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Details

Stereochemistry ABSOLUTE
Molecular Formula C7H11N3O6S
Molecular Weight 265.244
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of AVIBACTAM

SMILES

NC(=O)[C@@H]1CC[C@@H]2C[N@]1C(=O)N2OS(O)(=O)=O

InChI

InChIKey=NDCUAPJVLWFHHB-UHNVWZDZSA-N
InChI=1S/C7H11N3O6S/c8-6(11)5-2-1-4-3-9(5)7(12)10(4)16-17(13,14)15/h4-5H,1-3H2,(H2,8,11)(H,13,14,15)/t4-,5+/m1/s1

HIDE SMILES / InChI
Avibactam (formerly NXL104, AVE1330A) is a synthetic non-β-lactam, covalent, slowly reversible β-lactamase inhibitor that inhibits the activities of Ambler class A and C β-lactamases and some Ambler class D enzymes. The combination of ceftazidime with avibactam exhibited broad-spectrum activity against Ambler class A- and class C-producing Enterobacteriaceae. AVYCAZ is a combination of ceftazidime, a cephalosporin, and avibactam indicated for the treatment of patients with the following infections caused by designated susceptible microorganisms: Complicated Intra-abdominal Infections, used in combination with metronidazole and Complicated Urinary Tract Infections, including Pyelonephritis.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
8.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
AVYCAZ

Approved Use

AVYCAZ is a combination of ceftazidime, a cephalosporin, and avibactam, a beta-lactamase inhibitor, indicated for the treatment of patients 18 years or older with the following infections caused by designated susceptible microorganisms: complicated Intra-abdominal Infections (cIAI), used in combination with metronidazole and complicated Urinary Tract Infections (cUTI), including Pyelonephritis.

Launch Date

2015
Curative
AVYCAZ

Approved Use

AVYCAZ is a combination of ceftazidime, a cephalosporin, and avibactam, a beta-lactamase inhibitor, indicated for the treatment of patients 18 years or older with the following infections caused by designated susceptible microorganisms: complicated Intra-abdominal Infections (cIAI), used in combination with metronidazole and complicated Urinary Tract Infections (cUTI), including Pyelonephritis.

Launch Date

2015
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
14.6 mg/L
0.5 g 3 times / day multiple, intravenous
dose: 0.5 g
route of administration: Intravenous
experiment type: MULTIPLE
co-administered: CEFTAZIDIME
AVIBACTAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
15.2 mg/L
0.5 g single, intravenous
dose: 0.5 g
route of administration: Intravenous
experiment type: SINGLE
co-administered: Ceftazidime
[NO STEREO] AVE-1330A FREE ACID|[NO STEREO] AVIBACTAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
38.2 mg × h/L
0.5 g 3 times / day multiple, intravenous
dose: 0.5 g
route of administration: Intravenous
experiment type: MULTIPLE
co-administered: CEFTAZIDIME
AVIBACTAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
42.1 mg × h/L
0.5 g single, intravenous
dose: 0.5 g
route of administration: Intravenous
experiment type: SINGLE
co-administered: Ceftazidime
[NO STEREO] AVE-1330A FREE ACID|[NO STEREO] AVIBACTAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
2.71 h
0.5 g 3 times / day multiple, intravenous
dose: 0.5 g
route of administration: Intravenous
experiment type: MULTIPLE
co-administered: CEFTAZIDIME
AVIBACTAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
2.22 h
0.5 g single, intravenous
dose: 0.5 g
route of administration: Intravenous
experiment type: SINGLE
co-administered: Ceftazidime
[NO STEREO] AVE-1330A FREE ACID|[NO STEREO] AVIBACTAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
93%
0.5 g single, intravenous
dose: 0.5 g
route of administration: Intravenous
experiment type: SINGLE
co-administered: Ceftazidime
[NO STEREO] AVE-1330A FREE ACID|[NO STEREO] AVIBACTAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
1000 mg 3 times / day multiple, intravenous
Highest studied dose
Dose: 1000 mg, 3 times / day
Route: intravenous
Route: multiple
Dose: 1000 mg, 3 times / day
Sources:
healthy, 18–45 years
n = 6
Health Status: healthy
Age Group: 18–45 years
Sex: M
Population Size: 6
Sources:
2000 mg single, intravenous
Highest studied dose
Dose: 2000 mg
Route: intravenous
Route: single
Dose: 2000 mg
Sources:
healthy, 18–45 years
n = 6
Health Status: healthy
Age Group: 18–45 years
Sex: M
Population Size: 6
Sources:
500 mg single, oral
Dose: 500 mg
Route: oral
Route: single
Dose: 500 mg
Sources:
healthy, 28.9 years
n = 8
Health Status: healthy
Age Group: 28.9 years
Sex: M
Population Size: 8
Sources:
OverviewDrug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
no
no
no
no
no
no
no
no
no
no
no
no
no
no
no
no
no
no
no
no
no
no
no
no
no
yes
Drug as victimTox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
PubMed

