Drug Information
| Drug General Information | Top | |||
|---|---|---|---|---|
| Drug ID |
D05CHI
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| Former ID |
DAP000656
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| Drug Name |
Rifabutin
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| Synonyms |
Alfacid; Ansamycin; Ansatipin; Ansatipine; Assatipin; Mycobutin; RBT; Rifabutina; Rifabutine; Rifabutinum; Grunenthal Brand of Rifabutin; Kenfarma Brand of Rifabutin; Pfizer Brand of Rifabutin; Rifabutin Pfizer Brand; Rifabutina [Spanish]; Rifabutine [French]; Rifabutinum [Latin]; Antibiotic LM 427; LM 427; LM427; DRG-0085; LM-427; Mycobutin (TN); Rifabutin [USAN:BAN:INN]; Rifabutin (JAN/USP/INN); Mycobutin, Ansamycin, LM 427, Ansatipine, Rifabutin; (9S,12E,14S,15R,16S,17R,18R,19R,20S,21S,22E,24Z)-6,18,20-trihydroxy-1'-isobutyl-14-methoxy-7,9,15,17,19,21,25-heptamethyl-5,10,26-trioxo-3,5,9,10-tetrahydrospiro[9,4-(epoxypentadeca[1,11,13]trienoimino)furo[2',3':7,8]naphtho[1,2-d]imidazole-2,4'-piperidin; Spiro[9,4-(epoxypentadeca[1,11,13]trienimino)-2H-furo[2',3':7,8]naphth[1,2-d]imidazole-2,4'-piperidine]-5,10,26(3H,9H)-trione, 16-(acetyloxy)-6,18,20-trihydroxy-14-methoxy-7,9,15,17,19,21,25-heptameth; 1,4-Dihydro-1-deoxy-1',4-didehydro-5'-(2-methylpropyl)-1-oxorifamycin XIV; 4-Deoxo-3,4-(2-spiro(N-isobutyl-4-piperidyl)-2,5-dihydro-1H-imidazo)-rifamycin S; 4-N-isobutylspiropiperidylrifamycin S
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| Drug Type |
Small molecular drug
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| Indication | Mycobacterium infection [ICD-11: 1B10-1B21] | Approved | [1] | |
| Tuberculosis [ICD-11: 1B10-1B14] | Approved | [1] | ||
| Therapeutic Class |
Antibiotics
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| Company |
Adria Laboratories
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| Structure |
 |
Download2D MOL
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| Formula |
C46H62N4O11
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| Canonical SMILES |
CC1C=CC=C(C(=O)N=C2C(=C3C(=C4C2=NC5(N4)CCN(CC5)CC(C)C)C6=C(C(=C3O)C)OC(C6=O)(OC=CC(C(C(C(C(C(C1O)C)O)C)OC(=O)C)C)OC)C)O)C
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| InChI |
1S/C46H62N4O11/c1-22(2)21-50-18-16-46(17-19-50)48-34-31-32-39(54)28(8)42-33(31)43(56)45(10,61-42)59-20-15-30(58-11)25(5)41(60-29(9)51)27(7)38(53)26(6)37(52)23(3)13-12-14-24(4)44(57)47-36(40(32)55)35(34)49-46/h12-15,20,22-23,25-27,30,37-38,41,48,52-55H,16-19,21H2,1-11H3/b13-12+,20-15+,24-14-,47-36?/t23-,25+,26+,27+,30-,37-,38+,41+,45-/m0/s1
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| InChIKey |
ZWBTYMGEBZUQTK-PVLSIAFMSA-N
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| CAS Number |
CAS 72559-06-9
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| PubChem Compound ID | ||||
| PubChem Substance ID |
9444, 596006, 7847490, 7890228, 7980515, 11599530, 12012943, 14791636, 17388744, 26697101, 37101863, 46506468, 48244710, 48425598, 50044776, 53787673, 56323065, 57288827, 57365629, 75049157, 92126064, 92717216, 103535182, 103914671, 104170218, 104253353, 119526090, 121362422, 124757471, 124766242, 124889959, 125164275, 126592920, 126628917, 126659394, 126684731, 134337945, 135011172, 135692257, 139945728, 144204563, 144207956, 152102452, 152343628, 160963960, 172080843, 173905832, 175267510, 175612152, 176484810
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| ADReCS Drug ID | BADD_D01935 | |||
| SuperDrug ATC ID |
J04AB04
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| SuperDrug CAS ID |
cas=072559069
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| Interaction between the Drug and Microbe | Top | |||
|---|---|---|---|---|
| The Metabolism of Drug Affected by Studied Microbe(s) | ||||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Gut microbiota | ||||
| Studied Microbe: Gut microbiota unspecific | [2] | |||
| Experimental Method | High-throughput screening | |||
| Description | Rifabutin can be metabolized by gut microbiota. | |||
| The Abundace of Studied Microbe(s) Regulated by Drug | ||||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Bacteroidales | ||||
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Studied Microbe: Bacteroides caccae
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[3] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Bacteroides caccae was decreased by Rifabutin (adjusted p-values: 5.04E-06). | |||
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Studied Microbe: Bacteroides fragilis enterotoxigenic
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[3] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Bacteroides fragilis enterotoxigenic was decreased by Rifabutin (adjusted p-values: 8.05E-06). | |||
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Studied Microbe: Bacteroides fragilis nontoxigenic
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[3] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Bacteroides fragilis nontoxigenic was decreased by Rifabutin (adjusted p-values: 8.82E-06). | |||
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Studied Microbe: Bacteroides ovatus
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[3] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Bacteroides ovatus was decreased by Rifabutin (adjusted p-values: 5.04E-06). | |||
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Studied Microbe: Bacteroides thetaiotaomicron
