Fidaxomicin Metabolite OP-1118

A summary of the most common chemical descriptors (InChI Key and SMILES codes) for Fidaxomicin Metabolite OP-1118 are summarized together with 3D and 2D structures and relevant physico-chemical properties.

What is the Fidaxomicin Metabolite OP-1118?

The molecule Fidaxomicin Metabolite OP-1118 presents a molecular formula of C48H68Cl2O17 and its IUPAC name is [(2R,3S,4S,5S,6R)-6-[[(3E,5E,8S,9E,11S,12R,13E,15E,18S)-11-ethyl-8-hydroxy-18-[(1R)-1-hydroxyethyl]-9,13,15-trimethyl-2-oxo-12-[(2R,3S,4S,5S)-3,4,5-trihydroxy-6,6-dimethyloxan-2-yl]oxy-1-oxacyclooctadeca-3,5,9,13,15-pentaen-3-yl]methoxy]-4-hydroxy-5-methoxy-2-methyloxan-3-yl] 3,5-dichloro-2-ethyl-4,6-dihydroxybenzoate.

Fidaxomicin (trade name Dificid) is an antibiotic used to treat certain infections caused by bacteria. It is a narrow-spectrum antibiotic that is a macrocyclic lactone derivative of rifamycin B. Fidaxomicin was approved for use in the United States in 2011, and in the European Union in 2012..

The main metabolite of fidaxomicin is OP-1118. OP-1118 is produced by the action of enzymes in the gut flora on fidaxomicin. OP-1118 is then absorbed and metabolized by the liver. The main route of elimination of OP-1118 is through the bile..

OP-1118 has bactericidal activity against a variety of Gram-positive bacteria, including Clostridium difficile, Staphylococcus aureus, and Streptococcus pneumoniae. The minimum inhibitory concentration (MIC) of OP-1118 against C. difficile is 0.015-0.03 μg/ml. The MIC of OP-1118 against S. aureus is 0.12 μg/ml. The MIC of OP-1118 against S. pneumoniae is 0.25 μg/ml..

The efficacy of OP-1118 against C. difficile has been demonstrated in animal models of infection. OP-1118 was also effective in a Phase II clinical trial in humans with C. difficile infection. The most common side effects of OP-1118 in humans are nausea and vomiting..

OP-1118 has the potential to be used as an alternative to existing antibiotics for the treatment of a variety of Gram-positive infections..

3D structure

Cartesian coordinates

Geometry of Fidaxomicin Metabolite OP-1118 in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

 

Fidaxomicin Metabolite OP-1118 MWZWKUKATWMWGS-KJJILEKPSA-N chemical compound 2D structure molecule svg
Fidaxomicin Metabolite OP-1118

 

Molecule descriptors

 
IUPAC name[(2R,3S,4S,5S,6R)-6-[[(3E,5E,8S,9E,11S,12R,13E,15E,18S)-11-ethyl-8-hydroxy-18-[(1R)-1-hydroxyethyl]-9,13,15-trimethyl-2-oxo-12-[(2R,3S,4S,5S)-3,4,5-trihydroxy-6,6-dimethyloxan-2-yl]oxy-1-oxacyclooctadeca-3,5,9,13,15-pentaen-3-yl]methoxy]-4-hydroxy-5-methoxy-2-methyloxan-3-yl] 3,5-dichloro-2-ethyl-4,6-dihydroxybenzoate
InChI codeInChI=1S/C48H68Cl2O17/c1-11-27-20-23(4)30(52)16-14-13-15-28(21-62-47-42(61-10)39(57)41(26(7)63-47)65-45(60)32-29(12-2)33(49)36(54)34(50)35(32)53)44(59)64-31(25(6)51)18-17-22(3)19-24(5)40(27)66-46-38(56)37(55)43(58)48(8,9)67-46/h13-15,17,19-20,25-27,30-31,37-43,46-47,51-58H,11-12,16,18,21H2,1-10H3/b14-13+,22-17+,23-20+,24-19+,28-15+/t25-,26-,27+,30+,31+,37-,38+,39+,40+,41-,42+,43+,46-,47-/m1/s1
InChI KeyMWZWKUKATWMWGS-KJJILEKPSA-N
SMILESCCc1c(Cl)c(O)c(Cl)c(O)c1C(=O)O[C@H]1[C@H](O)[C@H](OC)[C@H](OC/C2=C\C=C\C[C@H](O)/C(C)=C/[C@H](CC)[C@@H](O[C@@H]3OC(C)(C)[C@@H](O)[C@H](O)[C@@H]3O)/C(C)=C/C(C)=C/C[C@@H]([C@@H](C)O)OC2=O)O[C@@H]1C

Other names (synonyms)

IUPAC nomenclature provides a standardized method for naming chemical compounds. Although this system is widely used in chemistry, many chemical compounds have also other names commonly used in different contexts. These synonyms can come from a variety of sources and are used for a variety of purposes.

One common source of synonyms for chemical compounds is the common or trivial names, assigned on the basis of appearance, properties, or origin of the molecule.

Another source of synonyms are historical or obsolete names employed in the past, however replaced nowadays by more modern or standardized names.

In addition to common and historical names, chemical compounds may also have synonyms that are specific to a particular field or industry.

  • 1030825-28-5
  • Fidaxomicin Metabolite OP-1118
  • OP-1118
  • [(2R,3S,4S,5S,6R)-6-[[(3E,5E,8S,9E,11S,12R,13E,15E,18S)-11-ethyl-8-hydroxy-18-[(1R)-1-hydroxyethyl]-9,13,15-trimethyl-2-oxo-12-[(2R,3S,4S,5S)-3,4,5-trihydroxy-6,6-dimethyloxan-2-yl]oxy-1-oxacyclooctadeca-3,5,9,13,15-pentaen-3-yl]methoxy]-4-hydroxy-5-methoxy-2-methyloxan-3-yl] 3,5-dichloro-2-ethyl-4,6-dihydroxybenzoate

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • CHEMBL1631108
  • SCHEMBL10029729

Physico-Chemical properties

IUPAC name[(2R,3S,4S,5S,6R)-6-[[(3E,5E,8S,9E,11S,12R,13E,15E,18S)-11-ethyl-8-hydroxy-18-[(1R)-1-hydroxyethyl]-9,13,15-trimethyl-2-oxo-12-[(2R,3S,4S,5S)-3,4,5-trihydroxy-6,6-dimethyloxan-2-yl]oxy-1-oxacyclooctadeca-3,5,9,13,15-pentaen-3-yl]methoxy]-4-hydroxy-5-methoxy-2-methyloxan-3-yl] 3,5-dichloro-2-ethyl-4,6-dihydroxybenzoate
Molecular formulaC48H68Cl2O17
Molecular weight987.949
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity249.23
LogP5.0
Topological polar surface area260.6

LogP and topological polar surface area (TPSA) values were estimated using Open Babel software.

The n-octanol/water partition coeficient (Kow) data is applied in toxicology and drug research. Kow values are used, to guess the environmental fate of persistent organic pollutants. High partition coefficients values, tend to accumulate in the fatty tissue of organisms. Molecules with a log(Kow) (or LogP) greater than 5 are considered to bioaccumulate.

TPSA values are the sum of the surface area over all polar atoms or molecules, mainly oxygen and nitrogen, also including hydrogen atoms.

In medicinal chemistry, TPSA is used to assess the ability of a drug to permeabilise cells.

For molecules to penetrate the blood-brain barrier (and act on receptors in the central nervous system), TPSA values below 90 Å2 are required. Thus, molecules with a polar surface area greater than 140 Å2 tend to be poorly permeable to cell membranes.