RELEBACTAM

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C12H20N4O6S.H2O
Molecular Weight	366.391
Optical Activity	UNSPECIFIED
Defined Stereocenters	3 / 3
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

O.OS(=O)(=O)ON1[C@H]2C[N@]([C@@H](CC2)C(=O)NC3CCNCC3)C1=O

InChI

InChIKey=TWFRCSHLWKJBQH-UXQCFNEQSA-N

InChI=1S/C12H20N4O6S.H2O/c17-11(14-8-3-5-13-6-4-8)10-2-1-9-7-15(10)12(18)16(9)22-23(19,20)21;/h8-10,13H,1-7H2,(H,14,17)(H,19,20,21);1H2/t9-,10+;/m1./s1

HIDE SMILES / InChI

Molecular Formula	C12H20N4O6S
Molecular Weight	348.375
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Molecular Formula	H2O
Molecular Weight	18.0153
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description

Relebactum sodium (MK-7655) is a piperidine analog 3 that inhibits class A and C β-lactamases (in vitro). It is being investigated for use in treatment of infectious diseases, such as treatment of gram-negative bacterial infections. Its potential as an alternative to existing medicines in the treatment of drug-resistant bacterial infections is being studied. Clinical trials have been conducted and are still ongoing to evaluate the efficacy and safety of relebactum sodium in treatment of intra-abdominal infections, urinary tract infections (such as pyelonephritis), hospital-acquired and ventilator-associated bacterial pneumonias, and gram-negative bacterial infections.

Approval Year

Targets

Targets

Primary Target	Pharmacology	Condition	Potency
Class A carbapenemase 3	Inhibitor 8,504		210.0 nM [IC50]
beta-lactamase 3	Inhibitor 8,504		410.0 nM [IC50]

C_max

Value	Dose	Co-administered	Analyte	Population
64 μM	250 mg 4 times / day multiple, intravenous	IMIPENEM	RELEBACTAM ANHYDROUS plasma	Homo sapiens

AUC

Value	Dose	Co-administered	Analyte	Population
7.97 μM × h	25 mg single, intravenous		RELEBACTAM ANHYDROUS plasma	Homo sapiens
81.8 μM × h	250 mg single, intravenous		RELEBACTAM ANHYDROUS plasma	Homo sapiens
396 μM × h	1150 mg single, intravenous		RELEBACTAM ANHYDROUS plasma	Homo sapiens
427.3 μM × h	250 mg 4 times / day multiple, intravenous	IMIPENEM	RELEBACTAM ANHYDROUS plasma	Homo sapiens

T_1/2

Value	Dose	Co-administered	Analyte	Population
1.39 h	25 mg single, intravenous		RELEBACTAM ANHYDROUS plasma	Homo sapiens
1.63 h	250 mg single, intravenous		RELEBACTAM ANHYDROUS plasma	Homo sapiens
1.78 h	1150 mg single, intravenous		RELEBACTAM ANHYDROUS plasma	Homo sapiens
1.2 h	250 mg 4 times / day multiple, intravenous	IMIPENEM	RELEBACTAM ANHYDROUS plasma	Homo sapiens

F_unbound

Value	Dose	Co-administered	Analyte	Population
78%	250 mg 4 times / day multiple, intravenous	IMIPENEM	RELEBACTAM ANHYDROUS plasma	Homo sapiens

Doses

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Dose	Population	Adverse events
250 mg 4 times / day multiple, intravenous Recommended	healthy, 24 to 42 years	Disc. AE: Diarrhea, Nausea... Other AEs: Fatigue, Blood creatinine increased...
125 mg 4 times / day multiple, intravenous	unhealthy, mean age 49.7 years	Disc. AE: Decreased creatinine clearance... Other AEs: Diarrhea, Nausea...
250 mg 4 times / day multiple, intravenous Recommended	unhealthy, mean age 56.4 years and 49.1 years	Other AEs: Anemia, Diarrhea...
625 mg 4 times / day multiple, intravenous MTD	healthy, median age 27 years	Other AEs: Upper abdominal pain, Diarrhea...
1150 mg 1 times / day single, intravenous MTD\|Highest studied dose	healthy, median age 28.5 years	Other AEs: Feeling of body temperature change...

