Zoliflodacin

Zoliflodacin (development codes AZD0914 and ETX0914) is an experimental antibiotic that is being studied for the treatment of infection with Neisseria gonorrhoeae (gonorrhea).[1] It has a novel mechanism of action which involves inhibition of bacterial type II topoisomerases.[2] It is being developed by Entasis Therapeutics and is (as of 2020) in Phase III clinical trials.[3]

Zoliflodacin

Clinical data
Other names	AZD0914; ETX0914
Pregnancy category	Not classified yet
Routes of administration	Oral
Drug class	Antibiotic
Legal status
Legal status	US: Investigational New Drug Investigational
Pharmacokinetic data
Bioavailability	97.8%
Metabolism	Hepatic
Onset of action	Fasted: 1.5–2.3 h Fed: 4 h
Elimination half-life	5.3–6.3 h
Excretion	Faeces (79.6%) Urine (18.2%)
Identifiers
CAS Number	1620458-09-4
PubChem CID	76685216
DrugBank	12817
UNII	FWL2263R77
KEGG	D11726
Chemical and physical data
Formula	C22H22FN5O7
Molar mass	487.444 g·mol^−1
3D model (JSmol)	Interactive image
SMILES C[C@@H]1CN2[C@H]([C@@H](O1)C)C3(CC4=C2C(=C5C(=C4)C(=NO5)N6[C@H](COC6=O)C)F)C(=O)NC(=O)NC3=O
InChI InChI=1S/C22H22FN5O7/c1-8-7-33-21(32)28(8)17-12-4-11-5-22(18(29)24-20(31)25-19(22)30)16-10(3)34-9(2)6-27(16)14(11)13(23)15(12)35-26-17/h4,8-10,16H,5-7H2,1-3H3,(H2,24,25,29,30,31)/t8-,9+,10-,16+/m0/s1 Key:ZSWMIFNWDQEXDT-ZESJGQACSA-N

References

1. Taylor SN, Marrazzo J, Batteiger BE, Hook EW, Seña AC, Long J, et al. (November 2018). "Single-Dose Zoliflodacin (ETX0914) for Treatment of Urogenital Gonorrhea". The New England Journal of Medicine. 379 (19): 1835–1845. doi:10.1056/NEJMoa1706988. PMID 30403954.
2. Basarab GS, Kern GH, McNulty J, Mueller JP, Lawrence K, Vishwanathan K, et al. (July 2015). "Responding to the challenge of untreatable gonorrhea: ETX0914, a first-in-class agent with a distinct mechanism-of-action against bacterial Type II topoisomerases". Scientific Reports. 5: 11827. Bibcode:2015NatSR...511827B. doi:10.1038/srep11827. PMC 4501059. PMID 26168713.
3. "Pipeline". Entasis Therapeutics.