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- Approved, Investigational, Withdrawn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
Structure for Halcinonide (DB06786)
- 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.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Management of Dermatoses •••••••••••• Used in combination to treat Dermatosis Combination Product in combination with: Neomycin (DB00994) •••••••••••• ••••• Used in combination to treat Corticosteroid-responsive dermatosis Combination Product in combination with: Salicylic acid (DB00936) •••••••••••• •••••••• - Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- 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.
Target Actions Organism USmoothened homolog agonistactivatorHumans - 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
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- 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 Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAbametapir The serum concentration of Halcinonide can be increased when it is combined with Abametapir. Acarbose The risk or severity of hyperglycemia can be increased when Halcinonide is combined with Acarbose. Acetohexamide The risk or severity of hyperglycemia can be increased when Halcinonide is combined with Acetohexamide. Acetyldigitoxin The risk or severity of adverse effects can be increased when Halcinonide is combined with Acetyldigitoxin. Albiglutide The risk or severity of hyperglycemia can be increased when Halcinonide is combined with Albiglutide. - Food Interactions
- No interactions found.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- 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
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Halog Cream 1 mg/1g Topical Physicians Total Care, Inc. 2009-02-10 2011-05-31 US 
Halog Ointment 1 mg/1g Topical Sun Pharmaceutical Industries, Inc. 2009-05-19 Not applicable US Halog Ointment 1 mg/1g Topical E.R. Squibb & Sons, L.L.C. 2008-01-01 2008-06-30 US Halog Cream 1 mg/1g Topical E.R. Squibb & Sons, L.L.C. 2009-06-01 2011-01-31 US Halog Cream 1 mg/1g Topical Sun Pharmaceutical Industries, Inc. 2009-02-10 Not applicable US - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Halcinonide Cream 1 mg/1g Topical Sun Pharmaceutical Industries, Inc. 2021-05-22 Not applicable US Halcinonide Cream 1 mg/1g Topical Mylan Pharmaceuticals Inc. 2019-08-15 Not applicable US Halcinonide Cream 1 mg/1g Topical Glasshouse Pharmaceuticals Limited Canada 2021-12-08 Not applicable US - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image HALCIDERM Halcinonide (0.1 %) + Salicylic acid (2 %) Solution Teofarma S.R.L. 2014-07-08 Not applicable Italy 
Categories
- ATC Codes
- D07AD02 — Halcinonide
- Drug Categories
- Adrenal Cortex Hormones
- Anti-Inflammatory Agents
- Corticosteroid Hormone Receptor Agonists
- Corticosteroids
- Corticosteroids, Dermatological Preparations
- Corticosteroids, Very Potent (Group IV)
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 Substrates
- Dermatologicals
- Fused-Ring Compounds
- Immunosuppressive Agents
- Pregnanes
- Pregnenediones
- Pregnenes
- Steroids
- 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 show 9 more
- 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
- Draelos ZD: Demonstration of the biphasic release of 0.1% halcinonide cream. J Drugs Dermatol. 2015 Jan;14(1):89-90. [Article]
- Ellis CN, Van Scott EJ: Clobetasol propionate cream versus halcinonide cream in psoriasis. Int J Dermatol. 1986 Jun;25(5):332-3. [Article]
- 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]
- External Links
- KEGG Drug
- D01308
- PubChem Compound
- 443943
- PubChem Substance
- 347827796
- ChemSpider
- 391997
- BindingDB
- 50240097
- 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 Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Bristol-Myers Squibb Co.
- Ranbaxy Laboratories
- Dosage Forms
Form Route Strength Solution Cream Topical Cream Topical 1 mg/1g Ointment Topical 1 mg/1g Solution Topical 1 mg/1mL Cream Topical 0.1 % Liquid Topical .1 % Ointment Topical 0.1 % - Prices
- Not Available
- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US3892857 No 1972-11-24 1992-11-24 US
Properties
- State
- Liquid
- Experimental Properties
Property Value Source melting point (°C) 276-277 U.S. Patent 3,892,857. - Predicted Properties
Property Value Source Water Solubility 0.0112 mg/mL ALOGPS logP 3.31 ALOGPS logP 3.3 Chemaxon logS -4.6 ALOGPS pKa (Strongest Acidic) 13.63 Chemaxon pKa (Strongest Basic) -3.4 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 5 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 72.83 Å2 Chemaxon Rotatable Bond Count 2 Chemaxon Refractivity 113.55 m3·mol-1 Chemaxon Polarizability 46.61 Å3 Chemaxon Number of Rings 5 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-052s-0003900000-387010fb384d098121ae Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0udi-0000900000-e5a7563dd1e66d652c26 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0gb9-3001900000-a90f07d0151b2d8a217a Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0a4s-0529600000-c5a94fe624ebf55352f6 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0uk9-2501900000-203732568bde6d284223 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-00p1-4779100000-7ab6df4dc2557c1e3163 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 205.8811 predictedDeepCCS 1.0 (2019) [M+H]+ 207.7765 predictedDeepCCS 1.0 (2019) [M+Na]+ 214.42009 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- AgonistActivator
- 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
- 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
- NCI/NIH [Link]
Drug created at September 14, 2010 16:21 / Updated at February 21, 2021 18:52