Identification

Name
Halcinonide
Accession Number
DB06786
Type
Small Molecule
Groups
Approved, Investigational, Withdrawn
Description

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.

Structure
Thumb
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
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
HalogCream1 mg/1gTopicalE.R. Squibb & Sons, L.L.C.2009-06-012011-01-31Us
HalogCream1 mg/1gTopicalSun Pharmaceutical Industries Limited2009-02-10Not applicableUs
HalogSolution1 mg/1mLTopicalE.R. Squibb & Sons, L.L.C.2009-01-012009-02-28Us
HalogCream1 mg/1gTopicalPhysicians Total Care, Inc.2009-02-102011-05-31Us
HalogOintment1 mg/1gTopicalSun Pharmaceutical Industries Limited2009-05-19Not applicableUs
HalogOintment1 mg/1gTopicalE.R. Squibb & Sons, L.L.C.2008-01-012008-06-30Us
Halog Cream 0.1%Cream0.1 %TopicalBristol Myers Squibb1994-12-312010-02-05Canada
Halog Liq 0.1%Liquid.1 %TopicalWestwood Squibb, Division Of Bristol Myers Squibb Canada Inc.1972-12-312005-08-01Canada
Halog Ont 0.1%Ointment0.1 %TopicalBristol Myers Squibb1977-12-312008-05-09Canada
Halog-ECream1 mg/1gTopicalE.R. Squibb & Sons, L.L.C.2009-06-012009-11-30Us
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)
Categories
UNII
SI86V6QNEG
CAS number
3093-35-4
Weight
Average: 454.96
Monoisotopic: 454.19223
Chemical Formula
C24H32ClFO5
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

Pharmacology

Indication

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

Associated Conditions
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
Human
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
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.

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(4R)-limoneneThe risk or severity of adverse effects can be increased when (4R)-limonene is combined with Halcinonide.
1,10-PhenanthrolineThe risk or severity of adverse effects can be increased when Halcinonide is combined with 1,10-Phenanthroline.
AceclofenacThe risk or severity of adverse effects can be increased when Aceclofenac is combined with Halcinonide.
AcemetacinThe risk or severity of adverse effects can be increased when Acemetacin is combined with Halcinonide.
Acetylsalicylic acidThe risk or severity of adverse effects can be increased when Acetylsalicylic acid is combined with Halcinonide.
AdalimumabThe risk or severity of adverse effects can be increased when Adalimumab is combined with Halcinonide.
AlclofenacThe risk or severity of adverse effects can be increased when Alclofenac is combined with Halcinonide.
AlclometasoneThe risk or severity of adverse effects can be increased when Alclometasone is combined with Halcinonide.
AldesleukinThe risk or severity of adverse effects can be increased when Aldesleukin is combined with Halcinonide.
AlemtuzumabThe risk or severity of adverse effects can be increased when Alemtuzumab is combined with Halcinonide.
Food Interactions
Not Available

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. [PubMed:25607913]
  2. Ellis CN, Van Scott EJ: Clobetasol propionate cream versus halcinonide cream in psoriasis. Int J Dermatol. 1986 Jun;25(5):332-3. [PubMed:3522448]
  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. [PubMed:26658258]
External Links
KEGG Drug
D01308
PubChem Compound
443943
PubChem Substance
347827796
ChemSpider
391997
ChEBI
31663
ChEMBL
CHEMBL1200845
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Halcinonide
ATC Codes
D07AD02 — Halcinonide
FDA label
Download (135 KB)
MSDS
Download (44.6 KB)

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

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

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

Taxonomy

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
show 9 more
Substituents
Progestogin-skeleton / 20-oxosteroid / Oxosteroid / Hydroxysteroid / 11-beta-hydroxysteroid / 11-hydroxysteroid / Halo-steroid / 9-halo-steroid / 3-oxosteroid / 3-oxo-delta-4-steroid
show 28 more
Molecular Framework
Aliphatic heteropolycyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Human
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. [PubMed:26658258]

Enzymes

Kind
Protein
Organism
Human
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 10:21 / Updated on August 02, 2018 05:39