Drug Information
| Drug General Information | Top | |||
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| Drug ID |
D0CT9C
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| Former ID |
DAP000532
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| Drug Name |
Cyclophosphamide
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| Synonyms |
ASTA; Ciclofosfamida; Ciclophosphamide; Clafen; Claphene; Cycloblastin; Cyclophosphamid; Cyclophosphamides; Cyclophosphamidum; Cyclophosphan; Cyclophosphane; Cyclophosphanum; Cyclophosphoramide; Cyclostin; Cyklofosfamid; Cytophosphan; Cytophosphane; Cytoxan; Endoxan; Endoxana; Endoxanal; Endoxane; Enduxan; Genoxal; Mitoxan; Neosar; Procytox; Revimmune; Semdoxan; Sendoxan; Senduxan; Zyklophosphamid; Ciclophosphamide [INN]; Cyclophosphamide Sterile; Cyclophosphamide anhydrous; Cyklofosfamid [Czech]; Cytoxan Lyoph; Endoxan R; Lyophilized Cytoxan; Zyklophosphamid [German]; ASTA B518; Asta B 518; B 518; C 0768; CB 4564; SK 20501; B-518; CB-4564; Ciclofosfamida [INN-Spanish]; Cyclophosphamide (INN); Cyclophosphamide (TN); Cyclophosphamide (anhydrous form); Cyclophosphamide (anhydrous); Cyclophosphamidum [INN-Latin]; Cytoxan (TN); Endoxan (TN); Endoxan-Asta; Neosar (TN); Occupation, cyclophosphamide exposure; Procytox (TN); Revimmune (TN); Bis(2-Chloroethyl)phosphami de cyclic propanolamide; Bis(2-Chloroethyl)phosphamide cyclic propanolamide ester; Bis(2-chloroethyl)phosphoramide cyclic propanolamide ester; D,L-Cyclophosphamide; Cyclophosphamide, (+-)-Isomer; N,N-Bis(2-chloroethyl)-1,3,2-oxazaphosphinan-2-amine 2-oxide; (+-)-Cyclophosphamide; (-)-Cyclophosphamide; (RS)-Cyclophosphamide; 1-(bis(2-chloroethyl)amino)-1-oxo-2-aza-5-oxaphosphoridine; 1-Bis(2-chloroethyl)amino-1-oxo-2-aza-5-oxaphosphoridin; 4-Hydroxy-cyclophosphan-mamophosphatide
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| Drug Type |
Small molecular drug
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| Indication | Solid tumour/cancer [ICD-11: 2A00-2F9Z; ICD-10: C76-C80; ICD-9: 140-229] | Approved | [1], [2] | |
| Therapeutic Class |
Anticancer Agents
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| Company |
Baxter International Inc
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| Structure |
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Download2D MOL |
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| Formula |
C7H15Cl2N2O2P
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| Canonical SMILES |
C1CNP(=O)(OC1)N(CCCl)CCCl
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| InChI |
1S/C7H15Cl2N2O2P/c8-2-5-11(6-3-9)14(12)10-4-1-7-13-14/h1-7H2,(H,10,12)
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| InChIKey |
CMSMOCZEIVJLDB-UHFFFAOYSA-N
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| CAS Number |
CAS 50-18-0
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| PubChem Compound ID | ||||
| PubChem Substance ID |
10090, 87150, 141705, 141706, 598053, 5080187, 7979009, 8151862, 10524283, 11110909, 11335421, 11360660, 11363752, 11366314, 11368876, 11371419, 11374027, 11377038, 11406490, 11461632, 11484807, 11488962, 11490186, 11492119, 11494672, 11533313, 14848034, 17404801, 25765844, 29222060, 46505441, 47365072, 47440141, 47515205, 48334372, 48413505, 48415829, 48423195, 49855451, 50000789, 50105634, 50105635, 51092052, 53777344, 53788477, 56310899, 56311422, 56313326, 56313987, 57288588
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| ChEBI ID |
CHEBI:4027
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| ADReCS Drug ID | BADD_D00549 | |||
| SuperDrug ATC ID |
L01AA01
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| SuperDrug CAS ID |
cas=000050180
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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): Bacteroidales | ||||
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Studied Microbe: Alistipes indistinctus
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[3] | |||
| Hierarchy | ||||
| Description | Cyclophosphamide can be metabolized by Alistipes indistinctus. | |||
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Studied Microbe: Alistipes indistinctus DSM22520
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[4] | |||
| Hierarchy | ||||
| Experimental Method | High-throughput screening | |||
| Description | Cyclophosphamide can be metabolized by Alistipes indistinctus DSM22520 (log2FC = -0.327; p = 0.003). | |||
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Studied Microbe: Bacteroides fragilis HMW 615
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[4] | |||
| Hierarchy | ||||
| Experimental Method | High-throughput screening | |||
| Description | Cyclophosphamide can be metabolized by Bacteroides fragilis HMW 615 (log2FC = -0.335; p = 0.046). | |||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Erysipelotrichales | ||||
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Studied Microbe: Eubacterium biforme DSM 3989
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[4] | |||
| Hierarchy | ||||
| Experimental Method | High-throughput screening | |||
| Description | Cyclophosphamide can be metabolized by Eubacterium biforme DSM 3989 (log2FC = -0.34; p = 0.032). | |||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Eubacteriales | ||||
