Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C16H19N3O4S |
Molecular Weight | 349.405 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 4 / 4 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)[C@H](N)C3=CC=CC=C3)C(O)=O
InChI
InChIKey=AVKUERGKIZMTKX-NJBDSQKTSA-N
InChI=1S/C16H19N3O4S/c1-16(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/h3-7,9-11,14H,17H2,1-2H3,(H,18,20)(H,22,23)/t9-,10-,11+,14-/m1/s1
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 |
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.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2354204 |
|||
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Curative | AMPICILLIN SODIUM Approved UseAmpicillin 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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/20399996 |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
58.74 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/20399996 |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/20399996 |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
72% |
AMPICILLIN serum | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse 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%) Sources: Page: nda/pre96/050608Orig1s000rev.pdf - p.40Creatine phosphokinase increased (100%) |
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) Sources: Page: nda/pre96/050608Orig1s000rev.pdf - p.160probenecid(1 g; single) |
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%) Sources: Page: nda/pre96/050608Orig1s000rev.pdf - p.160Rash (1%) Diarrhea (5%) Fatigue (3%) Chills (1%) Headache (1%) AST increased (3%) Bilirubin increased (1%) Creatinine increased (1%) |
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%) Sources: Page: nda/pre96/050608Orig1s000rev.pdf - p.53Flatulence (5%) Diarrhea (10%) 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.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%) Sources: Page: nda/pre96/050608Orig1s000rev.pdf - p.57Phlebitis (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%) |
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%) Sources: Page: nda/pre96/050608Orig1s000rev.pdf - p.155Nausea (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%) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
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) Sources: Page: nda/pre96/050608Orig1s000rev.pdf - p.160probenecid(1 g; single) |
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) Sources: Page: nda/pre96/050608Orig1s000rev.pdf - p.160probenecid(1 g; single) |
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) Sources: Page: nda/pre96/050608Orig1s000rev.pdf - p.160probenecid(1 g; single) |
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) Sources: Page: nda/pre96/050608Orig1s000rev.pdf - p.160probenecid(1 g; single) |
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) Sources: Page: nda/pre96/050608Orig1s000rev.pdf - p.160probenecid(1 g; single) |
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) Sources: Page: nda/pre96/050608Orig1s000rev.pdf - p.160probenecid(1 g; single) |
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) Sources: Page: nda/pre96/050608Orig1s000rev.pdf - p.160probenecid(1 g; single) |
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) Sources: Page: nda/pre96/050608Orig1s000rev.pdf - p.160probenecid(1 g; single) |
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) Sources: Page: nda/pre96/050608Orig1s000rev.pdf - p.160probenecid(1 g; single) |
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 |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 1.0 |
no | |||
Page: 1.0 |
no | |||
Page: 1.0 |
no | |||
Page: 1.0 |
no | |||
Page: 1.0 |
no | |||
Page: 1.0 |
no | |||
Page: 1.0 |
no | |||
Page: 1.0 |
no | |||
Page: 2.0 |
yes [Inhibition 1000 uM] |
PubMed
Title | Date | PubMed |
---|---|---|
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 |
|
[Achromobacter xylosoxidans bacteremia in a patient with community-acquired pneumonia]. | 2001 |
|
Effect of granulocyte-macrophage colony-stimulating factor on treatment of acute osteomyelitis. An experimental investigation in rats. | 2001 |
|
Bilateral femoral osteomyelitis with knee arthritis due to Salmonella enteritidis in a patient with systemic lupus erythematosus. | 2001 |
|
Prevalence of penicillin-resistant Streptococcus pneumoniae in Kuwait. | 2001 Apr |
|
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 |
|
An outbreak of Salmonella enteritidis infection in pygmy hogs (Sus salvanius). | 2001 Apr |
|
Isolation and identification of bacteria associated with adult laboratory Mexican fruit flies, Anastrepha ludens (Diptera: Tephritidae). | 2001 Apr |
|
Serogroups and antimicrobial susceptibility of non-typhoidal salmonellas in children. | 2001 Feb |
|
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 |
|
Epidemiology, resistance, and outcomes of Acinetobacter baumannii bacteremia treated with imipenem-cilastatin or ampicillin-sulbactam. | 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 |
|
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 |
|
Adhesion to a polymeric biomaterial affects the antibiotic resistance of Staphylococcus epidermidis. | 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 |
|
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 |
|
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 |
|
[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 |
|
Acinetobacter infections in patients with human immunodeficiency virus infection: microbiological and clinical epidemiology. | 2001 Jan-Feb |
|
Antibiotic-resistant bacteria in pediatric chronic sinusitis. | 2001 Mar |
|
Antimicrobial resistance of Enterococci in Lebanon. | 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 |
|
Expanding the genetic code: selection of efficient suppressors of four-base codons and identification of "shifty" four-base codons with a library approach in Escherichia coli. | 2001 Mar 30 |
|
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 |
|
Molecular epidemiology and mutations at gyrA and parC genes of ciprofloxacin-resistant Escherichia coli isolates from a Taiwan medical center. | 2001 Spring |
|
In vitro activity of 19 antimicrobial agents against enterococci from healthy subjects and hospitalized patients and use of an ace gene probe from Enterococcus faecalis for species identification. | 2001 Spring |
|
Variation in clonality and antibiotic-resistance genes among multiresistant Salmonella enterica serotype typhimurium phage-type U302 (MR U302) from humans, animals, and foods. | 2001 Spring |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.drugs.com/pro/ampicillin.html
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/14195635
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
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on
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Record UNII |
7C782967RD
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Record Status |
Validated (UNII)
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Classification Tree | Code System | Code | ||
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NDF-RT |
N0000011281
Created by
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WHO-VATC |
QJ51RC20
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CFR |
21 CFR 522.90
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LIVERTOX |
NBK547894
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NDF-RT |
N0000011281
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NDF-RT |
N0000011281
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WHO-ATC |
J01CR01
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WHO-VATC |
QJ51CA51
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NDF-RT |
N0000011281
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WHO-VATC |
QJ51CA01
Created by
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CFR |
