Haloprogin

Identification

Name
Haloprogin
Accession Number
DB00793  (APRD01011)
Type
Small Molecule
Groups
Approved, Withdrawn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
  • Haloprogin
  • Haloprogina
  • Haloprogine
  • Haloproginum
External IDs
M-1028 (MEIJI) / NSC-100071
International/Other Brands
Aloprogen (Westwood) / Halotex (Westwood) / Mycanden (Schering) / Mycilan (Schering-Plough) / Polik (Meiji)
Categories
UNII
AIU7053OWL
CAS number
777-11-7
Weight
Average: 361.391
Monoisotopic: 359.837241291
Chemical Formula
C9H4Cl3IO
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

Pharmacology

Indication

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

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
Toxicity
Not Available
Affected organisms
  • Dermatophytic fungi including Trichophyton, Microsporum and Epidermophyton
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
AgmatineThe therapeutic efficacy of Haloprogin can be increased when used in combination with Agmatine.Experimental, Investigational
AmiodaroneThe therapeutic efficacy of Haloprogin can be increased when used in combination with Amiodarone.Approved, Investigational
AmlodipineThe therapeutic efficacy of Haloprogin can be increased when used in combination with Amlodipine.Approved
Amphotericin BThe therapeutic efficacy of Amphotericin B can be decreased when used in combination with Haloprogin.Approved, Investigational
AmrinoneThe therapeutic efficacy of Haloprogin can be increased when used in combination with Amrinone.Approved
AranidipineThe therapeutic efficacy of Haloprogin can be increased when used in combination with Aranidipine.Approved, Investigational
AzelnidipineThe therapeutic efficacy of Haloprogin can be increased when used in combination with Azelnidipine.Approved, Investigational
AzimilideThe therapeutic efficacy of Haloprogin can be increased when used in combination with Azimilide.Investigational
BarnidipineThe therapeutic efficacy of Haloprogin can be increased when used in combination with Barnidipine.Approved
BencyclaneThe therapeutic efficacy of Haloprogin can be increased when used in combination with Bencyclane.Experimental
BenidipineThe therapeutic efficacy of Haloprogin can be increased when used in combination with Benidipine.Approved, Investigational
BepridilThe therapeutic efficacy of Haloprogin can be increased when used in combination with Bepridil.Approved, Withdrawn
BioallethrinThe therapeutic efficacy of Haloprogin can be increased when used in combination with Bioallethrin.Approved, Experimental
BuspironeThe metabolism of Buspirone can be decreased when combined with Haloprogin.Approved, Investigational
BusulfanThe serum concentration of Busulfan can be increased when it is combined with Haloprogin.Approved, Investigational
CarboxyamidotriazoleThe therapeutic efficacy of Haloprogin can be increased when used in combination with Carboxyamidotriazole.Investigational
CaroverineThe therapeutic efficacy of Haloprogin can be increased when used in combination with Caroverine.Experimental
CilnidipineThe therapeutic efficacy of Haloprogin can be increased when used in combination with Cilnidipine.Approved, Investigational
CinnarizineThe therapeutic efficacy of Haloprogin can be increased when used in combination with Cinnarizine.Approved, Investigational
CisaprideThe serum concentration of Cisapride can be increased when it is combined with Haloprogin.Approved, Investigational, Withdrawn
ClevidipineThe therapeutic efficacy of Haloprogin can be increased when used in combination with Clevidipine.Approved, Investigational
CyclandelateThe therapeutic efficacy of Haloprogin can be increased when used in combination with Cyclandelate.Approved
CyclosporineThe metabolism of Cyclosporine can be decreased when combined with Haloprogin.Approved, Investigational, Vet Approved
DarodipineThe therapeutic efficacy of Haloprogin can be increased when used in combination with Darodipine.Experimental
DidanosineDidanosine can cause a decrease in the absorption of Haloprogin resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
DiltiazemThe therapeutic efficacy of Haloprogin can be increased when used in combination with Diltiazem.Approved, Investigational
DocetaxelThe metabolism of Docetaxel can be decreased when combined with Haloprogin.Approved, Investigational
DofetilideThe serum concentration of Dofetilide can be increased when it is combined with Haloprogin.Approved, Investigational
