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

• ChemBase ID: 173
• Molecular Formular: C28H35FO7
• Molecular Mass: 502.5717032
• Monoisotopic Mass: 502.23668168
• 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

NAMES AND DATABASE IDS

Names

• 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,^8.0^1^3,^1^8]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^{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
• IUPAC Traditional name: cyclocort; amcinonide
• Brand Name: Cyclocort
• Synonyms: Amcinonide; 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; Visderm; 安西奈德

Database IDs

• CAS Number: 51022-69-6
• EC Number: 256-915-2
• MDL Number: MFCD00213379
• PubChem SID: 24890657; 160963636; 46506705
• PubChem CID: 443958

CALCULATED PROPERTIES

ALOGPS 2.1

• Log P: 3.16
• LOG S: -4.81
• Solubility (Water): 7.74e-03 g/l

JChem

• Log P: 3.1952636
• Molar Refractivity: 127.8767 cm^3
• Polarizability: 50.165337 Å^3
• Polar Surface Area: 99.13 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false
• Acid pKa: 13.633899
• H Acceptors: 6
• H Donor: 1
• LogD (pH = 5.5): 3.1952636
• LogD (pH = 7.4): 3.1952634

PROPERTIES

Physical Property

• Hydrophobicity(logP): 2.3

Safety Information

• RTECS: TU3682500
• German water hazard class: 2
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Grade: analytical standard, for drug analysis
• Empirical Formula (Hill Notation): C28H35FO7

DETAILS

DrugBank - DB00288

• 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

Toronto Research Chemicals - A576150

Glucocorticoid.

REFERENCES

• Woodford, R., et al.: Curr. Ther. Res., 26, 301 (1979)