Ketoconazole

(BAN, USAN, rINN)
Ketoconazole Chemical formula
Synonyms: Ketoconazol; Kétoconazole; Ketoconazolum; Ketokonatsoli; Ketokonazol; Ketokonazolas; R-41400. (±)cis-1-Acetyl-4-{4-[2(2,4-dichlorophenyl)-2-imidazol-1-ylmethyl-1,3-dioxolan-4-ylmethoxy]phenyl}piperazine.
Cyrillic synonym: Кетоконазол.

💊 Chemical information

Chemical formula: C26H28Cl2N4O4 = 531.4.
CAS — 65277-42-1.
ATC — D01AC08; G01AF11; J02AB02.
ATC Vet — QD01AC08; QG01AF11; QJ02AB02.

Pharmacopoeias.

In Chin., Eur., Int., and US.

Ph. Eur. 6.2

(Ketoconazole). A white or almost white powder. Practically insoluble in water; sparingly soluble in alcohol; freely soluble in dichloromethane; soluble in methyl alcohol. Protect from light.

💊 Adverse Effects

Gastrointestinal disturbances are the most frequently reported adverse effect after the oral use of ketoconazole. Nausea and vomiting have been reported in about 3% of patients, and abdominal pain in about 1%. These adverse effects are dose-related and may be minimised by giving ketoconazole with food. 3,4 It has also been tried in cutaneous leishmaniasis. A cure rate of 70% was reported in over 100 patients with Leishmania major infections treated with oral ketoconazole 200 to 400 mg daily for 4 to 6 weeks. Ketoconazole was not considered to be effective in infections due to L. tropica, L. aethiopica,5 or L. guyanensis.6Ketoconazole 600 mg daily for 28 days has produced similar results to sodium stibogluconate intramuscularly for 20 days in patients with cutaneous leishmaniasis due to L. panamensis.7 A further comparative study8 of 96 patients being treated for cutaneous leishmaniasis, caused mainly by L. major or L. tropica, found ketoconazole given in doses of 600 mg in adults or 10 mg/kg in children for 30 days to be more effective than 6 to 8 bi-weekly intralesional injections of meglumine antimonate. In another study,9 ketoconazole was less effective than sodium stibogluconate when cutaneous leishmaniasis was due to L. braziliensis, but more effective when L. mexicana was the cause.
1. Wali JP, et al. Ketoconazole in treatment of visceral leishmaniasis. Lancet 1990; 330: 810–11
2. Wali JP, et al. Ketoconazole in the treatment of antimony- and pentamidine-resistant Kala-azar. J Infect Dis 1992; 166: 215–16
3. Sundar S, et al. Ketoconazole in visceral leishmaniasis. Lancet 1990; 336: 1582–3
4. Rashid JR, et al. The efficacy and safety of ketoconazole in visceral leishmaniasis. East Afr Med J 1994; 71: 392–5
5. Weinrauch L, et al. Ketoconazole in cutaneous leishmaniasis. Br J Dermatol 1987; 117: 666–7
6. Dedet J-P, et al. Failure to cure Leishmania braziliensis guyanensis cutaneous leishmaniasis with oral ketoconazole. Trans R Soc Trop Med Hyg 1986; 80: 176
7. Saenz RE, et al. Efficacy of ketoconazole against Leishmania braziliensis panamensis cutaneous leishmaniasis. Am J Med 1990; 89: 147–55
8. Salmanpour R, et al. Comparative study of the efficacy of oral ketoconazole with intra-lesional meglumine antimoniate (Glucantime) for the treatment of cutaneous leishmaniasis. J Dermatol Treat 2001; 12: 159–62
9. Navin TR, et al. Placebo-controlled clinical trial of sodium stibogluconate (Pentostam) versus ketoconazole for treating cutaneous leishmaniasis in Guatemala. J Infect Dis 1992; 165: 528–34.

💊 Preparations

USP 31: Ketoconazole Oral Suspension; Ketoconazole Tablets.

