Compounds > dsm 74
Page last updated: 2024-11-13

dsm 74

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

Cross-References

ID SourceID
PubMed CID25263414
CHEMBL ID492529
SCHEMBL ID4099123
MeSH IDM0535126

Synonyms (20)

Synonym
triazolopyrimidine-based compound, dsm74
bdbm28817
5-methyl-n-[4-(trifluoromethyl)phenyl]-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine
5-methyl-n-[4-(trifluoromethyl)phenyl][1,2,4]triazolo[1,5-a]pyrimidin-7-amine
DB08008
BRD-K89082768-001-01-7
CHEMBL492529
dsm-74
DSM74 ,
SCHEMBL4099123
Q27097235
unii-a94akh2dcp
898743-92-5
(5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)-(4-trifluoromethyl-phenyl)-amine
(1,2,4)triazolo(1,5-a)pyrimidin-7-amine, 5-methyl-n-(4-(trifluoromethyl)phenyl)-
5-methyl-n-(4-(trifluoromethyl)phenyl)(1,2,4)triazolo(1,5-a)pyrimidin-7-amine
A94AKH2DCP ,
lrhhxkbkrnnfrv-uhfffaoysa-n
PD005258
AKOS040746782
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (5)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Dihydroorotate dehydrogenase (quinone), mitochondrialMus musculus (house mouse)IC50 (µMol)100.00000.03000.10300.1560AID1152593
Dihydroorotate dehydrogenase (quinone), mitochondrialHomo sapiens (human)IC50 (µMol)47.29140.00050.742710.0000AID1152596; AID1798932; AID1802883; AID414582
Dihydroorotate dehydrogenase (quinone), mitochondrialPlasmodium falciparum 3D7IC50 (µMol)26.20800.28001.07804.0000AID1798932; AID1802883
Dihydroorotate dehydrogenase Plasmodium falciparum (malaria parasite P. falciparum)IC50 (µMol)0.27500.23002.64439.4800AID1152595; AID414599
Dihydroorotate dehydrogenase (quinone), mitochondrialRattus norvegicus (Norway rat)IC50 (µMol)100.00000.00900.14100.7000AID1152597
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Activation Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Dihydroorotate dehydrogenase Plasmodium falciparum (malaria parasite P. falciparum)Kd0.17000.17000.17000.1700AID1152599
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (4)

Processvia Protein(s)Taxonomy
UDP biosynthetic processDihydroorotate dehydrogenase (quinone), mitochondrialHomo sapiens (human)
'de novo' UMP biosynthetic processDihydroorotate dehydrogenase (quinone), mitochondrialHomo sapiens (human)
pyrimidine ribonucleotide biosynthetic processDihydroorotate dehydrogenase (quinone), mitochondrialHomo sapiens (human)
'de novo' pyrimidine nucleobase biosynthetic processDihydroorotate dehydrogenase (quinone), mitochondrialHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (4)

Processvia Protein(s)Taxonomy
dihydroorotase activityDihydroorotate dehydrogenase (quinone), mitochondrialHomo sapiens (human)
protein bindingDihydroorotate dehydrogenase (quinone), mitochondrialHomo sapiens (human)
dihydroorotate dehydrogenase (quinone) activityDihydroorotate dehydrogenase (quinone), mitochondrialHomo sapiens (human)
dihydroorotate dehydrogenase activityDihydroorotate dehydrogenase (quinone), mitochondrialHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (4)

Processvia Protein(s)Taxonomy
nucleoplasmDihydroorotate dehydrogenase (quinone), mitochondrialHomo sapiens (human)
mitochondrionDihydroorotate dehydrogenase (quinone), mitochondrialHomo sapiens (human)
mitochondrial inner membraneDihydroorotate dehydrogenase (quinone), mitochondrialHomo sapiens (human)
cytosolDihydroorotate dehydrogenase (quinone), mitochondrialHomo sapiens (human)
mitochondrial inner membraneDihydroorotate dehydrogenase (quinone), mitochondrialHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (38)

Assay IDTitleYearJournalArticle
AID1152599Binding affinity to Plasmodium falciparum DHODH by isothermal titration calorimetry2014Journal of medicinal chemistry, Jun-26, Volume: 57, Issue:12
Fluorine modulates species selectivity in the triazolopyrimidine class of Plasmodium falciparum dihydroorotate dehydrogenase inhibitors.
