Oxiconazole

Names
Trade names| Oxistat, Oxizole, others

IUPAC name

* (E)-[1-(2,4-Dichlorophenyl)-2-(1H-imidazol-1-yl)ethylidene][(2,4-dichlorophenyl)methoxy]amine

Clinical data
Drug class| Antifungal
Main uses| Athlete's foot, jock itch, ringworm, tinea versicolor, yeast infections[1]
Side effects| Irritation, burning, itching[1]
External links
AHFS/Drugs.com| Monograph
MedlinePlus| a689004
Chemical and physical data
Formula| C18H13Cl4N3O
Molar mass| 429.12 g·mol−1
3D model (JSmol)|

* Interactive image

SMILES

* Clc3ccc(/C(=N\OCc1ccc(Cl)cc1Cl)Cn2ccnc2)c(Cl)c3

InChI

* InChI=1S/C18H13Cl4N3O/c19-13-2-1-12(16(21)7-13)10-26-24-18(9-25-6-5-23-11-25)15-4-3-14(20)8-17(15)22/h1-8,11H,9-10H2/b24-18- Y

* Key:QRJJEGAJXVEBNE-MOHJPFBDSA-N Y

Oxiconazole, sold under the brand name Oxistat among others, is an antifungal medication used to treat athlete's foot, jock itch, ringworm, tinea versicolor, and yeast infections.[1] It is typically applied to the skin as a cream or lotion.[1]

Common side effects include irritation, burning, and itching.[1] Other side effects may include contact dermatitis.[1] Use appears to be safe in pregnancy, though has not been well studied.[2] It is in the azole family of medications.[1] It is believed to work by increasing the permeability of the cellular membrane.[1]

Oxiconazole was patented in 1975 and approved for medical use in 1983.[3] It is available as a generic medication.[4] In the United States a tube of 30 grams costs about 110 USD.[4]

## See also[edit | edit source]

* Fluconazole

## References[edit | edit source]

1. ↑ 1.0 1.1 1.2 1.3 1.4 1.5 1.6 1.7 "Oxiconazole Monograph for Professionals". Drugs.com. Archived from the original on 18 January 2021. Retrieved 10 November 2021.
2. ↑ "Oxiconazole topical (Oxistat) Use During Pregnancy". Drugs.com. Archived from the original on 25 January 2021. Retrieved 10 November 2021.
3. ↑ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 503\. ISBN 9783527607495. Archived from the original on 2017-09-10. Retrieved 2020-09-20.
4. ↑ 4.0 4.1 "Oxiconazole Prices, Coupons & Savings Tips - GoodRx". GoodRx. Archived from the original on 5 May 2016. Retrieved 10 November 2021.

## External links[edit | edit source]

Identifiers:|

* ATC code:

* D01AC11 (WHO) G01AF17 (WHO)

* CAS Number: 64211-46-7 Y
* PubChem CID: 5361463
* DrugBank:

* DB00239 Y

* ChemSpider:

* 4514745 Y

* UNII:

* RQ8UL4C17S

* KEGG:

* D00885 Y

* ChEBI:

* CHEBI:7825

* ChEMBL:

* ChEMBL1262 N

|

* MedlinePlus Archived 2008-10-01 at the Wayback Machine \- Oxiconazole

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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#
* hexaconazole‡
* fosfluconazole
* fosravuconazole
* isavuconazonium
* itraconazole#
* 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|

* Systemic: echinocandins (anidulafungin
* biafungin
* caspofungin
* cilofungin
* micafungin)

Intracellular|

| Pyrimidine analogues/
thymidylate synthase inhibitors|

* Systemic: flucytosine#

|

Mitotic inhibitors|

* Systemic: griseofulvin#

Aminoacyl tRNA synthetase inhibitors|

* Topical: tavaborole

Others|

* bromochlorosalicylanilide
* chlorophetanol
* chlorphenesin
* ciclopirox
* crystal violet
* dimazole
* ethylparaben
* haloprogin‡
* polynoxylin
* potassium iodide#
* salicylic acid
* selenium disulfide#
* sodium thiosulfate#
* sulbentine
* taurolidine
* ticlatone
* tolciclate
* tolnaftate
* tribromometacresol
* undecylenic acid
* Whitfield's ointment#

* citronella oil
* lemon grass
* lemon myrtle
* orange oil
* patchouli
* tea tree oil
* PCP: atovaquone
* dapsone
* pentamidine

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

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Gynecological anti-infectives and antiseptics (G01)

Antibiotics|

* Candicidin
* Chloramphenicol
* Hachimycin
* Oxytetracycline
* Carfecillin
* Mepartricin
* Clindamycin
* Pentamycin

Arsenic compounds|

* Acetarsol

Quinoline derivatives|

* Diiodohydroxyquinoline
* Clioquinol
* Chlorquinaldol
* Dequalinium
* Broxyquinoline
* Oxyquinoline

Organic acids|

* Lactic acid
* Acetic acid
* Ascorbic acid

Sulfonamides|

* Sulfatolamide

Antifungals|

| Imidazoles|

* Metronidazole
* Clotrimazole
* Miconazole
* Econazole
* Ornidazole
* Isoconazole
* Tioconazole
* Ketoconazole
* Fenticonazole
* Azanidazole
* Propenidazole
* Butoconazole
* Omoconazole
* Oxiconazole
* Flutrimazole

|

Triazoles|

* Terconazole

Polyenes|

* Nystatin
* Natamycin
* Amphotericin B

Other|

* Ciclopirox
* Methylrosaniline

Other|

* Clodantoin
* Inosine
* Policresulen
* Nifuratel
* Furazolidone
* Povidone-iodine
* Protiofate
* Lactobacillus fermentum
* Copper usnate

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