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Studied Microbe: Blautia hansenii DSM20583
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[4] | |||
| Hierarchy | ||||
| Experimental Method | High-throughput screening | |||
| Description | Cyclophosphamide can be metabolized by Blautia hansenii DSM20583 (log2FC = -0.325; p = 0.017). | |||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Gut microbiota | ||||
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Studied Microbe: Firmicutes
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[5] | |||
| Hierarchy | ||||
| Metabolic Effect | Increase activity | |||
| Description | Cyclophosphamide can be metabolized by Firmicutes, which results in the increase of the drug's activity. | |||
| Studied Microbe: Gut microbiota unspecific | [6] | |||
| Metabolic Effect | Increase activity | |||
| Description | Cyclophosphamide can be metabolized by gut microbiota, which results in the increase of the drug's activity. | |||
| The Abundace of Studied Microbe(s) Regulated by Drug | ||||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Bacillales | ||||
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Studied Microbe: Staphylococcaceae
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[7] | |||
| Hierarchy | ||||
| Abundance Change | Increase | |||
| Experimental Species | C57BL/6 mice | Experimental Sample | Faeces | |
| Disease or Condition | Healthy | |||
| Description | The abundance of Staphylococcaceae was increased by Cyclophosphamide (p < 0.05). | |||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Bacteroidales | ||||
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Studied Microbe: Prevotellaceae
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[7] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experimental Species | C57BL/6 mice | Experimental Sample | Faeces | |
| Disease or Condition | Healthy | |||
| Description | The abundance of Prevotellaceae was decreased by Cyclophosphamide (p < 0.05). | |||
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Studied Microbe: S24-7
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[7] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experimental Species | C57BL/6 mice | Experimental Sample | Faeces | |
| Disease or Condition | Healthy | |||
| Description | The abundance of S24-7 was decreased by Cyclophosphamide (p < 0.05). | |||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Burkholderiales | ||||
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Studied Microbe: Alcaligenaceae
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[7] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experimental Species | C57BL/6 mice | Experimental Sample | Faeces | |
| Disease or Condition | Healthy | |||
| Description | The abundance of Alcaligenaceae was decreased by Cyclophosphamide (p < 0.05). | |||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Coriobacteriales | ||||
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Studied Microbe: Coriobacteriaceae
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[7] | |||
| Hierarchy | ||||
| Abundance Change | Increase | |||
| Experimental Species | C57BL/6 mice | Experimental Sample | Faeces | |
| Disease or Condition | Healthy | |||
| Description | The abundance of Coriobacteriaceae was increased by Cyclophosphamide (p < 0.05). | |||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Enterobacterales | ||||
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Studied Microbe: Enterobacteriaceae
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[8] | |||
| Hierarchy | ||||
| Abundance Change | Increase | |||
| Experimental Species | BALB/c mice | Experimental Sample | Faeces | |
| Disease or Condition | Healthy | |||
| Description | The abundance of Enterobacteriaceae was increased by Cyclophosphamide. | |||
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Studied Microbe: Escherichia coli
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[8] | |||
| Hierarchy | ||||
| Abundance Change | Increase | |||
| Experimental Species | BALB/c mice | Experimental Sample | Faeces | |
| Disease or Condition | Healthy | |||
| Description | The abundance of Escherichia coli was increased by Cyclophosphamide. | |||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Eubacteriales | ||||
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Studied Microbe: Coprococcus
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[9] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experimental Species | C57BL/6 mice | Experimental Sample | Faeces | |
| Disease or Condition | Melanoma | |||
| Description | The abundance of Coprococcus was decreased by Cyclophosphamide. | |||
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Studied Microbe: Lachnospiraceae
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[7] | |||
| Hierarchy | ||||
| Abundance Change | Increase | |||
| Experimental Species | C57BL/6 mice | Experimental Sample | Faeces | |
| Disease or Condition | Healthy | |||
| Description | The abundance of Lachnospiraceae was increased by Cyclophosphamide (p < 0.05). | |||
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Studied Microbe: Lachnospiraceae
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[9] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experimental Species | C57BL/6 mice | Experimental Sample | Faeces | |
| Disease or Condition | Melanoma | |||
| Description | The abundance of Lachnospiraceae was decreased by Cyclophosphamide. | |||
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Studied Microbe: Roseburia
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[9] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experimental Species | C57BL/6 mice | Experimental Sample | Faeces | |
| Disease or Condition | Melanoma | |||
| Description | The abundance of Roseburia was decreased by Cyclophosphamide. | |||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Lactobacillales | ||||
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Studied Microbe: Enterococcus
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[8] | |||
| Hierarchy | ||||
| Abundance Change | Increase | |||
| Experimental Species | BALB/c mice | Experimental Sample | Faeces | |
| Disease or Condition | Healthy | |||
| Description | The abundance of Enterococcus was increased by Cyclophosphamide. | |||
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Studied Microbe: Enterococcus
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[9] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experimental Species | C57BL/6 mice | Experimental Sample | Faeces | |
| Disease or Condition | Melanoma | |||
| Description | The abundance of Enterococcus was decreased by Cyclophosphamide. | |||
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Studied Microbe: Lactobacillaceae
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[7] | |||
| Hierarchy | ||||
| Abundance Change | Increase | |||
| Experimental Species | C57BL/6 mice | Experimental Sample | Faeces | |
| Disease or Condition | Healthy | |||
| Description | The abundance of Lactobacillaceae was increased by Cyclophosphamide (p < 0.05). | |||
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Studied Microbe: Lactobacillus
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[9] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experimental Species | C57BL/6 mice | Experimental Sample | Faeces | |
| Disease or Condition | Melanoma | |||
| Description | The abundance of Lactobacillus was decreased by Cyclophosphamide. | |||
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Studied Microbe: Streptococcaceae
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[7] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experimental Species | C57BL/6 mice | Experimental Sample | Faeces | |
| Disease or Condition | Healthy | |||
| Description | The abundance of Streptococcaceae was decreased by Cyclophosphamide. | |||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Pseudomonadales | ||||
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Studied Microbe: Pseudomonas
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[8] | |||
| Hierarchy | ||||
| Abundance Change | Increase | |||
| Experimental Species | BALB/c mice | Experimental Sample | Faeces | |
| Disease or Condition | Healthy | |||
| Description | The abundance of Pseudomonas was increased by Cyclophosphamide. | |||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Rhodospirillales | ||||
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Studied Microbe: Rhodospirillaceae
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[7] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experimental Species | C57BL/6 mice | Experimental Sample | Faeces | |
| Disease or Condition | Healthy | |||
| Description | The abundance of Rhodospirillaceae was decreased by Cyclophosphamide (p < 0.05). | |||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Gut microbiota | ||||
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Studied Microbe: Actinobacteria
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[7] | |||
| Hierarchy | ||||
| Abundance Change | Increase | |||
| Experimental Species | C57BL/6 mice | Experimental Sample | Faeces | |
| Disease or Condition | Healthy | |||
| Description | The abundance of Actinobacteria was increased by Cyclophosphamide (p < 0.01). | |||
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Studied Microbe: Alphaproteobacteria
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[7] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experimental Species | C57BL/6 mice | Experimental Sample | Faeces | |
| Disease or Condition | Healthy | |||
| Description | The abundance of Alphaproteobacteria was decreased by Cyclophosphamide (p < 0.05). | |||
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Studied Microbe: Bacilli
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[7] | |||
| Hierarchy | ||||
| Abundance Change | Increase | |||
| Experimental Species | C57BL/6 mice | Experimental Sample | Faeces | |
| Disease or Condition | Healthy | |||
| Description | The abundance of Bacilli was increased by Cyclophosphamide. | |||
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Studied Microbe: Bacteroidetes
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[10] | |||
| Hierarchy | ||||
| Abundance Change | Increase | |||
| Experimental Species | BALB/c mice | Experimental Sample | Faeces | |
| Disease or Condition | Healthy | |||
