Chemical Component Summary

Name1-alpha-hydroxy-vitamin D3
Identifiers(1~{R},3~{S},5~{Z})-5-[(2~{E})-2-[(1~{R},3~{a}~{S},7~{a}~{R})-7~{a}-methyl-1-[(2~{R})-6-methylheptan-2-yl]-2,3,3~{a},5,6,7-hexahydro-1~{H}-inden-4-ylidene]ethylidene]-4-methylidene-cyclohexane-1,3-diol
FormulaC27 H44 O2
Molecular Weight400.637
TypeNON-POLYMER
Isomeric SMILESC[C@H](CCCC(C)C)[C@H]1CC[C@@H]\2[C@@]1(CCC/C2=C\C=C/3\C[C@H](C[C@@H](C3=C)O)O)C
InChIInChI=1S/C27H44O2/c1-18(2)8-6-9-19(3)24-13-14-25-21(10-7-15-27(24,25)5)11-12-22-16-23(28)17-26(29)20(22)4/h11-12,18-19,23-26,28-29H,4,6-10,13-17H2,1-3,5H3/b21-11+,22-12-/t19-,23-,24-,25+,26+,27-/m1/s1
InChIKeyOFHCOWSQAMBJIW-AVJTYSNKSA-N

Chemical Details

Formal Charge0
Atom Count73
Chiral Atom Count6
Bond Count75
Aromatic Bond Count0

Drug Info: DrugBank

DrugBank IDDB01436 
NameAlfacalcidol
Groups
  • nutraceutical
  • approved
DescriptionAlfacalcidol, or 1-alpha-hydroxycholecalciferol or 1-alpha-hydroxyvitamin D3, is a non-endogenous analogue of [vitamin D].[A234044] It plays an essential function in calcium homeostasis and bone metabolism. Alfacaldisol is activated by the enzyme 25-hydroxylase in the liver to mediate its effects in the body, or most importantly, the kidneys and bones. The pharmacological actions of alfacalcidol are prolonged than vitamin D because a negative feedback mechanism regulates the final activation step of vitamin D in the kidneys.[A175348,A175351] Alfacalcidol is available in oral and intravenous formulations. In Canada, it is marketed as ONE-ALPHA, which manages hypocalcemia, secondary hyperparathyroidism, and osteodystrophy in adults with chronic renal failure.[L33284] In approving European countries, alfacalcidol is also indicated for managing nutritional and malabsorptive rickets and osteomalacia, vitamin D-dependent rickets and osteomalacia, and hypophosphataemic vitamin D resistant rickets and osteomalacia.[L33364,L33369]
Synonyms
  • Alfacalcidolum
  • 1α-hydroxyvitamin D3
  • Alfacalcidol
  • (5Z,7E)-9,10-seco-5,7,10(19)-cholestatrien-1α,3β-diol
  • 1α-hydroxycholecalciferol
Brand Names
  • Sandoz Alfacalcidol
  • Alfacalcidol Capsules
  • One-alpha Sol 0.2mcg/ml
  • One-alpha
IndicationAlfacalcidol is indicated in adult patients with chronic renal failure for the management of hypocalcemia, secondary hyperparathyroidism, or osteodystrophy.[L33284] Alfacalcidol is indicated in the management of nutritional and malabsorptive rickets and osteomalacia, vitamin D-dependent rickets and osteomalacia, and hypophosphataemic vitamin D resistant rickets and osteomalacia.[L33364,L33369]
Categories
  • Alimentary Tract and Metabolism
  • Bone Density Conservation Agents
  • Cholestanes
  • Cholestenes
  • Drugs Affecting Bone Structure and Mineralization
ATC-Code
  • A11CC03
  • M05BB06
CAS number41294-56-8

Drug Targets

NameTarget SequencePharmacological ActionActions
Vitamin D3 receptorMEAMAASTSLPDPGDFDRNVPRICGVCGDRATGFHFNAMTCEGCKGFFRR...unknownagonist
25-hydroxyvitamin D-1 alpha hydroxylase, mitochondrialMTQTLKYASRVFHRVRWAPELGASLGYREYHSARRSLADIPGPSTPSFLA...unknown
Retinoic acid receptor RXR-alphaMDTKHFLPLDFSTQVNSSLTSPTGRGSMAAPSLHPSLGPGIGSPGQLHSP...unknown
Vitamin D-binding proteinMKRVLVLLLAVAFGHALERGRDYEKNKVCKEFSHLGKEDFTSLSLVLYSR...unknownsubstrate
Alpha globinMVLSPADKTNVKAAWGKVGAHAGEYGAEALERHFDLSHGSAQVKGHGKKV...unknownbinder
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
Pharos CHEMBL1601669
PubChem 5282181
ChEMBL CHEMBL1601669
ChEBI CHEBI:31186, CHEBI:94779