Fidaxomicin

Molecular Formula

C52H74Cl2O18

M.W.

1 058.00

CAS number

873857-62-6

MSDS

Download

Details

Source

Dactylosporangium aurantiacum (An Actinobecterium)

Fermentek product Code

FID-001

Brand/grade

For research

Specifications

Appearance

White to Off-White powder

Purity by HPLC

≥98% ; refer to CoA for more data

Purity By TLC

≥98% ; refer to CoA for more data

Melting point

160°C-170°C

Solubility test

Clear colorless to faint yellow solution at 1mg/ml of DMSO;
Clear colorless to faint yellow solution at 5 mg/ml of Methanol

Chemical identification

Names and identifiers

Synonyms:

Dificid,
Dificlir,
Clostomicin B1,
lipiarmicin,
lipiarmycin,
lipiarmycin A3,
tiacumicin B

Chemical names:

IUPAC: [(2R,3S,4S,5S,6R)-6-[[(3E,5E,8S,9E,11S,12R,13E,15E,18S)-12-[(2R,3S,4R,5S)-3,4-dihydroxy-6,6-dimethyl-5-(2-methylpropanoyloxy)oxan-2-yl]oxy-11-ethyl-8-hydroxy-18-[(1R)-1-hydroxyethyl]-9,13,15-trimethyl-2-oxo-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

RTECS# Not available

EU number

692-555-6

Chemical name

Fidaxomicin

Description

Fidaxomicin is a narrow spectrum macrocyclic antibiotic, sourced from actinomycete Dactylosporangium aurantiacum. Fidaxomicin is non-systemic, meaning it is minimally absorbed into the bloodstream. This anti-bacterial agent selectively acts against pathogenic Clostridium difficile bacteria which may infect the colon, while causing minimal damage to the natural intestinal microbial flora.

InChl Key

ZVGNESXIJDCBKN-UUEYKCAUSA-N

Canonical SMILES

CCC1C=C(C(CC=CC=C(C(=O)OC(CC=C(C=C(C1OC2C(C(C(C(O2)(C)C)OC(=O)C(C)C)O)O)C)C)C(C)O)COC3C(C(C(C(O3)C)OC(=O)C4=C(C(=C(C(=C4O)Cl)O)Cl)CC)O)OC)O)C

Isomeric SMILES

CC[C@H]1/C=C(/[C@H](C/C=C/C=C(/C(=O)O[C@@H](C/C=C(/C=C(/[C@@H]1O[C@H]2[C@H]([C@H]([C@@H](C(O2)(C)C)OC(=O)C(C)C)O)O)\C)\C)[C@@H](C)O)\CO[C@H]3[C@H]([C@H]([C@@H]([C@H](O3)C)OC(=O)C4=C(C(=C(C(=C4O)Cl)O)Cl)CC)O)OC)O)\C

Further Information

Solubility ( literature )

Reportedly, Fidaxomicin is soluble in CHCl3(10 mg/ml), methanol(10 mg/ml), DMSO(1mg/ml); poor water solubility.

Compound Classification

UNSPSC: