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Details

Stereochemistry ABSOLUTE
Molecular Formula C23H16O6.2C22H29N3O6S
Molecular Weight 1315.464
Optical Activity UNSPECIFIED
Defined Stereocenters 8 / 8
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PIVAMPICILLIN PAMOATE

SMILES

OC(=O)C1=CC2=C(C=CC=C2)C(CC3=C4C=CC=CC4=CC(C(O)=O)=C3O)=C1O.[H][C@]56SC(C)(C)[C@@H](N5C(=O)[C@H]6NC(=O)[C@H](N)C7=CC=CC=C7)C(=O)OCOC(=O)C(C)(C)C.[H][C@]89SC(C)(C)[C@@H](N8C(=O)[C@H]9NC(=O)[C@H](N)C%10=CC=CC=C%10)C(=O)OCOC(=O)C(C)(C)C

InChI

InChIKey=RYPIBFIQHKWKBM-WDPVPZODSA-N
InChI=1S/C23H16O6.2C22H29N3O6S/c24-20-16(14-7-3-1-5-12(14)9-18(20)22(26)27)11-17-15-8-4-2-6-13(15)10-19(21(17)25)23(28)29;2*1-21(2,3)20(29)31-11-30-19(28)15-22(4,5)32-18-14(17(27)25(15)18)24-16(26)13(23)12-9-7-6-8-10-12/h1-10,24-25H,11H2,(H,26,27)(H,28,29);2*6-10,13-15,18H,11,23H2,1-5H3,(H,24,26)/t;2*13-,14-,15+,18-/m.11/s1

