Compound ID | 148

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Meropenem + Vaborbactam

Synonym(s): RPX7009 + meropenem  |  Vabomere/ Carbavance

Class: Beta-lactam + beta-lactamase inhibitor

Agent Type: Semisynthetic; Small molecule; Direct acting; Indirect acting; Antibiotic adjuvant;
Spectrum of activity: Gram-negative
Mechanism of action: Cell wall synthesis inhibitor
Target Pathogen: Active against Gram-negatives causing complicated urinary tract infections, complicated intra-abdominal infections, hospital-acquired bacterial pneumonia/ ventilator-associated bacterial pneumonia, febrile neutropenia, bacteraemia, acute pyelonephritis; some indications specifically target infections caused by carbapenem- resistant Enterobacteriaceae
Combined with other compounds: Yes
Description: A carbapenem and a heterocyclic boron beta-lactamase inhibitor
Institute where first reported: Rempex Pharmaceuticals (wholly owned subsidiary of The Medicines Co.), USA
Year first mentioned: 2013
Highest developmental phase: Approved by FDA in 2017
Development status: Approved
Chemical structure(s):
Meropenem
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Molecular weight:
Iso. SMILES: C[C@@H]1[C@@H]2[C@H](C(=O)N2C(=C1S[C@H]3C[C@H](NC3)C(=O)N(C)C)C(=O)O)[C@@H](C)O
InChI Key: DMJNNHOOLUXYBV-PQTSNVLCSA-N
Can. SMILES: C[C@@H]1[C@@H]2[C@@H]([C@@H](C)O)C(=O)N2C(=C1S[C@H]3C[C@@H](C(=O)N(C)C)NC3)C(=O)O
InChI: InChI=1S/C17H25N3O5S/c1-7-12-11(8(2)21)16(23)20(12)13(17(24)25)14(7)26-9-5-10(18-6-9)15(22)19(3)4/h7-12,18,21H,5-6H2,1-4H3,(H,24,25)/t7-,8-,9+,10+,11-,12-/m1/s1
Vaborbactam
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Molecular weight:
Iso. SMILES: B1([C@H](CC[C@H](O1)CC(=O)O)NC(=O)CC2=CC=CS2)O
InChI Key: IOOWNWLVCOUUEX-WPRPVWTQSA-N
Can. SMILES: C1=CSC(=C1)CC(=O)N[C@H]2CC[C@@H](CC(=O)O)OB2O
InChI: InChI=1S/C12H16BNO5S/c15-11(7-9-2-1-5-20-9)14-10-4-3-8(6-12(16)17)19-13(10)18/h1-2,5,8,10,18H,3-4,6-7H2,(H,14,15)(H,16,17)/t8-,10-/m0/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/441130
Guide to Pharmacology: vaborbactam
Citations:
  • https://aac.asm.org/content/62/1/e01904-17
  • https://journals.sagepub.com/doi/abs/10.1177/1060028018763288?rfr_dat=cr_pub%3Dpubmed&url_ver=Z39.88-2003&rfr_id=ori%3Arid%3Acrossref.org&journalCode=aopd
  • http://www.vabomere.com

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