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Details

Stereochemistry ABSOLUTE
Molecular Formula C16H20N2.2C16H19N3O4S
Molecular Weight 939.153
Optical Activity UNSPECIFIED
Defined Stereocenters 8 / 8
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of AMPICILLIN BENZATHINE

SMILES

C(CNCC1=CC=CC=C1)NCC2=CC=CC=C2.[H][C@]34SC(C)(C)[C@@H](N3C(=O)[C@H]4NC(=O)[C@H](N)C5=CC=CC=C5)C(O)=O.[H][C@]67SC(C)(C)[C@@H](N6C(=O)[C@H]7NC(=O)[C@H](N)C8=CC=CC=C8)C(O)=O

InChI

InChIKey=RHKWJSNGCNASTF-PHGYPNQBSA-N
InChI=1S/2C16H19N3O4S.C16H20N2/c2*1-16(2)11(15(22)23)19-13(21)10(14(19)24-16)18-12(20)9(17)8-6-4-3-5-7-8;1-3-7-15(8-4-1)13-17-11-12-18-14-16-9-5-2-6-10-16/h2*3-7,9-11,14H,17H2,1-2H3,(H,18,20)(H,22,23);1-10,17-18H,11-14H2/t2*9-,10-,11+,14-;/m11./s1

HIDE SMILES / InChI

Molecular Formula C16H19N3O4S
Molecular Weight 349.405
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula C16H20N2
Molecular Weight 240.3434
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Ampicillin is a penicillin beta-lactam antibiotic. The following gram-negative and gram-positive bacteria have been shown in in vitro studies to be susceptible to ampicillin: Hemolytic and nonhemolytic streptococci, Streptococcus pneumoniae, Nonpenicillinase-producing staphylococci, Clostridium spp., B. anthracis, Listeria monocytogenes, most strains of enterococci, H. influenzae, N. gonorrhoeae, N. meningitidis, Proteus mirabilis, many strains of Salmonella, Shigella, and E. coli. Ampicillin is indicated in the treatment of bacterial meningitis, septicemia, endocarditis, urinary tract, gastrointestinal, respiratory tract infections caused by susceptible strains of the designated organisms.

CNS Activity

Curator's Comment: Ampicillin penetration into the cerebrospinal fluid and brain occurs only when the meninges are inflamed.

Originator

Sources: DOYLE, F.P., NAYLER, J.H.C. & SMITH, H. (1961). British Patent Specification No. 873049.
Curator's Comment: reference retrieved from https://www.ncbi.nlm.nih.gov/pubmed/13859205