DotarizineThe therapeutic efficacy of Haloprogin can be increased when used in combination with Dotarizine.Investigational
EfonidipineThe therapeutic efficacy of Haloprogin can be increased when used in combination with Efonidipine.Approved, Investigational
EperisoneThe therapeutic efficacy of Haloprogin can be increased when used in combination with Eperisone.Approved, Investigational
EthosuximideThe therapeutic efficacy of Haloprogin can be increased when used in combination with Ethosuximide.Approved
EtravirineThe serum concentration of Etravirine can be increased when it is combined with Haloprogin.Approved
FelodipineThe therapeutic efficacy of Haloprogin can be increased when used in combination with Felodipine.Approved, Investigational
FendilineThe therapeutic efficacy of Haloprogin can be increased when used in combination with Fendiline.Withdrawn
Fish oilThe therapeutic efficacy of Haloprogin can be increased when used in combination with Fish oil.Approved, Nutraceutical
FlunarizineThe therapeutic efficacy of Haloprogin can be increased when used in combination with Flunarizine.Approved
FluspirileneThe therapeutic efficacy of Haloprogin can be increased when used in combination with Fluspirilene.Approved, Investigational
FosphenytoinThe serum concentration of Haloprogin can be decreased when it is combined with Fosphenytoin.Approved, Investigational
GabapentinThe therapeutic efficacy of Haloprogin can be increased when used in combination with Gabapentin.Approved, Investigational
GallopamilThe therapeutic efficacy of Haloprogin can be increased when used in combination with Gallopamil.Investigational
IsradipineThe therapeutic efficacy of Haloprogin can be increased when used in combination with Isradipine.Approved, Investigational
LacidipineThe therapeutic efficacy of Haloprogin can be increased when used in combination with Lacidipine.Approved, Investigational
LamotrigineThe therapeutic efficacy of Haloprogin can be increased when used in combination with Lamotrigine.Approved, Investigational
LercanidipineThe therapeutic efficacy of Haloprogin can be increased when used in combination with Lercanidipine.Approved, Investigational
LevetiracetamThe therapeutic efficacy of Haloprogin can be increased when used in combination with Levetiracetam.Approved, Investigational
LidoflazineThe therapeutic efficacy of Haloprogin can be increased when used in combination with Lidoflazine.Experimental
LoperamideThe therapeutic efficacy of Haloprogin can be increased when used in combination with Loperamide.Approved
LosartanThe metabolism of Losartan can be decreased when combined with Haloprogin.Approved
Magnesium sulfateThe therapeutic efficacy of Haloprogin can be increased when used in combination with Magnesium sulfate.Approved, Investigational, Vet Approved
ManidipineThe therapeutic efficacy of Haloprogin can be increased when used in combination with Manidipine.Approved, Investigational
MentholThe therapeutic efficacy of Haloprogin can be increased when used in combination with Menthol.Approved
MethsuximideThe therapeutic efficacy of Haloprogin can be increased when used in combination with Methsuximide.Approved
MibefradilThe therapeutic efficacy of Haloprogin can be increased when used in combination with Mibefradil.Investigational, Withdrawn
NaftopidilThe therapeutic efficacy of Haloprogin can be increased when used in combination with Naftopidil.Investigational
NicardipineThe therapeutic efficacy of Haloprogin can be increased when used in combination with Nicardipine.Approved, Investigational
NifedipineThe therapeutic efficacy of Haloprogin can be increased when used in combination with Nifedipine.Approved
NiguldipineThe therapeutic efficacy of Haloprogin can be increased when used in combination with Niguldipine.Experimental
NiludipineThe therapeutic efficacy of Haloprogin can be increased when used in combination with Niludipine.Experimental
NilvadipineThe therapeutic efficacy of Haloprogin can be increased when used in combination with Nilvadipine.Approved, Investigational
NimesulideThe therapeutic efficacy of Haloprogin can be increased when used in combination with Nimesulide.Approved, Investigational, Withdrawn
NimodipineThe therapeutic efficacy of Haloprogin can be increased when used in combination with Nimodipine.Approved, Investigational
NisoldipineThe therapeutic efficacy of Haloprogin can be increased when used in combination with Nisoldipine.Approved
NitrendipineThe therapeutic efficacy of Haloprogin can be increased when used in combination with Nitrendipine.Approved, Investigational
