ContaminantDB: Haloprogin

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-22 06:00:41 UTC

Update Date

2026-05-14 16:49:08 UTC

Accession Number

CHEM019314

Identification

Common Name

Haloprogin

Class

Small Molecule

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.

Contaminant Sources

HMDB Contaminants - Urine
STOFF IDENT Compounds
ToxCast & Tox21 Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Halotex	Kegg
Théraplix brand OF haloprogin	HMDB
Mycilan	HMDB
Westwood squibb brand OF haloprogin	HMDB
3-Iodo-2-propynyl 2,4,5-trichlorophenyl ether	HMDB

Chemical Formula

C₉H₄Cl₃IO

Average Molecular Mass

361.391 g/mol

Monoisotopic Mass

359.837 g/mol

CAS Registry Number

777-11-7

IUPAC Name

1,2,4-trichloro-5-[(3-iodoprop-2-yn-1-yl)oxy]benzene

Traditional Name

haloprogin

SMILES

ClC1=CC(Cl)=C(Cl)C=C1OCC#CI

InChI Identifier

InChI=1S/C9H4Cl3IO/c10-6-4-8(12)9(5-7(6)11)14-3-1-2-13/h4-5H,3H2

InChI Key

CTETYYAZBPJBHE-UHFFFAOYSA-N

Chemical Taxonomy

Description

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

Substituents

Phenoxy compound
Phenol ether
Alkyl aryl ether
Chlorobenzene
Halobenzene
Aryl chloride
Aryl halide
Monocyclic benzene moiety
Ether
Haloacetylene or derivatives
Organohalogen compound
Hydrocarbon derivative
Organic oxygen compound
Organochloride
Organoiodide
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.006 g/L	ALOGPS
logP	4.69	ALOGPS
logP	4.85	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Basic)	-5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	9.23 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	66.88 m³·mol⁻¹	ChemAxon
Polarizability	26.82 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0nvi-2937000000-e0fbc50dec2df8a7392c	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0009000000-205241bf6f19269ac44f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-0009000000-685736b870ca3a5b7396	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01q9-0904000000-0fa7f51cc65c247bc53e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0009000000-613da8314566eab0ea09	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-0009000000-5526c9d6e567956ca1c8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a6r-0639000000-48169dabf0e58c7b946c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0009000000-13123a05c84264f3a263	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-0029000000-82363b16547174d03783	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-06w9-4296000000-43a5c95da82f2b836304	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0009000000-c2d55deaed82c6582a92	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-0009000000-c2d55deaed82c6582a92	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-2249000000-3d6d4d91ac564a883d2b	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not Available

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

DB00793

HMDB ID

HMDB0014931

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

1. Harrison EF, Zygmunt WA: Haloprogin: mode of action studies in Candida albicans. Can J Microbiol. 1974 Sep;20(9):1241-5.

2. 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.

Haloprogin (CHEM019314)

Structure for CHEM019314: Haloprogin