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52-21-1 molecular structure
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2-[(1S,2R,10S,11S,14R,15S,17S)-14,17-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,6-dien-14-yl]-2-oxoethyl acetate

ChemBase ID: 73158
Molecular Formular: C23H30O6
Molecular Mass: 402.4807
Monoisotopic Mass: 402.20423868
SMILES and InChIs

SMILES:
C1=C[C@]2(C(=CC1=O)CC[C@@H]1[C@@H]2[C@H](C[C@]2([C@H]1CC[C@@]2(C(=O)COC(=O)C)O)C)O)C
Canonical SMILES:
CC(=O)OCC(=O)[C@@]1(O)CC[C@@H]2[C@]1(C)C[C@H](O)[C@H]1[C@H]2CCC2=CC(=O)C=C[C@]12C
InChI:
InChI=1S/C23H30O6/c1-13(24)29-12-19(27)23(28)9-7-17-16-5-4-14-10-15(25)6-8-21(14,2)20(16)18(26)11-22(17,23)3/h6,8,10,16-18,20,26,28H,4-5,7,9,11-12H2,1-3H3/t16-,17-,18-,20+,21-,22-,23-/m0/s1
InChIKey:
LRJOMUJRLNCICJ-JZYPGELDSA-N

Cite this record

CBID:73158 http://www.chembase.cn/molecule-73158.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
2-[(1S,2R,10S,11S,14R,15S,17S)-14,17-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,6-dien-14-yl]-2-oxoethyl acetate
2-[(1S,2R,10S,11S,14R,15S,17S)-14,17-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.02,7.011,15]heptadeca-3,6-dien-14-yl]-2-oxoethyl acetate
2-[(1S,2R,10S,11S,14R,15S,17S)-14,17-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0?,?.0??,??]heptadeca-3,6-dien-14-yl]-2-oxoethyl acetate
IUPAC Traditional name
prednisolone acetate
2-[(1S,2R,10S,11S,14R,15S,17S)-14,17-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.02,7.011,15]heptadeca-3,6-dien-14-yl]-2-oxoethyl acetate
Synonyms
Omnipred
Prednisolone acetate
1,4-Pregnadiene-11β,17α,21-triol-3,20-dione 21-acetate
11β,17α,21-Trihydroxy-1,4-pregnadiene-3,20-dione 21-acetate
21-Acetoxy-1,4-pregnadiene-11β,17α-diol-3,20-dione
Prednisolone 21-acetate
PREDNISOLONE-21-ACETATE
Prednelan
Inflanefran Forte
Nisolone
Prednisolone acetate
(11β)-21-(Acetyloxy)-11,17-dihydroxypregna-1,4-diene-3,20-dione
11β,17α,21-Trihydroxypregna-1,4-diene-3,20-dione 21-acetate
21-(Acetoxy)-11β,17α-dihydroxypregna-1,4-diene-3,20-dione
Cormalone
Cortipred
Deltilen
Econopred
Falcon
Meticortelone Acetate
Predalone 50
Prediacortin
Predicort
Prednelan N
Prednidoren
Prenema
Supercortyl
1,4-孕甾二烯-11β,17α,21-三醇-3,20-二酮 21-醋酸酯
11β,17α,21-三羟基-1,4-孕甾二烯-3,20-二酮 21-醋酸酯
21-乙酰氧基-1,4-孕甾二烯-11β,17α-二醇-3,20-二酮
醋酸泼尼松龙
CAS Number
52-21-1
EC Number
200-134-1
MDL Number
MFCD00037710
Beilstein Number
3111798
PubChem SID
24898962
24887840
24870352
162038078
PubChem CID
5834