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
AMPICILLIN SODIUM

Approved Use

Ampicillin is indicated in the treatment of bacterial meningitis, septicemia, endocarditis, urinary tract, gastrointestinal, respiratory tracti nfections caused by susceptible strains of bacteria (Hemolytic and nonhemolytic streptococci, Streptococcus pneumoniae, Nonpenicillinase-producing staphylococci, Clostridium spp., B. anthracis, Listeria monocytogenes, most strains of enterococci, H. influenzae, N. gonorrhoeae, N. meningitidis, Proteus mirabilis, many strains of Salmonella, Shigella, and E. coli.)
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
129.5 μg/mL
2000 mg single, intravenous
dose: 2000 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered: SULBACTAM
AMPICILLIN plasma
Homo sapiens
population: UNKNOWN
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
15.04 μg/mL
1500 mg single, oral
dose: 1500 mg
route of administration: Oral
experiment type: SINGLE
co-administered: PROBENECID
AMPICILLIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
58.74 μg × h/mL
1500 mg single, oral
dose: 1500 mg
route of administration: Oral
experiment type: SINGLE
co-administered: PROBENECID
AMPICILLIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
1 h
2000 mg single, intravenous
dose: 2000 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered: SULBACTAM
AMPICILLIN plasma
Homo sapiens
population: UNKNOWN
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
1.82 h
1500 mg single, oral
dose: 1500 mg
route of administration: Oral
experiment type: SINGLE
co-administered: PROBENECID
AMPICILLIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
72%
AMPICILLIN serum
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
650 mg 3 times / day multiple, intravenous (mean)
Studied dose
Dose: 650 mg, 3 times / day
Route: intravenous
Route: multiple
Dose: 650 mg, 3 times / day
Co-administed with::
Sulbactam(300-350 mg; 3/day)
Sources: Page: nda/pre96/050608Orig1s000rev.pdf - p.48
unhealthy, 11 to 18 months
n = 4
Health Status: unhealthy
Condition: acute pyelonephritis
Age Group: 11 to 18 months
Sex: M+F
Population Size: 4
Sources: Page: nda/pre96/050608Orig1s000rev.pdf - p.48
Disc. AE: Skin rash...
AEs leading to
discontinuation/dose reduction:
Skin rash (25%)
Sources: Page: nda/pre96/050608Orig1s000rev.pdf - p.48
5 g 3 times / day multiple, intravenous
Highest studied dose
Dose: 5 g, 3 times / day
Route: intravenous
Route: multiple
Dose: 5 g, 3 times / day
Co-administed with::
Sulbactam(500 mg; 3/day)
Sources: Page: nda/pre96/050608Orig1s000rev.pdf - p.161
unhealthy, adult
n = 9
Health Status: unhealthy
Condition: Bacterial infections
Age Group: adult
Sex: M+F
Population Size: 9
Sources: Page: nda/pre96/050608Orig1s000rev.pdf - p.161
Sources: Page: nda/pre96/050608Orig1s000rev.pdf - p.161
0.5 g 1 times / day single, intramuscular
Recommended
Dose: 0.5 g, 1 times / day
Route: intramuscular
Route: single
Dose: 0.5 g, 1 times / day
Sources: Page: nda/pre96/050608Orig1s000rev.pdf - p.36
healthy, adult
n = 12
Health Status: healthy
Age Group: adult
Sex: M
Population Size: 12
Sources: Page: nda/pre96/050608Orig1s000rev.pdf - p.36
Other AEs: Injection site pain...
Other AEs:
Injection site pain
Sources: Page: nda/pre96/050608Orig1s000rev.pdf - p.36
1 g 1 times / day single, intramuscular
Studied dose
Dose: 1 g, 1 times / day
Route: intramuscular
Route: single
Dose: 1 g, 1 times / day
Co-administed with::
Sulbactam(0.5 g; single dose)
Sources: Page: nda/pre96/050608Orig1s000rev.pdf - p.40
healthy, adult
n = 11
Health Status: healthy
Age Group: adult
Sex: M
Population Size: 11
Sources: Page: nda/pre96/050608Orig1s000rev.pdf - p.40
Other AEs: Injection site pain, Creatine phosphokinase increased...
Other AEs:
Injection site pain (grade 3-4, 100%)
Creatine phosphokinase increased (100%)
Sources: Page: nda/pre96/050608Orig1s000rev.pdf - p.40
2 g 1 times / day single, intramuscular
Studied dose
Dose: 2 g, 1 times / day
Route: intramuscular
Route: single
Dose: 2 g, 1 times / day
Co-administed with::
Sulbactam(1 g; single)
probenecid(1 g; single)
Sources: Page: nda/pre96/050608Orig1s000rev.pdf - p.160
unhealthy, mean age 25.8 years
n = 101
Health Status: unhealthy
Condition: Acute uncomplicated gonorrhea
Age Group: mean age 25.8 years
Sex: M+F
Population Size: 101
Sources: Page: nda/pre96/050608Orig1s000rev.pdf - p.160
Other AEs: Injection site pain, Rash...
Other AEs:
Injection site pain (1%)
Rash (1%)
Diarrhea (5%)
Fatigue (3%)
Chills (1%)
Headache (1%)
AST increased (3%)
Bilirubin increased (1%)
Creatinine increased (1%)
Sources: Page: nda/pre96/050608Orig1s000rev.pdf - p.160
2 g 3 times / day multiple, intravenous
Studied dose
Dose: 2 g, 3 times / day
Route: intravenous
Route: multiple
Dose: 2 g, 3 times / day
Co-administed with::
Sulbactam(1 g; 3/day)
Sources: Page: nda/pre96/050608Orig1s000rev.pdf - p.53
unhealthy, mean age 27.1 years
n = 21
Health Status: unhealthy
Condition: Endomyometritis
Age Group: mean age 27.1 years
Sex: F
Population Size: 21
Sources: Page: nda/pre96/050608Orig1s000rev.pdf - p.53
Other AEs: Chest pain, Flatulence...
Other AEs:
Chest pain (5%)
Flatulence (5%)
Diarrhea (10%)
Injection site pain (5%)
Sources: Page: nda/pre96/050608Orig1s000rev.pdf - p.53
2 g 3 times / day multiple, intravenous
Studied dose
Dose: 2 g, 3 times / day
Route: intravenous
Route: multiple
Dose: 2 g, 3 times / day
Co-administed with::
Sulbactam(1 g; 3/day)
Sources: Page: nda/pre96/050608Orig1s000rev.pdf - p.57
unhealthy, mean age 27.4 years
n = 131
Health Status: unhealthy
Condition: Peritonitis associated with appendicitis
Age Group: mean age 27.4 years
Sex: M+F
Population Size: 131
Sources: Page: nda/pre96/050608Orig1s000rev.pdf - p.57
Other AEs: Injection site pain, Phlebitis...
Other AEs:
Injection site pain (0.8%)
Phlebitis (5.3%)
Chest pain (0.8%)
Diarrhea (6.8%)
Vomiting (0.8%)
Retention of urine (0.8%)
Rash (0.8%)
Epistaxis (0.8%)
Edema (0.8%)
Sources: Page: nda/pre96/050608Orig1s000rev.pdf - p.57
2 g 3 times / day multiple, intravenous
Studied dose
Dose: 2 g, 3 times / day
Route: intravenous
Route: multiple
Dose: 2 g, 3 times / day
Co-administed with::
Sulbactam(1 g; 3/day)
Sources: Page: nda/pre96/050608Orig1s000rev.pdf - p.155
unhealthy, mean age 60.1 years
n = 15
Health Status: unhealthy
Condition: Pneumonia
Age Group: mean age 60.1 years
Sex: M+F
Population Size: 15
Sources: Page: nda/pre96/050608Orig1s000rev.pdf - p.155
Other AEs: Thrombophlebitis, Nausea...
Other AEs:
Thrombophlebitis (6.7%)
Nausea (6.7%)
Diarrhea (6.7%)
Rash (6.7%)
Blood eosinophils increased (6.7%)
AST increased (6.7%)
ALT increased (13.3%)
GGT increased (13.3%)
Alkaline phosphatase increased (6.7%)
Sources: Page: nda/pre96/050608Orig1s000rev.pdf - p.155
AEs

