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Identification
NameHaloprogin
Accession NumberDB00793  (APRD01011)
TypeSmall Molecule
GroupsApproved, Withdrawn
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.

Structure
Thumb
Synonyms
SynonymLanguageCode
HaloproginNot AvailableINN, USAN, JAN
HaloproginaSpanishINN
HaloprogineFrenchINN
HaloproginumLatinINN
HalotexNot AvailableNot Available
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International Brands
NameCompany
AloprogenWestwood
HalotexWestwood
MycandenSchering
MycilanSchering-Plough
PolikMeiji
Brand mixturesNot Available
SaltsNot Available
Categories
CAS number777-11-7
WeightAverage: 361.391
Monoisotopic: 359.837241291
Chemical FormulaC9H4Cl3IO
InChI KeyCTETYYAZBPJBHE-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
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenol ethers
Direct ParentPhenol ethers
Alternative Parents
Substituents
  • Phenol ether
  • Halobenzene
  • Chlorobenzene
  • Alkyl aryl ether
  • Aryl halide
  • Aryl chloride
  • Ether
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organoiodide
  • Organochloride
  • Organohalogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationUsed to treat fungal (Tinea) skin infections such as athlete's foot, jock itch, ringworm, and tinea versicolor.
PharmacodynamicsUsed 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 actionHaloprogin 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.
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Dermatophytic fungi including Trichophyton, Microsporum and Epidermophyton
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 substrateNon-inhibitor0.6083
CYP450 2D6 substrateNon-inhibitor0.9101
CYP450 2C19 substrateInhibitor0.6549
CYP450 3A4 substrateNon-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
Pharmacoeconomics
Manufacturers
  • Westwood squibb pharmaceuticals inc
Packagers
  • Norega Laboratories Inc.
Dosage formsNot Available
Prices
Unit descriptionCostUnit
Halotin 1% cream1.53USD g
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point114-115U.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 FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis Reference

U.S. Patent 3,322,813.

General Reference
  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
  2. Harrison EF, Zygmunt WA: Haloprogin: mode of action studies in Candida albicans. Can J Microbiol. 1974 Sep;20(9):1241-5. Pubmed
External Links
ATC CodesD01AE11
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (43.8 KB)
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available
Comments
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Drug created on June 13, 2005 07:24 / Updated on April 25, 2014 16:51