CAS 67-97-0|CAS 22350-41-0|(+)-维生素 D3|活化7-脱氢胆甾醇|胆钙化醇|活化7-脱氢胆固醇|vitamin D3|Cholecalciferol|(1S,3Z)-3-{2-[(1R,3aS,4E,7aR)-7a-methyl-1-[(2R)-6-methylheptan-2-yl]-octahydro-1H-inden...

General Information

Structure

Molecular Formula

C₂₇H₄₄O

Molecular Mass

384.63766

Exact Mass

384.33921603

Charge

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/t21-,24+,25-,26+,27-/m1/s1

InChIKey

QYSXJUFSXHHAJI-RWDMXNMGSA-N

Canonic Smiles

CC(CCC[C@H]([C@H]1CC[C@@H]2[C@]1(C)CCCC2=CC=C1C[C@@H](O)CCC1=C)C)C

Isomeric Smiles

O[C@@H]1CC(=CC=C2[C@H]3[C@@]([C@H](CC3)[C@@H](CCCC(C)C)C)(CCC2)C)C(=C)CC1

Calculated Properties

JChem

Acid pKa

18.384342

H Acceptors

H Donor

LogD (pH = 5.5)

7.1254606

LogD (pH = 7.4)

7.1254606

Log P

7.1254606

Molar Refractivity

123.2245

Polarizability

48.251457

Polar Surface Area

20.23

Rotatable Bonds

Lipinski's Rule of Five

false

ALOGPS 2.1

Log P

7.98

LOG S

-6.01

Solubility (Water)

3.80e-04 g/l

Data Source

Names and Identifiers

Synonyms

(+)-维生素 D3活化7-脱氢胆甾醇胆钙化醇活化7-脱氢胆固醇Cholecalciferol胆骨化醇Vitamin D3 solutionCholecalciferol solution胆钙化醇溶液(+)-Vitamin D3Calciol胆钙化醇Cholecalciferol胆钙化固醇（维生素 D3）7-Dehydrocholesterol activatedActivated 7-dehydrocholesterolCholecalciferol (D3)CholecalciferolCCCholecalciferol, D3ColecalciferolVitamin D3CholecalciferolumVigorsanProvitinaVitamin D3VidekholDeparalVi-De3EbivitRicketonDuphafral D3 1000Oleovitamin D3DelsterolVitinc Dan-Dee-3(3β,5Z,7E)-9,10-Secocholesta-5,7,10(19)-trien-3-olColecalciferol(3β,5E,7E)-9,10-Secocholesta-5,7,10(19)-trien-3-olVitamin D3trans-Vitamin D35,6-trans-Vitamin D3 (1S,3E)-3-[(2E)-2-[(1R,3aS,7aR)-1-[(1R)-1,5-Dimethylhexyl]octahydro-7a-methyl-4H-inden-4-ylidene]ethylidene]-4-methylenecyclohexanol(E,E)-9,10-Secocholesta-5,7,10(19)-trien-3β-ol5,6-trans-Cholecalciferol维生素D3

IUPAC Traditional name

vitamin D3 cholecalciferol (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 delta-D

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

Brand Name

Micro-DeeRicketonProvitamin D3TrivitanVigantolOleovitamin D3DelsterolDelta-DEbivitVigorsanCalciolDeparalProvitinaProvitamine

Names and Identifiers

Registration numbers

Beilstein Number

2339331

PubChem SID

2489319724893192248924042488919216096351724871395

MDL Number

CAS Number

EC Number

Merck Index

PubChem CID

Registration numbers

Properties

Safety Information

H301-H311-H330-H372

H225

Pharmacology Properties

Calcium homeostasis regulator

Properties

Related Proteins

No Data Available

Click here to submit data

Molecular Spectra

No Data Available

Click here to submit data

Molecule Details

DrugBank

DB00169

Drug Groups

approved; 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]

Indication

For 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.

Pharmacology

Cholecalciferol (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.

Toxicity

Hypercalcemia - 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

Biotransformation

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.