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 12.610176  H Acceptors
H Donor LogD (pH = 5.5) 1.7141153 
LogD (pH = 7.4) 1.7141126  Log P 1.7141154 
Molar Refractivity 107.6448 cm3 Polarizability 41.884506 Å3
Polar Surface Area 100.9 Å2 Rotatable Bonds
Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Melting Point
240-244 °C expand Show data source
Optical Rotation
[α]20/D +116±2°, c = 1% in dioxane expand Show data source
Storage Condition
-20°C expand Show data source
RTECS
TU4152500 expand Show data source
European Hazard Symbols
Toxic Toxic (T) expand Show data source
UN Number
2811 expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Hazard Class
6.1 expand Show data source
Packing Group
3 expand Show data source
Risk Statements
25 expand Show data source
Safety Statements
45 expand Show data source
GHS Pictograms
GHS06 expand Show data source
GHS Signal Word
Danger expand Show data source
GHS Hazard statements
H300 expand Show data source
GHS Precautionary statements
P264-P301 + P310 expand Show data source
Personal Protective Equipment
Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges expand Show data source
RID/ADR
UN 2811 6.1/PG 3 expand Show data source
Mechanism of Action
ACTH antagonist expand Show data source
ACTH secretion inhibitor expand Show data source
Calcium mobilizer expand Show data source
Corticosteroid expand Show data source
Gluconeogenesis promoter expand Show data source
Glycogen deposition inhibitor expand Show data source
Phosphorus mobilizer expand Show data source
Purity
≥97% expand Show data source
≥97.0% (HPLC) expand Show data source
Grade
VETRANAL™, analytical standard expand Show data source
Salt Data
Free Base expand Show data source
Certificate of Analysis
Download expand Show data source
Download expand Show data source
Application(s)
Antiinflammatory agent expand Show data source
Immunosuppressive expand Show data source
Empirical Formula (Hill Notation)
C23H30O6 expand Show data source

DETAILS

DETAILS

MP Biomedicals MP Biomedicals Selleck Chemicals Selleck Chemicals Sigma Aldrich Sigma Aldrich TRC TRC
Selleck Chemicals - S2570 external link
Research Area: Inflammation
Biological Activity:
Prednisolone acetate is a synthetic corticosteroid drug that is particularly effective as an immunosuppressant agent. Prednisolone is converted from prednisone by the liver.Prednisolone is used to achieve prompt suppression of inflammation in many inflammatory and allergic conditions. Examples of inflammatory conditions include rheumatoid arthritis, systemic lupus, acute gouty arthritis, psoriatic arthritis, ulcerative colitis, and Crohn’s disease. Severe allergic conditions that fail conventional treatment may also respond to prednisolone. Prednisolone also is used in the treatment of blood cell cancers (leukemiias), and lymph gland cancers (lymphomas). [1][2]
Sigma Aldrich - 46657 external link
Legal Information
VETRANAL is a trademark of Sigma-Aldrich Co. LLC
Toronto Research Chemicals - P703750 external link
Synthetic corticosteroid; metabolically interconvertible with prednisone.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Proksch J et al. Drug Metab Dispos. 2011 Mar 25.
  • • Jusko, W.J., et al.: Ther. Drug Monit., 2, 169 (1980)
  • • Ali, S.L., et al.: Anal. Profiles Drug Subs. Excip., 21, 415 (1980)
  • • Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 3, 585B, (nmr)
  • • Nobile, A. et al., J.A.C.S., 1955, 77, 4184, (biosynth)
  • • Herzog, H.L. et al., Science (Washington, D.C.), 1955, 121, 176, (struct)
  • • Poos, G.I. et al., Chem. Ind. (London), 1958, 1260, (phosphate)
  • • Hirschmann, R. et al., J.A.C.S., 1964, 86, 3903, (synth)
  • • Toft, P. et al., Can. J. Spectrosc., 1970, 15, 137, (ms)
  • • Gambertoglis, J.G. et al., J. Pharmacokinet. Biopharm., 1980, 8, 1, (rev, pharmacol)
  • • Jusko, W.J. et al., Ther. Drug Monit., 1980, 2, 169, (rev, pharmacol)
  • • Gonzalez, M.D. et al., Org. Magn. Reson., 1984, 22, 586, (cmr)
  • • Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 6297; 6321; 6941
  • • Kirk, D.N. et al., J.C.S. Perkin 2, 1990, 1567, (pmr)
  • • Ali, S.L., Anal. Profiles Drug Subst., 1992, 21, 415, (rev)
  • • Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 737
  • • Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, AAF625; PMA000; PMA100; SOV100; PLY300
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PATENTS

PATENTS

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INTERNET

INTERNET

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