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

• ChemBase ID: 672
• Molecular Formular: C9H4Cl3IO
• Molecular Mass: 361.39093
• Monoisotopic Mass: 359.83724579
• SMILES: IC#CCOc1c(Cl)cc(Cl)c(Cl)c1
• Canonical SMILES: Clc1cc(Cl)c(cc1OCC#CI)Cl
• InChI: InChI=1S/C9H4Cl3IO/c10-6-4-8(12)9(5-7(6)11)14-3-1-2-13/h4-5H,3H2
• InChIKey: CTETYYAZBPJBHE-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1,2,4-trichloro-5-[(3-iodoprop-2-yn-1-yl)oxy]benzene
• IUPAC Traditional name: haloprogin
• Brand Name: Aloprogen; Haloprogin [USAN:INN:JAN]; Haloprogina [INN-Spanish]; Haloprogine [INN-French]; Haloproginum [INN-Latin]; Halotex; Mycanden; Mycilan; Polik
• Synonyms: Haloprogin

Database IDs

• CAS Number: 777-11-7
• PubChem SID: 160964135; 46504892
• PubChem CID: 3561

CALCULATED PROPERTIES

JChem

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 4.8453
• LogD (pH = 7.4): 4.8453
• Log P: 4.8453
• Molar Refractivity: 66.879 cm^3
• Polarizability: 26.488203 Å^3
• Polar Surface Area: 9.23 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 4.69
• LOG S: -4.78
• Solubility (Water): 6.01e-03 g/l

PROPERTIES

Physical Property

• Hydrophobicity(logP): 5.3

DETAILS

DrugBank - DB00793

• Drug Groups: approved
• 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.
• Indication: Used to treat fungal (Tinea) skin infections such as athlete's foot, jock itch, ringworm, and tinea versicolor.
• Pharmacology: 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).
• Affected Organisms: Dermatophytic fungi including Trichophyton, Microsporum and Epidermophyton
• References: 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] ; Harrison EF, Zygmunt WA: Haloprogin: mode of action studies in Candida albicans. Can J Microbiol. 1974 Sep;20(9):1241-5. [Pubmed]
• External Links: Wikipedia; Drugs.com

REFERENCES

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