Details of the Drug

General Information of Drug (ID: DMDCFXJ)

Drug Name

Vaborbactam

Synonyms

RPX-7009; 1360457-46-0; RPX7009; UNII-1C75676F8V; 2-((3R,6S)-2-hydroxy-3-(2-(thiophen-2-yl)acetamido)-1,2-oxaborinan-6-yl)acetic acid; CHEMBL3317857; 1C75676F8V; 2-[(3R,6S)-2-hydroxy-3-[(2-thiophen-2-ylacetyl)amino]oxaborinan-6-yl]acetic acid; Vaborbactam [INN]; RPX 7009; Vaborbactam. RPX7009; Vaborbactam (USAN/INN); Vaborbactam [USAN:INN]; SCHEMBL620289; GTPL10871; Vabomere (vaborbactam + meropenem); EX-A2589; BDBM50089084; MFCD28502176; AKOS032961376; CS-6445; DB12107; SB17184; 1,2-Oxaborinane-6-acetic acid, 2-hydroxy-3-((2-(2-thienyl)acetyl)amino)-, (3R,6S)-; compound 9f [PMID: 25782055]; NCGC00510003-01; HY-19930; 2-hydroxy-3-((2-(2-thienyl)acetyl)amino)-; D10998; Q27252228; {(3R,6S)-2-hydroxy-3-[(thiophen-2-ylacetyl)amino]-1,2-oxaborinan-6-yl}acetic acid; 2-((3R,6S)-2-hydroxy-3-(2-(thiophen-2-yl)acetamido)-1,2-oxaborinan-6-yl)acetic acid; 2-[(3R,6S)-2-hydroxy-3-[(2-thiophen-2-ylacetyl)amino]oxaborinan-6-yl]acetic acid; 1,2-Oxaborinane-6-acetic acid

Indication

Disease Entry	ICD 11	Status	REF
Urinary tract infection	GC08	Phase 3	[1]

Drug Type

Small molecular drug

Structure

3D MOL is unavailable

2D MOL

#Ro5 Violations (Lipinski):
0

Molecular Weight

297.14

Topological Polar Surface Area

Not Available

Rotatable Bond Count

Hydrogen Bond Donor Count

Hydrogen Bond Acceptor Count

ADMET Property

Absorption AUC: The area under the plot of plasma concentration (AUC) of drug is 588 mgh/L [2]
Absorption Cmax: The maximum plasma concentration (Cmax) of drug is 55.6 mg/L [2]
Clearance: The renal clearance of drug is 8.9 L/h [3]
Elimination: About 75 to 95% of the dose is excreted unchanged in the urine over a 24 to 48 hour period [3]
Half-life: The concentration or amount of drug in body reduced by one-half in 1.68 hours (in healthy subjects following multiple 2 g dose adminutesistration as a 3 - hours infusion) [4]
Metabolism: The drug is not metabolised [4]
Unbound Fraction: The unbound fraction of drug in plasma is 0.67% [5]
Vd: The volume of distribution (Vd) of drug is 18.6 L [3]

Chemical Identifiers

Formula: C12H16BNO5S
IUPAC Name: 2-[(3R,6S)-2-hydroxy-3-[(2-thiophen-2-ylacetyl)amino]oxaborinan-6-yl]acetic acid
Canonical SMILES: B1([C@H](CC[C@H](O1)CC(=O)O)NC(=O)CC2=CC=CS2)O
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
InChIKey: IOOWNWLVCOUUEX-WPRPVWTQSA-N

Cross-matching ID

PubChem CID: 56649692
CAS Number: 1360457-46-0
DrugBank ID: DB12107
TTD ID: DR6BU1

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Staphylococcus Beta-lactamase (Stap-coc blaZ)	TTHI19T	BLAC_STAAU	Inhibitor	[6]

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Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction Atlas of This Drug

References

1	ClinicalTrials.gov (NCT02166476) Efficacy/Safety of Meropenem-Vaborbactam Compared to Piperacillin-Tazobactam in Adults With cUTI and AP. U.S. National Institutes of Health.
2	Griffith DC, Loutit JS, Morgan EE, Durso S, Dudley MN: Phase 1 Study of the Safety, Tolerability, and Pharmacokinetics of the beta-Lactamase Inhibitor Vaborbactam (RPX7009) in Healthy Adult Subjects. Antimicrob Agents Chemother. 2016 Sep 23;60(10):6326-32. doi: 10.1128/AAC.00568-16. Print 2016 Oct.
3	An FDA phase I clinical trial of quinacrine sterilization (QS). Int J Gynaecol Obstet. 2003 Oct;83 Suppl 2:S45-9.
4	FDA approval: ado-trastuzumab emtansine for the treatment of patients with HER2-positive metastatic breast cancer. Clin Cancer Res. 2014 Sep 1;20(17):4436-41.
5	Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
6	Vaborbactam: Spectrum of Beta-Lactamase Inhibition and Impact of Resistance Mechanisms on Activity in Enterobacteriaceae. Antimicrob Agents Chemother. 2017 Oct 24;61(11):e01443-17.
7	Selection of TNF-alpha binding affibody molecules using a beta-lactamase protein fragment complementation assay. N Biotechnol. 2009 Nov 30;26(5):251-9.
8	2014 FDA drug approvals. Nat Rev Drug Discov. 2015 Feb;14(2):77-81.
9	2017 FDA drug approvals.Nat Rev Drug Discov. 2018 Feb;17(2):81-85.
10	A sensitive coupled HPLC/electrospray mass spectrometry assay for SPM-1 metallo-beta-lactamase inhibitors. Assay Drug Dev Technol. 2009 Apr;7(2):170-9.
11	NXL104 irreversibly inhibits the -lactamase from Mycobacterium tuberculosis. Biochemistry. 2012 Jun 5;51(22):4551-7.
12	Pharmacodynamics of Cefepime Combined with the Novel Extended-Spectrum--Lactamase (ESBL) Inhibitor Enmetazobactam for Murine Pneumonia Caused by ESBL-Producing Klebsiella pneumoniae. Antimicrob Agents Chemother. 2020 May 21;64(6):e00180-20.
13	Discovery of MK-7655, a beta-lactamase inhibitor for combination with Primaxin . Bioorg Med Chem Lett. 2014 Feb 1;24(3):780-5.
14	Beta-Lactam Antibiotics Renaissance. Antibiotics. 2014, 3(2), 193-215.
15	WO patent application no. 2010,0456,20, Recombinant bacterium capable of eliciting an immune response against streptococcus pneumoniae.
16	Multidrug-resistant Gram-negative bacterial infections: are you ready for the challenge. Curr Clin Pharmacol. 2014 Feb;9(1):27-38.