HIDE SMILES / InChI
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
Hearing loss as a sequel to chloramphenicol and ampicillin treatment of Haemophilus influenzae meningitis.
1976
Tone audiometry control of children treated for meningitis with large intravenous doses of ampicillin.
1976 Nov
Fresh vs aged benzylpenicillin on non-IgE responses in mice.
1998 Jan
Immunologic response to different determinants of benzylpenicillin, amoxicillin, and ampicillin. Comparison between urticaria and anaphylactic shock.
1999 Sep
Protective effect of lafutidine against indomethacin-induced intestinal ulceration in rats: relation to capsaicin-sensitive sensory neurons.
2000
Ampicillin-resistant enterococci in a Swedish university hospital: nosocomial spread and risk factors for infection.
2001
Superantigen antagonist peptides.
2001
Effect of granulocyte-macrophage colony-stimulating factor on treatment of acute osteomyelitis. An experimental investigation in rats.
2001
The frequency of silencing in Arabidopsis thaliana varies highly between progeny of siblings and can be influenced by environmental factors.
2001
Enterobacter spp. infections complicating the course of HIV disease.
2001 Apr
Prevalence of penicillin-resistant Streptococcus pneumoniae in Kuwait.
2001 Apr
Antimicrobial resistance of Streptococcus pneumoniae at a university hospital in Saudi Arabia.
2001 Apr
The isolation and characterization of Campylobacter jejuni subsp. jejuni from domestic geese (Anser anser).
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
An outbreak of Salmonella enteritidis infection in pygmy hogs (Sus salvanius).
2001 Apr
Simultaneous determination of five beta-lactam antibiotics in bovine milk using liquid chromatography coupled with electrospray ionization tandem mass spectrometry.
2001 Apr 1
Spectrophotometric determination of ampicillin, dicluxacillin, flucloxacillin and amoxicillin antibiotic drugs: ion-pair formation with molybdenum and thiocyanate.
2001 Feb
Syntheses and hydrolysis of basic and dibasic ampicillin esters tailored for intracellular accumulation.
2001 Feb
Synergistic effect of gentamicin plus ampicillin on enterococci.
2001 Feb
Vibrio parahaemolyticus associated with cholera-like diarrhea among patients in North Jakarta, Indonesia.
2001 Feb
Incidence of beta-lactamase production and antimicrobial susceptibility of anaerobic gram-negative rods isolated from pus specimens of orofacial odontogenic infections.
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
Shigella and Salmonella strains isolated from children under 5 years in Gaborone, Botswana, and their antibiotic susceptibility patterns.
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
Salmonella typhimurium-endocarditis secondary to an acquired environmental infection: a case report.
2001 Jan
In vitro Gram-positive antimicrobial activity of evernimicin (SCH 27899), a novel oligosaccharide, compared with other antimicrobials: a multicentre international trial.
2001 Jan
In vivo application of biodegradable controlled antibiotic release systems for the treatment of implant-related osteomyelitis.
2001 Jan
A suicide-substrate mechanism for hydrolysis of beta-lactams by an anti-idiotypic catalytic antibody.
2001 Jan 26
[Prevalence of Moraxella catarrhalis colonization in asymptomatic carriers under 6 years of age].
2001 Jan-Feb
Charm Safe-Level beta-Lactam Test for amoxicillin, ampicillin, ceftiofur, cephapirin, and penicillin G in raw commingled milk.
2001 Jan-Feb
Standard case management of pneumonia in hospitalized children in Uruguay, 1997 to 1998.
2001 Mar
Screening method for identification of beta-lactams in bovine urine by use of liquid chromatography and a microbial inhibition test.
2001 Mar
Improved agar diffusion method for detecting residual antimicrobial agents.
2001 Mar
Chryseobacterium (Flavobacterium) meningosepticum outbreak associated with colonization of water taps in a neonatal intensive care unit.
2001 Mar
Antimicrobial resistance in salmonellae from humans, food and animals in Spain in 1998.
2001 Mar
Factors associated with antibiotic resistance in coliform organisms from community urinary tract infection in Wales.
2001 Mar
Serogroups and antimicrobial susceptibility among Escherichia coli isolated from farmed mink (Mustela vison Schreiber) in Denmark.
2001 Mar 20
Association between antibiotic resistance and the expression of Dr adhesin among uropathogenic Escherichia coli.
2001 Mar-Apr
Ureidopenicillins and risk of Clostridium difficile infection.
2001 May
Antibiotic resistance and antibiotic sensitivity based treatment in Helicobacter pylori infection: advantages and outcome.
2001 May
Ampicillin-resistant Escherichia coli in gestational pyelonephritis: increased occurrence and association with the colonization factor Dr adhesin.
2001 May 15
The ddcA gene from Streptomyces fradiae encodes an extracellular beta-lactamase with penicillinase and cephalosporinase activities.
2001 Nov 30
A multicenter study of the antimicrobial susceptibility of Haemophilus influenzae, Streptococcus pneumoniae, and Moraxella catarrhalis isolated from patients with community-acquired lower respiratory tract infections in 1999 in Portugal.
2001 Spring
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.
Name Type Language
PIVAMPICILLIN PAMOATE
USAN  
USAN  
Official 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-, (2,2-DIMETHYL-1-OXOPROPOXY)METHYL ESTER, (2S,5R,6R)-, 4,4'-METHYLENEBIS(3-HYDROXY-2-NAPHTHALENECARBOXYLATE) (2:1)
Systematic Name English
PIVAMPICILLIN PAMOATE [USAN]
Common Name English
HYDROXYMETHYL D-(-)-6-(2-AMINO-2-PHENYLACETAMIDO)-3,3-DIMETHYL-7-OXO-4-THIA-1-AZABICYCLO(3.2.0)HEPTANE-2-CARBOXYLATE PIVALATE (ESTER) COMPOUND WITH 4,4'-METHYLENEBIS(3-HYDROXY-2-NAPHTHOIC ACID) (2:1)
Common Name English
PIVAMPICILLIN EMBONATE
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C1500
Created by admin on Fri Dec 15 16:24:14 GMT 2023 , Edited by admin on Fri Dec 15 16:24:14 GMT 2023
Code System Code Type Description
CAS
39030-72-3
Created by admin on Fri Dec 15 16:24:14 GMT 2023 , Edited by admin on Fri Dec 15 16:24:14 GMT 2023
PRIMARY
FDA UNII
5Z5TRG74EY
Created by admin on Fri Dec 15 16:24:14 GMT 2023 , Edited by admin on Fri Dec 15 16:24:14 GMT 2023
PRIMARY
PUBCHEM
20055543
Created by admin on Fri Dec 15 16:24:14 GMT 2023 , Edited by admin on Fri Dec 15 16:24:14 GMT 2023
PRIMARY
ChEMBL
CHEMBL323354
Created by admin on Fri Dec 15 16:24:14 GMT 2023 , Edited by admin on Fri Dec 15 16:24:14 GMT 2023
PRIMARY
NCI_THESAURUS
C73835
Created by admin on Fri Dec 15 16:24:14 GMT 2023 , Edited by admin on Fri Dec 15 16:24:14 GMT 2023
PRIMARY