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Rifalazil

CAT: 0804-HY-105099-01Size: 5 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-105099-01Size:5 mg
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24/48H Stock Items & 2 to 6 Weeks non Stock Items.
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Description
Rifalazil (KRM-1648; ABI-1648), a rifamycin derivative, inhibits the bacterial DNA-dependent RNA polymerase and kills bacterial cells by blocking off the β-subunit in RNA polymerase[1]. Rifalazil (KRM-1648; ABI-1648) is an antibiotic, exhibits high potency against mycobacteria, gram-positive bacteria, Helicobacter pylori, C. pneumoniae and C. trachomatis with MIC values from 0.00025 to 0.0025 μg/ml[3]. Rifalazil (KRM-1648; ABI-1648) has the potential for the treatment of Chlamydia infection, Clostridium difficile associated diarrhea (CDAD), and tuberculosis (TB) [2].
CAS Number
129791-92-0
Product Name Alternative
KRM-1648; ABI-1648
UNSPSC
12352005
Target
Antibiotic; Bacterial; DNA/RNA Synthesis
Type
Reference compound
Related Pathways
Anti-infection; Cell Cycle/DNA Damage
Applications
COVID-19-anti-virus
Field of Research
Infection; Inflammation/Immunology
Assay Protocol
https://www.medchemexpress.com/rifalazil.html
Purity
99.64
Solubility
DMSO : 8.33 mg/mL (ultrasonic)
Smiles
CC(C)CN(CC1)CCN1C2=CC(O3)=C(C(O)=C2)N=C(C3=C(NC(/C(C)=C\C=C\[C@@H]([C@H](O)[C@@H](C)[C@@H](O)[C@@H](C)[C@@H]([C@@H]([C@H](/C=C/O[C@@]4(C)O5)OC)C)OC(C)=O)C)=O)C6=O)C7=C6C(O)=C(C)C5=C7C4=O
Molecular Formula
C51H64N4O13
Molecular Weight
941.07
References & Citations
[1]Suchland RJ, et al. Rifalazil pretreatment of mammalian cell cultures prevents subsequent Chlamydia infection.Antimicrob Agents Chemother. 2006 Feb;50 (2) :439-44.|[2]Shoen CM, et al. Evaluation of rifalazil in long-term treatment regimens for tuberculosis in mice.Antimicrob Agents Chemother. 2000 Jun;44 (6) :1458-62.|[3]Rothstein DM, et al. Development potential of rifalazil.Expert Opin Investig Drugs. 2003 Feb;12 (2) :255-71.
Shipping Conditions
Room Temperature
Storage Conditions
4°C (Powder, sealed storage, away from moisture)
Scientific Category
Reference compound1
Clinical Information
Phase 3

Chemical Information

Rifalazil

Rifalazil is a phenoxazine.

CAS Number129791-92-0
PubChem CID135431094
IUPAC Name[(7S,9E,11S,12R,13S,14R,15R,16R,17S,18S,19E,21Z)-2,6,15,17-tetrahydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-30-[4-(2-methylpropyl)piperazin-1-yl]-23,32,37-trioxo-8,27,38-trioxa-24,34-diazahexacyclo[23.11.1.14,7.05,36.026,35.028,33]octatriaconta-1,3,5,9,19,21,25,28,30,33,35-undecaen-13-yl] acetate
Molecular FormulaC51H64N4O13
Molecular Weight941.1
XLogP3.3
Topological Polar Surface Area226
Hydrogen Bond Donor Count5
Hydrogen Bond Acceptor Count16
Rotatable Bond Count6
Heavy Atom Count68
Formal Charge0
Complexity2510
SMILES
C[C@H]1/C=C/C=C(\C(=O)NC2=C3C(=C4C(=C(C(=C5C4=C([C@](O5)(O/C=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)O)C)O)C2=O)N=C6C(=CC(=CC6=O)N7CCN(CC7)CC(C)C)O3)/C
InChI
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/h12-15,20-22,24-25,27-29,34,42-43,46,58-60,62H,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
InChIKey
IXSVOCGZBUJEPI-HTQYORAHSA-N
Chemical Structure
2D Structure
2D structure of Rifalazil
CAS: 129791-92-0
CID: 135431094
Formula: C51H64N4O13
MW: 941.1
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight941.1
XLogP33.3
Hydrogen Bond Donor Count5
Hydrogen Bond Acceptor Count16
Rotatable Bond Count6
Exact Mass940.44698811
Monoisotopic Mass940.44698811
Topological Polar Surface Area226 Ų
Heavy Atom Count68
Formal Charge0
Complexity2510
Isotope Atom Count0
Defined Atom Stereocenter Count9
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count3
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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