U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C65H81FN6O15
Molecular Weight 1205.3682
Optical Activity UNSPECIFIED
Defined Stereocenters 10 / 10
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of Rifaquizinone

SMILES

CO[C@H]1\C=C\O[C@@]2(C)OC3=C(C2=O)C4=C(O)C(\C=N\N5CCC(CC5)N(C)C6(CC6)[C@@H]7CCN(C7)C8=C(C)C9=C(C=C(C(O)=O)C(=O)N9C=C8F)C%10CC%10)=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)=C4C(O)=C3C

InChI

InChIKey=OPZFMLLAJBIKAN-KYGXCNJYSA-N
InChI=1S/C65H81FN6O15/c1-31-13-12-14-32(2)61(80)68-50-44(56(77)47-48(57(50)78)55(76)37(7)59-49(47)60(79)64(9,87-59)85-26-20-46(84-11)33(3)58(86-38(8)73)36(6)54(75)35(5)53(31)74)28-67-71-24-18-41(19-25-71)69(10)65(21-22-65)40-17-23-70(29-40)52-34(4)51-42(39-15-16-39)27-43(63(82)83)62(81)72(51)30-45(52)66/h12-14,20,26-28,30-31,33,35-36,39-41,46,53-54,58,74-78H,15-19,21-25,29H2,1-11H3,(H,68,80)(H,82,83)/b13-12+,26-20+,32-14-,67-28+/t31-,33+,35+,36+,40+,46-,53-,54+,58+,64-/m0/s1

HIDE SMILES / InChI

Molecular Formula C65H81FN6O15
Molecular Weight 1205.3682
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 10 / 10
E/Z Centers 1
Optical Activity UNSPECIFIED

Approval Year

Substance Class Chemical
Created
by admin
on Sat Dec 16 11:31:17 GMT 2023
Edited
by admin
on Sat Dec 16 11:31:17 GMT 2023
Record UNII
W2P7EF7O6O
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
Rifaquizinone
INN  
Official Name English
Rifamycin, 3-[(E)-[[4-[[1-[(3R)-1-(3-carboxy-1-cyclopropyl-7-fluoro-9-methyl-4-oxo-4H-quinolizin-8-yl)-3-pyrrolidinyl]cyclopropyl]methylamino]-1-piperidinyl]imino]methyl]-
Systematic Name English
3-[(E)-[[4-[[1-[(3R)-1-(3-Carboxy-1-cyclopropyl-7-fluoro-9-methyl-4-oxo-4H-quinolizin-8-yl)-3-pyrrolidinyl]cyclopropyl]methylamino]-1-piperidinyl]imino]methyl]rifamycin
Systematic Name English
rifaquizinone [INN]
Common Name English
TNP-2092
Common Name English
CBR-2092
Common Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 704419
Created by admin on Sat Dec 16 11:31:17 GMT 2023 , Edited by admin on Sat Dec 16 11:31:17 GMT 2023
Code System Code Type Description
INN
12336
Created by admin on Sat Dec 16 11:31:17 GMT 2023 , Edited by admin on Sat Dec 16 11:31:17 GMT 2023
PRIMARY
CAS
922717-97-3
Created by admin on Sat Dec 16 11:31:17 GMT 2023 , Edited by admin on Sat Dec 16 11:31:17 GMT 2023
PRIMARY
FDA UNII
W2P7EF7O6O
Created by admin on Sat Dec 16 11:31:17 GMT 2023 , Edited by admin on Sat Dec 16 11:31:17 GMT 2023
PRIMARY
NCI_THESAURUS
C190491
Created by admin on Sat Dec 16 11:31:17 GMT 2023 , Edited by admin on Sat Dec 16 11:31:17 GMT 2023
PRIMARY
SMS_ID
300000045598
Created by admin on Sat Dec 16 11:31:17 GMT 2023 , Edited by admin on Sat Dec 16 11:31:17 GMT 2023
PRIMARY
PUBCHEM
145722022
Created by admin on Sat Dec 16 11:31:17 GMT 2023 , Edited by admin on Sat Dec 16 11:31:17 GMT 2023
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR
TARGET ORGANISM->INHIBITOR
TARGET ORGANISM->INHIBITOR
TARGET ORGANISM->INHIBITOR
Related Record Type Details
ACTIVE MOIETY
In biochemical studies, CBR-2092 exhibited rifampin-like potency as an inhibitor of RNA polymerase, was an equipotent (balanced) inhibitor of DNA gyrase and DNA topoisomerase IV, and retained activity against a prevalent quinolone-resistant variant. Macromolecular biosynthesis studies confirmed that CBR-2092 has rifampin-like effects on RNA synthesis in rifampin-susceptible strains and quinolone-like effects on DNA synthesis in rifampin-resistant strains. Studies of mutant strains that exhibited reduced susceptibility to CBR-2092 further substantiated RNA polymerase as the primary cellular target of CBR-2092, with DNA gyrase and DNA topoisomerase IV being secondary and tertiary targets, respectively, in strains exhibiting preexisting rifampin resistance. In contrast to quinolone comparator agents, no strains with altered susceptibility to CBR-2092 were found to exhibit changes consistent with altered efflux properties. The combined data indicate that CBR-2092 may have potential utility in monotherapy for the treatment of persistent S. aureus infections.