Rifaximin

Basic Info

Common NameRifaximin(F05945)
2D Structure
FRCD IDF05945
CAS Number
PubChem CID6436173
FormulaC43H51N3O11
IUPAC Name

None

InChI Key

NZCRJKRKKOLAOJ-XRCRFVBUSA-N

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

Canonical SMILES

CC1C=CC=C(C(=O)NC2=C(C3=C(C4=C(C(=C3O)C)OC(C4=O)(OC=CC(C(C(C(C(C(C1O)C)O)C)OC(=O)C)C)OC)C)C5=C2N6C=CC(=CC6=N5)C)O)C

Isomeric 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

Synonyms
        
            Rifaximine
        
            Rifaximin
        
            Rifaxidin
        
            Rifacol
        
            Xifaxan
        
            Rifamycin L 105
        
            Rifamycin L 105SV
        
            Fatroximin
        
            Rifaximina
        
            Normix
Classifies
                

                  
                    Predicted: Plant Toxin
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassPhenylpropanoids and polyketides
ClassMacrolactams
SubclassNot available
Intermediate Tree NodesNot available
Direct ParentMacrolactams
Alternative Parents
Molecular FrameworkAromatic heteropolycyclic compounds
SubstituentsMacrolactam - Naphthofuran - 1-naphthol - Naphthalene - Benzimidazole - Benzofuran - Coumaran - Imidazo[1,2-a]pyridine - Aryl alkyl ketone - Aryl ketone - Methylpyridine - Ketal - Pyridine - N-substituted imidazole - Benzenoid - Azole - Heteroaromatic compound - Imidazole - Secondary alcohol - Secondary carboxylic acid amide - Lactam - Ketone - Carboxylic acid ester - Carboxamide group - Acetal - Carboxylic acid derivative - Dialkyl ether - Ether - Oxacycle - Azacycle - Organoheterocyclic compound - Polyol - Monocarboxylic acid or derivatives - Hydrocarbon derivative - Organic nitrogen compound - Organic oxygen compound - Organopnictogen compound - Carbonyl group - Organic oxide - Alcohol - Organooxygen compound - Organonitrogen compound - Aromatic heteropolycyclic compound
DescriptionThis compound belongs to the class of organic compounds known as macrolactams. These are cyclic amides of amino carboxylic acids, having a 1-azacycloalkan-2-one structure, or analogues having unsaturation or heteroatoms replacing one or more carbon atoms of the ring. They are nitrogen analogues (the a nitrogen atom replacing the o atom of the cyclic carboxylic acid group ) of the naturally occurring macrolides.

Properties

Property NameProperty Value
Molecular Weight785.891
Hydrogen Bond Donor Count5
Hydrogen Bond Acceptor Count12
Rotatable Bond Count3
Complexity1590
Monoisotopic Mass785.352
Exact Mass785.352
XLogP6.9
Formal Charge0
Heavy Atom Count57
Defined Atom Stereocenter Count9
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count3
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

ADMET

Model Result Probability
Absorption
Blood-Brain BarrierBBB-0.9730
Human Intestinal AbsorptionHIA-0.6460
Caco-2 PermeabilityCaco2-0.6301
P-glycoprotein SubstrateSubstrate0.6681
P-glycoprotein InhibitorNon-inhibitor0.6985
Non-inhibitor0.7134
Renal Organic Cation TransporterNon-inhibitor0.9533
Distribution
Subcellular localizationMitochondria0.3349
Metabolism
CYP450 2C9 SubstrateNon-substrate0.8256
CYP450 2D6 SubstrateNon-substrate0.8783
CYP450 3A4 SubstrateSubstrate0.5651
CYP450 1A2 InhibitorNon-inhibitor0.7129
CYP450 2C9 InhibitorNon-inhibitor0.7393
CYP450 2D6 InhibitorNon-inhibitor0.8750
CYP450 2C19 InhibitorNon-inhibitor0.7684
CYP450 3A4 InhibitorNon-inhibitor0.8904
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.7729
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9940
Non-inhibitor0.7210
AMES ToxicityNon AMES toxic0.6276
CarcinogensNon-carcinogens0.9055
Fish ToxicityHigh FHMT0.7957
Tetrahymena Pyriformis ToxicityHigh TPT0.9699
Honey Bee ToxicityLow HBT0.6796
BiodegradationNot ready biodegradable1.0000
Acute Oral ToxicityIII0.7720
Carcinogenicity (Three-class)Non-required0.4955
Model Value Unit
Absorption
Aqueous solubility-3.2053LogS
Caco-2 Permeability0.5483LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity2.6259LD50, mol/kg
Fish Toxicity0.9429pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.6366pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
MilkJapan0.06ppm

References

TitleJournalDatePubmed ID
Gut : liver : brain axis: the microbial challenge in the hepatic encephalopathy.Food Funct2018 Mar 129485654
Natural plant products inhibits growth and alters the swarming motility, biofilm formation, and expression of virulence genes in enteroaggregative and enterohemorrhagic Escherichia coli.Food Microbiol2016 Oct27375253
Effect of antibiotics on cellular stress generated in Shiga toxin-producing Escherichia coli O157:H7 and non-O157 biofilms.Toxicol In Vitro2015 Oct26130220
Clostridium difficile colitis: review of the therapeutic approach.Am J Ther2014 Sep-Oct22990077
Challenges and opportunities in the management of Clostridium difficile infection.Expert Rev Gastroenterol Hepatol2014 Nov25012255
The potential for emerging therapeutic options for Clostridium difficile infection.Gut Microbes201425564777
Evolving concepts: the negative effect of minimal hepatic encephalopathy and role for prophylaxis in patients with cirrhosis.Clin Ther2013 Sep23972578
Best strategies in recurrent or persistent Clostridium difficile infection.Surg Infect (Larchmt)2011 Jun21767157
Recurrent Clostridium difficile infection: causality and therapeutic approaches.Int J Antimicrob Agents2009 Mar19303567
Clostridium difficile: controversies and approaches to management.Curr Opin Infect Dis2009 Dec19738464
Treatment of Clostridium difficile infection.Clin Infect Dis2008 Jan 1518177219
Advances in defining etiology and new therapeutic approaches in acute diarrhea.J Infect2007 Nov17825422
Clostridium difficile: recent epidemiologic findings and advances in therapy.Pharmacotherapy2007 Jul17594209
A review of an emerging enteric pathogen: enteroaggregative Escherichia coli.J Med Microbiol2006 Oct17005776