AEs

AESignificanceDosePopulation
Skin rash 25%
Disc. AE
650 mg 3 times / day multiple, intravenous (mean)
Studied dose
Dose: 650 mg, 3 times / day
Route: intravenous
Route: multiple
Dose: 650 mg, 3 times / day
Co-administed with::
Sulbactam(300-350 mg; 3/day)
Sources: Page: nda/pre96/050608Orig1s000rev.pdf - p.48
unhealthy, 11 to 18 months
n = 4
Health Status: unhealthy
Condition: acute pyelonephritis
Age Group: 11 to 18 months
Sex: M+F
Population Size: 4
Sources: Page: nda/pre96/050608Orig1s000rev.pdf - p.48
Injection site pain
0.5 g 1 times / day single, intramuscular
Recommended
Dose: 0.5 g, 1 times / day
Route: intramuscular
Route: single
Dose: 0.5 g, 1 times / day
Sources: Page: nda/pre96/050608Orig1s000rev.pdf - p.36
healthy, adult
n = 12
Health Status: healthy
Age Group: adult
Sex: M
Population Size: 12
Sources: Page: nda/pre96/050608Orig1s000rev.pdf - p.36
Creatine phosphokinase increased 100%
1 g 1 times / day single, intramuscular
Studied dose
Dose: 1 g, 1 times / day
Route: intramuscular
Route: single
Dose: 1 g, 1 times / day
Co-administed with::
Sulbactam(0.5 g; single dose)
Sources: Page: nda/pre96/050608Orig1s000rev.pdf - p.40
healthy, adult
n = 11
Health Status: healthy
Age Group: adult
Sex: M
Population Size: 11
Sources: Page: nda/pre96/050608Orig1s000rev.pdf - p.40
Injection site pain grade 3-4, 100%
1 g 1 times / day single, intramuscular
Studied dose
Dose: 1 g, 1 times / day
Route: intramuscular
Route: single
Dose: 1 g, 1 times / day
Co-administed with::
Sulbactam(0.5 g; single dose)
Sources: Page: nda/pre96/050608Orig1s000rev.pdf - p.40
healthy, adult
n = 11
Health Status: healthy
Age Group: adult
Sex: M
Population Size: 11
Sources: Page: nda/pre96/050608Orig1s000rev.pdf - p.40
Bilirubin increased 1%
2 g 1 times / day single, intramuscular
Studied dose
Dose: 2 g, 1 times / day
Route: intramuscular
Route: single
Dose: 2 g, 1 times / day
Co-administed with::
Sulbactam(1 g; single)
probenecid(1 g; single)
Sources: Page: nda/pre96/050608Orig1s000rev.pdf - p.160
unhealthy, mean age 25.8 years
n = 101
Health Status: unhealthy
Condition: Acute uncomplicated gonorrhea
Age Group: mean age 25.8 years
Sex: M+F
Population Size: 101
Sources: Page: nda/pre96/050608Orig1s000rev.pdf - p.160
Chills 1%
2 g 1 times / day single, intramuscular
Studied dose
Dose: 2 g, 1 times / day
Route: intramuscular
Route: single
Dose: 2 g, 1 times / day
Co-administed with::
Sulbactam(1 g; single)
probenecid(1 g; single)
Sources: Page: nda/pre96/050608Orig1s000rev.pdf - p.160
unhealthy, mean age 25.8 years
n = 101
Health Status: unhealthy
Condition: Acute uncomplicated gonorrhea
Age Group: mean age 25.8 years
Sex: M+F
Population Size: 101
Sources: Page: nda/pre96/050608Orig1s000rev.pdf - p.160
Creatinine increased 1%
2 g 1 times / day single, intramuscular
Studied dose
Dose: 2 g, 1 times / day
Route: intramuscular
Route: single
Dose: 2 g, 1 times / day
Co-administed with::
Sulbactam(1 g; single)
probenecid(1 g; single)
Sources: Page: nda/pre96/050608Orig1s000rev.pdf - p.160
unhealthy, mean age 25.8 years
n = 101
Health Status: unhealthy
Condition: Acute uncomplicated gonorrhea
Age Group: mean age 25.8 years
Sex: M+F
Population Size: 101
Sources: Page: nda/pre96/050608Orig1s000rev.pdf - p.160
Headache 1%
2 g 1 times / day single, intramuscular
Studied dose
Dose: 2 g, 1 times / day
Route: intramuscular
Route: single
Dose: 2 g, 1 times / day
Co-administed with::
Sulbactam(1 g; single)
probenecid(1 g; single)
Sources: Page: nda/pre96/050608Orig1s000rev.pdf - p.160
unhealthy, mean age 25.8 years
n = 101
Health Status: unhealthy
Condition: Acute uncomplicated gonorrhea
Age Group: mean age 25.8 years
Sex: M+F
Population Size: 101
Sources: Page: nda/pre96/050608Orig1s000rev.pdf - p.160
Injection site pain 1%
2 g 1 times / day single, intramuscular
Studied dose
Dose: 2 g, 1 times / day
Route: intramuscular
Route: single
Dose: 2 g, 1 times / day
Co-administed with::
Sulbactam(1 g; single)
probenecid(1 g; single)
Sources: Page: nda/pre96/050608Orig1s000rev.pdf - p.160
unhealthy, mean age 25.8 years
n = 101
Health Status: unhealthy
Condition: Acute uncomplicated gonorrhea
