WC, Price,and more, enabling you to easily find the right Vitamin D manufacturer or Vitamin D supplier for your needs.

    Send us enquiries for free, and we will assist you in establishing a direct connection with your preferred Vitamin D manufacturer or Vitamin D supplier.

    PharmaCompass also assists you with knowing the Vitamin D API Price utilized in the formulation of products. Vitamin D API Price is not always fixed or binding as the Vitamin D Price is obtained through a variety of data sources. The Vitamin D Price can also vary due to multiple factors, including market conditions, regulatory modifications, or negotiated pricing deals.

    API | Excipient name

    Vitamin D

    Synonyms

    Vitamin d2, Calciferol, 50-14-6, Viosterol, Ergorone, Ercalciol

    Cas Number

    50-14-6

    Unique Ingredient Identifier (UNII)

    VS041H42XC

    About Vitamin D

    Derivatives of ERGOSTEROL formed by ULTRAVIOLET RAYS breaking of the C9-C10 bond. They differ from CHOLECALCIFEROL in having a double bond between C22 and C23 and a methyl group at C24.

    Viosterol Manufacturers

    A Viosterol manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of Viosterol, including repackagers and relabelers. The FDA regulates Viosterol manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. Viosterol API Manufacturers are required to adhere to Good Manufacturing Practices (GMP) to ensure that their products are consistently manufactured to meet established quality criteria.

    click here to find a list of Viosterol manufacturers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PhamaCompass.

    Viosterol Suppliers

    A Viosterol supplier is an individual or a company that provides Viosterol active pharmaceutical ingredient (API) or Viosterol finished formulations upon request. The Viosterol suppliers may include Viosterol API manufacturers, exporters, distributors and traders.

    click here to find a list of Viosterol suppliers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PharmaCompass.

    Viosterol USDMF

    A Viosterol DMF (Drug Master File) is a document detailing the whole manufacturing process of Viosterol active pharmaceutical ingredient (API) in detail. Different forms of Viosterol DMFs exist exist since differing nations have different regulations, such as Viosterol USDMF, ASMF (EDMF), JDMF, CDMF, etc.

    A Viosterol DMF submitted to regulatory agencies in the US is known as a USDMF. Viosterol USDMF includes data on Viosterol's chemical properties, information on the facilities and procedures used, and details about packaging and storage. The Viosterol USDMF is kept confidential to protect the manufacturer’s intellectual property.

    click here to find a list of Viosterol suppliers with USDMF on PharmaCompass.

    Viosterol JDMF

    The Pharmaceuticals and Medical Devices Agency (PMDA) established the Japan Drug Master File (JDMF), also known as the Master File (MF), to permit Japanese and foreign manufacturers of drug substances, intermediates, excipients, raw materials, and packaging materials (‘Products’) to voluntarily register confidential information about the production and management of their products in Japan.

    The Viosterol Drug Master File in Japan (Viosterol JDMF) empowers Viosterol API manufacturers to present comprehensive information (e.g., production methods, data, etc.) to the review authority, i.e., PMDA (Pharmaceuticals & Medical Devices Agency).

    PMDA reviews the Viosterol JDMF during the approval evaluation for pharmaceutical products. At the time of Viosterol JDMF registration, PMDA checks if the format is accurate, if the necessary items have been included (application), and if data has been attached.

    click here to find a list of Viosterol suppliers with JDMF on PharmaCompass.

    Viosterol NDC

    National Drug Code is a comprehensive database maintained by the FDA that contains information on all drugs marketed in the US. This directory includes information about finished drug products, unfinished drug products, and compounded drug products, including those containing Viosterol as an active pharmaceutical ingredient (API).

    Finished drug products

    The FDA updates the NDC directory daily. The NDC numbers for Viosterol API and other APIs are published in this directory by the FDA.

    Unfinished drugs

    The NDC unfinished drugs database includes product listing information submitted for all unfinished drugs, such as active pharmaceutical ingredients (APIs), drugs intended for further processing and bulk drug substances for compounding.

    Pharmaceutical companies that manufacture Viosterol as an active pharmaceutical ingredient (API) must furnish the FDA with an updated record of all drugs that they produce, prepare, propagate, compound, or process for commercial distribution in the US at their facilities.

    Compounded drug products

    The NDC directory also contains data on finished compounded human drug products that contain Viosterol and are produced by outsourcing facilities. While these outsourcing facilities are not mandated to assign a Viosterol NDC to their finished compounded human drug products, they may choose to do so.

    click here to find a list of Viosterol suppliers with NDC on PharmaCompass.

    Viosterol GMP

    Viosterol Active pharmaceutical ingredient (API) is produced in GMP-certified manufacturing facility.

    GMP stands for Good Manufacturing Practices, which is a system used in the pharmaceutical industry to make sure that goods are regularly produced and monitored in accordance with quality standards. The FDA’s current Good Manufacturing Practices requirements are referred to as cGMP or current GMP which indicates that the company follows the most recent GMP specifications. The World Health Organization (WHO) has its own set of GMP guidelines, called the WHO GMP. Different countries can also set their own guidelines for GMP like China (Chinese GMP) or the EU (EU GMP).

    PharmaCompass offers a list of Viosterol GMP manufacturers, exporters & distributors, which can be sorted by USDMF, JDMF, KDMF, CEP (COS), WC, API price, and more, enabling you to easily find the right Viosterol GMP manufacturer or Viosterol GMP API supplier for your needs.

    Viosterol CoA

    A Viosterol CoA (Certificate of Analysis) is a formal document that attests to Viosterol's compliance with Viosterol specifications and serves as a tool for batch-level quality control.

    Viosterol CoA mostly includes findings from lab analyses of a specific batch. For each Viosterol CoA document that a company creates, the USFDA specifies specific requirements, such as supplier information, material identification, transportation data, evidence of conformity and signature data.

    Viosterol may be tested according to a variety of international standards, such as European Pharmacopoeia (Viosterol EP), Viosterol JP (Japanese Pharmacopeia) and the US Pharmacopoeia (Viosterol USP).

    Inform the supplier about your product requirements, specifying if you need a product with particular monograph like EP (Ph. Eur.), USP, JP, BP, or any other quality. In addition, clarify whether you need hydrochloride (HCl), anhydricum, base, micronisatum or a specific level of purity. To find reputable suppliers, utilize the filters and select those certified by GMP, FDA, or any other certification as per your requirement.
    For your convenience, we have listed synonyms and CAS numbers to help you find the best supplier. The use of synonyms and CAS numbers can be helpful in identifying potential suppliers, but it is crucial to note that they might not always indicate the exact same product. It is important to confirm the product details with the supplier before making a purchase to ensure that it meets your requirements.
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