Page last updated: 2024-11-08

sm 8668

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

Sch 39304: Sch 42427 is the active entantiomer of the antifungal agent Sch 39304 which consists of Sch 42426 & Sch 42427; Sch 42426, the (S,S)-isomer, is inactive [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID452261
CHEMBL ID34139
SCHEMBL ID8937940
MeSH IDM0158490

Synonyms (41)

Synonym
sm-9164
sch-39304
sch-42427
sm8668 (*r isomer*)
sm-8668
genaconazole
sch39304
(2r,3r)-2-(2,4-difluorophenyl)-3-methylsulfonyl-1-(1,2,4-triazol-1-yl)butan-2-ol
sch42427
(r,r)1-[1-(methylsulfonyl)ethyl]-1-[1- triazolomethyl]-2,4-difluorophenylmethanol
rr-sch39304
sch 39304
rac-(2r*,3r*)-2-(2,4-difluorophenyl)-3-(methylsulfonyl)-1-(1,2,4-triazol-1-yl)-2-butanol
121650-83-7
120924-80-3
(r,r)-sch 39304
1h-1,2,4-triazole-1-ethanol, alpha-(2,4-difluorophenyl)-alpha-((1r)-1-(methylsulfonyl)ethyl)-, (alphar)-
1h-1,2,4-triazole-1-ethanol, alpha-(2,4-difluorophenyl)-alpha-(1-(methylsulfonyl)ethyl)-, (r-(r*,r*))-
drg-0078
sm 9164
sch 42427
CHEMBL34139
1h-1,2,4-triazole-1-ethanol, alpha-(2,4-difluorophenyl)-alpha-((1r)-1- (methylsulfonyl)ethyl)-, (alphar)-rel-
unii-1bfz5cm687
sm 8668
1bfz5cm687 ,
sch-39304, (r,r)-
i87rhm3o1j ,
unii-i87rhm3o1j
SCHEMBL8937940
1h-1,2,4-triazole-1-ethanol, .alpha.-(2,4-difluorophenyl)-.alpha.-((1r)-1-(methylsulfonyl)ethyl)-, (.alpha.r)-rel-
1h-1,2,4-triazole-1-ethanol, .alpha.-(2,4-difluorophenyl)-.alpha.-(1-(methylsulfonyl)ethyl)-, (r*,r*)-(+/-)-
sm8668
(.alpha.r)-.alpha.-(2,4-difluorophenyl)-.alpha.-((1r)-1-(methylsulfonyl)ethyl)-1h-1,2,4-triazole-1-ethanol
genaconazole, (r,r)-
1h-1,2,4-triazole-1-ethanol, .alpha.-(2,4-difluorophenyl)-.alpha.-((1r)-1-(methylsulfonyl)ethyl)-, (.alpha.r)-
1h-1,2,4-triazole-1-ethanol, .alpha.-(2,4-difluorophenyl)-.alpha.-(1-(methylsulfonyl)ethyl)-, (r-(r*,r*))-
sch-39304, (+)-
sm1964
1h-1,2,4-triazole-1-ethanol, alpha-(2,4-difluorophenyl)-alpha-((1r)-1- (methylsulfonyl)ethyl)-, (alphar)-rel-
Q27252196

