Econazole

D01A - Antifungals for topical use ATC G01AF05 Small molecule approved 1982 Topical Natural product

JFDA label: Eco-Cure Vaginal Ovule

Mechanism of Action

Alters fungal cell wall membrane permeability; may interfere with RNA and protein synthesis, and lipid metabolism

Indications

Approved

Cream
Foam
Fungal infection

Contraindications

Source: Lexicomp

Cream: Hypersensitivity to econazole or any component of the formulation Foam: There are no contraindications listed in the manufacturer’s labeling. Documentation of allergenic cross-reactivity for imidazole antifungals is limited. However, because of similarities in chemical structure and/or pharmacologic actions, the possibility of cross-sensitivity cannot be ruled out with certainty Absolute

Adverse Reactions

Very Common >10%Common 1–10%Uncommon 0.1–1% Rare 0.01–0.1%Very Rare <0.01%Not Known

Other (4)

Common Dermatologic: Burning sensation of skin · erythema · pruritus · stinging of the skin

Dosing

Source: Lexicomp

Tinea pedis: Topical: Cream, Foam: Apply sufficient amount to cover affected areas once daily for 4 weeks Tinea cruris, tinea corporis, tinea versicolor: Topical: Cream: Apply sufficient amount to cover affected areas once daily for 2 weeks Cutaneous candidiasis: Topical: Cream: Apply sufficient quantity twice daily (morning and evening) for 2 weeks

(For additional information see "Econazole: Pediatric drug information") Tinea pedis: Children ≥12 years and Adolescents: Topical: Foam: Apply sufficient amount to cover affected area once daily for 4 weeks

Refer to adult dosing.

There are no dosage adjustments provided in the manufacturer’s labeling.

Warnings & Precautions

Source: Lexicomp

Irritation

Discontinue if sensitivity or irritation occurs. Dosage form specific issues:

Foam

Avoid heat, flame, and smoking during and immediately following application; topical foam is flammable. Other warnings/precautions:

Appropriate use

For topical use only; avoid contact with eyes, mouth, nose, or other mucous membranes

Pregnancy & Lactation

Pregnancy

FDA category C

Adverse events were observed in some animal reproduction studies. The manufacturer recommends avoiding use during pregnancy, especially during the first trimester.

Lactation

It is not known if econazole is excreted in breast milk. The manufacturer recommends that caution be exercised when administering econazole to nursing women.

Monitoring

Clinical pearl	Reassess diagnosis if no clinical improvement after completion of treatment course.

Chemistry & Properties

Formula	C18H15Cl3N2O
Molecular weight	381.69 g/mol
IUPAC name	1-[2-[(4-chlorophenyl)methoxy]-2-(2,4-dichlorophenyl)ethyl]imidazole
CAS	27220-47-9
PubChem CID	3198
InChIKey	`LEZWWPYKPKIXLL-UHFFFAOYSA-N`
logP	5.8 (XLogP 5.3)
Polar surface area	27.05 Å²
H-bond acceptors / donors	3 / 0
Drug-likeness (QED)	0.54
Lipinski violations	1

SMILES

Clc1ccc(COC(Cn2ccnc2)c2ccc(Cl)cc2Cl)cc1

Biology & Pharmacokinetics

Pharmacokinetics

BBB penetrant	No

Enzyme interactions

Enzyme	Role	Detail
CYP1A2	Inhibitor	IC₅₀ 0.3000000000000001 µM
CYP1A2	Substrate	—
CYP2B6	Inhibitor	—
CYP2C19	Inhibitor	IC₅₀ 0.040000000000000015 µM
CYP2C8	Inhibitor	—
CYP2C9	Inhibitor	IC₅₀ 0.20000000000000004 µM
CYP2D6	Inhibitor	IC₅₀ 0.40000000000000013 µM
CYP3A4	Inhibitor	IC₅₀ 0.20996518697290756 µM
CYP3A4	Substrate	—

Receptor binding (top 2)

Target	Action	Affinity
CYP8B1 (CYP8B1)	Inhibitor	pKd 7.2
CYP8B1 (CYP8B1)	Inhibitor	pIC50 6.1

Transporters

BCRP (Inhibitor)BSEP (Inhibitor)BSEP (Inhibitor)MRP1 (Inhibitor)OATP1B1 (Inhibitor)OATP1B1 (Inhibitor)OATP1B3 (Inhibitor)P-gp (Inhibitor)P-gp (Substrate)

Registered Products (10)

Brand	Form / strength	Pack	Agent	Citizen (JOD)
Ecorex Plus Cream	Cream 1 %, 0.1 %	15 g tube pack varies	Hayat Pharmaceutical Industries CO.PLC/JORDAN	1.690
Ecorex Cream	Cream 1 %	30 g tube pack varies	Hayat Pharmaceutical Industries CO.PLC/JORDAN	2.000
Eco-Cure Vaginal Ovule	Vaginal 150 mg	3 Vaginal Ovules	MIDDLE EAST PHARMA&CHEMICAL IND/JORDAN	2.250
Ecorex ovules	Ovule 150 mg	3	Hayat Pharmaceutical Industries CO.PLC/JORDAN	2.610
Ecomi Ovules	Vaginal 150 mg	3 Ovules	Kurdi Drug Store	2.910
Ecorex Plus Cream	Cream 1 %, 0.1 %	30 g tube pack varies	Hayat Pharmaceutical Industries CO.PLC/JORDAN	3.210
Gyno-Pevaryl Depot	Tablet 150 mg	2 tab	Shawi & Rushedat Drug Store	3.460
Ecorex vaginal Cream	Cream 1 %	78 gm pack varies	Hayat Pharmaceutical Industries CO.PLC/JORDAN	5.480
Pevaryl Lipogel	Gel 1 %	15 mg	Ninos Drug Store	6.680
Gyno-Pevaryl 50 Vag Ovules	Ovule 50 mg	15	Ninos Drug Store	13.380