Absorption

Readily absorbed

Half Life

Several weeks

Protein Binding

50% to 80%

References

• 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

• [Wikipedia]

• [PDRhealth]

• [Drugs.com]

Sigma Aldrich

C9774

包装
Packaged in flame-sealed ampules under Argon
Biochem/physiol Actions
维生素 D 借以发挥作用的受体是配体依赖性转录因子超家族的成员。调控正常细胞和癌细胞的增殖和分化。对乳腺癌、结肠癌和前列腺癌细胞具有抗增殖和抗转移作用。肠和骨骼中的活化维生素 D 受体维持着钙的吸收和平衡。

C1357

Biochem/physiol Actions
维生素 D 借以发挥作用的受体是配体依赖性转录因子超家族的成员。调控正常细胞和癌细胞的增殖和分化。对乳腺癌、结肠癌和前列腺癌细胞具有抗增殖和抗转移作用。肠和骨骼中的活化维生素 D 受体维持着钙的吸收和平衡。

C9756

包装
1, 5 g in glass bottle
Biochem/physiol Actions
维生素 D 借以发挥作用的受体是配体依赖性转录因子超家族的成员。调控正常细胞和癌细胞的增殖和分化。对乳腺癌、结肠癌和前列腺癌细胞具有抗增殖和抗转移作用。肠和骨骼中的活化维生素 D 受体维持着钙的吸收和平衡。

89193

Biochem/physiol Actions
Vitamin D acts through a receptor that is a member of the ligand-dependent transcription factor superfamily. Modulates the proliferation and differentiation of both normal and cancer cells. Has antiproliferative and antimetastatic effects on breast, colon, and prostate cancer cells. Activated vitamin D receptors in intestine and bone maintain calcium absorbance and homeostasis.

95230

Other Notes
Review: Vitamin D: Recent advances1
Unit Definition
1 U corresponds to 1 international U according to commentary-DAB, 8th issue, 38 (1981)
Biochem/physiol Actions
Vitamin D acts through a receptor that is a member of the ligand-dependent transcription factor superfamily. Modulates the proliferation and differentiation of both normal and cancer cells. Has antiproliferative and antimetastatic effects on breast, colon, and prostate cancer cells. Activated vitamin D receptors in intestine and bone maintain calcium absorbance and homeostasis.

TRC

V676065

5,6-trans-Vitamin D3 is the major photoisomer of Vitamin D3 analog, as an impurity.

V676045

The vitamin that mediates intestinal calcium absorbtion, bone calcium metabolism and probably, muscle activity. Occurs in and is isolated from fish liver oils. Vitamin D acts through a receptor that is a member of the ligand-dependent transcription factor

Molecule Details

References

PubChem Literature

From Data Sources

• 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

• Welsh, J., et al.: J. Nutr., 133, 2425S (1972)

• Holick, M.F., Rec. Res. Canc. Res., 164, 3 (1972)

• Palmer, H.G., et al.: Cancer Res., 63, 7799 (1972)

• Haussler, R., et al.: J. Biol. Chem., 247, 2328 (1972)

• Bikle, D., et al.: Biochemistry, 25, 1545 (1986)

• Baran, D., et al.: J. Cell Biochem., 50, 124 (1986)

• Tian, X., et al.: J. Biol. Chem., 268, 14888 (1986)

• Webb, A., et al.: J. Clin. Endocrinol. Metab., 68, 882 (1986)

• Jankowski, P. et al., Tetrahedron, 1998, 54, 12071-12150, (rev, synth)

• Wing, R.M. et al., J.A.C.S., 1975, 97, 4980, (pmr, conformn)

• Wilson, S.R. et al., Tet. Lett., 1984, 25, 3147, (synth)

• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 1058

• Zhu, G.-D. et al., Chem. Rev., 1995, 95, 1877, (rev, synth)

• Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 3, 570C, (nmr)

• Coldwell, R.D. et al., Steroids, 1990, 55, 418, (rev)

• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, CMC750; HJV000

• Aldrich Library of FT-IR Spectra, 1st edn., 1985, 2, 1049D, (ir)

• Pure Appl. Chem., 1982, 54, 1511, (nomencl)

• Koshy, K.T. et al., Anal. Profiles Drug Subst., 1984, 13, 655, (rev)

• Nemoto, H. et al., Heterocycles, 1985, 23, 567, (synth)

• Borle, A.B., Annu. Rev. Physiol., 1974, 36, 361, (rev, metab)