Age Group: mean age 25.8 years
Sex: M+F
Population Size: 101
Sources: Page: nda/pre96/050608Orig1s000rev.pdf - p.160
Rash 1%
2 g 1 times / day single, intramuscular
Studied dose
Dose: 2 g, 1 times / day
Route: intramuscular
Route: single
Dose: 2 g, 1 times / day
Co-administed with::
Sulbactam(1 g; single)
probenecid(1 g; single)
Sources: Page: nda/pre96/050608Orig1s000rev.pdf - p.160
unhealthy, mean age 25.8 years
n = 101
Health Status: unhealthy
Condition: Acute uncomplicated gonorrhea
Age Group: mean age 25.8 years
Sex: M+F
Population Size: 101
Sources: Page: nda/pre96/050608Orig1s000rev.pdf - p.160
AST increased 3%
2 g 1 times / day single, intramuscular
Studied dose
Dose: 2 g, 1 times / day
Route: intramuscular
Route: single
Dose: 2 g, 1 times / day
Co-administed with::
Sulbactam(1 g; single)
probenecid(1 g; single)
Sources: Page: nda/pre96/050608Orig1s000rev.pdf - p.160
unhealthy, mean age 25.8 years
n = 101
Health Status: unhealthy
Condition: Acute uncomplicated gonorrhea
Age Group: mean age 25.8 years
Sex: M+F
Population Size: 101
Sources: Page: nda/pre96/050608Orig1s000rev.pdf - p.160
Fatigue 3%
2 g 1 times / day single, intramuscular
Studied dose
Dose: 2 g, 1 times / day
Route: intramuscular
Route: single
Dose: 2 g, 1 times / day
Co-administed with::
Sulbactam(1 g; single)
probenecid(1 g; single)
Sources: Page: nda/pre96/050608Orig1s000rev.pdf - p.160
unhealthy, mean age 25.8 years
n = 101
Health Status: unhealthy
Condition: Acute uncomplicated gonorrhea
Age Group: mean age 25.8 years
Sex: M+F
Population Size: 101
Sources: Page: nda/pre96/050608Orig1s000rev.pdf - p.160
Diarrhea 5%
2 g 1 times / day single, intramuscular
Studied dose
Dose: 2 g, 1 times / day
Route: intramuscular
Route: single
Dose: 2 g, 1 times / day
Co-administed with::
Sulbactam(1 g; single)
probenecid(1 g; single)
Sources: Page: nda/pre96/050608Orig1s000rev.pdf - p.160
unhealthy, mean age 25.8 years
n = 101
Health Status: unhealthy
Condition: Acute uncomplicated gonorrhea
Age Group: mean age 25.8 years
Sex: M+F
Population Size: 101
Sources: Page: nda/pre96/050608Orig1s000rev.pdf - p.160
Diarrhea 10%
2 g 3 times / day multiple, intravenous
Studied dose
Dose: 2 g, 3 times / day
Route: intravenous
Route: multiple
Dose: 2 g, 3 times / day
Co-administed with::
Sulbactam(1 g; 3/day)
Sources: Page: nda/pre96/050608Orig1s000rev.pdf - p.53
unhealthy, mean age 27.1 years
n = 21
Health Status: unhealthy
Condition: Endomyometritis
Age Group: mean age 27.1 years
Sex: F
Population Size: 21
Sources: Page: nda/pre96/050608Orig1s000rev.pdf - p.53
Chest pain 5%
2 g 3 times / day multiple, intravenous
Studied dose
Dose: 2 g, 3 times / day
Route: intravenous
Route: multiple
Dose: 2 g, 3 times / day
Co-administed with::
Sulbactam(1 g; 3/day)
Sources: Page: nda/pre96/050608Orig1s000rev.pdf - p.53
unhealthy, mean age 27.1 years
n = 21
Health Status: unhealthy
Condition: Endomyometritis
Age Group: mean age 27.1 years
Sex: F
Population Size: 21
Sources: Page: nda/pre96/050608Orig1s000rev.pdf - p.53
Flatulence 5%
2 g 3 times / day multiple, intravenous
Studied dose
Dose: 2 g, 3 times / day
Route: intravenous
Route: multiple
Dose: 2 g, 3 times / day
Co-administed with::
Sulbactam(1 g; 3/day)
Sources: Page: nda/pre96/050608Orig1s000rev.pdf - p.53
unhealthy, mean age 27.1 years
n = 21
Health Status: unhealthy
Condition: Endomyometritis
Age Group: mean age 27.1 years
Sex: F
Population Size: 21
Sources: Page: nda/pre96/050608Orig1s000rev.pdf - p.53
Injection site pain 5%
2 g 3 times / day multiple, intravenous
Studied dose
Dose: 2 g, 3 times / day
Route: intravenous
Route: multiple
Dose: 2 g, 3 times / day
Co-administed with::
Sulbactam(1 g; 3/day)
Sources: Page: nda/pre96/050608Orig1s000rev.pdf - p.53
unhealthy, mean age 27.1 years
n = 21
Health Status: unhealthy
Condition: Endomyometritis
Age Group: mean age 27.1 years
Sex: F
Population Size: 21
Sources: Page: nda/pre96/050608Orig1s000rev.pdf - p.53
Chest pain 0.8%
2 g 3 times / day multiple, intravenous
Studied dose
Dose: 2 g, 3 times / day
Route: intravenous
Route: multiple
Dose: 2 g, 3 times / day
Co-administed with::
Sulbactam(1 g; 3/day)
