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Details

Stereochemistry ABSOLUTE
Molecular Formula C37H47NO12
Molecular Weight 697.7686
Optical Activity UNSPECIFIED
Defined Stereocenters 9 / 9
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of RIFAMYCIN

SMILES

CO[C@H]1\C=C\O[C@@]2(C)OC3=C(C2=O)C4=C(O)C=C(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)C(O)=C4C(O)=C3C

InChI

InChIKey=HJYYPODYNSCCOU-ODRIEIDWSA-N
InChI=1S/C37H47NO12/c1-16-11-10-12-17(2)36(46)38-23-15-24(40)26-27(32(23)44)31(43)21(6)34-28(26)35(45)37(8,50-34)48-14-13-25(47-9)18(3)33(49-22(7)39)20(5)30(42)19(4)29(16)41/h10-16,18-20,25,29-30,33,40-44H,1-9H3,(H,38,46)/b11-10+,14-13+,17-12-/t16-,18+,19+,20+,25-,29-,30+,33+,37-/m0/s1

HIDE SMILES / InChI
Molecular Formula C37H47NO12
Molecular Weight 697.7686
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 9 / 9
E/Z Centers 0
Optical Activity UNSPECIFIED

Approval Year

Unknown
86413
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:02:07 UTC 2023
Edited
by admin
on Fri Dec 15 15:02:07 UTC 2023
Record UNII
DU69T8ZZPA
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
RIFAMYCIN
INN   USAN   WHO-DD  
USAN   INN  
Official Name English
RIFAMYCIN SV [EP IMPURITY]
Common Name English
Rifamycin [WHO-DD]
Common Name English
M-14
Code English
RIFAMYCIN SV
MI  
Common Name English
RIFAMICINE SV
Common Name English
5,6,9,17,19,21-HEXAHYDROXY-23-METHOXY-2,4,12,16,18,20,22-HEPTAMETHYL-2,7-(EPOXYPENTADECA(1,11,13)TRIENIMINO)NAPHTHO(2,1-B)FURAN-1,11(2H)-DIONE 21-ACETATE
Common Name English
RIFAMYCIN [USAN]
Common Name English
RIFAMYCIN SV, AN ANTIBIOTIC PRODUCED BY CERTAIN STRAINS OF STREPTOMYCES MEDITERRANEI, OR THE SAME SUBSTANCE PRODUCED BY ANY OTHER MEANS
Common Name English
rifamycin [INN]
Common Name English
RIFAMYCIN SV [MI]
Common Name English
RIFOMYCIN SV
Common Name English
RIFAXIMIN IMPURITY C [EP IMPURITY]
Common Name English
Classification Tree Code System Code
WHO-VATC QJ04AB03
Created by admin on Fri Dec 15 15:02:07 UTC 2023 , Edited by admin on Fri Dec 15 15:02:07 UTC 2023
WHO-ATC S01AA16
Created by admin on Fri Dec 15 15:02:07 UTC 2023 , Edited by admin on Fri Dec 15 15:02:07 UTC 2023
WHO-VATC QJ54AB03
Created by admin on Fri Dec 15 15:02:07 UTC 2023 , Edited by admin on Fri Dec 15 15:02:07 UTC 2023
WHO-ATC J04AB03
Created by admin on Fri Dec 15 15:02:07 UTC 2023 , Edited by admin on Fri Dec 15 15:02:07 UTC 2023
NCI_THESAURUS C280
Created by admin on Fri Dec 15 15:02:07 UTC 2023 , Edited by admin on Fri Dec 15 15:02:07 UTC 2023
WHO-ATC S02AA12
Created by admin on Fri Dec 15 15:02:07 UTC 2023 , Edited by admin on Fri Dec 15 15:02:07 UTC 2023
FDA ORPHAN DRUG 853821
Created by admin on Fri Dec 15 15:02:07 UTC 2023 , Edited by admin on Fri Dec 15 15:02:07 UTC 2023
WHO-VATC QS01AA16
Created by admin on Fri Dec 15 15:02:07 UTC 2023 , Edited by admin on Fri Dec 15 15:02:07 UTC 2023
WHO-VATC QS02AA12
Created by admin on Fri Dec 15 15:02:07 UTC 2023 , Edited by admin on Fri Dec 15 15:02:07 UTC 2023
Code System Code Type Description
CHEBI
26580
Created by admin on Fri Dec 15 15:02:07 UTC 2023 , Edited by admin on Fri Dec 15 15:02:07 UTC 2023
PRIMARY
SMS_ID
100000080581
Created by admin on Fri Dec 15 15:02:07 UTC 2023 , Edited by admin on Fri Dec 15 15:02:07 UTC 2023
PRIMARY
EVMPD
SUB10310MIG
Created by admin on Fri Dec 15 15:02:07 UTC 2023 , Edited by admin on Fri Dec 15 15:02:07 UTC 2023
PRIMARY
WIKIPEDIA
Rifamycin
Created by admin on Fri Dec 15 15:02:07 UTC 2023 , Edited by admin on Fri Dec 15 15:02:07 UTC 2023
PRIMARY
NCI_THESAURUS
C29406
Created by admin on Fri Dec 15 15:02:07 UTC 2023 , Edited by admin on Fri Dec 15 15:02:07 UTC 2023
