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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- Approved, Investigational, Withdrawn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 ASteroid hormone receptor ERR1 modulatorHumans ASteroid hormone receptor ERR2 modulatorHumans AEstrogen-related receptor gamma modulatorHumans UProtein smoothened 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
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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.
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 (Europe) B.V. 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 (Europe) B.V. 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 (Europe) B.V. 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 Halcinonide Topical Solution Solution 1 mg/1mL Topical Encube Ethicals Private Limited 2024-05-31 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
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample data
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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Use our structured and evidence-based datasets to unlock newinsights and accelerate drug research.
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Modulator
- General Function
- Binds to an ERR-alpha response element (ERRE) containing a single consensus half-site, 5'-TNAAGGTCA-3'. Can bind to the medium-chain acyl coenzyme A dehydrogenase (MCAD) response element NRRE-1 and may act as an important regulator of MCAD promoter. Binds to the C1 region of the lactoferrin gene promoter. Requires dimerization and the coactivator, PGC-1A, for full activity. The ERRalpha/PGC1alpha complex is a regulator of energy metabolism. Induces the expression of PERM1 in the skeletal muscle
- Specific Function
- DNA-binding transcription factor activity
- Gene Name
- ESRRA
- Uniprot ID
- P11474
- Uniprot Name
- Steroid hormone receptor ERR1
- Molecular Weight
- 45509.11 Da
References
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Modulator
- General Function
- Transcription factor that binds a canonical ESRRB recognition (ERRE) sequence 5'TCAAGGTCA-3' localized on promoter and enhancer of targets genes regulating their expression or their transcription activity (PubMed:17920186, PubMed:19755138). Plays a role, in a LIF-independent manner, in maintainance of self-renewal and pluripotency of embryonic and trophoblast stem cells through different signaling pathways including FGF signaling pathway and Wnt signaling pathways. Upon FGF signaling pathway activation, interacts with KDM1A by directly binding to enhancer site of ELF5 and EOMES and activating their transcription leading to self-renewal of trophoblast stem cells. Also regulates expression of multiple rod-specific genes and is required for survival of this cell type (By similarity). Plays a role as transcription factor activator of GATA6, NR0B1, POU5F1 and PERM1 (PubMed:23836911). Plays a role as transcription factor repressor of NFE2L2 transcriptional activity and ESR1 transcriptional activity (PubMed:17920186, PubMed:19755138). During mitosis remains bound to a subset of interphase target genes, including pluripotency regulators, through the canonical ESRRB recognition (ERRE) sequence, leading to their transcriptional activation in early G1 phase. Can coassemble on structured DNA elements with other transcription factors like SOX2, POU5F1, KDM1A and NCOA3 to trigger ESRRB-dependent gene activation. This mechanism, in the case of SOX2 corecruitment prevents the embryonic stem cells (ESCs) to epiblast stem cells (EpiSC) transition through positive regulation of NR0B1 that inhibits the EpiSC transcriptional program. Also plays a role inner ear development by controlling expression of ion channels and transporters and in early placentation (By similarity)
- Specific Function
- cis-regulatory region sequence-specific DNA binding
- Gene Name
- ESRRB
- Uniprot ID
- O95718
- Uniprot Name
- Steroid hormone receptor ERR2
- Molecular Weight
- 48053.14 Da
References
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Modulator
- General Function
- Orphan receptor that acts as a transcription activator in the absence of bound ligand. Binds specifically to an estrogen response element and activates reporter genes controlled by estrogen response elements (By similarity). Induces the expression of PERM1 in the skeletal muscle