Research Excerpts

Pharmacokinetics

ExcerptReferenceRelevance
" There were no significant differences between the pharmacokinetic parameters of G(+) and G(-) rabbits."( Pharmacokinetics and tissue penetration of Sch 39304 in granulocytopenic and nongranulocytopenic rabbits.
Lee, JW; Lin, C; Loebenberg, D; Pizzo, PA; Rubin, M; Walsh, TJ, 1989
)
0.28
" Pharmacokinetic evaluation following oral and intravenous doses indicated that mean values for the area under the concentration-time curve from 0 h to infinity (137 and 136 micrograms."( Pharmacokinetics of the triazole antifungal agent genaconazole in healthy men after oral and intravenous administration.
Affrime, MB; Cayen, MN; Lin, CC; Mojaverian, P; Radwanski, E, 1994
)
0.29
"7 micrograms/ml), times to Cmax (4."( Pharmacokinetics and metabolism of genaconazole, a potent antifungal drug, in men.
Affrime, M; Brannan, M; Cayen, MN; Kim, H; Lin, C; Radwanski, E, 1996
)
0.29
" The bioavailability and pharmacokinetic profiles of the two enantiomers after oral administration of the racemate (genaconazole) were very similar in cynomolgus monkeys."( Pharmacokinetics of the active antifungal enantiomer, SCH 42427 (RR), and evaluation of its chiral inversion in animals following its oral administration and the oral administration of its racemate genaconazole (RR/SS).
Kim, H; Lin, CC; Lovey, R; Nomeir, AA; Radwanski, E, 2002
)
0.31
" pharmacokinetic data on 670 drugs representing, to our knowledge, the largest publicly available set of human clinical pharmacokinetic data."( Trend analysis of a database of intravenous pharmacokinetic parameters in humans for 670 drug compounds.
Lombardo, F; Obach, RS; Waters, NJ, 2008
)
0.35

Bioavailability

ExcerptReferenceRelevance
"h/ml), suggesting the potential for reduced bioavailability at higher dosages."( Pharmacokinetics of SCH-39304 in human immunodeficiency virus-infected patients following chronic oral dosing.
Graybill, JR; Hardin, TC; Lam, YF; Rinaldi, MG; Sharkey, PK; Wallace, JE, 1992
)
0.28
" The oral and intravenous administrations of genaconazole yielded virtually superimposable plasma concentration-time curves, resulting in an absolute bioavailability of 100%."( Pharmacokinetics of the triazole antifungal agent genaconazole in healthy men after oral and intravenous administration.
Affrime, MB; Cayen, MN; Lin, CC; Mojaverian, P; Radwanski, E, 1994
)
0.29
" The bioavailability and pharmacokinetic profiles of the two enantiomers after oral administration of the racemate (genaconazole) were very similar in cynomolgus monkeys."( Pharmacokinetics of the active antifungal enantiomer, SCH 42427 (RR), and evaluation of its chiral inversion in animals following its oral administration and the oral administration of its racemate genaconazole (RR/SS).
Kim, H; Lin, CC; Lovey, R; Nomeir, AA; Radwanski, E, 2002
)
0.31
"Oral bioavailability (F) is a product of fraction absorbed (Fa), fraction escaping gut-wall elimination (Fg), and fraction escaping hepatic elimination (Fh)."( Physicochemical space for optimum oral bioavailability: contribution of human intestinal absorption and first-pass elimination.
Chang, G; El-Kattan, A; Miller, HR; Obach, RS; Rotter, C; Steyn, SJ; Troutman, MD; Varma, MV, 2010
)
0.36

Dosage Studied

ExcerptRelevanceReference
"25%, respectively, when dosed intravaginally."( Saperconazole: in vitro and in vivo anticandidal activity.
Foleno, B; Fu, KP; Isaacson, D; LoCoco, J, 1992
)
0.28
" The unique pharmacologic and pharmacokinetic properties of SCH 39304 (low incidence of toxicity, long serum half-life, and good penetration into the cerebrospinal fluid) lend promise to pursue other triazole antifungals at higher doses as primary therapy and less frequent dosing for maintenance therapy."( Oral SCH 39304 as primary, salvage, and maintenance therapy for cryptococcal meningitis in AIDS.
Chambers, HF; Lee, BL; Padula, AM; Sande, MA; Täuber, MG, 1992
)
0.28
" The differences in the efficacies of the triazoles appeared to be due to differences in their pharmacokinetics and the dosage schedule that was used."( In vitro and in vivo activities of Sch 39304, fluconazole, and amphotericin B against Histoplasma capsulatum.
Kobayashi, GS; Medoff, G; Rinaldi, MG; Travis, SJ, 1990
)
0.28
" CD-1 mice were infected with Coccidioides immitis and dosed with SCH at 2, 10, 25, or 50 mg/kg per day or FLU at 10 or 100 mg/kg per day."( Efficacy of SCH39304 and fluconazole in a murine model of disseminated coccidioidomycosis.
Clemons, KV; Hanson, LH; Perlman, AM; Stevens, DA, 1990
)
0.28
" Both dosage regimens were well tolerated."( Pharmacokinetics of the triazole antifungal agent genaconazole in healthy men after oral and intravenous administration.
Affrime, MB; Cayen, MN; Lin, CC; Mojaverian, P; Radwanski, E, 1994
)
0.29
" The results showed that the pharmacokinetic profiles of the two enantiomers were similar after a single oral dosing of the racemate."( Pharmacokinetics and metabolism of genaconazole, a potent antifungal drug, in men.
Affrime, M; Brannan, M; Cayen, MN; Kim, H; Lin, C; Radwanski, E, 1996
)
0.29
" In rats following dosing with genaconazole, the RR enantiomer had a lower C(max) and a longer t(1/2) than the SS enantiomer, while the AUC(I) values of the two enantiomers were similar."( Pharmacokinetics of the active antifungal enantiomer, SCH 42427 (RR), and evaluation of its chiral inversion in animals following its oral administration and the oral administration of its racemate genaconazole (RR/SS).
Kim, H; Lin, CC; Lovey, R; Nomeir, AA; Radwanski, E, 2002
)
0.31
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (46)