PRIMARY
DRUG CENTRAL
4817
Created by admin on Fri Dec 15 15:02:07 UTC 2023 , Edited by admin on Fri Dec 15 15:02:07 UTC 2023
PRIMARY
DRUG BANK
DB11753
Created by admin on Fri Dec 15 15:02:07 UTC 2023 , Edited by admin on Fri Dec 15 15:02:07 UTC 2023
PRIMARY
CHEBI
29673
Created by admin on Fri Dec 15 15:02:07 UTC 2023 , Edited by admin on Fri Dec 15 15:02:07 UTC 2023
PRIMARY
DAILYMED
DU69T8ZZPA
Created by admin on Fri Dec 15 15:02:07 UTC 2023 , Edited by admin on Fri Dec 15 15:02:07 UTC 2023
PRIMARY
MESH
C023808
Created by admin on Fri Dec 15 15:02:07 UTC 2023 , Edited by admin on Fri Dec 15 15:02:07 UTC 2023
PRIMARY
ECHA (EC/EINECS)
230-273-3
Created by admin on Fri Dec 15 15:02:07 UTC 2023 , Edited by admin on Fri Dec 15 15:02:07 UTC 2023
PRIMARY
CHEBI
84571
Created by admin on Fri Dec 15 15:02:07 UTC 2023 , Edited by admin on Fri Dec 15 15:02:07 UTC 2023
PRIMARY
EPA CompTox
DTXSID1032014
Created by admin on Fri Dec 15 15:02:07 UTC 2023 , Edited by admin on Fri Dec 15 15:02:07 UTC 2023
PRIMARY
USAN
XX-60
Created by admin on Fri Dec 15 15:02:07 UTC 2023 , Edited by admin on Fri Dec 15 15:02:07 UTC 2023
PRIMARY
RXCUI
35616
Created by admin on Fri Dec 15 15:02:07 UTC 2023 , Edited by admin on Fri Dec 15 15:02:07 UTC 2023
PRIMARY RxNorm
MERCK INDEX
m9613
Created by admin on Fri Dec 15 15:02:07 UTC 2023 , Edited by admin on Fri Dec 15 15:02:07 UTC 2023
PRIMARY Merck Index
PUBCHEM
6324616
Created by admin on Fri Dec 15 15:02:07 UTC 2023 , Edited by admin on Fri Dec 15 15:02:07 UTC 2023
PRIMARY
CAS
6998-60-3
Created by admin on Fri Dec 15 15:02:07 UTC 2023 , Edited by admin on Fri Dec 15 15:02:07 UTC 2023
PRIMARY
LACTMED
Rifamycin
Created by admin on Fri Dec 15 15:02:07 UTC 2023 , Edited by admin on Fri Dec 15 15:02:07 UTC 2023
PRIMARY
FDA UNII
DU69T8ZZPA
Created by admin on Fri Dec 15 15:02:07 UTC 2023 , Edited by admin on Fri Dec 15 15:02:07 UTC 2023
PRIMARY
ChEMBL
CHEMBL437765
Created by admin on Fri Dec 15 15:02:07 UTC 2023 , Edited by admin on Fri Dec 15 15:02:07 UTC 2023
PRIMARY
INN
2293
Created by admin on Fri Dec 15 15:02:07 UTC 2023 , Edited by admin on Fri Dec 15 15:02:07 UTC 2023
PRIMARY
Related Record Type Details
OAT-3
TRANSPORTER -> INHIBITOR
Rifamycin is an inhibitor of renal transporters organic anion transporter (OAT) 3, multidrug and toxin extrusion (MATE) 1, and MATE2-K transporters in vitro, however, based on systemic concentrations of rifamycin observed after administration of the recommended dose, clinically relevant inhibition of these transporters in vivo is unlikely.
SOLUTE CARRIER FAMILY 21 MEMBER 3
TRANSPORTER -> INHIBITOR
CYTOCHROME P450 3A4
METABOLIC ENZYME -> INDUCER
Rifamycin is an inducer of CYP3A4 and CYP2B6 but not CYP1A2 in vitro, however, based on systemic concentrations of rifamycin observed after administration of the recommended dose, clinically relevant induction of these enzymes in vivo is unlikely.
STAPHYLOCOCCUS AUREUS
TARGET ORGANISM->INHIBITOR
METHICILLIN-RESISTANT STAPHYLOCOCCUS AUREUS
TARGET ORGANISM->INHIBITOR
Structure of RIFALAZIL
DERIVATIVE -> PARENT
CYTOCHROME P450 2C9
METABOLIC ENZYME -> INHIBITOR
Rifamycin is an inhibitor of CYP1A2, 2B6, 2C8, 2C9, 2C19, 2D6 and 3A4/5 in vitro, however, based on systemic concentrations of rifamycin observed after administration of the recommended dose clinically relevant inhibition of these enzymes in vivo is unlikely.
CYTOCHROME P450 2C8
METABOLIC ENZYME -> INHIBITOR
Rifamycin is an inhibitor of CYP1A2, 2B6, 2C8, 2C9, 2C19, 2D6 and 3A4/5 in vitro, however, based on systemic concentrations of rifamycin observed after administration of the recommended dose clinically relevant inhibition of these enzymes in vivo is unlikely.
