Rifaquizinone

{{cs1 config |name-list-style=vanc |display-authors=6}}

{{Infobox drug

| image = Rifaquizinone_structure.png

| width = 300

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| routes_of_administration = Oral, intravenous

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| CAS_number = 922717-97-3

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| PubChem = 137253362

| IUPHAR_ligand = 11028

| DrugBank = DB16312

| ChemSpiderID = 26354547

| UNII = W2P7EF7O6O

| ChEMBL = 1275685

| synonyms = RFQ, CBR-2092, TNP-2092

| 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[23.3.1.1^4,7.0^5,28]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

| C = 65 | H = 81 | F = 1 | N = 6 | O = 15

| 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

| StdInChI = 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

| StdInChI_comment =

| StdInChIKey = 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.{{cite journal | vauthors = Surur AS, Sun D | title = Macrocycle-Antibiotic Hybrids: A Path to Clinical Candidates | journal = Frontiers in Chemistry | volume = 9 | issue = | pages = 659845 | date = 2021 | pmid = 33996753 | pmc = 8120311 | doi = 10.3389/fchem.2021.659845 | doi-access = free | bibcode = 2021FrCh....9..317S }}{{cite journal | vauthors = Scott Overcash J, Waters M, Wang H, Geng G, Ai C, Ma Z, Chen J |title=P-1090. Rifaquizinone for the Treatment of Acute Bacterial Skin and Skin Structure Infections: A Multicenter, Double-Blind, Randomized, Active-Controlled, Phase 2 Trial |journal=Open Forum Infectious Diseases |date=29 January 2025 |volume=12 |issue=Supplement_1 |pages=ofae631.1278 |doi=10.1093/ofid/ofae631.1278 | pmc = 11778548 }}{{cite journal | vauthors = Weiss WJ, Pulse ME, Nguyen P, Valtierra D, Peterson K, Ogbonna A, Beeman L, Dai T, Chen L, Wang H, Ma Z |title=P-1111. Efficacy of Intra-Articular Administration of Rifaquizinone in Rodent Models of Implant Infection Associated with Staphylococcus aureus |journal=Open Forum Infectious Diseases |date=29 January 2025 |volume=12 |issue=Supplement_1 |pages=ofae631.1299 |doi=10.1093/ofid/ofae631.1299 | pmc = 11777660 }}{{cite journal | vauthors = Douglas EJ, Laabei M | title = Staph wars: the antibiotic pipeline strikes back | journal = Microbiology | volume = 169 | issue = 9 | date = September 2023 | pmid = 37656158 | doi = 10.1099/mic.0.001387 | doi-access = free | pmc = 10569064 }}