Assay IDTitleYearJournalArticle
AID1079945Animal toxicity known. [column 'TOXIC' in source]
AID1079932Highest frequency of moderate liver toxicity observed during clinical trials, expressed as a percentage. [column '% BIOL' in source]
AID540213Half life in human after iv administration2008Drug metabolism and disposition: the biological fate of chemicals, Jul, Volume: 36, Issue:7
Trend analysis of a database of intravenous pharmacokinetic parameters in humans for 670 drug compounds.
AID540210Clearance in human after iv administration2008Drug metabolism and disposition: the biological fate of chemicals, Jul, Volume: 36, Issue:7
Trend analysis of a database of intravenous pharmacokinetic parameters in humans for 670 drug compounds.
AID547622Antitrypanosomal activity against Trypanosoma cruzi amastigotes infected in BESM cells measured after 88 hrs postinfection by HTS assay2010Antimicrobial agents and chemotherapy, Aug, Volume: 54, Issue:8
Image-based high-throughput drug screening targeting the intracellular stage of Trypanosoma cruzi, the agent of Chagas' disease.
AID1079943Malignant tumor, proven histopathologically. Value is number of references indexed. [column 'T.MAL' in source]
AID73613The compound was tested in vitro for antifungal activity against 6 filamentous fungi.1998Journal of medicinal chemistry, May-21, Volume: 41, Issue:11
New azole antifungals. 2. Synthesis and antifungal activity of heterocyclecarboxamide derivatives of 3-amino-2-aryl-1-azolyl-2-butanol.
AID1079931Moderate liver toxicity, defined via clinical-chemistry results: ALT or AST serum activity 6 times the normal upper limit (N) or alkaline phosphatase serum activity of 1.7 N. Value is number of references indexed. [column 'BIOL' in source]
AID118896In vivo antifungal activity against murine candidosis model after peroral administration with 1 mg/kg for 5 days.(percent protection for 100% mortality with fluconazole-treated group.)1998Journal of medicinal chemistry, May-21, Volume: 41, Issue:11
New azole antifungals. 2. Synthesis and antifungal activity of heterocyclecarboxamide derivatives of 3-amino-2-aryl-1-azolyl-2-butanol.
AID1079934Highest frequency of acute liver toxicity observed during clinical trials, expressed as a percentage. [column '% AIGUE' in source]
AID444058Volume of distribution at steady state in human2010Journal of medicinal chemistry, Feb-11, Volume: 53, Issue:3
Physicochemical space for optimum oral bioavailability: contribution of human intestinal absorption and first-pass elimination.
AID1079933Acute liver toxicity defined via clinical observations and clear clinical-chemistry results: serum ALT or AST activity > 6 N or serum alkaline phosphatases activity > 1.7 N. This category includes cytolytic, choleostatic and mixed liver toxicity. Value is
AID444054Oral bioavailability in human2010Journal of medicinal chemistry, Feb-11, Volume: 53, Issue:3
Physicochemical space for optimum oral bioavailability: contribution of human intestinal absorption and first-pass elimination.
AID1079944Benign tumor, proven histopathologically. Value is number of references indexed. [column 'T.BEN' in source]
AID73614In vitro antifungal activity against 6 filamentous fungi1998Journal of medicinal chemistry, May-21, Volume: 41, Issue:11
New azole antifungals. 3. Synthesis and antifungal activity of 3-substituted-4(3H)-quinazolinones.
AID1079949Proposed mechanism(s) of liver damage. [column 'MEC' in source]
AID119045The compound was tested in vivo for anti-candida activity in mice model 2(dose: 1 mg/kg, untreated group).1998Journal of medicinal chemistry, May-21, Volume: 41, Issue:11
New azole antifungals. 3. Synthesis and antifungal activity of 3-substituted-4(3H)-quinazolinones.