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AEs

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AE	Significance	Dose	Population
Blood creatinine increased	grade 1, 5.9%	250 mg 4 times / day multiple, intravenous Recommended	healthy, 24 to 42 years
Fatigue	grade 1, 5.9%	250 mg 4 times / day multiple, intravenous Recommended	healthy, 24 to 42 years
Diarrhea	grade 1, 5.9% Disc. AE	250 mg 4 times / day multiple, intravenous Recommended	healthy, 24 to 42 years
Nausea	grade 2, 5.9% Disc. AE	250 mg 4 times / day multiple, intravenous Recommended	healthy, 24 to 42 years
Vomiting	grade 2, 5.9% Disc. AE	250 mg 4 times / day multiple, intravenous Recommended	healthy, 24 to 42 years

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Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2,252 inducer 1,087	inhibitor 2,438		inhibitor 2,217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 2,153 CYP2B6 926 CYP2C8 1,057 CYP2C19 2,057 P-gp 1,741 OATP1B1 1,079 OATP1B3 961 OAT1 725 OAT3 747 OCT2 779 MATE1 415 MATE2 267 BCRP 910 BSEP 550 Nav1.5 116	OAT3 391 OAT4 93 OAT1 395 OCT2 434 P-gp 2,052 BCRP 697 MRP2 252 MRP4 91 MATE1 182 MATE2 98	CYP1A2 832 CYP2B6 669

Drug as perpetrator

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Target	Modality	Activity
BCRP 985	inhibitor 4,027	no [IC50 >300 uM]
BSEP 554	inhibitor 4,027	no [IC50 >300 uM]
MATE1 416	inhibitor 4,027	no [IC50 >300 uM]
MATE2 267	inhibitor 4,027	no [IC50 >300 uM]
OAT1 730	inhibitor 4,027	no [IC50 >300 uM]

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Drug as victim

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Target	Modality	Activity
BCRP 697	substrate 4,014	no
MRP2 252	substrate 4,014	no
MRP4 91	substrate 4,014	no
OAT1 395	substrate 4,014	no
OCT2 434	substrate 4,014	no

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Tox targets

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Target	Modality	Activity	Metabolite	Clinical evidence
Nav1.5 119	inhibitor 2,237
hERG 2,263	inhibitor 2,237

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Sourcing

Sourcing

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Vendor/Aggregator	ID	URL
AA Blocks	AA008TMP	https://www.aablocks.com/goods/Goods/detail?id=AA008TMP
Aaron Chemicals	AR008UEH	http://www.aaronchem.com/1174018-99-5
abcr GmbH	AB479629	http://www.abcr.com/shop/en/AB479629
BioSynth	J-690043	https://www.biosynth.com/en/products/all-products/products/J-690054.html
Chem Scene	CS-5391	http://www.chemscene.com/1174018-99-5.html

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Substance Class	Chemical
Record UNII	Y1MYA2UHFL
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

RELEBACTAM

Official Name

English

RELEBACTAM MONOHYDRATE

Preferred Name

English

RELEBACTAM [ORANGE BOOK]

Common Name

English

RECARBRIO COMPONENT RELEBACTAM MONOHYDRATE

Brand Name

English

RELEBACTAM [USAN]

Common Name

English

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Classification Tree

Code System

Code

Anti-Infective Agent

NCI_THESAURUS

C258

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Code System

Code

Type

Description

SMS_ID

100000179908

PRIMARY

EVMPD

SUB194532

PRIMARY

DRUG CENTRAL

5342

PRIMARY

RXCUI

2184137

PRIMARY

CAS

1174020-13-3

PRIMARY

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SMILES

InChI

Approval Year

Targets

Cmax

AUC

T1/2

Funbound

Doses

AEs

Overview

OverviewOther

Drug as perpetrator​

Drug as victim

Tox targets

Sourcing

C_max

T_1/2

F_unbound

Drug as perpetrator