CAS 873857-62-6

Fidaxomicin

Description:

Fidaxomicin is a macrolide antibiotic primarily used for the treatment of Clostridium difficile infections. It is characterized by its unique mechanism of action, which involves inhibiting bacterial RNA polymerase, thereby preventing bacterial protein synthesis. This selective inhibition allows fidaxomicin to effectively target C. difficile while sparing the normal gut flora, which is crucial for maintaining intestinal health. The compound is poorly absorbed systemically, leading to high concentrations in the gastrointestinal tract, which enhances its efficacy against intestinal infections. Fidaxomicin is typically administered orally and is known for its favorable safety profile, with fewer gastrointestinal side effects compared to other antibiotics. Its chemical structure features a complex macrocyclic lactone ring, contributing to its antibacterial properties. The drug is often preferred in cases of recurrent C. difficile infections due to its ability to reduce recurrence rates. Overall, fidaxomicin represents a significant advancement in the treatment of antibiotic-associated diarrhea caused by C. difficile, offering a targeted approach with minimal disruption to the gut microbiome.

Formula: C₅₂H₇₄Cl₂O₁₈

InChI: 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

InChI key: InChIKey=ZVGNESXIJDCBKN-UUEYKCAUSA-N

SMILES: C(O[C@H]1[C@H](O)[C@H](OC)[C@H](OC\C=2\C(=O)O[C@]([C@@H](C)O)(C/C=C(\C)/C=C(\C)/[C@H](O[C@H]3[C@@H](O)[C@@H](O)[C@H](OC(C(C)C)=O)C(C)(C)O3)[C@@H](CC)/C=C(\C)/[C@@H](O)C\C=C\C2)[H])O[C@@H]1C)(=O)C4=C(CC)C(Cl)=C(O)C(Cl)=C4O

Synonyms:

• (3E,5E,8S,9E,11S,12R,13E,15E,18S)-3-[[[6-Deoxy-4-O-(3,5-dichloro-2-ethyl-4,6-dihydroxybenzoyl)-2-O-methyl-β-<span class="text-smallcaps">D</smallcap>-mannopyranosyl]oxy]methyl]-12-[[6-deoxy-5-C-methyl-4-O-(2-methyl-1-oxopropyl)-β-<smallcap>D</span>-lyxo-hexopyranosyl]oxy]-11-ethyl-8-hydroxy-18-[(1R)-1-hydroxyethyl]-9,13,15-trimethyloxacyclooctadeca-3,5,9,13,15-pentaen-2-one
• 3-(((6-Deoxy-4-O-(3,5-dichloro-2-ethyl-4,6-dihydroxybenzoyl)-2-O-methyl-b-D-mannopyranosyl)oxy)-methyl)-12(R)-[(6-deoxy-5-C-methyl-4-O-(2-methyl-1-oxopropyl)-b-D-lyxo-hexopyranosyl)oxy]-11(S)-ethyl-8(S)-hydroxy-18(S)-(1(R)-hydroxyethyl)-9,13,15-trimethyloxacyclooctadeca-3,5,9,13,15-pentaene-2-one
• Clostomicin B₁
• Dificid
• Dificlir
• Fidaxomycin
• Lipiarmicin
• Lipiarmycin
• Lipiarmycin A 3
• Opt-80
• Oxacyclooctadeca-3,5,9,13,15-pentaen-2-one, 3-[[[6-deoxy-4-O-(3,5-dichloro-2-ethyl-4,6-dihydroxybenzoyl)-2-O-methyl-β-<span class="text-smallcaps">D</smallcap>-mannopyranosyl]oxy]methyl]-12-[[6-deoxy-5-C-methyl-4-O-(2-methyl-1-oxopropyl)-β-<smallcap>D</span>-lyxo-hexopyranosyl]oxy]-11-ethyl-8-hydroxy-18-[(1R)-1-hydroxyethyl]-9,13,15-trimethyl-, (3E,5E,8S,9E,11S,12R,13E,15E,18S)-
• Par 01
• Par-101
• R-Tiacumicin B
• Tiacumicin B
• (3E,5E,8S,9E,11S,12R,13E,15E,18S)-3-[[[6-Deoxy-4-O-(3,5-dichloro-2-ethyl-4,6-dihydroxybenzoyl)-2-O-methyl-β-D-mannopyranosyl]oxy]methyl]-12-[[6-deoxy-5-C-methyl-4-O-(2-methyl-1-oxopropyl)-β-D-lyxo-hexopyranosyl]oxy]-11-ethyl-8-hydroxy-18-[(1R)-1-hydroxyethyl]-9,13,15-trimethyloxacyclooctadeca-3,5,9,13,15-pentaen-2-one
• Oxacyclooctadeca-3,5,9,13,15-pentaen-2-one, 3-[[[6-deoxy-4-O-(3,5-dichloro-2-ethyl-4,6-dihydroxybenzoyl)-2-O-methyl-β-D-mannopyranosyl]oxy]methyl]-12-[[6-deoxy-5-C-methyl-4-O-(2-methyl-1-oxopropyl)-β-D-lyxo-hexopyranosyl]oxy]-11-ethyl-8-hydroxy-18-[(1R)-1-hydroxyethyl]-9,13,15-trimethyl-, (3E,5E,8S,9E,11S,12R,13E,15E,18S)-

