RELEBACTAM ANHYDROUS

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C12H20N4O6S
Molecular Weight	348.375
Optical Activity	UNSPECIFIED
Defined Stereocenters	3 / 3
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

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

InChI

InChIKey=SMOBCLHAZXOKDQ-ZJUUUORDSA-N

InChI=1S/C12H20N4O6S/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)/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

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 8,297		210.0 nM [IC50]
beta-lactamase 3	Inhibitor 8,297		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 1,587 inducer 781	inhibitor 1,767		inhibitor 1,612

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 1,524 CYP2B6 810 CYP2C8 911 CYP2C19 1,478 P-gp 1,461 OATP1B1 788 OATP1B3 706 OAT1 599 OAT3 642 OCT2 647 MATE1 306 MATE2 263 BCRP 699 BSEP 402 Nav1.5 97	OAT3 339 OAT4 78 OAT1 326 OCT2 355 P-gp 1,537 BCRP 561 MRP2 205 MRP4 77 MATE1 135 MATE2 96	CYP1A2 701 CYP2B6 547

Drug as perpetrator

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Target	Modality	Activity
BCRP 773	inhibitor 3,277	no [IC50 >300 uM]
BSEP 403	inhibitor 3,277	no [IC50 >300 uM]
MATE1 308	inhibitor 3,277	no [IC50 >300 uM]
MATE2 263	inhibitor 3,277	no [IC50 >300 uM]
OAT1 603	inhibitor 3,277	no [IC50 >300 uM]

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Drug as victim

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Target	Modality	Activity
BCRP 561	substrate 3,367	no
MRP2 205	substrate 3,367	no
MRP4 77	substrate 3,367	no
OAT1 326	substrate 3,367	no
OCT2 355	substrate 3,367	no

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Tox targets

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Target	Modality	Activity	Metabolite	Clinical evidence
Nav1.5 100	inhibitor 1,626
hERG 1,647	inhibitor 1,626

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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	1OQF7TT3PF
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

RELEBACTAM ANHYDROUS

Common Name

English

Relebactam [WHO-DD]

Common Name

English

relebactam [INN]

Common Name

English

MK-7655

Code

English

(-)-RELEBACTAM ANHYDROUS

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

MERCK INDEX

m12234

PRIMARY

EPA CompTox

DTXSID601027689

PRIMARY

WIKIPEDIA

Relebactam

PRIMARY

INN

10027

PRIMARY

FDA UNII

1OQF7TT3PF

PRIMARY

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Related Record

Type

Details


					6D53G0FD0Z

PLASMA PROTEIN FRACTION (HUMAN)

BINDER->LIGAND

Comments:

The binding of Relebactam to human plasma proteins is approxi mately22% and is independent ofconcentration at a range of 5 to 50 μM.

Interaction Type:

BINDING

Amount:

22 % (average)


					Y1MYA2UHFL

RELEBACTAM

SOLVATE->ANHYDROUS

Amount:


					4HZ67LW8L7

OAT-4

TRANSPORTER -> SUBSTRATE

Comments:

in vitro

Amount:


					ZWJ2Y6JZWY

OAT-3

TRANSPORTER -> SUBSTRATE

Comments:

in vitro

Amount:


					1OQF7TT3PF

RELEBACTAM ANHYDROUS

EXCRETED UNCHANGED

Comments:

In Study PN001, REL was 98.4% and 99.6% excreted in the urine as the parent drug in the two dosing groups that received a single dose of 250 mg.Similarly, in the multiple dose arm, the mean percentage of REL dose excreted unchanged in urine was 90.8% at 250 mg, 99.5% at 125 mg and 95.2% at 375 mg.These results indicate that Relebactam is cleared primarily (>90%) via urinary excretion of the parent drug in humans

Qualification:

URINE

Amount:

[>90] % (average)

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Related Record

Type

Details


					1OQF7TT3PF

RELEBACTAM ANHYDROUS

ACTIVE MOIETY

Amount:

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Name	Property Type	Amount
Biological Half-life	PHARMACOKINETIC	1.2 hours (average)

Volume of Distribution	PHARMACOKINETIC	19 LITERS (average)

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