AID414592Cmax in Swiss mouse at 20 mg/kg, po administered as single dose2009Journal of medicinal chemistry, Apr-09, Volume: 52, Issue:7
Identification of a metabolically stable triazolopyrimidine-based dihydroorotate dehydrogenase inhibitor with antimalarial activity in mice.
AID414604Toxicity in Swiss mouse at 20 mg/kg, po administered as single dose2009Journal of medicinal chemistry, Apr-09, Volume: 52, Issue:7
Identification of a metabolically stable triazolopyrimidine-based dihydroorotate dehydrogenase inhibitor with antimalarial activity in mice.
AID414581Inhibition of Plasmodium berghei ANKA DHODH2009Journal of medicinal chemistry, Apr-09, Volume: 52, Issue:7
Identification of a metabolically stable triazolopyrimidine-based dihydroorotate dehydrogenase inhibitor with antimalarial activity in mice.
AID414595AUC (0 to last) in Swiss mouse at 50 mg/kg, po administered as single dose2009Journal of medicinal chemistry, Apr-09, Volume: 52, Issue:7
Identification of a metabolically stable triazolopyrimidine-based dihydroorotate dehydrogenase inhibitor with antimalarial activity in mice.
AID601644Plasma protein binding in human by albumin chromatographic method2011Journal of medicinal chemistry, Jun-09, Volume: 54, Issue:11
Lead optimization of aryl and aralkyl amine-based triazolopyrimidine inhibitors of Plasmodium falciparum dihydroorotate dehydrogenase with antimalarial activity in mice.
AID414588Plasma concentration in Swiss mouse at 20 mg/kg, po administered as single dose2009Journal of medicinal chemistry, Apr-09, Volume: 52, Issue:7
Identification of a metabolically stable triazolopyrimidine-based dihydroorotate dehydrogenase inhibitor with antimalarial activity in mice.
AID414590Half life in Swiss mouse at 20 mg/kg, po administered as single dose2009Journal of medicinal chemistry, Apr-09, Volume: 52, Issue:7
Identification of a metabolically stable triazolopyrimidine-based dihydroorotate dehydrogenase inhibitor with antimalarial activity in mice.
AID1604304Inhibition of Plasmodium falciparum DHODH2019European journal of medicinal chemistry, Dec-01, Volume: 183Dihydroorotate dehydrogenase inhibitors in anti-infective drug research.
AID414583Antiplasmodial activity against Plasmodium falciparum 3D7 by [3H]hypoxanthine uptake2009Journal of medicinal chemistry, Apr-09, Volume: 52, Issue:7
Identification of a metabolically stable triazolopyrimidine-based dihydroorotate dehydrogenase inhibitor with antimalarial activity in mice.
AID414589Plasma concentration in Swiss mouse at 50 mg/kg, po administered as single dose for 16 hrs2009Journal of medicinal chemistry, Apr-09, Volume: 52, Issue:7
Identification of a metabolically stable triazolopyrimidine-based dihydroorotate dehydrogenase inhibitor with antimalarial activity in mice.
AID1152595Inhibition of N-terminal His6-tagged recombinant Plasmodium falciparum DHODH (amino acid residues 158 to 569) expressed in Escherichia coli BL21 cells assessed as orotic acid production using dihydroorotate as substrate by DCIP dye-based assay2014Journal of medicinal chemistry, Jun-26, Volume: 57, Issue:12
Fluorine modulates species selectivity in the triazolopyrimidine class of Plasmodium falciparum dihydroorotate dehydrogenase inhibitors.
