2-[(1S,2R,9R,10S,11S,13R,14R,15S,17S)-9-chloro-17-hydroxy-2,13,15-trimethyl-5-oxo-14-(propanoyloxy)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,6-dien-14-yl]-2-oxoethyl propanoate

• ChemBase ID: 125
• Molecular Formular: C28H37ClO7
• Molecular Mass: 521.04218
• Monoisotopic Mass: 520.2227812
• SMILES: Cl[C@H]1[C@H]2[C@H]3[C@@]([C@](OC(=O)CC)([C@@H](C3)C)C(=O)COC(=O)CC)(C[C@H](O)[C@@H]2[C@@]2(C(=CC(=O)C=C2)C1)C)C
• Canonical SMILES: CCC(=O)O[C@@]1([C@H](C)C[C@@H]2[C@]1(C)C[C@H](O)[C@H]1[C@H]2[C@H](Cl)CC2=CC(=O)C=C[C@]12C)C(=O)COC(=O)CC
• InChI: InChI=1S/C28H37ClO7/c1-6-22(33)35-14-21(32)28(36-23(34)7-2)15(3)10-18-24-19(29)12-16-11-17(30)8-9-26(16,4)25(24)20(31)13-27(18,28)5/h8-9,11,15,18-20,24-25,31H,6-7,10,12-14H2,1-5H3/t15-,18+,19-,20+,24-,25+,26+,27+,28+/m1/s1
• InChIKey: DJHCCTTVDRAMEH-DUUJBDRPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(1S,2R,9R,10S,11S,13R,14R,15S,17S)-9-chloro-17-hydroxy-2,13,15-trimethyl-5-oxo-14-(propanoyloxy)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,6-dien-14-yl]-2-oxoethyl propanoate; 2-[(1S,2R,9R,10S,11S,13R,14R,15S,17S)-9-chloro-17-hydroxy-2,13,15-trimethyl-5-oxo-14-(propanoyloxy)tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-dien-14-yl]-2-oxoethyl propanoate
• IUPAC Traditional name: modrasone; aclovate
• Brand Name: Aclovate
• Synonyms: Alclometasone dipropionate; Alclometasone; AlcloMetasone dipropionate

Database IDs

• CAS Number: 66734-13-2
• PubChem SID: 160963588
• PubChem CID: 636374

CALCULATED PROPERTIES

JChem

• Acid pKa: 14.795353
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 3.9671123
• LogD (pH = 7.4): 3.9671123
• Log P: 3.9671123
• Molar Refractivity: 135.1652 cm^3
• Polarizability: 53.096844 Å^3
• Polar Surface Area: 106.97 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 3.28
• LOG S: -5.27
• Solubility (Water): 2.81e-03 g/l

PROPERTIES

Physical Property

• Solubility: Insoluble
• Hydrophobicity(logP): 2.7

Product Information

• Purity: 97%

DETAILS

DrugBank - DB00240

• Drug Groups: approved
• Description: Alclometasone is synthetic glucocorticoid steroid for topical use in dermatology as anti-inflammatory, antipruritic, antiallergic, antiproliferative and vasoconstrictive agent. [Wikipedia]
• Indication: For the relief of the inflammatory and pruritic manifestations of corticosteroid-responsive dermatoses.
• Pharmacology: Alclometasone is a synthetic corticosteroid for topical dermatologic use. The corticosteroids constitute a class of primarily synthetic steroids used topically as anti-inflammatory and antipruritic agents. Alclometasone is a selective glucocorticoid receptor agonist.
• Toxicity: Symptoms of overdose include suppression of adrenal glands, temporary decrease in white blood cell counts, symptoms of hypersensitivity (such as skin rash, hives, itching, and difficulty breathing), and increased susceptibility to infection.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic.
• Absorption: Topical corticosteroids can be absorbed from normal intact skin. Studies have shown that approximately 3% of steroid is absorbed during 8 hours of contact with intact skin of normal volunteers.
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com