Fidaxomicin

CAS: 873857-62-6

Formula: C₅₂H₇₄Cl₂O₁₈

Purity: >98.0%(HPLC)

Color and Shape: White to Light yellow powder to crystal

Molecular weight: 1,058.05

Ref: 3B-F1216

Fidaxomycin; Lipiarmycin A3; Tiacumicin B; Chlostomicin B1;

CAS: 873857-62-6

Formula: C₅₂H₇₄CL₂O₁₈

Purity: 98.89%

Color and Shape: Off white. Powder

Molecular weight: 1056.0

Ref: 8R-CL0228

Fidaxomicin

CAS: 873857-62-6

Fidaxomicin

Formula: C₅₂H₇₄Cl₂O₁₇

Purity: By hplc: 98.48% (Typical Value in Batch COA)

Color and Shape: white to off-white powder

Molecular weight: 1,042.04g/mol

Ref: 54-BIW4203

Fidaxomicin

CAS: 873857-62-6

Fidaxomicin

Purity: ≥98%

Molecular weight: 1058.04g/mol

Ref: 54-BUP15040

Fidaxomicin

CAS: 873857-62-6

Formula: C₅₂H₇₄Cl₂O₁₈

Purity: ≥ 97.0%

Color and Shape: White to off-white powder

Molecular weight: 1058.0

Ref: 7W-GA3227

Fidaxomicin

CAS: 873857-62-6

Formula: C₅₂H₇₄Cl₂O₁₈

Color and Shape: White To Off-White Solid

Molecular weight: 1058.05

Ref: 4Z-F-076001

Fidaxomicin

CAS: 873857-62-6

Fidaxomicin (Tiacumicin B) is a semisynthetic macrolide antibiotic used to treat Clostridium difficile-associated diarrhea in adults.

Formula: C₅₂H₇₄Cl₂O₁₈

Purity: 99.76% - 99.82%

Color and Shape: Solid

Molecular weight: 1058.04

Ref: TM-T6194

Fidaxomicin

CAS: 873857-62-6

Applications Fidaxomicin is a nonabsorbed macrocyclic antibiotic, and is the first antimicrobial to be approved by the FDA for the treatment of Clostridium difficile infection (CDI) in 20 years. Fidaxomicin works by inhibiting sporulation by CDI, sustaining clinical response and reducing recurrences of this pathogen.
References Babakhani, F., et al.: Clin. Infect. Dis., 55, S162 (2012); Venugopal, A., et al.: Clin. Infect. Dis., 54, 568 (2012)

Formula: C₅₂H₇₄Cl₂O₁₈

Color and Shape: Neat

Molecular weight: 1058.04

Ref: TR-F335400

Fidaxomicin

CAS: 873857-62-6

Fidaxomicin is a macrocyclic antibiotic with action on bacterial RNA polymerase and is used for treating Clostridium difficile infections.

Formula: C₅₂H₇₄Cl₂O₁₈

Purity: Min. 98 Area-%

Color and Shape: White Powder

Molecular weight: 1,058.04 g/mol

Ref: 3D-AF31015