| Description | The abundance of Bacteroidetes was increased by Cyclophosphamide (p < 0.05). | |||
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Studied Microbe: Bacteroidetes
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[7] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experimental Species | C57BL/6 mice | Experimental Sample | Faeces | |
| Disease or Condition | Healthy | |||
| Description | The abundance of Bacteroidetes was decreased by Cyclophosphamide. | |||
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Studied Microbe: Bacteroidia
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[7] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experimental Species | C57BL/6 mice | Experimental Sample | Faeces | |
| Disease or Condition | Healthy | |||
| Description | The abundance of Bacteroidia was decreased by Cyclophosphamide (p < 0.05). | |||
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Studied Microbe: Clostridia
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[7] | |||
| Hierarchy | ||||
| Abundance Change | Increase | |||
| Experimental Species | C57BL/6 mice | Experimental Sample | Faeces | |
| Disease or Condition | Healthy | |||
| Description | The abundance of Clostridia was increased by Cyclophosphamide. | |||
| Studied Microbe: Clostridium cluster XIVa | [9] | |||
| Abundance Change | Decrease | |||
| Experimental Species | C57BL/6 mice | Experimental Sample | Faeces | |
| Disease or Condition | Melanoma | |||
| Description | The abundance of Clostridium cluster XIVa was decreased by Cyclophosphamide. | |||
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Studied Microbe: Coriobacteriia
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[7] | |||
| Hierarchy | ||||
| Abundance Change | Increase | |||
| Experimental Species | C57BL/6 mice | Experimental Sample | Faeces | |
| Disease or Condition | Healthy | |||
| Description | The abundance of Coriobacteriia was increased by Cyclophosphamide. | |||
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Studied Microbe: Firmicutes/Bacteroidetes ratio
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[7] | |||
| Hierarchy | ||||
| Abundance Change | Increase | |||
| Experimental Species | C57BL/6 mice | Experimental Sample | Faeces | |
| Disease or Condition | Healthy | |||
| Description | The abundance of Firmicutes/Bacteroidetes ratio was increased by Cyclophosphamide. | |||
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Studied Microbe: Mollicutes
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[7] | |||
| Hierarchy | ||||
| Abundance Change | Increase | |||
| Experimental Species | C57BL/6 mice | Experimental Sample | Faeces | |
| Disease or Condition | Healthy | |||
| Description | The abundance of Mollicutes was increased by Cyclophosphamide. | |||
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Studied Microbe: Verrucomicrobia
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[7] | |||
| Hierarchy | ||||
| Abundance Change | Decrease | |||
| Experimental Species | C57BL/6 mice | Experimental Sample | Faeces | |
| Disease or Condition | Healthy | |||
| Description | The abundance of Verrucomicrobia was decreased by Cyclophosphamide. | |||
| Target and Pathway | Top | |||
|---|---|---|---|---|
| Target(s) | Human Deoxyribonucleic acid (hDNA) | Target Info | Modulator | [11], [12] |
| References | Top | |||
|---|---|---|---|---|
| REF 1 | URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 7154). | |||
| REF 2 | Emerging drugs for idiopathic thrombocytopenic purpura in adults. Expert Opin Emerg Drugs. 2008 Jun;13(2):237-54. | |||
| REF 3 | Emerging Insights on the Interaction Between Anticancer and Immunosuppressant Drugs and Intestinal Microbiota in Pediatric Patients. Clin Transl Sci. 2020 Mar;13(2):238-259. | |||
| REF 4 | Mapping human microbiome drug metabolism by gut bacteria and their genes. Nature. 2019 Jun;570(7762):462-467. | |||
| REF 5 | Pharmacomicrobiomics: the impact of human microbiome variations on systems pharmacology and personalized therapeutics. OMICS. 2014 Jul;18(7):402-14. | |||
| REF 6 | Drug pharmacomicrobiomics and toxicomicrobiomics: from scattered reports to systematic studies of drug-microbiome interactions. Expert Opin Drug Metab Toxicol. 2018 Oct;14(10):1043-1055. | |||
| REF 7 | Effects of cyclophosphamide on immune system and gut microbiota in mice. Microbiol Res. 2015 Feb;171:97-106. | |||
| REF 8 | The changes induced by cyclophosphamide in intestinal barrier and microflora in mice. Eur J Pharmacol. 2013 Aug 15;714(1-3):120-4. | |||
| REF 9 | The intestinal microbiota modulates the anticancer immune effects of cyclophosphamide. Science. 2013 Nov 22;342(6161):971-6. | |||
| REF 10 | Dietary squid ink polysaccharides ameliorated the intestinal microflora dysfunction in mice undergoing chemotherapy. Food Funct. 2014 Oct;5(10):2529-35. | |||
| REF 11 | O6-methylguanine-DNA methyltransferase activity and sensitivity to cyclophosphamide and cisplatin in human lung tumor xenografts. Int J Cancer. 1998 Sep 11;77(6):919-22. | |||
| REF 12 | Cytotoxicity, DNA cross-linking, and single strand breaks induced by activated cyclophosphamide and acrolein in human leukemia cells. Cancer Res. 1986 Oct;46(10):5029-34. | |||
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