Sources: Page: nda/pre96/050608Orig1s000rev.pdf - p.57
unhealthy, mean age 27.4 years
n = 131
Health Status: unhealthy
Condition: Peritonitis associated with appendicitis
Age Group: mean age 27.4 years
Sex: M+F
Population Size: 131
Sources: Page: nda/pre96/050608Orig1s000rev.pdf - p.57
Edema 0.8%
2 g 3 times / day multiple, intravenous
Studied dose
Dose: 2 g, 3 times / day
Route: intravenous
Route: multiple
Dose: 2 g, 3 times / day
Co-administed with::
Sulbactam(1 g; 3/day)
Sources: Page: nda/pre96/050608Orig1s000rev.pdf - p.57
unhealthy, mean age 27.4 years
n = 131
Health Status: unhealthy
Condition: Peritonitis associated with appendicitis
Age Group: mean age 27.4 years
Sex: M+F
Population Size: 131
Sources: Page: nda/pre96/050608Orig1s000rev.pdf - p.57
Epistaxis 0.8%
2 g 3 times / day multiple, intravenous
Studied dose
Dose: 2 g, 3 times / day
Route: intravenous
Route: multiple
Dose: 2 g, 3 times / day
Co-administed with::
Sulbactam(1 g; 3/day)
Sources: Page: nda/pre96/050608Orig1s000rev.pdf - p.57
unhealthy, mean age 27.4 years
n = 131
Health Status: unhealthy
Condition: Peritonitis associated with appendicitis
Age Group: mean age 27.4 years
Sex: M+F
Population Size: 131
Sources: Page: nda/pre96/050608Orig1s000rev.pdf - p.57
Injection site pain 0.8%
2 g 3 times / day multiple, intravenous
Studied dose
Dose: 2 g, 3 times / day
Route: intravenous
Route: multiple
Dose: 2 g, 3 times / day
Co-administed with::
Sulbactam(1 g; 3/day)
Sources: Page: nda/pre96/050608Orig1s000rev.pdf - p.57
unhealthy, mean age 27.4 years
n = 131
Health Status: unhealthy
Condition: Peritonitis associated with appendicitis
Age Group: mean age 27.4 years
Sex: M+F
Population Size: 131
Sources: Page: nda/pre96/050608Orig1s000rev.pdf - p.57
Rash 0.8%
2 g 3 times / day multiple, intravenous
Studied dose
Dose: 2 g, 3 times / day
Route: intravenous
Route: multiple
Dose: 2 g, 3 times / day
Co-administed with::
Sulbactam(1 g; 3/day)
Sources: Page: nda/pre96/050608Orig1s000rev.pdf - p.57
unhealthy, mean age 27.4 years
n = 131
Health Status: unhealthy
Condition: Peritonitis associated with appendicitis
Age Group: mean age 27.4 years
Sex: M+F
Population Size: 131
Sources: Page: nda/pre96/050608Orig1s000rev.pdf - p.57
Retention of urine 0.8%
2 g 3 times / day multiple, intravenous
Studied dose
Dose: 2 g, 3 times / day
Route: intravenous
Route: multiple
Dose: 2 g, 3 times / day
Co-administed with::
Sulbactam(1 g; 3/day)
Sources: Page: nda/pre96/050608Orig1s000rev.pdf - p.57
unhealthy, mean age 27.4 years
n = 131
Health Status: unhealthy
Condition: Peritonitis associated with appendicitis
Age Group: mean age 27.4 years
Sex: M+F
Population Size: 131
Sources: Page: nda/pre96/050608Orig1s000rev.pdf - p.57
Vomiting 0.8%
2 g 3 times / day multiple, intravenous
Studied dose
Dose: 2 g, 3 times / day
Route: intravenous
Route: multiple
Dose: 2 g, 3 times / day
Co-administed with::
Sulbactam(1 g; 3/day)
Sources: Page: nda/pre96/050608Orig1s000rev.pdf - p.57
unhealthy, mean age 27.4 years
n = 131
Health Status: unhealthy
Condition: Peritonitis associated with appendicitis
Age Group: mean age 27.4 years
Sex: M+F
Population Size: 131
Sources: Page: nda/pre96/050608Orig1s000rev.pdf - p.57
Phlebitis 5.3%
2 g 3 times / day multiple, intravenous
Studied dose
Dose: 2 g, 3 times / day
Route: intravenous
Route: multiple
Dose: 2 g, 3 times / day
Co-administed with::
Sulbactam(1 g; 3/day)
Sources: Page: nda/pre96/050608Orig1s000rev.pdf - p.57
unhealthy, mean age 27.4 years
n = 131
Health Status: unhealthy
Condition: Peritonitis associated with appendicitis
Age Group: mean age 27.4 years
Sex: M+F
Population Size: 131
Sources: Page: nda/pre96/050608Orig1s000rev.pdf - p.57
Diarrhea 6.8%
2 g 3 times / day multiple, intravenous
Studied dose
Dose: 2 g, 3 times / day
Route: intravenous
Route: multiple
Dose: 2 g, 3 times / day
Co-administed with::
Sulbactam(1 g; 3/day)
Sources: Page: nda/pre96/050608Orig1s000rev.pdf - p.57
unhealthy, mean age 27.4 years
n = 131
Health Status: unhealthy
Condition: Peritonitis associated with appendicitis
Age Group: mean age 27.4 years
Sex: M+F
Population Size: 131
Sources: Page: nda/pre96/050608Orig1s000rev.pdf - p.57
