U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS
This repository is under review for potential modification in compliance with Administration directives.

Details

Stereochemistry ABSOLUTE
Molecular Formula C52H74Cl2O18
Molecular Weight 1058.039
Optical Activity UNSPECIFIED
Defined Stereocenters 14 / 14
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of FIDAXOMICIN

SMILES

CC[C@H]1\C=C(C)\[C@@H](O)C\C=C\C=C(CO[C@@H]2O[C@H](C)[C@@H](OC(=O)C3=C(O)C(Cl)=C(O)C(Cl)=C3CC)[C@H](O)[C@@H]2OC)\C(=O)O[C@@H](C\C=C(C)\C=C(C)\[C@@H]1O[C@@H]4OC(C)(C)[C@@H](OC(=O)C(C)C)[C@H](O)[C@@H]4O)[C@@H](C)O

InChI

InChIKey=ZVGNESXIJDCBKN-UUEYKCAUSA-N
InChI=1S/C52H74Cl2O18/c1-13-30-22-26(6)33(56)18-16-15-17-31(23-66-51-45(65-12)42(61)44(29(9)67-51)69-49(64)35-32(14-2)36(53)39(58)37(54)38(35)57)48(63)68-34(28(8)55)20-19-25(5)21-27(7)43(30)70-50-41(60)40(59)46(52(10,11)72-50)71-47(62)24(3)4/h15-17,19,21-22,24,28-30,33-34,40-46,50-51,55-61H,13-14,18,20,23H2,1-12H3/b16-15+,25-19+,26-22+,27-21+,31-17+/t28-,29-,30+,33+,34+,40-,41+,42+,43+,44-,45+,46+,50-,51-/m1/s1

HIDE SMILES / InChI

Description

Fidaxomicin (trade names Dificid, Dificlir in Europe) is the first in a new class of narrow spectrum macrocyclic antibiotic drugs indicated for treatment of Clostridium difficile-associated diarrhea. Lipiarmycin (fidaxomicin), a metabolite of Actinoplanes deccanensis nov. sp. was first isolated in pure form in 1970s and was considered as antibiotic from its chemical and physico-chemical characteristics. It demonstrated high activity against Gram-positive bacteria, including strains resistant to the medically important antibiotics and protected mice experimentally infected with Streptococcus haemolyticus. Fidaxomicin is non-systemic, meaning it is minimally absorbed into the bloodstream, it is bactericidal, and it has demonstrated selective eradication of pathogenic Clostridium difficile with minimal disruption to the multiple species of bacteria that make up the normal, healthy intestinal flora. Although the exact mechanism of action has yet to be fully elucidated, fidaxomicin may bind to and inhibit bacterial DNA-dependent RNA polymerase, thereby inhibiting the initiation of bacterial RNA synthesis. When orally administered, this agent is minimally absorbed into the systemic circulation, acting locally in the gastrointestinal tract. Fidaxomicin appears to be active against pathogenic Gram-positive bacteria, such as clostridia, enterococci, and staphylococci, but does not appear to be active against other beneficial intestinal bacteria. The maintenance of normal physiological conditions in the colon can reduce the probability of Clostridium difficile infection recurrence. It is marketed by Cubist Pharmaceuticals after acquisition of its originating company Optimer Pharmaceuticals.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
DIFICID

Cmax

ValueDoseCo-administeredAnalytePopulation
5.2 ng/mL
200 mg single, oral
FIDAXOMICIN plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
62.9 ng × h/mL
200 mg single, oral
FIDAXOMICIN plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
11.7 h
200 mg single, oral
FIDAXOMICIN plasma
Homo sapiens

Doses

AEs

Drug as perpetrator​

Drug as victim

Tox targets

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
One 200 mg tablet orally twice daily for 10 days with or without food
Route of Administration: Oral
In Vitro Use Guide
In in vitro susceptibility test developed for fidaxomicin so that laboratories determining the susceptibility of C. difficile isolates to fidaxomicin can ascertain whether the susceptibility test is performing correctly the MICs were 0.03–0.25 ug/ml for C. difficile (ATCC 700057)