PubMed

TitleDatePubMed
In vitro activity of AVE1330A, an innovative broad-spectrum non-beta-lactam beta-lactamase inhibitor.
2004 Aug
Avibactam is a covalent, reversible, non-β-lactam β-lactamase inhibitor.
2012 Jul 17
Patents

Patents

Sample Use Guides

AVYCAZ 2.5 grams (ceftazidime 2 grams and avibactam 0.5 grams) for injection administered every 8 hours by intravenous (IV) infusion over 2 hours in patients 18 years of age and older with creatinine clearance (CrCl) greater than 50 mL/min. For treatment of Complicated Intra-abdominal Infections (cIAI), metronidazole should be given concurrently. Recommended duration of treatment: cIAI: 5 to 14 days, Complicated Urinary Tract Infections (cUTI) including pyelonephritis: 7 to 14 days.
Route of Administration: Intravenous
MICs of ceftazidime/AVE1330A(avibactam) for Enterobacteriaceae were at least eight-fold lower than those of ceftazidime alone. All of the Escherichia coli, Klebsiella pneumoniae, Citrobacter and Proteus mirabilis strains, including ceftazidime-resistant isolates, were inhibited at 4-8 mg/L. Only 2 mg/L were required to inhibit other Proteeae, Enterobacter, Salmonella and Serratia.
Name Type Language
AVIBACTAM
DASH   INN   MI   USAN   WHO-DD  
USAN   INN  
Official Name English
Avibactam [WHO-DD]
Common Name English
(1R,2S,5R)-7-OXO-6-SULFOOXY-1,6-DIAZABICYCLO(3.2.1)OCTANE-2-CARBOXAMIDE
Common Name English
ZAVICEFTA COMPONENT AVIBACTAM
Brand Name English
SULFURIC ACID, MONO((1R,2S,5R)-2-(AMINOCARBONYL)-7-OXO-1,6-DIAZABICYCLO(3.2.1)OCT-6-YL) ESTER
Common Name English
AVIBACTAM COMPONENT OF ZAVICEFTA
Brand Name English
NXL-104 FREE ACID
Code English
avibactam [INN]
Common Name English
AVIBACTAM [USAN]
Common Name English
AVIBACTAM [MI]
Common Name English
Classification Tree Code System Code
NDF-RT N0000175930
Created by admin on Fri Dec 15 20:13:18 GMT 2023 , Edited by admin on Fri Dec 15 20:13:18 GMT 2023
Code System Code Type Description
DRUG BANK
DB09060
Created by admin on Fri Dec 15 20:13:18 GMT 2023 , Edited by admin on Fri Dec 15 20:13:18 GMT 2023
PRIMARY
ChEMBL
CHEMBL1689063
Created by admin on Fri Dec 15 20:13:18 GMT 2023 , Edited by admin on Fri Dec 15 20:13:18 GMT 2023
PRIMARY
LACTMED
Ceftazidime and Avibactam
Created by admin on Fri Dec 15 20:13:18 GMT 2023 , Edited by admin on Fri Dec 15 20:13:18 GMT 2023
PRIMARY
WIKIPEDIA
Avibactam
Created by admin on Fri Dec 15 20:13:18 GMT 2023 , Edited by admin on Fri Dec 15 20:13:18 GMT 2023
PRIMARY
INN
8972
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PRIMARY
EVMPD
SUB72111
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PRIMARY
FDA UNII
7352665165
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PRIMARY
PUBCHEM
9835049
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PRIMARY
CAS
1192500-31-4
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PRIMARY
EPA CompTox
DTXSID901026066
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PRIMARY
NCI_THESAURUS
C171777
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PRIMARY
SMS_ID
100000135830
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PRIMARY
RXCUI
1603834
Created by admin on Fri Dec 15 20:13:18 GMT 2023 , Edited by admin on Fri Dec 15 20:13:18 GMT 2023
PRIMARY RxNorm
DAILYMED
7352665165
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PRIMARY
MERCK INDEX
m2148
Created by admin on Fri Dec 15 20:13:18 GMT 2023 , Edited by admin on Fri Dec 15 20:13:18 GMT 2023
PRIMARY Merck Index
DRUG CENTRAL
4946
Created by admin on Fri Dec 15 20:13:18 GMT 2023 , Edited by admin on Fri Dec 15 20:13:18 GMT 2023
PRIMARY