Haloprogin

Chemical compound

D01AE11 (WHO)

Legal statusLegal status

US: Not available

Identifiers

IUPAC name

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

CAS Number

777-11-7^Y

PubChem CID

3561

DrugBank

DB00793^Y

ChemSpider

3440^Y

UNII

AIU7053OWL

KEGG

D00339^Y

ChEMBL

ChEMBL1289^Y

CompTox Dashboard (EPA)

DTXSID9046865

ECHA InfoCard100.011.169

Chemical and physical dataFormulaC₉H₄Cl₃IOMolar mass361.38 g·mol⁻¹3D model (JSmol)

Interactive image

Melting point113.5 °C (236.3 °F)Solubility in waterInsoluble mg/mL (20 °C)

SMILES

Clc1cc(OCC#CI)c(Cl)cc1Cl

InChI

InChI=1S/C9H4Cl3IO/c10-6-4-8(12)9(5-7(6)11)14-3-1-2-13/h4-5H,3H2^Y
Key:CTETYYAZBPJBHE-UHFFFAOYSA-N^Y

(verify)

Haloprogin is an antifungal drug used to treat athlete's foot and other fungal infections.^[1] It is marketed in creams under the trade names Halotex, Mycanden, Mycilan, and Polik.

Action

Haloprogin was previously used in 1% topical creams as an antifungal agent. It was marketed over-the-counter primarily to treat tinea infections of the skin. The mechanism of action is unknown.^[2]

Haloprogin had a high incidence of side effects including: irritation, burning, vesiculation (blisters), scaling, and itching. It has since been discontinued due to the emergence of more modern antifungals with fewer side effects.^[3]

References

^ Rudolph RI (December 1979). "Haloprogin as treatment for fungal infections". Clinical and Experimental Dermatology. 4 (4): 548. doi:10.1111/j.1365-2230.1979.tb01656.x. PMID 161212. S2CID 71471801.
^ "Haloprogin". Drugs@FDA. Food and Drug Administration. Retrieved 2007-02-17.
^ "Haloprogin". DrugBank. University of Alberta. Nov 6, 2006. Retrieved 2007-02-17.

Antifungals (D01 and J02)

Wall/
membrane

Ergosterol
inhibitors

Azoles (lanosterol 14α-
demethylase inhibitors)

Imidazoles	Topical: bifonazole^‡ butoconazole chlormidazole^‡ climbazole clotrimazole^# croconazole^‡ eberconazole econazole fenticonazole^‡ flutrimazole isoconazole ketoconazole luliconazole miconazole^# neticonazole^‡ omoconazole^‡ oxiconazole sertaconazole sulconazole tioconazole Systemic: ketoconazole
Triazoles	Topical: efinaconazole fluconazole^# terconazole Systemic: fluconazole^# fosfluconazole fosravuconazole hexaconazole^‡ isavuconazole itraconazole^# oteseconazole posaconazole voriconazole^# Unknown: albaconazole^‡ ravuconazole^†
Thiazoles	Topical: abafungin^‡

Polyene antimycotics
(ergosterol binding)

Topical: hamycin^‡
natamycin
nystatin^#
Systemic: amphotericin B^#, hamycin^‡

Squalene monooxygenase
inhibitors

Allylamines	Topical: naftifine terbinafine Systemic: terbinafine
Benzylamines	Topical: butenafine

Others

Topical: amorolfine

β-glucan synthase
inhibitors

Intracellular

Pyrimidine analogues/ thymidylate synthase inhibitors	Systemic: flucytosine^#
Mitotic inhibitors	Systemic: griseofulvin^#
Aminoacyl tRNA synthetase inhibitors	Topical: tavaborole

Others

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

v t e Xenobiotic-sensing receptor modulators
CARTooltip Constitutive androstane receptor	Agonists: 6,7-Dimethylesculetin Amiodarone Artemisinin Benfuracarb Carbamazepine Carvedilol Chlorpromazine Chrysin CITCO Clotrimazole Cyclophosphamide Cypermethrin DHEA (prasterone) Efavirenz Ellagic acid Griseofulvin Methoxychlor Mifepristone Nefazodone Nevirapine Nicardipine Octicizer Permethrin Phenobarbital Phenytoin Pregnanedione (5β-dihydroprogesterone) Reserpine TCPOBOP Telmisartan Tolnaftate Troglitazone Valproic acid Antagonists: 3,17β-Estradiol 3α-Androstanol 3α-Androstenol 3β-Androstanol 17-Androstanol AITC Ethinylestradiol Meclizine Nigramide J Okadaic acid PK-11195 S-07662 T-0901317
PXRTooltip Pregnane X receptor	Agonists: 17α-Hydroxypregnenolone 17α-Hydroxyprogesterone Δ⁴-Androstenedione Δ⁵-Androstenediol Δ⁵-Androstenedione AA-861 Allopregnanediol Allopregnanedione (5α-dihydroprogesterone) Allopregnanolone (brexanolone) Alpha-Lipoic acid Ambrisentan AMI-193 Amlodipine besylate Antimycotics Artemisinin Aurothioglucose Bile acids Bithionol Bosentan Bumecaine Cafestol Cephaloridine Cephradine Chlorpromazine Ciglitazone Clindamycin Clofenvinfos Chloroxine Clotrimazole Colforsin Corticosterone Cyclophosphamide Cyproterone acetate Demecolcine Dexamethasone DHEA (prasterone) DHEA-S (prasterone sulfate) Dibunate sodium Diclazuril Dicloxacillin Dimercaprol Dinaline Docetaxel Docusate calcium Dodecylbenzenesulfonic acid Dronabinol Droxidopa Eburnamonine Ecopipam Enzacamene Epothilone B Erythromycin Famprofazone Febantel Felodipine Fenbendazole Fentanyl Flucloxacillin Fluorometholone Griseofulvin Guggulsterone Haloprogin Hetacillin potassium Hyperforin Hypericum perforatum (St John's wort) Indinavir sulfate Lasalocid sodium Levothyroxine Linolenic acid: α-Linolenic acid and γ-linolenic acid LOE-908 Loratadine Lovastatin Meclizine Metacycline Methylprednisolone Metyrapone Mevastatin Mifepristone Nafcillin Nicardipine Nicotine Nifedipine Nilvadipine Nisoldipine Norelgestromin Omeprazole Orlistat Oxatomide Paclitaxel Phenobarbital Piperine Plicamycin Prednisolone Pregnanediol Pregnanedione (5β-dihydroprogesterone) Pregnanolone Pregnenolone Pregnenolone 16α-carbonitrile Proadifen Progesterone Quingestrone Reserpine Reverse triiodothyronine Rifampicin Rifaximin Rimexolone Riodipine Ritonavir Simvastatin Sirolimus Spironolactone Spiroxatrine SR-12813 Suberoylanilide Sulfisoxazole Suramin Tacrolimus Tenylidone Terconazole Testosterone isocaproate Tetracycline Thiamylal sodium Thiothixene Thonzonium bromide Tianeptine Troglitazone Troleandomycin Tropanyl 3,5-dimethulbenzoate Zafirlukast Zeranol Antagonists: Ketoconazole Sesamin
See also Receptor/signaling modulators