Haloprogin

Identification

Name
Haloprogin
Accession Number
DB00793
Description

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Approved, Withdrawn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
Thumb
Weight
Average: 361.391
Monoisotopic: 359.837241291
Chemical Formula
C9H4Cl3IO
Synonyms
  • Haloprogin
  • Haloprogina
  • Haloprogine
  • Haloproginum
External IDs
  • M-1028 (MEIJI)
  • NSC-100071

Pharmacology

Pharmacology
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Indication

Used to treat fungal (Tinea) skin infections such as athlete's foot, jock itch, ringworm, and tinea versicolor.

Contraindications & Blackbox Warnings
Contraindications
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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
Medicalerrors
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Toxicity
Not Available
Affected organisms
  • Dermatophytic fungi including Trichophyton, Microsporum and Epidermophyton
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
AcenocoumarolThe therapeutic efficacy of Acenocoumarol can be increased when used in combination with Haloprogin.
DicoumarolThe therapeutic efficacy of Dicoumarol can be increased when used in combination with Haloprogin.
FluindioneThe therapeutic efficacy of Fluindione can be increased when used in combination with Haloprogin.
PhenindioneThe therapeutic efficacy of Phenindione can be increased when used in combination with Haloprogin.
PhenprocoumonThe therapeutic efficacy of Phenprocoumon can be increased when used in combination with Haloprogin.
WarfarinThe therapeutic efficacy of Warfarin can be increased when used in combination with Haloprogin.
Interactions
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Food Interactions
Not Available

Products

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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

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
  1. Harrison EF, Zwadyk P Jr, Bequette RJ, Hamlow EE, Tavormina PA, Zygmunt WA: Haloprogin: a topical antifungal agent. Appl Microbiol. 1970 May;19(5):746-50. [PubMed:5422306]
  2. Harrison EF, Zygmunt WA: Haloprogin: mode of action studies in Candida albicans. Can J Microbiol. 1974 Sep;20(9):1241-5. [PubMed:4608935]
Human Metabolome Database
HMDB0014931
KEGG Drug
D00339
PubChem Compound
3561
PubChem Substance
46504892
ChemSpider
3440
BindingDB
50194601
RxNav
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

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
  • Westwood squibb pharmaceuticals inc
Packagers
  • Norega Laboratories Inc.
Dosage Forms
Not Available
Prices
Unit descriptionCostUnit
Halotin 1% cream1.53USD g
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)114-115U.S. Patent 3,322,813.
logP5.3Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00601 mg/mLALOGPS
logP4.69ALOGPS
logP4.85ChemAxon
logS-4.8ALOGPS
pKa (Strongest Basic)-5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area9.23 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity66.88 m3·mol-1ChemAxon
Polarizability26.82 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.971
Blood Brain Barrier+0.9801
Caco-2 permeable+0.7613
P-glycoprotein substrateNon-substrate0.8197
P-glycoprotein inhibitor INon-inhibitor0.8892
P-glycoprotein inhibitor IINon-inhibitor0.9614
Renal organic cation transporterNon-inhibitor0.8024
CYP450 2C9 substrateNon-substrate0.8017
CYP450 2D6 substrateNon-substrate0.817
CYP450 3A4 substrateNon-substrate0.6163
CYP450 1A2 substrateInhibitor0.9082
CYP450 2C9 inhibitorNon-inhibitor0.6083
CYP450 2D6 inhibitorNon-inhibitor0.9101
CYP450 2C19 inhibitorInhibitor0.6549
CYP450 3A4 inhibitorNon-inhibitor0.8235
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.7712
Ames testNon AMES toxic0.6364
CarcinogenicityNon-carcinogens0.731
BiodegradationNot ready biodegradable0.9606
Rat acute toxicity1.8412 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.7112
hERG inhibition (predictor II)Non-inhibitor0.9133
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
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

Drug created on June 13, 2005 13:24 / Updated on April 03, 2021 09:38