- Specific Function
- AF-2 domain binding
- Gene Name
- ESRRG
- Uniprot ID
- P62508
- Uniprot Name
- Estrogen-related receptor gamma
- Molecular Weight
- 51305.485 Da
References
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- AgonistActivator
- General Function
- G protein-coupled receptor which associates with the patched protein (PTCH) to transduce hedgehog protein signaling. Binding of sonic hedgehog (SHH) to its receptor patched prevents inhibition of smoothened (SMO) by patched. When active, SMO binds to and sequesters protein kinase A catalytic subunit PRKACA at the cell membrane, preventing PRKACA-mediated phosphorylation of GLI transcription factors which releases the GLI proteins from PRKACA-mediated inhibition and allows for transcriptional activation of hedgehog pathway target genes (By similarity). Required for the accumulation of KIF7, GLI2 and GLI3 in the cilia (PubMed:19592253). Interacts with DLG5 at the ciliary base to induce the accumulation of KIF7 and GLI2 at the ciliary tip for GLI2 activation (By similarity)
- Specific Function
- cAMP-dependent protein kinase inhibitor activity
- Gene Name
- SMO
- Uniprot ID
- Q99835
- Uniprot Name
- Protein smoothened
- 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
- A cytochrome P450 monooxygenase involved in the metabolism of sterols, steroid hormones, retinoids and fatty acids (PubMed:10681376, PubMed:11093772, PubMed:11555828, PubMed:12865317, PubMed:14559847, PubMed:15373842, PubMed:15764715, PubMed:19965576, PubMed:20702771, PubMed:21490593, PubMed:21576599). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase). Catalyzes the hydroxylation of carbon-hydrogen bonds (PubMed:12865317, PubMed:14559847, PubMed:15373842, PubMed:15764715, PubMed:21490593, PubMed:21576599, PubMed:2732228). Exhibits high catalytic activity for the formation of hydroxyestrogens from estrone (E1) and 17beta-estradiol (E2), namely 2-hydroxy E1 and E2, as well as D-ring hydroxylated E1 and E2 at the C-16 position (PubMed:11555828, PubMed:12865317, PubMed:14559847). Plays a role in the metabolism of androgens, particularly in oxidative deactivation of testosterone (PubMed:15373842, PubMed:15764715, PubMed:22773874, PubMed:2732228). Metabolizes testosterone to less biologically active 2beta- and 6beta-hydroxytestosterones (PubMed:15373842, PubMed:15764715, PubMed:2732228). Contributes to the formation of hydroxycholesterols (oxysterols), particularly A-ring hydroxylated cholesterol at the C-4beta position, and side chain hydroxylated cholesterol at the C-25 position, likely contributing to cholesterol degradation and bile acid biosynthesis (PubMed:21576599). Catalyzes bisallylic hydroxylation of polyunsaturated fatty acids (PUFA) (PubMed:9435160). Catalyzes the epoxidation of double bonds of PUFA with a preference for the last double bond (PubMed:19965576). Metabolizes endocannabinoid arachidonoylethanolamide (anandamide) to 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acid ethanolamides (EpETrE-EAs), potentially modulating endocannabinoid system signaling (PubMed:20702771). Plays a role in the metabolism of retinoids. Displays high catalytic activity for oxidation of all-trans-retinol to all-trans-retinal, a rate-limiting step for the biosynthesis of all-trans-retinoic acid (atRA) (PubMed:10681376). Further metabolizes atRA toward 4-hydroxyretinoate and may play a role in hepatic atRA clearance (PubMed:11093772). Responsible for oxidative metabolism of xenobiotics. Acts as a 2-exo-monooxygenase for plant lipid 1,8-cineole (eucalyptol) (PubMed:11159812). Metabolizes the majority of the administered drugs. Catalyzes sulfoxidation of the anthelmintics albendazole and fenbendazole (PubMed:10759686). Hydroxylates antimalarial drug quinine (PubMed:8968357). Acts as a 1,4-cineole 2-exo-monooxygenase (PubMed:11695850). Also involved in vitamin D catabolism and calcium homeostasis. Catalyzes the inactivation of the active hormone calcitriol (1-alpha,25-dihydroxyvitamin D(3)) (PubMed:29461981)
- Specific Function
- 1,8-cineole 2-exo-monooxygenase activity
- 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 August 26, 2024 19:24