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51022-69-6 molecular structure
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2-[(1'S,2'S,4'R,8'S,9'S,11'S,12'R,13'S)-12'-fluoro-11'-hydroxy-9',13'-dimethyl-16'-oxo-5',7'-dioxaspiro[cyclopentane-1,6'-pentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icosane]-14',17'-dien-8'-yl]-2-oxoethyl acetate

ChemBase ID: 173
Molecular Formular: C28H35FO7
Molecular Mass: 502.5717032
Monoisotopic Mass: 502.23668168
SMILES and InChIs

SMILES:
F[C@@]12[C@H]([C@H]3[C@@]([C@@]4(OC5(O[C@@H]4C3)CCCC5)C(=O)COC(=O)C)(C[C@@H]1O)C)CCC1=CC(=O)C=C[C@]21C
Canonical SMILES:
CC(=O)OCC(=O)[C@@]12OC3(O[C@@H]1C[C@@H]1[C@]2(C)C[C@H](O)[C@]2([C@H]1CCC1=CC(=O)C=C[C@]21C)F)CCCC3
InChI:
InChI=1S/C28H35FO7/c1-16(30)34-15-22(33)28-23(35-26(36-28)9-4-5-10-26)13-20-19-7-6-17-12-18(31)8-11-24(17,2)27(19,29)21(32)14-25(20,28)3/h8,11-12,19-21,23,32H,4-7,9-10,13-15H2,1-3H3/t19-,20-,21-,23+,24-,25-,27-,28+/m0/s1
InChIKey:
ILKJAFIWWBXGDU-MOGDOJJUSA-N

Cite this record

CBID:173 http://www.chembase.cn/molecule-173.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
2-[(1'S,2'S,4'R,8'S,9'S,11'S,12'R,13'S)-12'-fluoro-11'-hydroxy-9',13'-dimethyl-16'-oxo-5',7'-dioxaspiro[cyclopentane-1,6'-pentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icosane]-14',17'-dien-8'-yl]-2-oxoethyl acetate
2-[(1'S,2'S,4'R,8'S,9'S,11'S,12'R,13'S)-12'-fluoro-11'-hydroxy-9',13'-dimethyl-16'-oxo-5',7'-dioxaspiro[cyclopentane-1,6'-pentacyclo[10.8.0.0?,?.0?,?.0??,??]icosane]-14',17'-dien-8'-yl]-2-oxoethyl acetate
2-[(1'S,2'S,4'R,8'S,9'S,11'S,12'R,13'S)-12'-fluoro-11'-hydroxy-9',13'-dimethyl-16'-oxo-5',7'-dioxaspiro[cyclopentane-1,6'-pentacyclo[10.8.0.02,9.04,8.013,18]icosane]-14',17'-dien-8'-yl]-2-oxoethyl acetate
IUPAC Traditional name
cyclocort
amcinonide
Brand Name
Cyclocort
Synonyms
Amcinonide
(11β,16α)-21-(Acetyloxy)-16,17-[cyclopentylidenebis(oxy)]-9-fluoro-11-hydroxypregna-1,4-diene-3,20-dione
Amciderm
Amcinonid
Amcinonide
CL 34699
Cyclocort
Penticort
Amcinonide
Visderm
安西奈德
CAS Number
51022-69-6
EC Number
256-915-2
MDL Number
MFCD00213379
PubChem SID
46506705
24890657
160963636
PubChem CID
443958

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 13.633899  H Acceptors
H Donor LogD (pH = 5.5) 3.1952636 
LogD (pH = 7.4) 3.1952634  Log P 3.1952636 
Molar Refractivity 127.8767 cm3 Polarizability 50.165337 Å3
Polar Surface Area 99.13 Å2 Rotatable Bonds
Lipinski's Rule of Five false 
Log P 3.16  LOG S -4.81 
Solubility (Water) 7.74e-03 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Hydrophobicity(logP)
2.3 expand Show data source
RTECS
TU3682500 expand Show data source
MSDS Link
Download expand Show data source
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German water hazard class
2 expand Show data source
Personal Protective Equipment
Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter expand Show data source
Grade
analytical standard, for drug analysis expand Show data source
Certificate of Analysis
Download expand Show data source
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Empirical Formula (Hill Notation)
C28H35FO7 expand Show data source

DETAILS

DETAILS

DrugBank DrugBank TRC TRC
DrugBank - DB00288 external link
Item Information
Drug Groups approved
Description Amcinonide is a corticosteroid. [Wikipedia]
Indication For the relief of the inflammatory and pruritic manifestations of corticosteroid-responsive dermatoses.
Pharmacology Amcinonide is a topical corticosteroid. The topical corticosteroids constitute a class of primarily synthetic steroids used as anti-inflammatory and antipruritic agents. Amcinonide reduces or inhibits the actions of chemicals in the body that cause inflammation, redness, and swelling. The mechanism of anti-inflammatory activity of the topical corticosteroids is unclear. Various laboratory methods, including vasoconstrictor assays, are used to compare and predict potencies and/or clinical efficacies of the topical corticosteroids. There is some evidence to suggest that a recognizable correlation exists between vasoconstrictor potency and therapeutic efficacy in man. When in an ointment form, amcinonide also helps the skin maintain moisture.
Toxicity Results from acute toxicity studies do not indicate that any risk of acute intoxication is to be expected following a single dermal application of an overdose (application over a large area under conditions favorable to absorption) or inadvertent oral ingestion.
Affected Organisms
Humans and other mammals
Biotransformation Once absorbed through the skin, topical corticosteroids are handled through pharmacokinetic pathways similar to systemically administered corticosteroids. Corticosteroids are metabolized primarily in the liver and are then excreted by the kidneys.
Absorption Topical corticosteroids can be absorbed from normal intact skin. Inflammation and/or other disease processes in the skin increase percutaneous absorption.
Elimination Corticosteroids are metabolized primarily in the liver and are then excreted by the kidneys.
Some of the topical corticosteroids and their metabolites are also excreted into the bile.
External Links
Wikipedia
RxList
PDRhealth
Drugs.com

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Woodford, R., et al.: Curr. Ther. Res., 26, 301 (1979)
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PATENTS

PATENTS

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INTERNET

INTERNET

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