Halcinonide

Identification

Summary

Halcinonide is a corticosteroid used for the management and symptomatic relief of the inflammatory and pruritic manifestations of corticosteroid-responsive dermatoses.

Brand Names
Halog
Generic Name
Halcinonide
DrugBank Accession Number
DB06786
Background

Halcinonide is a corticosteroid indicated for the relief of the inflammatory and pruritic manifestations of corticosteroid-responsive dermatoses, and is distributed as a cream and ointment. Halcinonide is marketed under the brand name Halog® by Ranbaxy Laboratories Inc. Research suggests that clobetasol propionate demonstrates superior pharmacologic efficacy in the treatment of psoriasis when compared to halcinonide.

Type
Small Molecule
Groups
Approved, Investigational, Withdrawn
Structure
Thumb
Weight
Average: 454.96
Monoisotopic: 454.19223
Chemical Formula
C24H32ClFO5
Synonyms
  • (4aS,4bR,5S,6aS,6bS,9aR,10aS,10bS)-6b-(chloroacetyl)-4b-fluoro-5-hydroxy-4a,6a,8,8-tetramethyl-3,4,4a,4b,5,6,6a,6b,9a,10,10a,10b,11,12-tetradecahydro-2H-naphtho[2',1':4,5]indeno[1,2-d][1,3]dioxol-2-one
  • Halcinonid
  • Halcinonida
  • Halcinonide
  • Halcinonidum
External IDs
  • SQ 18566
  • SQ-18566

Pharmacology

Indication

Indicated for the relief of the inflammatory and pruritic manifestations of corticosteroid-responsive dermatoses.

Pharmacology
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Associated Conditions
Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

Not Available

Mechanism of action

The precise mechanism of action of topical corticosteroids is unclear. However they possess anti-inflammatory, antipruritic, and vasoconstrictive actions.

New research indicates that halcinonide activates MBP (myelin basic protein) expression via smoothened receptor activation. This finding suggests that halcinonide could be used in the treatment of multiple sclerosis therapy as an alternative to Dexamethasone or Methylprednisolone.

TargetActionsOrganism
USmoothened homolog
agonist
activator
Humans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Systemic absorption of topical corticosteroids has produced reversible hypothalamicpituitary-adrenal (HPA) axis suppression, manifestations of Cushing’s syndrome, hyperglycemia, and glucosuria in some patients. Conditions which augment systemic absorption include the application of the more potent steroids, use over large surface areas, prolonged use, and the addition of occlusive dressings.

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbametapirThe serum concentration of Halcinonide can be increased when it is combined with Abametapir.
AcarboseThe risk or severity of hyperglycemia can be increased when Halcinonide is combined with Acarbose.
AcetohexamideThe risk or severity of hyperglycemia can be increased when Halcinonide is combined with Acetohexamide.
AcetyldigitoxinThe risk or severity of adverse effects can be increased when Halcinonide is combined with Acetyldigitoxin.
AlbiglutideThe risk or severity of hyperglycemia can be increased when Halcinonide is combined with Albiglutide.
AlogliptinThe risk or severity of hyperglycemia can be increased when Halcinonide is combined with Alogliptin.
AminoglutethimideThe therapeutic efficacy of Halcinonide can be decreased when used in combination with Aminoglutethimide.
BendroflumethiazideThe risk or severity of electrolyte imbalance can be increased when Halcinonide is combined with Bendroflumethiazide.
BenzthiazideThe risk or severity of electrolyte imbalance can be increased when Halcinonide is combined with Benzthiazide.
BromocriptineThe risk or severity of hyperglycemia can be increased when Halcinonide is combined with Bromocriptine.
Interactions
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Food Interactions
No interactions found.

Products

Products
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International/Other Brands
Adcortin (Daiichi Sankyo) / Berodan (Dong Sung) / Betacorton (Spirig) / Confumin (Hwang's) / Cortilate (Micro Gratia) / Ha Le Te (Tianjin Pharmaceutical Group Xinzheng) / Halciderm (Teofarma) / Halcinonide-Pacific Pharm (Pacific) / Sawastin (Sawai Seiyaku)
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
HalogCream1 mg/1gTopicalE.R. Squibb & Sons, L.L.C.2009-06-012011-01-31US flag
HalogCream1 mg/1gTopicalSun Pharmaceutical Industries, Inc.2009-02-10Not applicableUS flag
HalogSolution1 mg/1mLTopicalE.R. Squibb & Sons, L.L.C.2009-01-012009-02-28US flag
HalogSolution1 mg/1mLTopicalSun Pharmaceutical Industries, Inc.2020-03-18Not applicableUS flag
HalogCream1 mg/1gTopicalPhysicians Total Care, Inc.2009-02-102011-05-31US flag
HalogOintment1 mg/1gTopicalSun Pharmaceutical Industries, Inc.2009-05-19Not applicableUS flag
HalogOintment1 mg/1gTopicalE.R. Squibb & Sons, L.L.C.2008-01-012008-06-30US flag
Halog Cream 0.1%Cream0.1 %TopicalBristol Myers Squibb1994-12-312010-02-05Canada flag
Halog Liq 0.1%Liquid.1 %TopicalWestwood Squibb, Division Of Bristol Myers Squibb Canada Inc.1972-12-312005-08-01Canada flag
Halog Ont 0.1%Ointment0.1 %TopicalBristol Myers Squibb1977-12-312008-05-09Canada flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
HalcinonideCream1 mg/1gTopicalMylan Pharmaceuticals Inc.2019-08-15Not applicableUS flag
HalcinonideCream1 mg/1gTopicalSun Pharmaceutical Industries, Inc.2021-05-22Not applicableUS flag