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[3] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Bacteroides thetaiotaomicron was decreased by Rifabutin (adjusted p-values: 9.34E-06). | |||
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Studied Microbe: Bacteroides uniformis
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[3] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Bacteroides uniformis was decreased by Rifabutin (adjusted p-values: 7.64E-07). | |||
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Studied Microbe: Bacteroides vulgatus
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[3] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Bacteroides vulgatus was decreased by Rifabutin (adjusted p-values: 4.58E-06). | |||
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Studied Microbe: Bacteroides xylanisolvens
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[3] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Bacteroides xylanisolvens was decreased by Rifabutin (adjusted p-values: 4.93E-07). | |||
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Studied Microbe: Odoribacter splanchnicus
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[3] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Odoribacter splanchnicus was decreased by Rifabutin (adjusted p-values: 5.04E-06). | |||
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Studied Microbe: Parabacteroides distasonis
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[3] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Parabacteroides distasonis was decreased by Rifabutin (adjusted p-values: 2.74E-07). | |||
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Studied Microbe: Parabacteroides merdae
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[3] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Parabacteroides merdae was decreased by Rifabutin (adjusted p-values: 4.93E-07). | |||
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Studied Microbe: Prevotella copri
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[3] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Prevotella copri was decreased by Rifabutin (adjusted p-values: 1.05E-04). | |||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Bifidobacteriales | ||||
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Studied Microbe: Bifidobacterium adolescentis
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[3] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Bifidobacterium adolescentis was decreased by Rifabutin (adjusted p-values: 5.04E-06). | |||
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Studied Microbe: Bifidobacterium longum
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[3] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Bifidobacterium longum was decreased by Rifabutin (adjusted p-values: 5.04E-06). | |||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Coriobacteriales | ||||
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Studied Microbe: Collinsella aerofaciens
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[3] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Collinsella aerofaciens was decreased by Rifabutin (adjusted p-values: 2.73E-07). | |||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Eggerthellales | ||||
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Studied Microbe: Eggerthella lenta
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[3] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Eggerthella lenta was decreased by Rifabutin (adjusted p-values: 9.87E-06). | |||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Enterobacterales | ||||
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Studied Microbe: Escherichia coli ED1a
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[3] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Escherichia coli ED1a was decreased by Rifabutin (adjusted p-values: 5.18E-06). | |||
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Studied Microbe: Escherichia coli IAI1
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[3] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Escherichia coli IAI1 was decreased by Rifabutin (adjusted p-values: 5.22E-07). | |||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Erysipelotrichales | ||||
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Studied Microbe: Erysipelatoclostridium ramosum
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[3] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Erysipelatoclostridium ramosum was decreased by Rifabutin (adjusted p-values: 5.04E-06). | |||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Eubacteriales | ||||
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Studied Microbe: Blautia obeum
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[3] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Blautia obeum was decreased by Rifabutin (adjusted p-values: 9.50E-07). | |||
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Studied Microbe: Clostridioides difficile
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[3] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Clostridioides difficile was decreased by Rifabutin (adjusted p-values: 5.61E-06). | |||
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Studied Microbe: Clostridium perfringens
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[3] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Clostridium perfringens was decreased by Rifabutin (adjusted p-values: 5.96E-07). | |||
