PDN

17,21-DIHYDROXYPREGNA-1,4-DIENE-3,11,20-TRIONE

Created: 2001-06-04
Last modified:  2020-06-05

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Chemical Details

Formal Charge0
Atom Count52
Chiral Atom Count6
Bond Count55
Aromatic Bond Count0
2D diagram of PDN
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Chemical Component Summary

Name17,21-DIHYDROXYPREGNA-1,4-DIENE-3,11,20-TRIONE
SynonymsPREDNISONE; 1,4 PREGNADIENE-17ALPHA,21-DIOL-3,11,20-TRIONE; 1-CORTISONE; DEHYDROCORTISONE
Systematic Name (OpenEye OEToolkits)(8S,9S,10R,13S,14S,17R)-17-(1,2-dihydroxyethenyl)-17-hydroxy-10,13-dimethyl-6,7,8,9,12,14,15,16-octahydrocyclopenta[a]phenanthrene-3,11-dione
FormulaC21 H26 O5
Molecular Weight358.428
TypeNON-POLYMER

Chemical Descriptors

TypeProgram Version Descriptor
SMILESACDLabs10.04O=C2CC4(C(C3CCC1=CC(=O)C=CC1(C)C23)CCC4(O)C(\O)=C\O)C
SMILESCACTVS3.341C[C]12CC(=O)[CH]3[CH](CCC4=CC(=O)C=C[C]34C)[CH]1CC[C]2(O)C(O)=CO
SMILESOpenEye OEToolkits1.5.0CC12CC(=O)C3C(C1CCC2(C(=CO)O)O)CCC4=CC(=O)C=CC34C
Canonical SMILESCACTVS3.341 C[C@]12CC(=O)[C@H]3[C@@H](CCC4=CC(=O)C=C[C@]34C)[C@@H]1CC[C@]2(O)\C(O)=C\O
Canonical SMILESOpenEye OEToolkits1.5.0 C[C@]12CC(=O)[C@H]3[C@H]([C@@H]1CC[C@@]2(C(=CO)O)O)CCC4=CC(=O)C=C[C@]34C
InChIInChI1.03 InChI=1S/C21H26O5/c1-19-7-5-13(23)9-12(19)3-4-14-15-6-8-21(26,17(25)11-22)20(15,2)10-16(24)18(14)19/h5,7,9,11,14-15,18,22,25-26H,3-4,6,8,10H2,1-2H3/b17-11-/t14-,15-,18+,19-,20-,21-/m0/s1
InChIKeyInChI1.03 WZTZVUUYKIOIRV-LMZHSBCYSA-N

Drug Info: DrugBank

DrugBank IDDB00635 
NamePrednisone
Groups
  • approved
  • vet_approved
DescriptionA synthetic anti-inflammatory glucocorticoid derived from [cortisone].[A187463] It is biologically inert and converted to [prednisolone] in the liver.[L10502] Prednisone was granted FDA approval on 21 February 1955.[L10496]
Synonyms
  • Dehydrocortisone
  • Prednisonum
  • Prednisone
  • Prednisona
  • 17,21-Dihydroxypregna-1,4-diene-3,11,20-trione
Brand Names
  • Prednisone Tab 5mg
  • Apo Prednisone Tab 50mg
  • Contrast Allergy PreMed Pack
  • Jaa Prednisone Tab 50mg USP
  • PredniSONE
IndicationPrednisone is indicated as an anti-inflammatory or immunosuppressive drug for allergic, dermatologic, gastrointestinal, hematologic, ophthalmologic, nervous system, renal, respiratory, rheumatologic, infectious, endocrine, or neoplastic conditions as well as in organ transplant.[L10502]
Categories
  • Adrenal Cortex Hormones
  • Adrenals
  • Alimentary Tract and Metabolism
  • Anti-Inflammatory Agents
  • Antidiarrheals, Intestinal Antiinflammatory/antiinfective Agents
ATC-Code
  • A07EA03
  • H02AB07
CAS number53-03-2

Drug Targets

NameTarget SequencePharmacological ActionActions
Glucocorticoid receptorMDSKESLTPGREENPSSVLAQERGDVMDFYKTLRGGATVKVSASSPSLAV...unknownagonist
Cytochrome P450 2C19MDPFVVLVLCLSCLLLLSIWRQSSGRGKLPPGPTPLPVIGNILQIDIKDV...unknowninducer
Cytochrome P450 3A5MDLIPNLAVETWLLLAVSLVLLYLYGTRTHGLFKRLGIPGPTPLPLLGNV...unknowninducer
Cytochrome P450 3A SubfamilyMALIPDLAMETWLLLAVSLVLLYLYGTHSHGLFKKLGIPGPTPLPFLGNI...unknowninducer
Cytochrome P450 2A6MLASGMLLVALLVCLTVMVLMSVWQQRKSKGKLPPGPTPLPFIGNYLQLN...unknowninducer
View More
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
PubChem 5289127