Proprietary Preparations

Arg.: C-86; Cetonil; Eumicel; Faction; Fangan; Fitonal; Fungicil†; Grenfung; Keduo; Ketogel†; Ketolef; Ketonazol; Ketozol†; Krol†; Micoespec K; Micoral; Orifungal; Perative; Quadion; Socosep; Tersoderm Plus†; Tikl; Triatop†; Austral.: Daktagold†; Hexal Konazol Shampoo; Nizoral; Sebizole; Austria: Fungoral; Nizoral; Belg.: Docketoral; Nizoral; Braz.: Aciderm; Arcolan; Candiderm; Candoral; Cetocona†; Cetoconalab; Cetohexal†; Cetomed; Cetomicoss†; Cetomizol; Cetonax; Cetoneo; Cetonil; Cetonin; Cetozan; Cetozaz†; Cetozol; Fungoral†; Ketomicol†; Ketonan†; Ketonazol; Lozan; Miconan; Micoral; Nizoral; Nizoretic; Noriderm; Noronal; Sioconazol†; Tonazox†; Zanoc; Zolmicol; Canad.: Ketoderm; Nizoral; Chile: Arcolane; Biogel; Eprofil†; Fungarest; Fungium; Ketonil†; Soridermal; TKC; Cz.: Asquam; Nizoral; Orozanol†; Denm.: Kezoral; Nizoral; Fin.: Nizoral; Fr.: Ketoderm; Ketolium; Nizoral; Ger.: Nizoral; Terzolin; Gr.: Abba; Adenosan; Aquarius; Botaderm; Cezolin; Ebersept; Flidaphen; Fungoral; Ilgem; Libroman; Mycofebrin; Neo-egmol; Nyoxep; Scalpin; Sostatin; Vafluson†; Hong Kong: Diazon; Fluzoral; Fungazol; Ketozol; Ketozole; Larry; Nizoral; Pristine; Pristinex; Sebizole†; Stada K; Synizoral; Hung.: Ketospor; Nizoral; India: Arcolane; Danfree; Danruf; Funazole; Fungicide; Hyphoral; Keto; Indon.: Anfuhex; Dermaral; Dexazol; Dysfungal; Fexazol; Formyco; Funet; Fungasol; Fungoral; Interzol; Ketomed; Lusanoc; Micoticum; Muzoral; Mycoderm; Mycoral; Mycozid; Nizol; Nizoral; Nofung; Picamic; Profungal; Solinfec; Sporex; Thicazol; Wizol; Zoloral; Zoralin; Zumazol; Irl.: Nizoral; Israel: Nizoral; Ital.: Nizoral; Triatop; Malaysia: Dezor; Fungazol; Funginox; Ketozole†; Kezoral; Larry; Nizoral; Pristine†; Pristinex†; Sebizole†; Sunazol†; Yucomy; Ziconal†; Mex.: Akorazol; Apo-Kesol†; Biozoral; Conazol; Cremosan; Ergomicon; Eurolat; Fungipar; Fungoral; Fungosine; Honzil; Keprobiozol†; Kestomicol†; Ketofar; Ketomed; Ketomizol; Ketoril; Konaderm; Konaturil; Lemyken†; Lizovag; Lornazol†; Messelzol; Mi-Ke-Sons; Micoser; Micozol; Mycodib; Nastil; Nazolfarm; Nazoltec; Nizoral; Onofin-K; Prenalon; Remecon; Strizole; Termizol; Tiniasil; Tiniazol; Tocomizol†; Toconal; Tolcrem; Tomiko; Triatop; Neth.: Nizoral; Norw.: Fungoral; Konazal; NZ: Daktagold; Ketopine; Nizoral; Sebizole; Philipp.: Ketovid; Nizoral; Pol.: Fungores; Nizoral; Noell; Port.: Farmorol; Frisol†; Frisolac; Micopar; Nizale; Nizoral; Rapamic; Tedol; Rus.: Livarole (Ливарол); Mycosoral (Микозорал); Nizoral (Низорал); S.Afr.: Adco-Dermed; Ketazol; Kez; Nizcreme; Nizoral; Nizorelle; Nizovules; Nizshampoo; Singapore: Antanazol; Beatoconazole; Dezor; Dezoral†; Diazon; Ketozole; Kezoral; Nicozone; Nitozol; Nizoral; Pristine; Pristinex; Profungal†; Sebizole; Yucomy; Spain: Fungarest; Fungo Farmasierra; Fungo Zeus; Keto-Cure; Ketoderma; Ketoisdin; Medezol; Micoticum; Panfungol; Swed.: Fundan; Fungoral; Ketoson; Switz.: Ketozol; Nizoral; Terzolin; Thai.: AC-FA; Chintaral; Dezor; Diazon; Fungazol; Fungiderm-K; Funginox; Kara†; Katsin; Kazinal; Kenalyn; Kenazol; Kenazole†; Kenoral; Ketazol†; Ketazon; Ketocine; Ketolan; Ketomed; Ketonazole; Ketoral†; Ketosil; Ketozal; Kezon; Konazol†; Lama; Larry; Manoketo; Masarol; Mizoron; Mycella; Myco; Mycoral; Ninazol; Nizoral; Nora†; Pasalen; Sporaxyl; Sporoxyl; Triatop†; Turk.: Fungoral; Ketoral; Konazol; Nizoral; UK: Daktarin Gold; Dandrazol; Dandrid; Nizoral; USA: Extina; Nizoral; Xolegel; Venez.: Arcolane; Danfree†; Freetop; Kenazol; Ketazol; Ketocoval†; Ketomed; Napox†; Nizoral; Noractin†; Topstar†. Multi-ingredient: Arg.: Aeromicrosona C†; Bactisona; Ciprocort; Dercotex; Duo Minoxi†; Gentacler; Gynerium; Ketohair†; Linfol Dermico; Micozol Compuesto†; Microsona C; Ovogin; Prurisedan Biotic†; Start NP†; Torgyn Duo; Tricur; Tridermal; Triefect†; Braz.: Betazol Cort; Candicort; Capel; Celocort; Cetobeta; Cetocort; Cetocorten; Cimecort; Emscort; Naderm; Novacort; Trok; Trok-N; Chile: KPL†; India: Hyphoral; Scalpe; Ital.: Keto Z; Ketomousse; Malaysia: Ketoplus; Mex.: Femisan; GynoclinV; Trexen Duo; Philipp.: Scalpex; Rus.: Keto Plus (Кето Плюс); USA: Xolegel Duo.
Published November 25, 2018.