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Details

Stereochemistry ABSOLUTE
Molecular Formula C24H32ClFO5
Molecular Weight 454.959
Optical Activity UNSPECIFIED
Defined Stereocenters 8 / 8
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of HALCINONIDE

SMILES

[H][C@@]12C[C@@]3([H])[C@]4([H])CCC5=CC(=O)CC[C@]5(C)[C@@]4(F)[C@@H](O)C[C@]3(C)[C@@]1(OC(C)(C)O2)C(=O)CCl

InChI

InChIKey=MUQNGPZZQDCDFT-JNQJZLCISA-N
InChI=1S/C24H32ClFO5/c1-20(2)30-19-10-16-15-6-5-13-9-14(27)7-8-21(13,3)23(15,26)17(28)11-22(16,4)24(19,31-20)18(29)12-25/h9,15-17,19,28H,5-8,10-12H2,1-4H3/t15-,16-,17-,19+,21-,22-,23-,24+/m0/s1

HIDE SMILES / InChI

Molecular Formula C24H32ClFO5
Molecular Weight 454.959
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 8 / 8
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Halcinonide is one of the available highly potent topical cor¬ticosteroids. It is a derivative of hydrocortisone and contains important modifications in its structure that alter its absorption, potency, and adverse effects compared with hydrocortisone. Halcinonide—along with desoximetasone, betamethasone, fluocinonide, and diflorasone diacetate—is classified as a Class II potency corticosteroid. Although similar in strength, halcinonide in Halog (the only topical product available that contains halcinonide) differs from many other compounds of this class in the formulation. Halcinonide cream is formulated in a biphasic base that allows for immediate-release of halcinonide upon application to the skin, followed by a delayed and sustained release of halcinonide over time. This “dual formulation” strategy allows for prolonged halcinonide activity. The formulation of halcinonide cream contains microcrystals of halcinonide. An equilibrium is established between dissolved halcinonide in the cream and non-dissolved halcinonide in the microcrystals. As soluble hal¬cinonide enters the skin, additional quantities of halcinonide from the microcrystals become available as a new equilibrium is established. This dynamic equilibrium serves to maintain a sustained level of halcinonide well beyond the time of application.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
HALOG

Cmax

ValueDoseCo-administeredAnalytePopulation
1350 ng/mL
0.1 % single, topical
HALCINONIDE skin
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
7440 ng × h/mL
0.1 % single, topical
HALCINONIDE skin
Homo sapiens

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as perpetrator​

PubMed

Sample Use Guides

In Vivo Use Guide
Apply the 0.1% HALOG (Halcinonide Cream, USP) to the affected area two to three times daily. Rub in gently.
Route of Administration: Topical
In Vitro Use Guide
U2OS cells were pretreated with 100 nM cyclopamine overnight. The cells were then treated with Halcinonide over a range of concentrations from 0–10 mkM for 2 h.
Substance Class Chemical
Record UNII
SI86V6QNEG
Record Status Validated (UNII)
Record Version