AID414597Antimalarial activity as reduced growth at day 5 in Plasmodium berghei NK65 infected BALB/c mice (Mus musculus) at 50 mg/kg peroral dose over 4 days2009Journal of medicinal chemistry, Apr-09, Volume: 52, Issue:7
Identification of a metabolically stable triazolopyrimidine-based dihydroorotate dehydrogenase inhibitor with antimalarial activity in mice.
AID1152600Binding affinity to rat DHODH by isothermal titration calorimetry2014Journal of medicinal chemistry, Jun-26, Volume: 57, Issue:12
Fluorine modulates species selectivity in the triazolopyrimidine class of Plasmodium falciparum dihydroorotate dehydrogenase inhibitors.
AID414593Cmax in Swiss mouse at 50 mg/kg, po administered as single dose2009Journal of medicinal chemistry, Apr-09, Volume: 52, Issue:7
Identification of a metabolically stable triazolopyrimidine-based dihydroorotate dehydrogenase inhibitor with antimalarial activity in mice.
AID414591Half life in Swiss mouse at 50 mg/kg, po administered as single dose2009Journal of medicinal chemistry, Apr-09, Volume: 52, Issue:7
Identification of a metabolically stable triazolopyrimidine-based dihydroorotate dehydrogenase inhibitor with antimalarial activity in mice.
AID601643Aqueous solubility of the compound in phosphate buffer at pH 6.52011Journal of medicinal chemistry, Jun-09, Volume: 54, Issue:11
Lead optimization of aryl and aralkyl amine-based triazolopyrimidine inhibitors of Plasmodium falciparum dihydroorotate dehydrogenase with antimalarial activity in mice.
AID414598Antimalarial activity as reduced growth at day 5 in Plasmodium berghei NK65 infected BALB/c mice (Mus musculus) at 50 mg/kg peroral dose over 4 days2009Journal of medicinal chemistry, Apr-09, Volume: 52, Issue:7
Identification of a metabolically stable triazolopyrimidine-based dihydroorotate dehydrogenase inhibitor with antimalarial activity in mice.
AID1152597Inhibition of rat DHODH (amino acid residues 30 to 396) expressed in Escherichia coli BL21 cells assessed as orotic acid production using dihydroorotate as substrate by DCIP dye-based assay2014Journal of medicinal chemistry, Jun-26, Volume: 57, Issue:12
Fluorine modulates species selectivity in the triazolopyrimidine class of Plasmodium falciparum dihydroorotate dehydrogenase inhibitors.
AID601642Partition coefficient, log D of the compound at pH 7.4 by UV-HPLC analysis2011Journal of medicinal chemistry, Jun-09, Volume: 54, Issue:11
Lead optimization of aryl and aralkyl amine-based triazolopyrimidine inhibitors of Plasmodium falciparum dihydroorotate dehydrogenase with antimalarial activity in mice.
AID414582Inhibition of human DHODH2009Journal of medicinal chemistry, Apr-09, Volume: 52, Issue:7
Identification of a metabolically stable triazolopyrimidine-based dihydroorotate dehydrogenase inhibitor with antimalarial activity in mice.
AID414599Inhibition of Plasmodium falciparum DHODH2009Journal of medicinal chemistry, Apr-09, Volume: 52, Issue:7
Identification of a metabolically stable triazolopyrimidine-based dihydroorotate dehydrogenase inhibitor with antimalarial activity in mice.
AID414851Plasma concentration in Swiss mouse at 50 mg/kg, po administered as single dose2009Journal of medicinal chemistry, Apr-09, Volume: 52, Issue:7
Identification of a metabolically stable triazolopyrimidine-based dihydroorotate dehydrogenase inhibitor with antimalarial activity in mice.
AID414603Toxicity in Swiss mouse at 50 mg/kg, po administered as single dose2009Journal of medicinal chemistry, Apr-09, Volume: 52, Issue:7
Identification of a metabolically stable triazolopyrimidine-based dihydroorotate dehydrogenase inhibitor with antimalarial activity in mice.
AID414596Toxicity in Plasmodium berghei NK65 infected BALB/c mice (Mus musculus) at 50 mg/kg, perorally qd for 4 days measured on day 5 postinfection2009Journal of medicinal chemistry, Apr-09, Volume: 52, Issue:7
Identification of a metabolically stable triazolopyrimidine-based dihydroorotate dehydrogenase inhibitor with antimalarial activity in mice.
AID414601Toxicity in Plasmodium berghei NK65 infected BALB/c mice (Mus musculus) at 50 mg/kg, perorally bid for 4 days measured on day 5 postinfection2009Journal of medicinal chemistry, Apr-09, Volume: 52, Issue:7
Identification of a metabolically stable triazolopyrimidine-based dihydroorotate dehydrogenase inhibitor with antimalarial activity in mice.
AID414594AUC (0 to last) in Swiss mouse at 20 mg/kg, po administered as single dose2009Journal of medicinal chemistry, Apr-09, Volume: 52, Issue:7
Identification of a metabolically stable triazolopyrimidine-based dihydroorotate dehydrogenase inhibitor with antimalarial activity in mice.
AID414585Intrinsic clearance in human liver microsomes at 1 uM2009Journal of medicinal chemistry, Apr-09, Volume: 52, Issue:7
Identification of a metabolically stable triazolopyrimidine-based dihydroorotate dehydrogenase inhibitor with antimalarial activity in mice.
AID414584Metabolic stability in human liver microsomes assessed as degradation half life at 1 uM2009Journal of medicinal chemistry, Apr-09, Volume: 52, Issue:7
Identification of a metabolically stable triazolopyrimidine-based dihydroorotate dehydrogenase inhibitor with antimalarial activity in mice.
AID1152596Inhibition of C-terminal His6-tagged human DHODH (amino acid residues 30 to 396) expressed in Escherichia coli BL21 cells assessed as orotic acid production using dihydroorotate as substrate by DCIP dye-based assay2014Journal of medicinal chemistry, Jun-26, Volume: 57, Issue:12
Fluorine modulates species selectivity in the triazolopyrimidine class of Plasmodium falciparum dihydroorotate dehydrogenase inhibitors.
AID1152594Antimalarial activity against Plasmodium falciparum 3D7 infected in RBC after 72 hrs by SYBR green dye based flow cytometry2014Journal of medicinal chemistry, Jun-26, Volume: 57, Issue:12
Fluorine modulates species selectivity in the triazolopyrimidine class of Plasmodium falciparum dihydroorotate dehydrogenase inhibitors.
AID1152598Inhibition of dog DHODH (amino acid residues 48 to 414) expressed in Escherichia coli BL21 cells assessed as orotic acid production using dihydroorotate as substrate by DCIP dye-based assay2014Journal of medicinal chemistry, Jun-26, Volume: 57, Issue:12
Fluorine modulates species selectivity in the triazolopyrimidine class of Plasmodium falciparum dihydroorotate dehydrogenase inhibitors.
AID1152601Partition coefficient, log D of the compound at pH 7.4 by chromatography2014Journal of medicinal chemistry, Jun-26, Volume: 57, Issue:12
Fluorine modulates species selectivity in the triazolopyrimidine class of Plasmodium falciparum dihydroorotate dehydrogenase inhibitors.
AID601645Intrinsic clearance in human liver microsome assessed per mg of protein at 1 uM after 60 mins by LC-MS analysis2011Journal of medicinal chemistry, Jun-09, Volume: 54, Issue:11
Lead optimization of aryl and aralkyl amine-based triazolopyrimidine inhibitors of Plasmodium falciparum dihydroorotate dehydrogenase with antimalarial activity in mice.