AID1079936Choleostatic liver toxicity, either proven histopathologically or where the ratio of maximal ALT or AST activity above normal to that of Alkaline Phosphatase is < 2 (see ACUTE). Value is number of references indexed. [column 'CHOLE' in source]
AID540209Volume of distribution at steady state in human after iv administration2008Drug metabolism and disposition: the biological fate of chemicals, Jul, Volume: 36, Issue:7
Trend analysis of a database of intravenous pharmacokinetic parameters in humans for 670 drug compounds.
AID1079939Cirrhosis, proven histopathologically. Value is number of references indexed. [column 'CIRRH' in source]
AID1079942Steatosis, proven histopathologically. Value is number of references indexed. [column 'STEAT' in source]
AID1079935Cytolytic liver toxicity, either proven histopathologically or where the ratio of maximal ALT or AST activity above normal to that of Alkaline Phosphatase is > 5 (see ACUTE). Value is number of references indexed. [column 'CYTOL' in source]
AID540212Mean residence time in human after iv administration2008Drug metabolism and disposition: the biological fate of chemicals, Jul, Volume: 36, Issue:7
Trend analysis of a database of intravenous pharmacokinetic parameters in humans for 670 drug compounds.
AID1079938Chronic liver disease either proven histopathologically, or through a chonic elevation of serum amino-transferase activity after 6 months. Value is number of references indexed. [column 'CHRON' in source]
AID220226In vitro for antifungal activity against 10 yeasts1998Journal of medicinal chemistry, May-21, Volume: 41, Issue:11
New azole antifungals. 3. Synthesis and antifungal activity of 3-substituted-4(3H)-quinazolinones.
AID1079937Severe hepatitis, defined as possibly life-threatening liver failure or through clinical observations. Value is number of references indexed. [column 'MASS' in source]
AID547804Selectivity window, ratio of EC50 for BESM cells to EC50 for Trypanosoma cruzi amastigotes infected in BESM cells2010Antimicrobial agents and chemotherapy, Aug, Volume: 54, Issue:8
Image-based high-throughput drug screening targeting the intracellular stage of Trypanosoma cruzi, the agent of Chagas' disease.
AID1079948Times to onset, minimal and maximal, observed in the indexed observations. [column 'DELAI' in source]
AID1079946Presence of at least one case with successful reintroduction. [column 'REINT' in source]
AID444055Fraction absorbed in human2010Journal of medicinal chemistry, Feb-11, Volume: 53, Issue:3
Physicochemical space for optimum oral bioavailability: contribution of human intestinal absorption and first-pass elimination.
AID444056Fraction escaping gut-wall elimination in human2010Journal of medicinal chemistry, Feb-11, Volume: 53, Issue:3
Physicochemical space for optimum oral bioavailability: contribution of human intestinal absorption and first-pass elimination.
AID118760In vivo antifungal activity against murine candidosis model after peroral administration with 0.5 mg/kg at various time intervals. (percent protection for 100% mortality with fluconazole-treated group.)1998Journal of medicinal chemistry, May-21, Volume: 41, Issue:11
New azole antifungals. 2. Synthesis and antifungal activity of heterocyclecarboxamide derivatives of 3-amino-2-aryl-1-azolyl-2-butanol.
AID444053Renal clearance in human2010Journal of medicinal chemistry, Feb-11, Volume: 53, Issue:3
Physicochemical space for optimum oral bioavailability: contribution of human intestinal absorption and first-pass elimination.
AID444057Fraction escaping hepatic elimination in human2010Journal of medicinal chemistry, Feb-11, Volume: 53, Issue:3
Physicochemical space for optimum oral bioavailability: contribution of human intestinal absorption and first-pass elimination.
