Rifabutin

SKU: orb1308428

Description

Rifabutin is a semisynthetic ansamycin antibiotic that potently inhibits bacterial DNA-dependent RNA polymerase, blocking transcription initiation. It is widely used in antimycobacterial research, including in vitro susceptibility assays and in vivo models for studying tuberculosis and MAC infections.

Research Area

Cell Biology, Infectious Disease & Virology, Metabolism Research, Molecular Biology, Signal Transduction

Key Properties

• CAS Number: 72559-06-9
• MW: 847
• Purity: 99.61%
• Formula: C₄₆H₆₂N₄O₁₁
• SMILES: CO[C@H]1\C=C/O[C@@]2(C)Oc3c(C2=O)c2C4=NC5(CCN(CC(C)C)CC5)NC4=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)c2c(O)c3C
• Target: HSP,DNA/RNA Synthesis,Antibiotic,Antibacterial
• Solubility: DMSO:50 mg/mL (59.03 mM);Ethanol:38 mg/mL (44.86 mM);10% DMSO+40% PEG300+5% Tween 80+45% Saline:2 mg/mL (2.36 mM)

Bioactivity

• In Vivo:
  Rifabutin exhibits broad-spectrum antimicrobial activity and, compared to rifampicin, demonstrates higher potency in vitro against the Mycobacterium avium complex (MAC), Mycobacterium tuberculosis, and Mycobacterium leprae. It is also effective against Group A Streptococcus, Campylobacter jejuni, Neisseria gonorrhoeae, Haemophilus influenzae, Staphylococcus species, Haemophilus ducreyi, Helicobacter pylori, Neisseria meningitidis, Chlamydia trachomatis, and Toxoplasma gondii. While rifabutin is active against most atypical mycobacteria, including Mycobacterium kansasii, it is less effective against Mycobacterium chelonae. Its isoenzyme selectivity closely resembles that of rifampicin, although rifampin induces to a greater extent, by 2-4 times. Furthermore, rifabutin enhances the glucuronidation of β-estradiol, 4-hydroxytamoxifen, and 1-naphthol by 2-3 times.
• In Vitro:
  In chimeric mice, the combined use of Rifabutin (100 mg/kg) and emtricitabine (10 mg/kg) resulted in a 75% survival rate among mice infected with either Toxoplasma or Plasmodium. Additionally, in these mice, Rifabutin significantly increased human CYP3A4 mRNA expression (by 7.4-fold), CYP3A4 protein levels (by 3.0-fold), testosterone 6β-hydroxylase activity (by 2.4-fold), and dexamethasone 6-hydroxylase activity (by 1.9-fold).

Storage & Handling

• Storage: Powder: -20°C for 3 years | In solvent: -80°C for 1 year | Shipping with blue ice/Shipping at ambient temperature.
• Expiration Date: 12 months from date of receipt.
• Disclaimer: For research use only

Alternative Names

Bacterial, Antibiotic, Ansamycin, DNA Synthesis, DNASynthesis, inhibit, LM 427, LM427, LM-427, HSP90, Inhibitor, Endoplasmin, Rifabutin, RNASynthesis, RNA polymerase, RNA Synthesis

Compound Identifiers

PubChem CID

137698378