AID1338073Inhibition of Plasmodium falciparum DHODH expressed in Escherichia coli using L-dihydroorotate as substrate by DCIP-based spectrophotometric method2017European journal of medicinal chemistry, Jan-05, Volume: 125Dihydroorotate dehydrogenase: A drug target for the development of antimalarials.
AID1152593Inhibition of mouse DHODH (amino acid residues 30 to 396) expressed in Escherichia coli BL21 cells assessed as orotic acid production using dihydroorotate as substrate by DCIP dye-based assay2014Journal of medicinal chemistry, Jun-26, Volume: 57, Issue:12
Fluorine modulates species selectivity in the triazolopyrimidine class of Plasmodium falciparum dihydroorotate dehydrogenase inhibitors.
AID1802883DHODH Biochemical Assay from Article 10.1074/jbc.M114.558353: \\In vitro resistance selections for Plasmodium falciparum dihydroorotate dehydrogenase inhibitors give mutants with multiple point mutations in the drug-binding site and altered growth.\\2014The Journal of biological chemistry, Jun-27, Volume: 289, Issue:26
In vitro resistance selections for Plasmodium falciparum dihydroorotate dehydrogenase inhibitors give mutants with multiple point mutations in the drug-binding site and altered growth.
AID1798932DHODH Inhibition Assay from Article 10.1021/jm801343r: \\Identification of a metabolically stable triazolopyrimidine-based dihydroorotate dehydrogenase inhibitor with antimalarial activity in mice.\\2009Journal of medicinal chemistry, Apr-09, Volume: 52, Issue:7
Identification of a metabolically stable triazolopyrimidine-based dihydroorotate dehydrogenase inhibitor with antimalarial activity in mice.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (6)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's1 (16.67)29.6817
2010's5 (83.33)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews2 (33.33%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other4 (66.67%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
chloroquine
Chloroquine: The prototypical antimalarial agent with a mechanism that is not well understood. It has also been used to treat rheumatoid arthritis, systemic lupus erythematosus, and in the systemic therapy of amebic liver abscesses.. chloroquine : An aminoquinoline that is quinoline which is substituted at position 4 by a [5-(diethylamino)pentan-2-yl]amino group at at position 7 by chlorine. It is used for the treatment of malaria, hepatic amoebiasis, lupus erythematosus, light-sensitive skin eruptions, and rheumatoid arthritis.		2.0610aminoquinoline;
organochlorine compound;
secondary amino compound;
tertiary amino compound		anticoronaviral agent;
antimalarial;
antirheumatic drug;
autophagy inhibitor;
dermatologic drug
leflunomide
Leflunomide: An isoxazole derivative that inhibits dihydroorotate dehydrogenase, the fourth enzyme in the pyrimidine biosynthetic pathway. It is used an immunosuppressive agent in the treatment of RHEUMATOID ARTHRITIS and PSORIATIC ARTHRITIS.. leflunomide : A monocarboxylic acid amide obtained by formal condensation of the carboxy group of 5-methyl-1,2-oxazole-4-carboxylic acid with the anilino group of 4-(trifluoromethyl)aniline. The prodrug of teriflunomide.		3.3110(trifluoromethyl)benzenes;
isoxazoles;
monocarboxylic acid amide		antineoplastic agent;
antiparasitic agent;
EC 1.3.98.1 [dihydroorotate oxidase (fumarate)] inhibitor;
EC 3.1.3.16 (phosphoprotein phosphatase) inhibitor;
hepatotoxic agent;
immunosuppressive agent;
non-steroidal anti-inflammatory drug;
prodrug;
pyrimidine synthesis inhibitor;
