Drug Information
| Drug General Information | Top | |||
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| Drug ID |
D06ZEE
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| Former ID |
DAP000156
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| Drug Name |
Atovaquone
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| Synonyms |
Acuvel; Atavaquone; Mepron; Pron; Wellvone; Atovaquone GlaxoSmithKline brand; Glaxo Wellcome brand of atovaquone; GlaxoSmithKline brand of atovaquone; Malarone Pediatric; BW 566C; BW 566C80; Hydroxynaphthoquinone 566C80; Atovaquone & Interleukin 12; BW 556C-80; BW 566C-80; BW-A 566C; DRG-0084; Hydroxynaphthoquinone, 566C80; Mepron (TN); Mepron (antipneumocystic); ATO & IL-12; Atovaquone (USP/INN); Atovaquone [USAN:BAN:INN]; CRL-8131 & Atovaquone; 2-(4-(4'-chlorophenyl)cyclohexyl)-3-hydroxy-1,4-naphthoquinone; 2-(4-(4-Chlorophenyl)cyclohexyl)-3-hydroxy-1,4-naphthoquinone; 2-(trans-4-(4-chlorophenyl)cyclohexyl)-3-hydroxy-1,4-naphthoquinone; 2-(trans-4-(p-Chlorophenyl)cyclohexyl)-3-hydroxy-1,4-naphthoquinone; 2-[trans-4-(4-chlorophenyl)cyclohexyl]-3-hydroxy-1,4-naphthoquinone; 2-[trans-4-(4-chlorophenyl)cyclohexyl]-3-hydroxynaphthalene-1,4-dione; 2-[trans-4-(p-Chlorophenyl)cyclohexyl]-3-hydroxy-1,4-naphthoquinone; 3-(4-(4-chlorophenyl)cyclohexyl)-4-hydroxy-naphthalene-1,2-dione; 3-[4-(4-chlorophenyl)cyclohexyl]-4-hydroxynaphthalene-1,2-dione; 566C80 hydroxynaphthoquinone; 566C80, hydroxynaphthoquinone; ATQ
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| Drug Type |
Small molecular drug
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| Indication | Fungal infection [ICD-11: 1F29-1F2F; ICD-10: B35-B49; ICD-9: 110-118] | Approved | [1] | |
| Therapeutic Class |
Antifungal Agents
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| Company |
GlaxoSmithKline
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| Structure |
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Download2D MOL |
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| Formula |
C22H19ClO3
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| Canonical SMILES |
C1CC(CCC1C2=CC=C(C=C2)Cl)C3=C(C4=CC=CC=C4C(=O)C3=O)O
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| InChI |
1S/C22H19ClO3/c23-16-11-9-14(10-12-16)13-5-7-15(8-6-13)19-20(24)17-3-1-2-4-18(17)21(25)22(19)26/h1-4,9-13,15,24H,5-8H2
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| InChIKey |
BSJMWHQBCZFXBR-UHFFFAOYSA-N
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| CAS Number |
CAS 94015-53-9
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| PubChem Compound ID | ||||
| PubChem Substance ID |
9053, 602773, 630991, 642443, 6268716, 7847303, 7978737, 11112877, 11341957, 11362140, 11364637, 11367199, 11369761, 11372000, 11374732, 11377923, 11466562, 11467682, 11485585, 11486204, 11487542, 11489481, 11490806, 11492931, 11495557, 11528793, 14803776, 14828617, 26608042, 26612671, 26680436, 26748932, 26748933, 37101820, 37347461, 43130769, 46507298, 47434353, 47656598, 47811034, 48104692, 48259503, 48328562, 48415589, 49699104, 50100533, 51002645, 56463626, 57319569, 81092863
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| ChEBI ID |
CHEBI:575568
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| ADReCS Drug ID | BADD_D00186 | |||
| SuperDrug ATC ID |
P01AX06
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| SuperDrug CAS ID |
cas=095233184
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| Interaction between the Drug and Microbe | Top | |||
|---|---|---|---|---|
| The Abundace of Studied Microbe(s) Regulated by Drug | ||||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Eubacteriales | ||||
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Studied Microbe: Blautia obeum
Show/Hide Hierarchy
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[2] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Blautia obeum was decreased by Atovaquone (adjusted p-values: 5.81E-03). | |||
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Studied Microbe: Ruminococcus torques
Show/Hide Hierarchy
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[2] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Ruminococcus torques was decreased by Atovaquone (adjusted p-values: 2.19E-03). | |||
| Drug Resistance Mutation (DRM) | Top | |||
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| DRM | DRM Info | |||
| Target and Pathway | Top | |||
|---|---|---|---|---|
| Target(s) | Plasmodium Dihydroorotate dehydrogenase (Malaria DHOdehase) | Target Info | Inhibitor | [3], [4], [5], [6] |
| KEGG Pathway | Pyrimidine metabolism | |||
| Metabolic pathways | ||||
| Pathwhiz Pathway | Pyrimidine Metabolism | |||
| Reactome | Pyrimidine biosynthesis | |||
| WikiPathways | Metabolism of nucleotides | |||
| References | Top | |||
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| REF 1 | The fight against drug-resistant malaria: novel plasmodial targets and antimalarial drugs. Curr Med Chem. 2008;15(2):161-71. | |||
| REF 2 | Extensive impact of non-antibiotic drugs on human gut bacteria. Nature. 2018 Mar 29;555(7698):623-628. | |||
| REF 3 | Inhibitor binding in a class 2 dihydroorotate dehydrogenase causes variations in the membrane-associated N-terminal domain. Protein Sci. 2004 Apr;13(4):1031-42. | |||
| REF 4 | Effects of atovaquone and diospyrin-based drugs on the cellular ATP of Pneumocystis carinii f. sp. carinii. Antimicrob Agents Chemother. 2000 Mar;44(3):713-9. | |||
| REF 5 | Kinetics of inhibition of human and rat dihydroorotate dehydrogenase by atovaquone, lawsone derivatives, brequinar sodium and polyporic acid. Chem Biol Interact. 2000 Jan 3;124(1):61-76. | |||
| REF 6 | The effects of antimalarials on the Plasmodium falciparum dihydroorotate dehydrogenase. Exp Parasitol. 1994 Aug;79(1):50-6. | |||
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