ALT increased 13.3%
2 g 3 times / day multiple, intravenous
Studied dose
Dose: 2 g, 3 times / day
Route: intravenous
Route: multiple
Dose: 2 g, 3 times / day
Co-administed with::
Sulbactam(1 g; 3/day)
Sources: Page: nda/pre96/050608Orig1s000rev.pdf - p.155
unhealthy, mean age 60.1 years
n = 15
Health Status: unhealthy
Condition: Pneumonia
Age Group: mean age 60.1 years
Sex: M+F
Population Size: 15
Sources: Page: nda/pre96/050608Orig1s000rev.pdf - p.155
GGT increased 13.3%
2 g 3 times / day multiple, intravenous
Studied dose
Dose: 2 g, 3 times / day
Route: intravenous
Route: multiple
Dose: 2 g, 3 times / day
Co-administed with::
Sulbactam(1 g; 3/day)
Sources: Page: nda/pre96/050608Orig1s000rev.pdf - p.155
unhealthy, mean age 60.1 years
n = 15
Health Status: unhealthy
Condition: Pneumonia
Age Group: mean age 60.1 years
Sex: M+F
Population Size: 15
Sources: Page: nda/pre96/050608Orig1s000rev.pdf - p.155
AST increased 6.7%
2 g 3 times / day multiple, intravenous
Studied dose
Dose: 2 g, 3 times / day
Route: intravenous
Route: multiple
Dose: 2 g, 3 times / day
Co-administed with::
Sulbactam(1 g; 3/day)
Sources: Page: nda/pre96/050608Orig1s000rev.pdf - p.155
unhealthy, mean age 60.1 years
n = 15
Health Status: unhealthy
Condition: Pneumonia
Age Group: mean age 60.1 years
Sex: M+F
Population Size: 15
Sources: Page: nda/pre96/050608Orig1s000rev.pdf - p.155
Alkaline phosphatase increased 6.7%
2 g 3 times / day multiple, intravenous
Studied dose
Dose: 2 g, 3 times / day
Route: intravenous
Route: multiple
Dose: 2 g, 3 times / day
Co-administed with::
Sulbactam(1 g; 3/day)
Sources: Page: nda/pre96/050608Orig1s000rev.pdf - p.155
unhealthy, mean age 60.1 years
n = 15
Health Status: unhealthy
Condition: Pneumonia
Age Group: mean age 60.1 years
Sex: M+F
Population Size: 15
Sources: Page: nda/pre96/050608Orig1s000rev.pdf - p.155
Blood eosinophils increased 6.7%
2 g 3 times / day multiple, intravenous
Studied dose
Dose: 2 g, 3 times / day
Route: intravenous
Route: multiple
Dose: 2 g, 3 times / day
Co-administed with::
Sulbactam(1 g; 3/day)
Sources: Page: nda/pre96/050608Orig1s000rev.pdf - p.155
unhealthy, mean age 60.1 years
n = 15
Health Status: unhealthy
Condition: Pneumonia
Age Group: mean age 60.1 years
Sex: M+F
Population Size: 15
Sources: Page: nda/pre96/050608Orig1s000rev.pdf - p.155
Diarrhea 6.7%
2 g 3 times / day multiple, intravenous
Studied dose
Dose: 2 g, 3 times / day
Route: intravenous
Route: multiple
Dose: 2 g, 3 times / day
Co-administed with::
Sulbactam(1 g; 3/day)
Sources: Page: nda/pre96/050608Orig1s000rev.pdf - p.155
unhealthy, mean age 60.1 years
n = 15
Health Status: unhealthy
Condition: Pneumonia
Age Group: mean age 60.1 years
Sex: M+F
Population Size: 15
Sources: Page: nda/pre96/050608Orig1s000rev.pdf - p.155
Nausea 6.7%
2 g 3 times / day multiple, intravenous
Studied dose
Dose: 2 g, 3 times / day
Route: intravenous
Route: multiple
Dose: 2 g, 3 times / day
Co-administed with::
Sulbactam(1 g; 3/day)
Sources: Page: nda/pre96/050608Orig1s000rev.pdf - p.155
unhealthy, mean age 60.1 years
n = 15
Health Status: unhealthy
Condition: Pneumonia
Age Group: mean age 60.1 years
Sex: M+F
Population Size: 15
Sources: Page: nda/pre96/050608Orig1s000rev.pdf - p.155
Rash 6.7%
2 g 3 times / day multiple, intravenous
Studied dose
Dose: 2 g, 3 times / day
Route: intravenous
Route: multiple
Dose: 2 g, 3 times / day
Co-administed with::
Sulbactam(1 g; 3/day)
Sources: Page: nda/pre96/050608Orig1s000rev.pdf - p.155
unhealthy, mean age 60.1 years
n = 15
Health Status: unhealthy
Condition: Pneumonia
Age Group: mean age 60.1 years
Sex: M+F
Population Size: 15
Sources: Page: nda/pre96/050608Orig1s000rev.pdf - p.155
Thrombophlebitis 6.7%
2 g 3 times / day multiple, intravenous
Studied dose
Dose: 2 g, 3 times / day
Route: intravenous
Route: multiple
Dose: 2 g, 3 times / day
Co-administed with::
Sulbactam(1 g; 3/day)
Sources: Page: nda/pre96/050608Orig1s000rev.pdf - p.155
unhealthy, mean age 60.1 years
n = 15
Health Status: unhealthy
Condition: Pneumonia
Age Group: mean age 60.1 years
Sex: M+F
Population Size: 15
Sources: Page: nda/pre96/050608Orig1s000rev.pdf - p.155
PubMed