ESCHERICHIA COLI
TARGET ORGANISM->INHIBITOR
Other
CYTOCHROME P450 2B6
METABOLIC ENZYME -> INDUCER
Rifamycin is an inducer of CYP3A4 and CYP2B6 but not CYP1A2 in vitro, however, based on systemic concentrations of rifamycin observed after administration of the recommended dose, clinically relevant induction of these enzymes in vivo is unlikely.
OATP-B
TRANSPORTER -> INHIBITOR
MULTIDRUG AND TOXIN EXTRUSION PROTEIN 1
TRANSPORTER -> INHIBITOR
Rifamycin is an inhibitor of renal transporters organic anion transporter (OAT) 3, multidrug and toxin extrusion (MATE) 1, and MATE2-K transporters in vitro, however, based on systemic concentrations of rifamycin observed after administration of the recommended dose, clinically relevant inhibition of these transporters in vivo is unlikely.
MULTIDRUG RESISTANCE PROTEIN 1
TRANSPORTER -> INHIBITOR
IC50
MYCOBACTERIUM TUBERCULOSIS
TARGET ORGANISM->INHIBITOR
CYTOCHROME P450 2B6
METABOLIC ENZYME -> INHIBITOR
Rifamycin is an inhibitor of CYP1A2, 2B6, 2C8, 2C9, 2C19, 2D6 and 3A4/5 in vitro, however, based on systemic concentrations of rifamycin observed after administration of the recommended dose clinically relevant inhibition of these enzymes in vivo is unlikely.
MULTIDRUG RESISTANCE PROTEIN 1
TRANSPORTER -> SUBSTRATE
Structure of RIFAMYCIN
EXCRETED UNCHANGED
After IV administration of rifamycin SV, > 90% of the dose is excreted as unchanged drug in feces via biliary secretion8
FECAL
Structure of RIFAMYCIN SODIUM
SALT/SOLVATE -> PARENT
ATP-BINDING CASSETTE SUB-FAMILY G MEMBER 2
TRANSPORTER -> INHIBITOR
IC50
CYTOCHROME P450 2D6
METABOLIC ENZYME -> INHIBITOR
Rifamycin is an inhibitor of CYP1A2, 2B6, 2C8, 2C9, 2C19, 2D6 and 3A4/5 in vitro, however, based on systemic concentrations of rifamycin observed after administration of the recommended dose clinically relevant inhibition of these enzymes in vivo is unlikely.
CYTOCHROME P450 3A4
METABOLIC ENZYME -> NON-SUBSTRATE
OATP-8
TRANSPORTER -> INHIBITOR
MATE-2
TRANSPORTER -> INHIBITOR
Rifamycin is an inhibitor of renal transporters organic anion transporter (OAT) 3, multidrug and toxin extrusion (MATE) 1, and MATE2-K transporters in vitro, however, based on systemic concentrations of rifamycin observed after administration of the recommended dose, clinically relevant inhibition of these transporters in vivo is unlikely.
CYTOCHROME P450 2C19
METABOLIC ENZYME -> INHIBITOR
Rifamycin is an inhibitor of CYP1A2, 2B6, 2C8, 2C9, 2C19, 2D6 and 3A4/5 in vitro, however, based on systemic concentrations of rifamycin observed after administration of the recommended dose clinically relevant inhibition of these enzymes in vivo is unlikely.
CYTOCHROME P450 3A4
METABOLIC ENZYME -> INHIBITOR
Rifamycin is an inhibitor of CYP1A2, 2B6, 2C8, 2C9, 2C19, 2D6 and 3A4/5 in vitro, however, based on systemic concentrations of rifamycin observed after administration of the recommended dose clinically relevant inhibition of these enzymes in vivo is unlikely.
CYTOCHROME P450 1A2
METABOLIC ENZYME -> INHIBITOR
Rifamycin is an inhibitor of CYP1A2, 2B6, 2C8, 2C9, 2C19, 2D6 and 3A4/5 in vitro, however, based on systemic concentrations of rifamycin observed after administration of the recommended dose clinically relevant inhibition of these enzymes in vivo is unlikely.
Related Record Type Details
Structure of RIFAXIMIN
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of RIFAMYCIN S
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
Structure of RIFAMYCIN
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