Haloprogin
Identification
- Generic Name
- Haloprogin
- DrugBank Accession Number
- DB00793
- Background
Haloprogin is used as a topical ointment or cream in the treatment of Tinea infections. Tinea infections are superficial fungal infections caused by three species of fungi collectively known as dermatophytes (Trichophyton, Microsporum and Epidermophyton). Commonly these infections are named for the body part affected, including tinea corporis (general skin), tinea cruris (groin), and tinea pedis (feet). Haloprogin is a halogenated phenolic ether administered topically for dermotaphytic infections. The mechanism of action is unknown, but it is thought to be via inhibition of oxygen uptake and disruption of yeast membrane structure and function. Haloprogin is no longer available in the United States and has been discontinued.
- Type
- Small Molecule
- Groups
- Approved, Withdrawn
- Structure
- Weight
- Average: 361.391
Monoisotopic: 359.837241291 - Chemical Formula
- C9H4Cl3IO
- Synonyms
- Haloprogin
- Haloprogina
- Haloprogine
- Haloproginum
- External IDs
- M-1028 (MEIJI)
- NSC-100071
Pharmacology
- Indication
Used to treat fungal (Tinea) skin infections such as athlete's foot, jock itch, ringworm, and tinea versicolor.
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- Pharmacodynamics
Used as a topical ointment or cream in the treatment of Tinea infections. Tinea infections are superficial fungal infections caused by three species of fungi collectively known as dermatophytes (Trichophyton, Microsporum and Epidermophyton). Commonly these infections are named for the body part affected, including tinea corporis (general skin), tinea cruris (groin), and tinea pedis (feet).
- Mechanism of action
Haloprogin is a halogenated phenolic ether administered topically for dermotaphytic infections. The mechanism of action is unknown, but is thought to be via inhibition of oxygen uptake and disruption of yeast membrane structure and function. There is a higher incidence of cutaneous side effects with haloprogin, including irritation, burning, vesiculation (blisters), scaling, and itching. It is generally used when the infection is unresponsive to other antifungals.
- 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
Not Available
- 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 softwareAcenocoumarol The therapeutic efficacy of Acenocoumarol can be increased when used in combination with Haloprogin. Dicoumarol The therapeutic efficacy of Dicoumarol can be increased when used in combination with Haloprogin. Fluindione The therapeutic efficacy of Fluindione can be increased when used in combination with Haloprogin. Phenindione The therapeutic efficacy of Phenindione can be increased when used in combination with Haloprogin. Phenprocoumon The therapeutic efficacy of Phenprocoumon can be increased when used in combination with Haloprogin. - Food Interactions
- Not Available
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
- Aloprogen (Westwood) / Halotex (Westwood) / Mycanden (Schering) / Mycilan (Schering-Plough) / Polik (Meiji)
Categories
- ATC Codes
- D01AE11 — Haloprogin
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as phenol ethers. These are aromatic compounds containing an ether group substituted with a benzene ring.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Phenol ethers
- Sub Class
- Not Available
- Direct Parent
- Phenol ethers
- Alternative Parents
- Phenoxy compounds / Chlorobenzenes / Alkyl aryl ethers / Aryl chlorides / Haloacetylenes and derivatives / Organoiodides / Organochlorides / Hydrocarbon derivatives
- Substituents
- Alkyl aryl ether / Aromatic homomonocyclic compound / Aryl chloride / Aryl halide / Chlorobenzene / Ether / Haloacetylene or derivatives / Halobenzene / Hydrocarbon derivative / Monocyclic benzene moiety
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Dermatophytic fungi including Trichophyton, Microsporum and Epidermophyton
Chemical Identifiers
- UNII
- AIU7053OWL
- CAS number
- 777-11-7
- InChI Key
- CTETYYAZBPJBHE-UHFFFAOYSA-N
- InChI
- InChI=1S/C9H4Cl3IO/c10-6-4-8(12)9(5-7(6)11)14-3-1-2-13/h4-5H,3H2
- IUPAC Name
- 1,2,4-trichloro-5-[(3-iodoprop-2-yn-1-yl)oxy]benzene
- SMILES
- ClC1=CC(Cl)=C(Cl)C=C1OCC#CI
References
- Synthesis Reference
U.S. Patent 3,322,813.
- General References
- External Links
- Human Metabolome Database
- HMDB0014931
- KEGG Drug
- D00339
- PubChem Compound
- 3561
- PubChem Substance
- 46504892
- ChemSpider
- 3440
- BindingDB
- 50194601
- 26422
- ChEBI
- 5614
- ChEMBL
- CHEMBL1289
- ZINC
- ZINC000001530649
- Therapeutic Targets Database
- DAP001332
- PharmGKB
- PA164768737
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Haloprogin
- MSDS
- Download (43.8 KB)
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Westwood squibb pharmaceuticals inc
- Packagers
- Norega Laboratories Inc.
- Dosage Forms
- Not Available
- Prices
Unit description Cost Unit Halotin 1% cream 1.53USD g DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 114-115 U.S. Patent 3,322,813. logP 5.3 Not Available - Predicted Properties
Property Value Source Water Solubility 0.00601 mg/mL ALOGPS logP 4.69 ALOGPS logP 4.85 Chemaxon logS -4.8 ALOGPS pKa (Strongest Basic) -5 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 1 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 9.23 Å2 Chemaxon Rotatable Bond Count 3 Chemaxon Refractivity 66.88 m3·mol-1 Chemaxon Polarizability 26.82 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.971 Blood Brain Barrier + 0.9801 Caco-2 permeable + 0.7613 P-glycoprotein substrate Non-substrate 0.8197 P-glycoprotein inhibitor I Non-inhibitor 0.8892 P-glycoprotein inhibitor II Non-inhibitor 0.9614 Renal organic cation transporter Non-inhibitor 0.8024 CYP450 2C9 substrate Non-substrate 0.8017 CYP450 2D6 substrate Non-substrate 0.817 CYP450 3A4 substrate Non-substrate 0.6163 CYP450 1A2 substrate Inhibitor 0.9082 CYP450 2C9 inhibitor Non-inhibitor 0.6083 CYP450 2D6 inhibitor Non-inhibitor 0.9101 CYP450 2C19 inhibitor Inhibitor 0.6549 CYP450 3A4 inhibitor Non-inhibitor 0.8235 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.7712 Ames test Non AMES toxic 0.6364 Carcinogenicity Non-carcinogens 0.731 Biodegradation Not ready biodegradable 0.9606 Rat acute toxicity 1.8412 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.7112 hERG inhibition (predictor II) Non-inhibitor 0.9133
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-0nvi-2937000000-e0fbc50dec2df8a7392c Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-03di-0009000000-8e8db9a24fe59dd038af Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0a4i-0009000000-7e4b5c230aa8e9ef2d8e Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-03di-0049000000-8e22e3ee3b74745c9e5a Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0a4i-0109000000-9874c32f90ed7c947713 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0089-0394000000-35ac5f852eed13b1e3a3 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-056r-2907000000-9be5f7148441d31ee896 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]- 135.3765845 predictedDarkChem Lite v0.1.0 [M-H]- 145.71458 predictedDeepCCS 1.0 (2019) [M+H]+ 135.9819845 predictedDarkChem Lite v0.1.0 [M+H]+ 148.07259 predictedDeepCCS 1.0 (2019) [M+Na]+ 135.8989845 predictedDarkChem Lite v0.1.0 [M+Na]+ 154.75566 predictedDeepCCS 1.0 (2019)
Drug created at June 13, 2005 13:24 / Updated at December 02, 2023 06:55