Categories

ATC Codes
D07AD02 — Halcinonide
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as gluco/mineralocorticoids, progestogins and derivatives. These are steroids with a structure based on a hydroxylated prostane moiety.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Steroids and steroid derivatives
Sub Class
Pregnane steroids
Direct Parent
Gluco/mineralocorticoids, progestogins and derivatives
Alternative Parents
20-oxosteroids / 11-beta-hydroxysteroids / 3-oxo delta-4-steroids / Halogenated steroids / Delta-4-steroids / Cyclohexenones / Ketals / 1,3-dioxolanes / Alpha-chloroketones / Fluorohydrins
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Substituents
11-beta-hydroxysteroid / 11-hydroxysteroid / 20-oxosteroid / 3-oxo-delta-4-steroid / 3-oxosteroid / 9-halo-steroid / Acetal / Alcohol / Aliphatic heteropolycyclic compound / Alkyl chloride
show 28 more
Molecular Framework
Aliphatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
SI86V6QNEG
CAS number
3093-35-4
InChI Key
MUQNGPZZQDCDFT-JNQJZLCISA-N
InChI
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
IUPAC Name
(1S,2S,4R,8S,9S,11S,12R,13S)-8-(2-chloroacetyl)-12-fluoro-11-hydroxy-6,6,9,13-tetramethyl-5,7-dioxapentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icos-17-en-16-one
SMILES
[H][C@@]12C[C@H]3OC(C)(C)O[C@@]3(C(=O)CCl)[C@@]1(C)C[C@H](O)[C@@]1(F)[C@@]2([H])CCC2=CC(=O)CC[C@]12C

References

Synthesis Reference

U.S. Patent 3,892,857.

General References
  1. Draelos ZD: Demonstration of the biphasic release of 0.1% halcinonide cream. J Drugs Dermatol. 2015 Jan;14(1):89-90. [Article]
  2. Ellis CN, Van Scott EJ: Clobetasol propionate cream versus halcinonide cream in psoriasis. Int J Dermatol. 1986 Jun;25(5):332-3. [Article]
  3. Porcu G, Serone E, De Nardis V, Di Giandomenico D, Lucisano G, Scardapane M, Poma A, Ragnini-Wilson A: Clobetasol and Halcinonide Act as Smoothened Agonists to Promote Myelin Gene Expression and RxRgamma Receptor Activation. PLoS One. 2015 Dec 10;10(12):e0144550. doi: 10.1371/journal.pone.0144550. eCollection 2015. [Article]
KEGG Drug
D01308
PubChem Compound
443943
PubChem Substance
347827796
ChemSpider
391997
BindingDB
50240097
RxNav
5084
ChEBI
31663
ChEMBL
CHEMBL1200845
ZINC
ZINC000004213474
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Halcinonide
FDA label
Download (135 KB)
MSDS
Download (44.6 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • Bristol-Myers Squibb Co.
  • Ranbaxy Laboratories
Dosage Forms
FormRouteStrength
CreamTopical
Solution
CreamTopical
CreamTopical1 mg/1g
OintmentTopical1 mg/1g
SolutionTopical1 mg/1mL
CreamTopical0.1 %
LiquidTopical.1 %
OintmentTopical0.1 %
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US3892857No1972-11-241992-11-24US flag

Properties

State
Liquid
Experimental Properties
PropertyValueSource
melting point (°C)276-277U.S. Patent 3,892,857.
Predicted Properties
PropertyValueSource
Water Solubility0.0112 mg/mLALOGPS
logP3.31ALOGPS
logP3.3ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)13.63ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area72.83 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity113.55 m3·mol-1ChemAxon
Polarizability46.61 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Targets

Drugtargets
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Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Agonist
Activator
General Function
Wnt-protein binding
Specific Function
G protein-coupled receptor that probably associates with the patched protein (PTCH) to transduce the hedgehog's proteins signal. Binding of sonic hedgehog (SHH) to its receptor patched is thought t...
Gene Name
SMO
Uniprot ID
Q99835
Uniprot Name
Smoothened homolog
Molecular Weight
86395.95 Da
References
  1. Porcu G, Serone E, De Nardis V, Di Giandomenico D, Lucisano G, Scardapane M, Poma A, Ragnini-Wilson A: Clobetasol and Halcinonide Act as Smoothened Agonists to Promote Myelin Gene Expression and RxRgamma Receptor Activation. PLoS One. 2015 Dec 10;10(12):e0144550. doi: 10.1371/journal.pone.0144550. eCollection 2015. [Article]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. NCI/NIH [Link]

Drug created on September 14, 2010 16:21 / Updated on February 21, 2021 18:52