tyrosine kinase inhibitor
mefloquine hydrochloride
[2,8-bis(trifluoromethyl)quinolin-4-yl]-(2-piperidyl)methanol : An organofluorine compound that consists of quinoline bearing trifluoromethyl substituents at positions 2 and 8 as well as a (2-piperidinyl)hydroxymethyl substituent at position 4.		2.0610organofluorine compound;
piperidines;
quinolines;
secondary alcohol
pyrimethamine
Maloprim: contains above 2 cpds		2.0610aminopyrimidine;
monochlorobenzenes		antimalarial;
antiprotozoal drug;
EC 1.5.1.3 (dihydrofolate reductase) inhibitor
brequinar
brequinar : A quinolinemonocarboxylic acid that is quinoline substituted by 2'-fluoro[1,1'-biphenyl]-4-yl, methyl, carboxy and fluoro groups at positions 2, 3, 4, and 6, respectively. It is an inhibitor of dihydroorotate dehydrogenase, an enzyme that is required for de novo pyrimidine biosynthesis. The compound exhibits antineoplastic and antiviral properties.		3.3110biphenyls;
monocarboxylic acid;
monofluorobenzenes;
quinolinemonocarboxylic acid		anticoronaviral agent;
antimetabolite;
antineoplastic agent;
antiviral agent;
EC 1.3.5.2 [dihydroorotate dehydrogenase (quinone)] inhibitor;
immunosuppressive agent;
pyrimidine synthesis inhibitor
atovaquone
Atovaquone: A hydroxynaphthoquinone that has antimicrobial activity and is being used in antimalarial protocols.. atovaquone : A naphthoquinone compound having a 4-(4-chlorophenyl)cyclohexyl group at the 2-position and a hydroxy substituent at the 3-position.		3.6120hydroxy-1,2-naphthoquinone
pd 156252
[no description available]		2.0510
n-(3,5-dichlorophenyl)-2-methyl-3-nitrobenzamide
N-(3,5-dichlorophenyl)-2-methyl-3-nitrobenzamide: inhibits dihydroorotate dehydrogenase from P. falciparum; structure in first source		3.2510
artesunate
artesunic acid: RN given for (3R-(3alpha,5abeta,6beta,8abeta,9alpha,10alpha,12beta,(2aR*))-isomer; succinic ester of artemether		2.0610artemisinin derivative;
cyclic acetal;
dicarboxylic acid monoester;
hemisuccinate;
semisynthetic derivative;
sesquiterpenoid		antimalarial;
antineoplastic agent;
ferroptosis inducer
teriflunomide
[no description available]		3.6420(trifluoromethyl)benzenes;
aromatic amide;
enamide;
enol;
nitrile;
secondary carboxamide		drug metabolite;
EC 1.3.98.1 [dihydroorotate oxidase (fumarate)] inhibitor;
hepatotoxic agent;
non-steroidal anti-inflammatory drug;
tyrosine kinase inhibitor
ConditionIndicatedRelationship StrengthStudiesTrials
Infections, Plasmodium
[description not available]		02.4620
Malaria
A protozoan disease caused in humans by four species of the PLASMODIUM genus: PLASMODIUM FALCIPARUM; PLASMODIUM VIVAX; PLASMODIUM OVALE; and PLASMODIUM MALARIAE; and transmitted by the bite of an infected female mosquito of the genus ANOPHELES. Malaria is endemic in parts of Asia, Africa, Central and South America, Oceania, and certain Caribbean islands. It is characterized by extreme exhaustion associated with paroxysms of high FEVER; SWEATING; shaking CHILLS; and ANEMIA. Malaria in ANIMALS is caused by other species of plasmodia.		02.4620
Disease Models, Animal
Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.		02.0610
Plasmodium falciparum Malaria
[description not available]		02.110
Malaria, Falciparum
Malaria caused by PLASMODIUM FALCIPARUM. This is the severest form of malaria and is associated with the highest levels of parasites in the blood. This disease is characterized by irregularly recurring febrile paroxysms that in extreme cases occur with acute cerebral, renal, or gastrointestinal manifestations.		02.110