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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


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CHINA 641005 CHINA, , China China","customerAddress":"401 4TH FL WINDSOR HOUSE CST RD"},{"dataSource":"API Import","activeIngredients":"","year":"2024","qtr":"Q2","strtotime":1718735400,"product":"VITAMIN D3 (CHOLECALCIFEROL)","address":"VILLAGE NAG KALAN,MAJITHA ROAD,MAJ","city":"AMRITSAR,PUNJAB","supplier":"YUANFANG CHEMICAL LIMITED","supplierCountry":"CHINA","foreign_port":"HONG KONG","customer":"KWALITY PHARMACEUTICALS","customerCountry":"INDIA","quantity":"7.00","actualQuantity":"7","unit":"KGS","unitRateFc":"980","totalValueFC":"6927.4","currency":"USD","unitRateINR":"82614","date":"19-Jun-2024","totalValueINR":"578298","totalValueInUsd":"6927.4","indian_port":"Delhi Air","hs_no":"29339990","bill_no":"4080023","productDescription":"API","marketType":"REGULATED MARKET","country":"CHINA","selfForZScoreResived":"Pharma Grade","supplierPort":"HONG KONG","supplierAddress":"ADD: 1601 BUILDING 9, NO. 1679NINGCHUAN ROAD NINGBOCHINA SDNF","customerAddress":"VILLAGE NAG KALAN,MAJITHA ROAD,MAJ"},{"dataSource":"API Import","activeIngredients":"","year":"2024","qtr":"Q2","strtotime":1718735400,"product":"ERGOCALCIFEROL (VITAMIN D2) (LOT NO. 240506)(QTY. 7000GRAM)","address":"DIL COMPLEX, S. 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ROAD,"},{"dataSource":"API Import","activeIngredients":"","year":"2024","qtr":"Q2","strtotime":1719167400,"product":"VITAMIN D2 (ERGOCALCIFEROL) 40 MIU\/G PURE CRYSTALS FCC","address":"PLOT NO.B11, PHASE-1, MEPZ-SEZ,","city":"CHENNAI, TAMIL NADU","supplier":"HEXAGON NUTRITION CHINA LIMITED","supplierCountry":"CHINA","foreign_port":"N\/A","customer":"HEXAGON NUTRITION PVT LTD","customerCountry":"INDIA","quantity":"5.00","actualQuantity":"5","unit":"KGS","unitRateFc":"6181.3","totalValueFC":"31210.1","currency":"USD","unitRateINR":"521079.4","date":"24-Jun-2024","totalValueINR":"2605397","totalValueInUsd":"31210.1","indian_port":"Madras-EPZ\/SEZ","hs_no":"29362940","bill_no":"1012432","productDescription":"API","marketType":"REGULATED MARKET","country":"CHINA","selfForZScoreResived":"Pharma Grade","supplierPort":"N\/A","supplierAddress":"N\/A","customerAddress":"PLOT NO.B11, PHASE-1, MEPZ-SEZ,"},{"dataSource":"API Import","activeIngredients":"","year":"2024","qtr":"Q2","strtotime":1719513000,"product":"VITAMIN D2 FCC (ERGOCALCIFEROL)NOT FOR MEDICINAL USE","address":"6-1-103\/41. 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CHINA","customerAddress":"K.C.RAGHU,NO.44\/2A, KODIGEHALLIGATE"},{"dataSource":"API Import","activeIngredients":"","year":"2024","qtr":"Q3","strtotime":1721845800,"product":"VITAMIN D3 CRYSTALLINE PH -FRANCE (FOR MEDICAL USE)","address":"401 4TH FL WINDSOR HOUSE CST RD","city":"MUMBAI, MAHARASHTRA.","supplier":"ROYAL DSM","supplierCountry":"FRANCE","foreign_port":"AMSTERDAM, SCHIPHOL","customer":"ROYAL DSM","customerCountry":"INDIA","quantity":"3.00","actualQuantity":"3","unit":"KGS","unitRateFc":"225916","totalValueFC":"8107.9","currency":"INR","unitRateINR":"225916","date":"25-Jul-2024","totalValueINR":"677748","totalValueInUsd":"8107.9","indian_port":"Bombay Air","hs_no":"29362940","bill_no":"4676658","productDescription":"API","marketType":"REGULATED MARKET","country":"FRANCE","selfForZScoreResived":"Crystalline","supplierPort":"AMSTERDAM, SCHIPHOL","supplierAddress":"30 PASIR PANJANG ROAD #13-31, MAPLETREE BUSINESS CITY, Singapore - 117440, , Singapore Singapore","customerAddress":"401 4TH FL WINDSOR HOUSE CST RD"},{"dataSource":"API Import","activeIngredients":"","year":"2024","qtr":"Q3","strtotime":1721845800,"product":"VITAMIN D2 (NOT FOR MEDICINAL USE)","address":"KHASRA NO.22 VILLAGE RAIPUR,BHAGWA","city":"ROORKEE,UTTARAKHAND","supplier":"SHANGHAI VIGOVITA BIOTECH CO.,LTD.","supplierCountry":"CHINA","foreign_port":"BEIJING","customer":"NATURAL HERBS AND ","customerCountry":"INDIA","quantity":"6.00","actualQuantity":"6","unit":"KGS","unitRateFc":"5650","totalValueFC":"34288.9","currency":"USD","unitRateINR":"477707.5","date":"25-Jul-2024","totalValueINR":"2866245","totalValueInUsd":"34288.9","indian_port":"Delhi Air","hs_no":"29362990","bill_no":"4700940","productDescription":"API","marketType":"REGULATED MARKET","country":"CHINA","selfForZScoreResived":"Non Pharma","supplierPort":"BEIJING","supplierAddress":"ROOM 1803 BUILDING 1 NO.2290 ZUCHO-(SHANGHAI) CHINA CN","customerAddress":"KHASRA NO.22 VILLAGE RAIPUR,BHAGWA"},{"dataSource":"API Import","activeIngredients":"","year":"2024","qtr":"Q3","strtotime":1723401000,"product":"CHOLECALCIFEROL USP(VITAMIN D3 40 MIU\/G)","address":"DIL COMPLEX, S. V. ROAD,","city":"THANE, MAHARASHTRA","supplier":"FERMENTA USA LLC","supplierCountry":"UNITED STATES","foreign_port":"O'HARE APT\/CHICAGO, IL","customer":"FERMENTA BIOTECH LIMITED","customerCountry":"INDIA","quantity":"17.00","actualQuantity":"17","unit":"KGS","unitRateFc":"1965.5","totalValueFC":"33701.1","currency":"USD","unitRateINR":"166282.3","date":"12-Aug-2024","totalValueINR":"2826799","totalValueInUsd":"33701.1","indian_port":"Dahez-SEZ","hs_no":"29362940","bill_no":"1003983","productDescription":"API","marketType":"REGULATED MARKET","country":"UNITED STATES","selfForZScoreResived":"Pharma Grade","supplierPort":"O'HARE APT\/CHICAGO, IL","supplierAddress":"N\/A","customerAddress":"DIL COMPLEX, S. V. 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04-Jan-2021
30-Sep-2024
KGS
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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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