AID1079941Liver damage due to vascular disease: peliosis hepatitis, hepatic veno-occlusive disease, Budd-Chiari syndrome. Value is number of references indexed. [column 'VASC' in source]
AID220225The compound was tested in vitro for antifungal activity against 10 yeasts.1998Journal of medicinal chemistry, May-21, Volume: 41, Issue:11
New azole antifungals. 2. Synthesis and antifungal activity of heterocyclecarboxamide derivatives of 3-amino-2-aryl-1-azolyl-2-butanol.
AID547621Cytotoxicity against BESM cells after 88 hrs by HTS assay2010Antimicrobial agents and chemotherapy, Aug, Volume: 54, Issue:8
Image-based high-throughput drug screening targeting the intracellular stage of Trypanosoma cruzi, the agent of Chagas' disease.
AID119047The compound was tested in vivo for anti-candida activity in mice model 2(dose :1 mg/kg,fluconazole-treated group)1998Journal of medicinal chemistry, May-21, Volume: 41, Issue:11
New azole antifungals. 3. Synthesis and antifungal activity of 3-substituted-4(3H)-quinazolinones.
AID444051Total clearance in human2010Journal of medicinal chemistry, Feb-11, Volume: 53, Issue:3
Physicochemical space for optimum oral bioavailability: contribution of human intestinal absorption and first-pass elimination.
AID119038Tested in vivo for anti-candida activity in mice model 1 (dose:0.5 mg/kg, fluconazole-treated group)1998Journal of medicinal chemistry, May-21, Volume: 41, Issue:11
New azole antifungals. 3. Synthesis and antifungal activity of 3-substituted-4(3H)-quinazolinones.
AID1079947Comments (NB not yet translated). [column 'COMMENTAIRES' in source]
AID119042Tested in vivo for anti-candida activity in mice model 1 (dose: 0.5 mg/kg, untreated group).1998Journal of medicinal chemistry, May-21, Volume: 41, Issue:11
New azole antifungals. 3. Synthesis and antifungal activity of 3-substituted-4(3H)-quinazolinones.
AID1079940Granulomatous liver disease, proven histopathologically. Value is number of references indexed. [column 'GRAN' in source]
AID444052Hepatic clearance in human2010Journal of medicinal chemistry, Feb-11, Volume: 53, Issue:3
Physicochemical space for optimum oral bioavailability: contribution of human intestinal absorption and first-pass elimination.
AID118765In vivo antifungal activity against murine candidosis model after peroral administration with 0.5 mg/kg at various time intervals. (percent protection for 100% mortality with untreated group)1998Journal of medicinal chemistry, May-21, Volume: 41, Issue:11
New azole antifungals. 2. Synthesis and antifungal activity of heterocyclecarboxamide derivatives of 3-amino-2-aryl-1-azolyl-2-butanol.
AID118898In vivo antifungal activity against murine candidosis model after peroral administration with 1 mg/kg for 5 days.(percent protection for 100% mortality with untreated group)1998Journal of medicinal chemistry, May-21, Volume: 41, Issue:11
New azole antifungals. 2. Synthesis and antifungal activity of heterocyclecarboxamide derivatives of 3-amino-2-aryl-1-azolyl-2-butanol.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (60)

TimeframeStudies, This Drug (%)All Drugs %
pre-19906 (10.00)18.7374
1990's50 (83.33)18.2507
2000's2 (3.33)29.6817
2010's2 (3.33)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 17.55

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index17.55 (24.57)
Research Supply Index4.25 (2.92)
Research Growth Index5.17 (4.65)
Search Engine Demand Index10.37 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (17.55)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials5 (7.81%)5.53%
Reviews4 (6.25%)6.00%
Case Studies1 (1.56%)4.05%
Observational0 (0.00%)0.25%
Other54 (84.38%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]