• Inhoffen, M. et al., Angew. Chem., 1960, 72, 875, (rev)

• Haussler, M.S. et al., J. Biol. Chem., 1972, 247, 2328, (rev)

• Okamura, W.H. et al., Tet. Lett., 1976, 4807, (ms)

• Fraser, D.R., Br. Med. Bull., 1981, 37, 37, (rev, metab)

• Nemoto, H. et al., J.O.C., 1986, 51, 5311, (synth)

• Encyclopedia of Food and Color Additives, (ed. Burdock, G.A.), CRC Press, 1997, 2935-2937, (props, use)

• Lythgoe, B. et al., Tet. Lett., 1977, 3685, (synth)

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

Synonyms

IUPAC Traditional name

vitamin D3 cholecalciferol (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 delta-D

IUPAC name

Brand Name

Micro-DeeRicketonProvitamin D3TrivitanVigantolOleovitamin D3DelsterolDelta-DEbivitVigorsanCalciolDeparalProvitinaProvitamine

Registration numbers

Beilstein Number

2339331

PubChem SID

2489319724893192248924042488919216096351724871395

MDL Number

CAS Number

EC Number

Merck Index

PubChem CID

References

PubChem Literature

From Data Sources

• 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

• Welsh, J., et al.: J. Nutr., 133, 2425S (1972)

• Holick, M.F., Rec. Res. Canc. Res., 164, 3 (1972)

• Palmer, H.G., et al.: Cancer Res., 63, 7799 (1972)

• Haussler, R., et al.: J. Biol. Chem., 247, 2328 (1972)

• Bikle, D., et al.: Biochemistry, 25, 1545 (1986)

• Baran, D., et al.: J. Cell Biochem., 50, 124 (1986)

• Tian, X., et al.: J. Biol. Chem., 268, 14888 (1986)

• Webb, A., et al.: J. Clin. Endocrinol. Metab., 68, 882 (1986)

• Jankowski, P. et al., Tetrahedron, 1998, 54, 12071-12150, (rev, synth)

• Wing, R.M. et al., J.A.C.S., 1975, 97, 4980, (pmr, conformn)

• Wilson, S.R. et al., Tet. Lett., 1984, 25, 3147, (synth)

• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 1058

• Zhu, G.-D. et al., Chem. Rev., 1995, 95, 1877, (rev, synth)

• Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 3, 570C, (nmr)

• Coldwell, R.D. et al., Steroids, 1990, 55, 418, (rev)

• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, CMC750; HJV000

• Aldrich Library of FT-IR Spectra, 1st edn., 1985, 2, 1049D, (ir)

• Pure Appl. Chem., 1982, 54, 1511, (nomencl)

• Koshy, K.T. et al., Anal. Profiles Drug Subst., 1984, 13, 655, (rev)

• Nemoto, H. et al., Heterocycles, 1985, 23, 567, (synth)

• Borle, A.B., Annu. Rev. Physiol., 1974, 36, 361, (rev, metab)

• Inhoffen, M. et al., Angew. Chem., 1960, 72, 875, (rev)

• Haussler, M.S. et al., J. Biol. Chem., 1972, 247, 2328, (rev)

• Okamura, W.H. et al., Tet. Lett., 1976, 4807, (ms)

• Fraser, D.R., Br. Med. Bull., 1981, 37, 37, (rev, metab)

• Nemoto, H. et al., J.O.C., 1986, 51, 5311, (synth)

• Encyclopedia of Food and Color Additives, (ed. Burdock, G.A.), CRC Press, 1997, 2935-2937, (props, use)

• Lythgoe, B. et al., Tet. Lett., 1977, 3685, (synth)

Bioactivity

PubChem BioAssay

Molecule Details

DrugBank

DB00169

Drug Groups

approved; nutraceutical

Description

Indication

Pharmacology

Toxicity

Affected Organisms

Humans and other mammals

Biotransformation

Absorption

Readily absorbed

Half Life

Several weeks

Protein Binding

50% to 80%

References

• 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

• [Wikipedia]

• [PDRhealth]

• [Drugs.com]

Sigma Aldrich

C9774

C1357

C9756

89193

95230

TRC

V676065