Details of the Drug

General Information of Drug (ID: DMW1TV2)

Drug Name
Rifaximin
Synonyms RCIFAX; Rifaximin (bioadhesive/ gastrointestinal extended release); Rifaximin (bioadhesive/ gastrointestinal extended release), Salix Pharmaceuticals
Indication
Disease Entry ICD 11 Status REF
Bacterial infection 1A00-1C4Z Approved [1]
Diarrhea-predominant irritable bowel syndrome DD91.01 Approved [2]
Hepatic encephalopathy DB99.5 Approved [2]
Drug Type
Small molecular drug
Structure
3D MOL is unavailable 2D MOL
#Ro5 Violations (Lipinski): 3 Molecular Weight (mw) 785.9
Logarithm of the Partition Coefficient (xlogp) 6.9
Rotatable Bond Count (rotbonds) 3
Hydrogen Bond Donor Count (hbonddonor) 5
Hydrogen Bond Acceptor Count (hbondacc) 12
ADMET Property
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 4: low solubility and low permeability [3]
Elimination
0.035% of drug is excreted from urine in the unchanged form [3]
Half-life
The concentration or amount of drug in body reduced by one-half in 6 hours [4]
Metabolism
The drug is metabolized via the hepatic []
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 10.9065 micromolar/kg/day [5]
Water Solubility
The ability of drug to dissolve in water is measured as 0.001 mg/mL [3]
Chemical Identifiers
Formula
C43H51N3O11
IUPAC Name
[(7S,9E,11S,12R,13S,14R,15R,16R,17S,18S,19E,21Z)-2,15,17,36-tetrahydroxy-11-methoxy-3,7,12,14,16,18,22,30-octamethyl-6,23-dioxo-8,37-dioxa-24,27,33-triazahexacyclo[23.10.1.14,7.05,35.026,34.027,32]heptatriaconta-1(35),2,4,9,19,21,25(36),26(34),28,30,32-undecaen-13-yl] acetate
Canonical SMILES
C[C@H]1/C=C/C=C(\\C(=O)NC2=C(C3=C(C4=C(C(=C3O)C)O[C@@](C4=O)(O/C=C/[C@@H]([C@H]([C@H]([C@@H]([C@@H]([C@@H]([C@H]1O)C)O)C)OC(=O)C)C)OC)C)C5=C2N6C=CC(=CC6=N5)C)O)/C
InChI
InChI=1S/C43H51N3O11/c1-19-14-16-46-28(18-19)44-32-29-30-37(50)25(7)40-31(29)41(52)43(9,57-40)55-17-15-27(54-10)22(4)39(56-26(8)47)24(6)36(49)23(5)35(48)20(2)12-11-13-21(3)42(53)45-33(34(32)46)38(30)51/h11-18,20,22-24,27,35-36,39,48-51H,1-10H3,(H,45,53)/b12-11+,17-15+,21-13-/t20-,22+,23+,24+,27-,35-,36+,39+,43-/m0/s1
InChIKey
NZCRJKRKKOLAOJ-XRCRFVBUSA-N
Cross-matching ID
PubChem CID
6436173
ChEBI ID
CHEBI:75246
CAS Number
80621-81-4
DrugBank ID
DB01220
TTD ID
D04ITO
VARIDT ID
DR00073
INTEDE ID
DR1422
ACDINA ID
D00593
Combinatorial Drugs (CBD) Click to Jump to the Detailed CBD Information of This Drug
Repurposed Drugs (RPD) Click to Jump to the Detailed RPD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Transporter (DTP)
DTP Name DTP ID UniProt ID MOA REF
P-glycoprotein 1 (ABCB1) DTUGYRD MDR1_HUMAN Substrate [6]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 3A4 (CYP3A4)
Main DME 		DE4LYSA CP3A4_HUMAN Substrate [7]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
ATP-dependent translocase ABCB1 (ABCB1) OTEJROBO MDR1_HUMAN Gene/Protein Processing [8]
Cytochrome P450 3A4 (CYP3A4) OTQGYY83 CP3A4_HUMAN Gene/Protein Processing [8]
Nuclear receptor subfamily 1 group I member 2 (NR1I2) OTC5U0N5 NR1I2_HUMAN Gene/Protein Processing [9]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Disease Different from Rifaximin (Comorbidity)
DDI Drug Name DDI Drug ID Severity Mechanism Comorbidity REF
Midostaurin DMI6E0R Moderate Decreased clearance of Rifaximin due to the transporter inhibition by Midostaurin. Acute myeloid leukaemia [2A60] [10]
Arn-509 DMT81LZ Moderate Accelerated clearance of Rifaximin due to the transporter induction by Arn-509. Acute myeloid leukaemia [2A60] [10]
Gilteritinib DMTI0ZO Moderate Decreased clearance of Rifaximin due to the transporter inhibition by Gilteritinib. Acute myeloid leukaemia [2A60] [11]
Erdafitinib DMI782S Moderate Decreased clearance of Rifaximin due to the transporter inhibition by Erdafitinib. Bladder cancer [2C94] [12]
Tucatinib DMBESUA Moderate Decreased clearance of Rifaximin due to the transporter inhibition by Tucatinib. Breast cancer [2C60-2C6Y] [13]
PF-04449913 DMSB068 Moderate Decreased clearance of Rifaximin due to the transporter inhibition by PF-04449913. Chronic myelomonocytic leukaemia [2A40] [10]
GS-5885 DMSL3DX Moderate Decreased clearance of Rifaximin due to the transporter inhibition by GS-5885. Hepatitis virus infection [1E50-1E51] [14]
Bempedoic acid DM1CI9R Moderate Decreased clearance of Rifaximin due to the transporter inhibition by Bempedoic acid. Hyper-lipoproteinaemia [5C80] [15]
Tolvaptan DMIWFRL Moderate Decreased clearance of Rifaximin due to the transporter inhibition by Tolvaptan. Hypo-osmolality/hyponatraemia [5C72] [11]
Capmatinib DMYCXKL Moderate Decreased clearance of Rifaximin due to the transporter inhibition by Capmatinib. Lung cancer [2C25] [16]
Ibrutinib DMHZCPO Moderate Decreased clearance of Rifaximin due to the transporter inhibition by Ibrutinib. Mature B-cell lymphoma [2A85] [10]
Nilotinib DM7HXWT Moderate Decreased clearance of Rifaximin due to the transporter inhibition by Nilotinib. Myeloproliferative neoplasm [2A20] [17]
Rolapitant DM8XP26 Moderate Decreased clearance of Rifaximin due to the transporter inhibition by Rolapitant. Nausea/vomiting [MD90] [18]
Lonafarnib DMGM2Z6 Moderate Decreased clearance of Rifaximin due to the transporter inhibition by Lonafarnib. Premature ageing appearance [LD2B] [19]
Enzalutamide DMGL19D Moderate Accelerated clearance of Rifaximin due to the transporter induction by Enzalutamide. Prostate cancer [2C82] [20]
Darolutamide DMV7YFT Moderate Decreased clearance of Rifaximin due to the transporter inhibition by Darolutamide. Prostate cancer [2C82] [10]
Fostamatinib DM6AUHV Moderate Decreased clearance of Rifaximin due to the transporter inhibition by Fostamatinib. Thrombocytopenia [3B64] [21]
⏷ Show the Full List of 17 DDI Information of This Drug

Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG
DIG Name DIG ID PubChem CID Functional Classification
Edetate disodium E00186 8759 Complexing agent
Eisenoxyd E00585 56841934 Colorant
Glyceryl palmitostearate E00396 114690 Coating agent; Diluent; Flavoring agent; Gelling agent; Modified-release agent; lubricant
Polyvinyl alcohol E00666 Not Available Coating agent; Emulsion stabilizing agent; Film/Membrane-forming agent
Propylene glycol E00040 1030 Antimicrobial preservative; Humectant; Plasticizing agent; Solvent
Silicon dioxide E00670 Not Available Anticaking agent; Opacifying agent; Viscosity-controlling agent
Talc E00520 16211421 Anticaking agent; Diluent; Glidant; lubricant
Titanium dioxide E00322 26042 Coating agent; Colorant; Opacifying agent
⏷ Show the Full List of 8 Pharmaceutical Excipients of This Drug
Pharmaceutical Formulation
Formulation Name Drug Dosage Dosage Form Route
Rifaximin 550 mg tablet 550 mg Oral Tablet Oral
Rifaximin 200 mg tablet 200 mg Oral Tablet Oral
Jump to Detail Pharmaceutical Formulation Page of This Drug

References

1 ClinicalTrials.gov (NCT01654939) Impact of an Antibiotic (Rifaximin) on Liver Scarring in HIV-Infected Patients With Liver Disease. U.S. National Institutes of Health.
2 Rifaximin FDA Label
3 BDDCS applied to over 900 drugs
4 Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
5 Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
6 Advantageous Solubility-Permeability Interplay When Using Amorphous Solid Dispersion (ASD) Formulation for the BCS Class IV P-gp Substrate Rifaximin: Simultaneous Increase of Both the Solubility and the Permeability. AAPS J. 2017 May;19(3):806-813.
7 Probable interaction between warfarin and rifaximin in a patient treated for small intestine bacterial overgrowth. Ann Pharmacother. 2011 May;45(5):e25.
8 Solomonsterols A and B from Theonella swinhoeiThe first example of C-24 and C-23 sulfated sterols from a marine source endowed with a PXR agonistic activity. J Med Chem. 2011 Jan 13;54(1):401-5.
9 Total synthesis and pharmacological characterization of solomonsterol A, a potent marine pregnane-X-receptor agonist endowed with anti-inflammatory activity. J Med Chem. 2011 Jul 14;54(13):4590-9. doi: 10.1021/jm200241s. Epub 2011 Jun 3.
10 Cerner Multum, Inc. "UK Summary of Product Characteristics.".
11 Cerner Multum, Inc. "Australian Product Information.".
12 Product Information. Balversa (erdafitinib). Janssen Products, LP, Horsham, PA.
13 Product Information. Tukysa (tucatinib). Seattle Genetics Inc, Bothell, WA.
14 Product Information. Harvoni (ledipasvir-sofosbuvir). Gilead Sciences, Foster City, CA.
15 Product Information. Nexletol (bempedoic acid). Esperion Therapeutics, Ann Arbor, MI.
16 Product Information. Tabrecta (capmatinib). Novartis Pharmaceuticals, East Hanover, NJ.
17 Product Information. Tasigna (nilotinib). Novartis Pharmaceuticals, East Hanover, NJ.
18 Product Information. Varubi (rolapitant). Tesaro Inc., Waltham, MA.
19 Product Information. Zokinvy (lonafarnib). Eiger BioPharmaceuticals, Palo Alto, CA.
20 Benoist G, van Oort I, et al "Drug-drug interaction potential in men treated with enzalutamide: Mind the gap." Br J Clin Pharmacol 0 (2017): epub. [PMID: 28881501]
21 Product Information. Tavalisse (fostamatinib). Rigel Pharmaceuticals, South San Francisco, CA.