NylidrinThe therapeutic efficacy of Haloprogin can be increased when used in combination with Nylidrin.Approved
OtiloniumThe therapeutic efficacy of Haloprogin can be increased when used in combination with Otilonium.Experimental, Investigational
PhenytoinThe serum concentration of Phenytoin can be increased when it is combined with Haloprogin.Approved, Vet Approved
PinaveriumThe therapeutic efficacy of Haloprogin can be increased when used in combination with Pinaverium.Approved
PrenylamineThe therapeutic efficacy of Haloprogin can be increased when used in combination with Prenylamine.Withdrawn
ProgesteroneThe absorption of Progesterone can be decreased when combined with Haloprogin.Approved, Vet Approved
QuinidineThe serum concentration of Quinidine can be increased when it is combined with Haloprogin.Approved, Investigational
RanolazineThe serum concentration of Ranolazine can be increased when it is combined with Haloprogin.Approved, Investigational
RifabutinThe serum concentration of Rifabutin can be increased when it is combined with Haloprogin.Approved, Investigational
RifampicinThe serum concentration of Rifampicin can be increased when it is combined with Haloprogin.Approved
RifapentineThe serum concentration of Rifapentine can be increased when it is combined with Haloprogin.Approved, Investigational
RifaximinThe serum concentration of Rifaximin can be increased when it is combined with Haloprogin.Approved, Investigational
SeletracetamThe therapeutic efficacy of Haloprogin can be increased when used in combination with Seletracetam.Investigational
SolifenacinThe metabolism of Solifenacin can be decreased when combined with Haloprogin.Approved
SucralfateSucralfate can cause a decrease in the absorption of Haloprogin resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
SunitinibThe metabolism of Sunitinib can be decreased when combined with Haloprogin.Approved, Investigational
TacrolimusThe metabolism of Tacrolimus can be decreased when combined with Haloprogin.Approved, Investigational
TerodilineThe therapeutic efficacy of Haloprogin can be increased when used in combination with Terodiline.Experimental
TetrahydropalmatineThe therapeutic efficacy of Haloprogin can be increased when used in combination with Tetrahydropalmatine.Investigational
Tolfenamic AcidThe therapeutic efficacy of Haloprogin can be increased when used in combination with Tolfenamic Acid.Approved, Investigational
TranilastThe therapeutic efficacy of Haloprogin can be increased when used in combination with Tranilast.Approved, Investigational
TrimebutineThe therapeutic efficacy of Haloprogin can be increased when used in combination with Trimebutine.Approved
TrimethadioneThe therapeutic efficacy of Haloprogin can be increased when used in combination with Trimethadione.Approved
VerapamilThe therapeutic efficacy of Haloprogin can be increased when used in combination with Verapamil.Approved
VinpocetineThe therapeutic efficacy of Haloprogin can be increased when used in combination with Vinpocetine.Investigational
WIN 55212-2The therapeutic efficacy of Haloprogin can be increased when used in combination with WIN 55212-2.Experimental
ZiconotideThe therapeutic efficacy of Haloprogin can be increased when used in combination with Ziconotide.Approved
ZolpidemThe serum concentration of Zolpidem can be increased when it is combined with Haloprogin.Approved
ZonisamideThe therapeutic efficacy of Haloprogin can be increased when used in combination with Zonisamide.Approved, Investigational
Food Interactions
Not Available

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]
External Links
Human Metabolome Database
HMDB0014931
KEGG Drug
D00339
PubChem Compound
3561
PubChem Substance
46504892
ChemSpider
3440
BindingDB
50194601
ChEBI
5614
ChEMBL
CHEMBL1289
Therapeutic Targets Database
DAP001332
PharmGKB
PA164768737
Drugs.com
Drugs.com Drug Page
Wikipedia
Haloprogin
ATC Codes
D01AE11 — Haloprogin
MSDS
Download (43.8 KB)

Clinical Trials

Clinical Trials
Not Available

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

Taxonomy

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
Phenoxy compound / Phenol ether / Alkyl aryl ether / Chlorobenzene / Halobenzene / Aryl chloride / Aryl halide / Monocyclic benzene moiety / Ether / Haloacetylene or derivatives
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available

Drug created on June 13, 2005 07:24 / Updated on June 02, 2018 06:40