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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GroupsApproved, Withdrawn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
SaltsNot Available
Brand names
NameCompany
AloprogenWestwood
HalotexWestwood
MycandenSchering
MycilanSchering-Plough
PolikMeiji
Brand mixturesNot 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
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassBenzenoids
ClassBenzene and Substituted Derivatives
SubclassPhenol Ethers
Direct parentPhenol Ethers
Alternative parentsAlkyl Aryl Ethers; Chlorobenzenes; Aryl Chlorides; Polyamines; Organoiodides; Organochlorides
Substituentsalkyl aryl ether; chlorobenzene; aryl halide; aryl chloride; ether; polyamine; organochloride; organoiodide; organohalogen
Classification descriptionThis compound belongs to the phenol ethers. These are aromatic compounds containing an ether group substituted with a benzene ring.
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
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 substrate Non-inhibitor 0.6083
CYP450 2D6 substrate Non-inhibitor 0.9101
CYP450 2C19 substrate Inhibitor 0.6549
CYP450 3A4 substrate 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
Pharmacoeconomics
Manufacturers
  • Westwood squibb pharmaceuticals inc
Packagers
  • Norega Laboratories Inc.
Dosage formsNot Available
Prices
Unit descriptionCostUnit
Halotin 1% cream1.53USDg
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 Solubility0.00601ALOGPS
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
Spectra
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
ResourceLink
KEGG DrugD00339
PubChem Compound3561
PubChem Substance46504892
ChemSpider3440
BindingDB50194601
Therapeutic Targets DatabaseDAP001332
PharmGKBPA164768737
Drugs.comhttp://www.drugs.com/mtm/haloprogin-topical.html
WikipediaHaloprogin
ATC CodesD01AE11
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSshow(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