Rifalazil

Rifalazil
Names
IUPAC name
(2S,16Z,18E,20S,21S,22R,23R,24R,25S,26R,27S,28E)-5,12,21,23-tetrahydroxy-27-methoxy-2,4,16,20,22,24,26-heptamethyl-10-[4-(2-methylpropyl)piperazin-1-yl]-1,6,15-trioxo-1,2-dihydro-6H-2,7-(epoxypentadeca[1,11,13]trienoimino)[1]benzofuro[4,5-a]phenoxazin-25-yl acetate
Systematic IUPAC name
(7S,9E,11S,12R,13S,14R,15R,16R,17S,18S,19E,21Z)-2,15,17,32-Tetrahydroxy-30-(4-isobutyl-1-piperazinyl)-11-methoxy-3,7,12,14,16,18,22-heptamethyl-6,23,37-trioxo-8,27,38-trioxa-24,34-diazahexacyclo[23.11;.1.14,7.05,36.026,35.028,33]octatriaconta-1(36),2,4,9,19,21,25,28,30,32,34-undecaen-13-yl acetate
Identifiers
3D model (JSmol)
ChemSpider
KEGG
UNII
  • InChI=1S/C51H64N4O13/c1-24(2)23-54-16-18-55(19-17-54)32-21-33(57)39-35(22-32)67-48-40(52-39)36-37-44(60)30(8)47-38(36)49(62)51(10,68-47)65-20-15-34(64-11)27(5)46(66-31(9)56)29(7)43(59)28(6)42(58)25(3)13-12-14-26(4)50(63)53-41(48)45(37)61/h12-15,20-22,24-25,27-29,34,42-43,46,57-60H,16-19,23H2,1-11H3,(H,53,63)/b13-12+,20-15+,26-14-/t25-,27+,28+,29+,34-,42-,43+,46+,51-/m0/s1
  • C[C@H]1C=CC=C(C(=O)N=C2C3=C(C4=C5C(=C(C(=C4C2=O)O)C)O[C@@](C5=O)(OC=C[C@@H]([C@H]([C@H]([C@@H]([C@@H]([C@@H]([C@H]1O)C)O)C)OC(=O)C)C)OC)C)NC6=C(O3)C=C(C=C6O)N7CCN(CC7)CC(C)C)C
Properties
C51H64N4O13
Molar mass 941.088 g·mol−1
Very high water solubility around 2000 mg/mL at a pH of 2 and a low solubility of 0.5 mg/mL at a pH of 5
Pharmacology
Pharmacokinetics:
8.7±2.7 hours[2]
Legal status
  • Development terminated
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Rifalazil (also known as KRM-1648 and AMI-1648)[2] is an antibiotic substance that kills bacterial cells by blocking off the β-subunit in RNA polymerase.[3] Rifalazil is used as a treatment for many different diseases. The most common are Chlamydia infection, Clostridioides difficile associated diarrhea (CDAD), and tuberculosis (TB). Using rifalazil and the effects that coincide with taking rifalazil for treating a bacterial disease vary from person to person, as does any drug put into the human body. Food interactions and genetic variation are a few causes for the variation in side effects from the use of rifalazil.[4] Its development was terminated in 2013 due to severe side effects.[5]

  1. ^ "Rifalazil - 129791-92-0".
  2. ^ a b "Rifalazil". Tuberculosis. 88 (2): 148–150. 2008. doi:10.1016/S1472-9792(08)70023-4. PMID 18486057.
  3. ^ Osburne, Marcia S; Murphy, Christopher K; Rothstein, David M (2006). "Enhanced Activity of Rifalazil in Combination with Levofloxacin, Linezolid, or Mupirocin against Staphylococcus aureus in vitro". The Journal of Antibiotics. 59 (5): 303–8. doi:10.1038/ja.2006.43. PMID 16883781.
  4. ^ "Cannabis Ministry Amsterdam : Home : THC Ministry Amsterdam".
  5. ^ "AdisInsight: Rifalazil (ABI 1648; KRM 1648; PA 1648)". Adis Insight. Springer International Publishing AG. Retrieved 30 January 2016.