Rifaquizinone

Rifaquizinone

Clinical data
Other names	RFQ, CBR-2092, TNP-2092
Routes of administration	Oral, intravenous
Identifiers
IUPAC name 8-[(3R)-3-[1-[[1-[(E)-[(7S,9E,11S,12R,13S,14R,15R,16R,17S,18S,19E,21Z)-13-acetyloxy-2,15,17,27,29-pentahydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-6,23-dioxo-8,30-dioxa-24-azatetracyclo[23.3.1.14,7.05,28]triaconta-1(29),2,4,9,19,21,25,27-octaen-26-yl]methylideneamino]piperidin-4-yl]-methylamino]cyclopropyl]pyrrolidin-1-yl]-1-cyclopropyl-7-fluoro-9-methyl-4-oxoquinolizine-3-carboxylic acid
CAS Number	922717-97-3
PubChem CID	137253362
IUPHAR/BPS	11028
DrugBank	DB16312
ChemSpider	26354547
UNII	W2P7EF7O6O
ChEMBL	ChEMBL1275685
Chemical and physical data
Formula	C65H81FN6O15
Molar mass	1205.388 g·mol−1
3D model (JSmol)	Interactive image
SMILES C[C@H]1/C=C/C=C(\C(=O)NC2=C(C(=C3C(=C2O)C(=C(C4=C3C(=O)[C@](O4)(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)C)O)O)/C=N/N5CCC(CC5)N(C)C6(CC6)[C@@H]7CCN(C7)C8=C(C9=C(C=C(C(=O)N9C=C8F)C(=O)O)C1CC1)C)/C
InChI 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 Key:OPZFMLLAJBIKAN-KYGXCNJYSA-N

Rifaquizinone (RFQ, CBR-2092, TNP-2092) is an experimental antibiotic medication developed in China for the treatment of bacterial infections such as drug-resistant strains of Staphylococcus aureus . It is an orally active prodrug which is also a codrug, being cleaved inside the body to two active components, with half of the molecule being a rifamycin derivative, and the other half a quinolone antibiotic. It is in clinical trials for joint infections following surgery and acute bacterial skin and skin structure infections. ^{[1] [2] [3] [4]}

See also

• Cefilavancin

References

1. Surur AS, Sun D (2021). "Macrocycle-Antibiotic Hybrids: A Path to Clinical Candidates". Frontiers in Chemistry. 9 659845. Bibcode:2021FrCh....9..317S. doi: 10.3389/fchem.2021.659845 . PMC   8120311 . PMID   33996753.
2. Scott Overcash J, Waters M, Wang H, Geng G, Ai C, Ma Z, et al. (29 January 2025). "P-1090. Rifaquizinone for the Treatment of Acute Bacterial Skin and Skin Structure Infections: A Multicenter, Double-Blind, Randomized, Active-Controlled, Phase 2 Trial". Open Forum Infectious Diseases. 12 (Supplement_1) ofae631.1278. doi:10.1093/ofid/ofae631.1278. PMC   11778548 .
3. Weiss WJ, Pulse ME, Nguyen P, Valtierra D, Peterson K, Ogbonna A, et al. (29 January 2025). "P-1111. Efficacy of Intra-Articular Administration of Rifaquizinone in Rodent Models of Implant Infection Associated with Staphylococcus aureus". Open Forum Infectious Diseases. 12 (Supplement_1) ofae631.1299. doi:10.1093/ofid/ofae631.1299. PMC   11777660 .
4. Douglas EJ, Laabei M (September 2023). "Staph wars: the antibiotic pipeline strikes back". Microbiology. 169 (9). doi: 10.1099/mic.0.001387 . PMC   10569064 . PMID   37656158.