RIFAXIMIN

/static/temp/default.svg

Search structure


Trade Names	XIFAXAN
Synonyms	L-105 NSC-758957 Normix Rifacol Rifamycin l 105 Rifaxidin Rifaximin Targaxan Xifaxan Xifaxanta Xifaxsan
Status
Molecule Category	UNKNOWN
ATC	A07AA11 D06AX11
UNII	L36O5T016N
EPA CompTox	DTXSID7045998


Active Pharmaceutical Ingredients Bioactive chemicals	Exact Similarity SubStructure	Threshold (%) >= 70

Structure


InChI Key	NZCRJKRKKOLAOJ-XRCRFVBUSA-N
Smiles	CO[C@H]1/C=C/O[C@@]2(C)Oc3c(C)c(O)c4c(O)c(c5c(nc6cc(C)ccn65)c4c3C2=O)NC(=O)/C(C)=C\C=C\[C@H](C)[C@H](O)[C@@H](C)[C@@H](O)[C@@H](C)[C@H](OC(C)=O)[C@@H]1C
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

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C43H51N3O11
Molecular Weight	785.89
AlogP	6.16
Hydrogen Bond Acceptor	13.0
Hydrogen Bond Donor	5.0
Number of Rotational Bond	2.0
Polar Surface Area	198.38
Molecular species	ACID
Aromatic Rings	4.0
Heavy Atoms	57.0

Bioactivity

Mechanism of Action	Action	Reference
Bacterial DNA-directed RNA polymerase inhibitor	INHIBITOR	DailyMed

Targets	EC50(nM)	IC50(nM)	Kd(nM)	Ki(nM)	Inhibition(%)
Transcription factor Nuclear receptor Nuclear hormone receptor subfamily 1 Nuclear hormone receptor subfamily 1 group I Nuclear hormone receptor subfamily 1 group I member 2	2200-14100	-	-	-	-
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides	-	-	-	-	63
Transporter Primary active transporter ATP-binding cassette ABCB subfamily	-	42000	-	-	-
Transporter Primary active transporter ATP-binding cassette ABCC subfamily	-	15400	-	-	-

Assay Description	Organism	Bioactivity	Reference
Inhibition of Staphylococcus epidermidis RNA polymerase mediated transcription	Staphylococcus epidermidis	0.07 ug.mL-1
Antimicrobial activity against Escherichia coli H10407 assessed as decrease in cell density at 16 ug/ml after 4 hrs in presence of 4 mM human bile acid	Escherichia coli ETEC H10407	72.8 %
Antimicrobial activity against Escherichia coli H10407 assessed as decrease in cell density at 16 ug/ml after 4 hrs in presence of 4 mM pooled synthetic bile acid	Escherichia coli ETEC H10407	70.6 %
Antimicrobial activity against Escherichia coli H10407 assessed as decrease in cell density at 16 ug/ml after 4 hrs in presence of 4 mM cholic acid	Escherichia coli ETEC H10407	95.5 %
Antimicrobial activity against Escherichia coli H10407 assessed as decrease in cell density at 16 ug/ml after 4 hrs in presence of 4 mM deoxycholic acid	Escherichia coli ETEC H10407	93.8 %
Antimicrobial activity against Escherichia coli H10407 assessed as decrease in cell density at 16 ug/ml after 4 hrs in presence of 4 mM chenodeoxycholic acid	Escherichia coli ETEC H10407	89.2 %
Antimicrobial activity against Escherichia coli H10407 assessed as decrease in cell density at 16 ug/ml after 4 hrs in presence of 4 mM glycocholic acid	Escherichia coli ETEC H10407	80.8 %
Antimicrobial activity against Escherichia coli H10407 assessed as decrease in cell density at 16 ug/ml after 4 hrs in presence of 4 mM taurocholic acid	Escherichia coli ETEC H10407	77.6 %
Antimicrobial activity against Escherichia coli H10407 assessed as decrease in cell density at 16 ug/ml after 4 hrs in presence of 4 mM lithocholic acid	Escherichia coli ETEC H10407	43.9 %
Inhibition of RNA synthesis in Escherichia coli H10407 assessed as inhibition of beta-galactosidase expression at 8 ug/ml in presence of 4 mM bile acid	Escherichia coli ETEC H10407	33.0 %
Inhibition of RNA synthesis in Escherichia coli H10407 assessed as inhibition of beta-galactosidase expression at 16 ug/ml in presence of 4nM bile acid	Escherichia coli ETEC H10407	49.0 %
Inhibition of RNA synthesis in Escherichia coli H10407 assessed as inhibition of beta-galactosidase expression at 32 ug/ml in presence of 4 mM bile acid	Escherichia coli ETEC H10407	82.0 %
Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM	Cricetulus griseus	63.34 %
Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM	Cricetulus griseus	81.07 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of Caco-2 cells at 10 uM after 48 hours by high content imaging	Homo sapiens	18.26 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	26.02 %		SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	11.89 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	0.11 %		Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	-0.11 %		Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	-0.11 %		Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	0.11 %

Related Entries

Environmental Exposure

Environmental Exposure Map

Countries
Romania

Cross References

Resources	Reference
ChEBI	75246
ChEMBL	CHEMBL1617
DrugBank	DB01220
DrugCentral	2379
FDA SRS	L36O5T016N
KEGG	D02554
PDB	RXM
PharmGKB	PA164752443
PubChem	6436173
SureChEMBL	SCHEMBL124066
ZINC	ZINC000169621200

CONTENTS

PREMIER has received funding from the Innovative Medicines Initiative 2 Joint Undertaking (JU) under grant agreement No 875508. The JU receives support from the EU’s Horizon 2020 research and innovation programme and the European Federation of Pharmaceutical Industries and Associations (EFPIA). The views reflect only the authors’ perspective and the JU is not responsible for any use that may be made of the information this manuscript contains.

Elements of the website have been developed under projects PREMIER and the Biocenter Finland Drug Discovery and Chemical Biology network. CSC-IT is thanked for providing computational resources. Content of the website is provided without guarantee for correctness. Data has been collected and integrated from multiple public sources, for the largest: FDA, HUGO Gene Nomenclature Committee, ChEMBL, IUPHAR/BPS guide to pharmacology, Reactome, UniProt, and Ensembl. Credit is given to Ensembl for collecting species images (provided under public domain licences such as Wikimedia and NHGRI).