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Approved, Withdrawn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.

Structured Indications
Not Available
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
AmlodipineThe risk or severity of adverse effects can be increased when Haloprogin is combined with Amlodipine.Approved
Amphotericin BThe therapeutic efficacy of Amphotericin B can be decreased when used in combination with Haloprogin.Approved, Investigational
AmrinoneThe risk or severity of adverse effects can be increased when Haloprogin is combined with Amrinone.Approved
AzelnidipineThe risk or severity of adverse effects can be increased when Haloprogin is combined with Azelnidipine.Approved, Investigational
AzimilideThe risk or severity of adverse effects can be increased when Haloprogin is combined with Azimilide.Investigational
BarnidipineThe risk or severity of adverse effects can be increased when Haloprogin is combined with Barnidipine.Approved
BencyclaneThe risk or severity of adverse effects can be increased when Haloprogin is combined with Bencyclane.Experimental
BenidipineThe risk or severity of adverse effects can be increased when Haloprogin is combined with Benidipine.Approved, Investigational
BepridilThe risk or severity of adverse effects can be increased when Haloprogin is combined with Bepridil.Approved, Withdrawn
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 risk or severity of adverse effects can be increased when Haloprogin is combined with Carboxyamidotriazole.Investigational
CaroverineThe risk or severity of adverse effects can be increased when Haloprogin is combined with Caroverine.Experimental
CilnidipineThe risk or severity of adverse effects can be increased when Haloprogin is combined with Cilnidipine.Approved, Investigational
CinnarizineThe risk or severity of adverse effects can be increased when Haloprogin is combined with Cinnarizine.Approved, Investigational
CisaprideThe serum concentration of Cisapride can be increased when it is combined with Haloprogin.Approved, Investigational, Withdrawn
ClevidipineThe risk or severity of adverse effects can be increased when Haloprogin is combined with Clevidipine.Approved
CyclosporineThe metabolism of Cyclosporine can be decreased when combined with Haloprogin.Approved, Investigational, Vet Approved
DarodipineThe risk or severity of adverse effects can be increased when Haloprogin is combined 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 risk or severity of adverse effects can be increased when Haloprogin is combined with Diltiazem.Approved
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
DotarizineThe risk or severity of adverse effects can be increased when Haloprogin is combined with Dotarizine.Investigational
EfonidipineThe risk or severity of adverse effects can be increased when Haloprogin is combined with Efonidipine.Approved, Investigational
EperisoneThe risk or severity of adverse effects can be increased when Haloprogin is combined with Eperisone.Approved, Investigational
EtravirineThe serum concentration of Etravirine can be increased when it is combined with Haloprogin.Approved
FelodipineThe risk or severity of adverse effects can be increased when Haloprogin is combined with Felodipine.Approved, Investigational
FendilineThe risk or severity of adverse effects can be increased when Haloprogin is combined with Fendiline.Withdrawn
FlunarizineThe risk or severity of adverse effects can be increased when Haloprogin is combined with Flunarizine.Approved
FosphenytoinThe serum concentration of Haloprogin can be decreased when it is combined with Fosphenytoin.Approved
GabapentinThe risk or severity of adverse effects can be increased when Haloprogin is combined with Gabapentin.Approved, Investigational
GallopamilThe risk or severity of adverse effects can be increased when Haloprogin is combined with Gallopamil.Investigational
IsradipineThe risk or severity of adverse effects can be increased when Haloprogin is combined with Isradipine.Approved
LacidipineThe risk or severity of adverse effects can be increased when Haloprogin is combined with Lacidipine.Approved, Investigational
LamotrigineThe risk or severity of adverse effects can be increased when Haloprogin is combined with Lamotrigine.Approved, Investigational
LercanidipineThe risk or severity of adverse effects can be increased when Haloprogin is combined with Lercanidipine.Approved, Investigational
LidoflazineThe risk or severity of adverse effects can be increased when Haloprogin is combined with Lidoflazine.Experimental
LosartanThe metabolism of Losartan can be decreased when combined with Haloprogin.Approved
Magnesium SulfateThe risk or severity of adverse effects can be increased when Haloprogin is combined with Magnesium Sulfate.Approved, Vet Approved
ManidipineThe risk or severity of adverse effects can be increased when Haloprogin is combined with Manidipine.Approved, Investigational
MibefradilThe risk or severity of adverse effects can be increased when Haloprogin is combined with Mibefradil.Investigational, Withdrawn
NaftopidilThe risk or severity of adverse effects can be increased when Haloprogin is combined with Naftopidil.Investigational
NicardipineThe risk or severity of adverse effects can be increased when Haloprogin is combined with Nicardipine.Approved
NifedipineThe risk or severity of adverse effects can be increased when Haloprogin is combined with Nifedipine.Approved
NiguldipineThe risk or severity of adverse effects can be increased when Haloprogin is combined with Niguldipine.Experimental
NiludipineThe risk or severity of adverse effects can be increased when Haloprogin is combined with Niludipine.Experimental
NilvadipineThe risk or severity of adverse effects can be increased when Haloprogin is combined with Nilvadipine.Approved, Investigational
NimesulideThe risk or severity of adverse effects can be increased when Haloprogin is combined with Nimesulide.Approved, Investigational, Withdrawn
NimodipineThe risk or severity of adverse effects can be increased when Haloprogin is combined with Nimodipine.Approved
NisoldipineThe risk or severity of adverse effects can be increased when Haloprogin is combined with Nisoldipine.Approved
NitrendipineThe risk or severity of adverse effects can be increased when Haloprogin is combined with Nitrendipine.Approved, Investigational
OtiloniumThe risk or severity of adverse effects can be increased when Haloprogin is combined with Otilonium.Experimental, Investigational
PerhexilineThe risk or severity of adverse effects can be increased when Haloprogin is combined with Perhexiline.Approved, Investigational
PhenytoinThe serum concentration of Phenytoin can be increased when it is combined with Haloprogin.Approved, Vet Approved
PinaveriumThe risk or severity of adverse effects can be increased when Haloprogin is combined with Pinaverium.Approved
PregabalinThe risk or severity of adverse effects can be increased when Haloprogin is combined with Pregabalin.Approved, Illicit, Investigational
PrenylamineThe risk or severity of adverse effects can be increased when Haloprogin is combined 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
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
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
RifaximinThe serum concentration of Rifaximin can be increased when it is combined with Haloprogin.Approved, Investigational
RisedronateThe risk or severity of adverse effects can be increased when Haloprogin is combined with Risedronate.Approved, 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 risk or severity of adverse effects can be increased when Haloprogin is combined with Terodiline.Experimental
TetrahydropalmatineThe risk or severity of adverse effects can be increased when Haloprogin is combined with Tetrahydropalmatine.Investigational
Tolfenamic AcidThe risk or severity of adverse effects can be increased when Haloprogin is combined with Tolfenamic Acid.Approved
TranilastThe risk or severity of adverse effects can be increased when Haloprogin is combined with Tranilast.Approved, Investigational
VerapamilThe risk or severity of adverse effects can be increased when Haloprogin is combined with Verapamil.Approved
VinpocetineThe risk or severity of adverse effects can be increased when Haloprogin is combined with Vinpocetine.Investigational
XylometazolineThe risk or severity of adverse effects can be increased when Haloprogin is combined with Xylometazoline.Approved
ZiconotideThe risk or severity of adverse effects can be increased when Haloprogin is combined with Ziconotide.Approved
ZolpidemThe serum concentration of Zolpidem can be increased when it is combined with Haloprogin.Approved
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
HMDB14931
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 November 07, 2017 01:42