PubMed

TitleDatePubMed
Therapeutic efficacy of tobramycin--a clinical and laboratory evaluation.
1975 Dec
Ampicillin-resistant enterococci in a Swedish university hospital: nosocomial spread and risk factors for infection.
2001
Superantigen antagonist peptides.
2001
The frequency of silencing in Arabidopsis thaliana varies highly between progeny of siblings and can be influenced by environmental factors.
2001
Effectiveness of specific RNA-mediated interference through ingested double-stranded RNA in Caenorhabditis elegans.
2001
Antibiotic resistance among Listeria, including Listeria monocytogenes, in retail foods.
2001 Apr
[Clinical characteristics of beta-lactamase negative ampicillin resistant Haemophilus influenzae (BLNAR) in respiratory tract].
2001 Apr
[Combination therapy against vancomycin-resistant enterococci].
2001 Apr
[Beta-lactamase negative ampicillin-resistant Haemophilus influenzae(BLNAR)].
2001 Apr
[Beta-lactam and macrolide resistance in Streptococcus pneumoniae].
2001 Apr
[Vancomycin-resistant enterococci(VRE)].
2001 Apr
Use of antibiotics to treat bacteriuria of pregnancy in the Nordic countries. Which antibiotics are appropriate to treat bacteriuria of pregnancy?
2001 Apr
Isolation and identification of bacteria associated with adult laboratory Mexican fruit flies, Anastrepha ludens (Diptera: Tephritidae).
2001 Apr
Enterococcus faecalis resistant to vancomycin and teicoplanin (VanA phenotype) isolated from a bone marrow transplanted patient in Brazil.
2001 Feb
Multicenter evaluation of resistance patterns of Klebsiella pneumoniae, Escherichia coli, Salmonella spp and Shigella spp isolated from clinical specimens in Brazil: RESISTNET Surveillance Program.
2001 Feb
Spectrophotometric determination of ampicillin, dicluxacillin, flucloxacillin and amoxicillin antibiotic drugs: ion-pair formation with molybdenum and thiocyanate.
2001 Feb
An unusual blood culture isolate in a 15-year-old boy.
2001 Feb
Resistance patterns of non-O157 Shiga toxin-producing Escherichia coli (STEC) strains isolated from animals, food and asymptomatic human carriers in Switzerland.
2001 Feb
[Streptococcus gallolyticus infections in racing pigeons, a literature review].
2001 Feb 1
Clostridium difficile--Associated diarrhea: A review.
2001 Feb 26
Immunization with plasmid DNA expressing the caprine arthritis-encephalitis virus envelope gene: quantitative and qualitative aspects of antibody response to viral surface glycoprotein.
2001 Feb 8
Synthesis and properties of dextran-linked ampicillin.
2001 Jan
Antibiotic susceptibilities among recent clinical isolates of Haemophilus influenzae and Moraxella catarrhalis from fifteen countries.
2001 Jan
Meropenem in neonatal severe infections due to multiresistant gram-negative bacteria.
2001 Jan
Fetal and neonatal death from maternally acquired infection.
2001 Jan
Carboxydobrachium pacificum gen. nov., sp. nov., a new anaerobic, thermophilic, CO-utilizing marine bacterium from Okinawa Trough.
2001 Jan
Salmonella typhimurium-endocarditis secondary to an acquired environmental infection: a case report.
2001 Jan
Adhesion to a polymeric biomaterial affects the antibiotic resistance of Staphylococcus epidermidis.
2001 Jan
Urinary tract infections in pregnancy.
2001 Jan
Effect of single-dose prophylactic ampicillin and sulbactam on wound infection after tension-free inguinal hernia repair with polypropylene mesh: the randomized, double-blind, prospective trial.
2001 Jan
In vivo application of biodegradable controlled antibiotic release systems for the treatment of implant-related osteomyelitis.
2001 Jan
Topological analysis of DctQ, the small integral membrane protein of the C4-dicarboxylate TRAP transporter of Rhodobacter capsulatus.
2001 Jan 1
The plasmid pcDNA3 differentially induces production of interferon-alpha and interleukin-6 in cultures of porcine leukocytes.
2001 Jan 10
A suicide-substrate mechanism for hydrolysis of beta-lactams by an anti-idiotypic catalytic antibody.
2001 Jan 26
Influence of ampicillin, ceftiofur, attenuated live PRRSV vaccine, and reduced dose Streptococcus suis exposure on disease associated with PRRSV and S. suis coinfection.
2001 Jan 5
Study of the in vitro activity of amoxicillin/clavulanic acid and other beta-lactam antibiotics against Escherichia coli isolated from urine specimens.
2001 Jan-Feb
[Immunocorrecting and protective effect of proteolytic enzymes on antibody formation in mice in staphylococcal infection and antibiotic treatment].
2001 Jan-Feb
Charm Safe-Level beta-Lactam Test for amoxicillin, ampicillin, ceftiofur, cephapirin, and penicillin G in raw commingled milk.
2001 Jan-Feb
Acinetobacter infections in patients with human immunodeficiency virus infection: microbiological and clinical epidemiology.
2001 Jan-Feb
Sepsis and multiple brain abscesses caused by Salmonella paratyphi B in an infant: successful treatment with sulbactam-ampicillin and surgical drainage.
2001 Jan-Mar
Standard case management of pneumonia in hospitalized children in Uruguay, 1997 to 1998.
2001 Mar
Antibiotic-resistant bacteria in pediatric chronic sinusitis.
2001 Mar
Neonatal sepsis and mortality in a regional hospital in Trinidad: aetiology and risk factors.
2001 Mar
Use of automated riboprinter and pulsed-field gel electrophoresis for epidemiological studies of invasive Haemophilus influenzae in Taiwan.
2001 Mar
Antimicrobial resistance in salmonellae from humans, food and animals in Spain in 1998.
2001 Mar
Serogroups and antimicrobial susceptibility among Escherichia coli isolated from farmed mink (Mustela vison Schreiber) in Denmark.
2001 Mar 20
Emergence of vancomycin-resistant enterococci.
2001 Mar-Apr
Association between antibiotic resistance and the expression of Dr adhesin among uropathogenic Escherichia coli.
2001 Mar-Apr
Carriage of antibiotic-resistant bacteria by healthy children.
2001 May
The ddcA gene from Streptomyces fradiae encodes an extracellular beta-lactamase with penicillinase and cephalosporinase activities.
2001 Nov 30
Patents

