A rifamycin antibiotic
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Labeled Version(s)
28904Rifabutin-d7
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Rifabutin

Item No. 16468

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(9S,12E,14S,15R,16S,17R,18R,19R,20S,21S,22E,24Z)-16-(acetyloxy)-6,18,20-trihydroxy-14-methoxy-7,9,15,17,19,21,25-heptamethyl-1’-(2-methylpropyl)-spiro[9,4-(epoxypentadeca[1,11,13]trienimino)-2H-furo[2’,3’:7,8]naphth[1,2-d]imidazole-2,4’-piperidine]-5,10,26(3H,9H)-trione
CAS Number
72559-06-9
Synonyms
  • Ansamycin
  • LM-427
Molecular Formula
C46H62N4O11
Formula Weight
847.0
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 30 mg/mlEthanol: 30 mg/mlEthanol:PBS(pH 7.2) (1:1): 0.5 mg/ml
λmax
239, 277, 315, 498 nm
SMILES
CC1=C2C3=C(C4=C1O)C5=NC6(CCN(CC(C)C)CC6)NC5=C(NC(/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](C)[C@@H](OC)/C=C/O[C@](O2)(C)C3=O)=O)C4=O
InChi Code
InChI=1S/C46H62N4O11/c1-22(2)21-50-18-16-46(17-19-50)48-34-31-32-39(54)28(8)42-33(31)43(56)45(10,61-42)59-20-15-30(58-11)25(5)41(60-29(9)51)27(7)38(53)26(6)37(52)23(3)13-12-14-24(4)44(57)47-36(40(32)55)35(34)49-46/h12-15,20,22-23,25-27,30,37-38,41,49
InChi Key
ATEBXHFBFRCZMA-NYGPAKPVSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    10 mg

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    Cayman Chemical
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    Product Description

    Rifabutin is a rifamycin antibiotic.1,2 It is active against a variety of Gram-positive and Gram-negative bacteria, including 81 clinical isolates of H. pylori (MIC50 = 0.25 µg/ml), as well as S. aureus, S. pyogenes, and C. trachomatis (MICs = 0.004, 0.005, and ~0.008 µg/ml, respectively). Rifabutin (0.5 µg/ml) is also active against 302 strains of M. tuberculosis.2 It inhibits protein synthesis via inhibition of DNA-dependent RNA polymerase (RNAP) activity.2 Rifabutin (10, 20, or 40 mg/kg) reduces the number of spleen, lung, and liver colony forming units (CFUs) in mouse models of disseminated Mycobacterium avium complex (MAC) infection.3 Formulations containing rifabutin have been used in the treatment of H. pylori infection.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Heep, M., Beck, D., Bayerdörffer, E., et al. Rifampin and rifabutin resistance mechanism in Helicobacter pylori. Antimicrob. Agents Chemother. 43(6), 1497-1499 (1999).

    2. Kunin, C.M. Antimicrobial activity of rifabutin. Clin. Infect. Dis. 22(Supp. 1), S3-S14 (1996).

    3. Klemens, S.P., Grossi, M.A., and Cynamon, M.H. Comparative in vivo activities of rifabutin and rifapentine against Mycobacterium avium complex. Antimicrob. Agents Chemother. 38(2), (1994).