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Studied Microbe: Coprococcus comes
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[3] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Coprococcus comes was decreased by Rifabutin (adjusted p-values: 5.04E-06). | |||
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Studied Microbe: Dorea formicigenerans
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[3] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Dorea formicigenerans was decreased by Rifabutin (adjusted p-values: 5.04E-06). | |||
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Studied Microbe: Enterocloster bolteae
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[3] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Enterocloster bolteae was decreased by Rifabutin (adjusted p-values: 5.85E-06). | |||
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Studied Microbe: Eubacterium eligens
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[3] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Eubacterium eligens was decreased by Rifabutin (adjusted p-values: 1.73E-04). | |||
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Studied Microbe: Eubacterium rectale
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[3] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Eubacterium rectale was decreased by Rifabutin (adjusted p-values: 3.78E-04). | |||
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Studied Microbe: Lacrimispora saccharolytica
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[3] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Lacrimispora saccharolytica was decreased by Rifabutin (adjusted p-values: 4.93E-07). | |||
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Studied Microbe: Roseburia hominis
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[3] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Roseburia hominis was decreased by Rifabutin (adjusted p-values: 3.12E-05). | |||
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Studied Microbe: Roseburia intestinalis
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[3] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Roseburia intestinalis was decreased by Rifabutin (adjusted p-values: 2.25E-04). | |||
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Studied Microbe: Ruminococcus bromii
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[3] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Ruminococcus bromii was decreased by Rifabutin (adjusted p-values: 2.06E-05). | |||
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Studied Microbe: Ruminococcus gnavus
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[3] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Ruminococcus gnavus was decreased by Rifabutin (adjusted p-values: 5.04E-06). | |||
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Studied Microbe: Ruminococcus torques
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[3] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Ruminococcus torques was decreased by Rifabutin (adjusted p-values: 2.33E-06). | |||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Lactobacillales | ||||
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Studied Microbe: Lactobacillus paracasei
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[3] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Lactobacillus paracasei was decreased by Rifabutin (adjusted p-values: 5.51E-07). | |||
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Studied Microbe: Streptococcus parasanguinis
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[3] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Streptococcus parasanguinis was decreased by Rifabutin (adjusted p-values: 1.67E-06). | |||
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Studied Microbe: Streptococcus salivarius
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[3] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Streptococcus salivarius was decreased by Rifabutin (adjusted p-values: 8.82E-07). | |||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Veillonellales | ||||
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Studied Microbe: Veillonella parvula
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[3] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Veillonella parvula was decreased by Rifabutin (adjusted p-values: 5.04E-06). | |||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Verrucomicrobiales | ||||
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Studied Microbe: Akkermansia muciniphila
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[3] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experiment Method | High-throughput screening | |||
| Description | The abundance of Akkermansia muciniphila was decreased by Rifabutin (adjusted p-values: 9.58E-06). | |||
| Target and Pathway | Top | |||
|---|---|---|---|---|
| Target(s) | DNA-directed RNA polymerase (RNAP) | Target Info | Modulator | [4] |
| References | Top | |||
|---|---|---|---|---|
| REF 1 | Novel agents in the management of Mycobacterium tuberculosis disease. Curr Med Chem. 2007;14(18):2000-8. | |||
| REF 2 | Personalized Mapping of Drug Metabolism by the Human Gut Microbiome. Cell. 2020 Jun 25;181(7):1661-1679.e22. | |||
| REF 3 | Extensive impact of non-antibiotic drugs on human gut bacteria. Nature. 2018 Mar 29;555(7698):623-628. | |||
| REF 4 | Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. | |||
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