Patents

Sample Use Guides

In Vivo Use Guide
Ampicillin Dosage and Administration This insert is for a Pharmacy Bulk Package and is intended for preparing IV admixtures only. Dosage recommendations for intramuscular or direct intravenous injection are for informational purposes only. Infections of the respiratory tract and soft tissues. Patients weighing 40 kg (88 lbs) or more: 250 to 500 mg every 6 hours. Patients weighing less than 40 kg (88 lbs): 25 to 50 mg/kg/day in equally divided doses at 6- to 8- hour intervals. Infections of the gastrointestinal and genitourinary tracts (including those caused by Neisseria gonorrhoeae in females). Patients weighing 40 kg (88 lbs) or more: 500 mg every 6 hours. Patients weighing less than 40 kg (88 lbs): 50 mg/kg/day in equally divided doses at 6- to 8- hour intervals. In the treatment of chronic urinary tract and intestinal infections, frequent bacteriological and clinical appraisal is necessary. Smaller doses than those recommended above should not be used. Higher doses should be used for stubborn or severe infections. In stubborn infections, therapy may be required for several weeks. It may be necessary to continue clinical and/or bacteriological follow-up for several months after cessation of therapy. Urethritis in males due to N. gonorrhoeae. Adults – Two doses of 500 mg each at an interval of 8 to 12 hours. Treatment may be repeated if necessary or extended if required. In the treatment of complications of gonorrheal urethritis, such as prostatitis and epididymitis, prolonged and intensive therapy is recommended. Cases of gonorrhea with a suspected primary lesion of syphilis should have darkfield examinations before receiving treatment. In all other cases where concomitant syphilis is suspected, monthly serological tests should be made for a minimum of four months. The doses for the preceding infections may be given by either the intramuscular or intravenous route. A change to oral Ampicillin may be made when appropriate. Bacterial Meningitis Adults and children – 150 to 200 mg/kg/day in equally divided doses every 3 to 4 hours. (Treatment may be initiated with intravenous drip therapy and continued with intramuscular injections.) The doses for other infections may be given by either the intravenous or intramuscular route. Septicemia Adults and children – 150 to 200 mg/kg/day. Start with intravenous administration for at least three days and continue with the intramuscular route every 3 to 4 hours. Treatment of all infections should be continued for a minimum of 48 to 72 hours beyond the time that the patient becomes asymptomatic or evidence of bacterial eradication has been obtained. A minimum of 10-days treatment is recommended for any infection caused by Group A beta-hemolytic streptococci to help prevent the occurrence of acute rheumatic fever or acute glomerulonephritis.
Route of Administration: Other
Ampicillin was tested in vitro for antibacterial activity against 673 clinical isolates of Gram-negative bacilli and Streptococcus faecalis. Taking the group of 673 isolates tested as a whole, 448 (67 %) were inhibited by ampicillin at a concentration of 5 ug/ml.
Substance Class Chemical
Created
by admin
on Fri Dec 15 17:09:18 GMT 2023
Edited
by admin
on Fri Dec 15 17:09:18 GMT 2023
Record UNII
E1TD7AM884
Record Status Validated (UNII)
Record Version
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Name Type Language
AMPICILLIN BENZATHINE
WHO-DD  
Common Name English
4-THIA-1-AZABICYCLO(3.2.0)HEPTANE-2-CARBOXYLIC ACID, 6-(((2R)-AMINOPHENYLACETYL)AMINO)-3,3-DIMETHYL-7-OXO-, (2S,5R,6R)-, COMPD WITH N,N'-BIS(PHENYLMETHYL)-1,2-ETHANEDIAMINE (2:1)
Common Name English
AMPICILLIN N,N'-DIBENZYLETHYLENEDIAMINE SALT
Common Name English
BENZATHINE AMPICILLIN
Common Name English
4-THIA-1-AZABICYCLO(3.2.0)HEPTANE-2-CARBOXYLIC ACID, 6-(((2R)-2-AMINO-2-PHENYLACETYL)AMINO)-3,3-DIMETHYL-7-OXO-, (2S,5R,6R)-, COMPD. WITH N,N'-BIS(PHENYLMETHYL)-1,2-ETHANEDIAMINE (2:1)
Common Name English
Ampicillin benzathine [WHO-DD]
Common Name English
Code System Code Type Description
EVMPD
SUB00506MIG
Created by admin on Fri Dec 15 17:09:18 GMT 2023 , Edited by admin on Fri Dec 15 17:09:18 GMT 2023
PRIMARY
FDA UNII
E1TD7AM884
Created by admin on Fri Dec 15 17:09:18 GMT 2023 , Edited by admin on Fri Dec 15 17:09:18 GMT 2023
PRIMARY
CAS
33276-75-4
Created by admin on Fri Dec 15 17:09:18 GMT 2023 , Edited by admin on Fri Dec 15 17:09:18 GMT 2023
PRIMARY
PUBCHEM
94447
Created by admin on Fri Dec 15 17:09:18 GMT 2023 , Edited by admin on Fri Dec 15 17:09:18 GMT 2023
PRIMARY
CHEBI
51343
Created by admin on Fri Dec 15 17:09:18 GMT 2023 , Edited by admin on Fri Dec 15 17:09:18 GMT 2023
PRIMARY
ECHA (EC/EINECS)
251-438-6
Created by admin on Fri Dec 15 17:09:18 GMT 2023 , Edited by admin on Fri Dec 15 17:09:18 GMT 2023
PRIMARY
SMS_ID
100000085161
Created by admin on Fri Dec 15 17:09:18 GMT 2023 , Edited by admin on Fri Dec 15 17:09:18 GMT 2023
PRIMARY
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