21 CFR 520.90E
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NCI_THESAURUS |
C1500
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WHO-VATC |
QJ01CR01
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WHO-VATC |
QJ51CR01
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NDF-RT |
N0000175497
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WHO-ATC |
J01CA51
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NDF-RT |
N0000011281
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CFR |
21 CFR 520.90B
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WHO-VATC |
QG51AG04
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WHO-VATC |
QJ01CA01
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WHO-VATC |
QJ01CA51
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CFR |
21 CFR 520.90F
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WHO-ATC |
S01AA19
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NDF-RT |
N0000011281
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IARC | Ampicillin | ||
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WHO-VATC |
QS01AA19
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NDF-RT |
N0000011281
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CFR |
21 CFR 556.40
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WHO-VATC |
QG51AG05
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WHO-ESSENTIAL MEDICINES LIST |
6.2.1
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CFR |
21 CFR 520.90
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CFR |
21 CFR 520.90D
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NDF-RT |
N0000011281
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NDF-RT |
N0000011281
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WHO-ATC |
J01CA01
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WHO-VATC |
QG51AG07
Created by
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CFR |
21 CFR 520.90C
Created by
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Code System | Code | Type | Description | ||
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SUB05487MIG
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PRIMARY | |||
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C239
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PRIMARY | |||
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AMPICILLIN
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PRIMARY | |||
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AMPICILLIN
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PRIMARY | Description: A white or almost white, crystalline powder; odourless or almost odourless. Solubility: Slightly soluble in water; practically insoluble in ethanol (~750 g/l) TS and ether R. Category: Antibiotic. Storage: Ampicillin should be kept in a tightly closed container, protected from light. Labelling: The designation on the container of Ampicillin should state whether the substance is in the anhydrous form or is the trihydrate. Additional information: Even in the absence of light, Ampicillin is gradually degraded on exposure to a humid atmosphere, the decomposition being faster at higher temperatures. Definition: Ampicillin contains not less than 95.0% and not more than 102.0% of C16H19N3O4S, calculated with reference to the anhydrous substance. | ||
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Ampicillin
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PRIMARY | |||
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31209
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221058
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DB00415
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198
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SUB11710MIG
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DTXSID4022602
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1033000
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PRIMARY | |||
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D000667
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PRIMARY | |||
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7C782967RD
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PRIMARY | |||
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Ampicillin and Sulbactam
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PRIMARY | |||
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733
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ALTERNATIVE | |||
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6249
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PRIMARY | |||
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100000092323
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200-709-7
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7C782967RD
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28971
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528986
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m1853
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PRIMARY | Merck Index | ||
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CHEMBL174
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3009
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1339
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69-53-4
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PRIMARY |
Related Record | Type | Details | ||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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TRANSPORTER -> SUBSTRATE | |||
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BINDER->LIGAND |
BINDING
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||
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (HPLC)
EP
|
||
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SALT/SOLVATE -> PARENT | |||
|
BASIS OF STRENGTH->SUBSTANCE |
Ampicillin is anhydrous or contains three molecules of water of hydration
ASSAY (HPLC)
USP
|
||
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SALT/SOLVATE -> PARENT | |||
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ENZYME->SUBSTRATE |
Leads to resistance to the antibiotic.
|
||
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PARENT -> DEGRADENT | |||
|
SOLVATE->ANHYDROUS | |||
|
SALT/SOLVATE -> PARENT |
For the trihydrate use about 0.1 g of the substance; the water content is not less than 120 mg/g and not more than 150 mg/g.
|
Related Record | Type | Details | ||
---|---|---|---|---|
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PRODRUG -> METABOLITE ACTIVE | |||
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PRODRUG -> METABOLITE ACTIVE | |||
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PRODRUG -> METABOLITE ACTIVE |
Related Record | Type | Details | ||
---|---|---|---|---|
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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||
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IMPURITY -> PARENT | |||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
|
||
|
IMPURITY -> PARENT | |||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
|
||
|
IMPURITY -> PARENT | |||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
|
||
|
PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
|
||
|
IMPURITY -> PARENT | |||
|
PARENT -> IMPURITY | |||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
|
||
|
IMPURITY -> PARENT | |||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
IMPURITY -> PARENT |
|
||
|
PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
Related Record | Type | Details | ||
---|---|---|---|---|
|
ACTIVE MOIETY |
For the anhydrous form use about 0.8 g of the substance; the water content is not more than 15 mg/g.
|
Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
---|---|---|---|---|---|---|
Biological Half-life | PHARMACOKINETIC |
|
|
|||
Volume of Distribution | PHARMACOKINETIC |
|
|
|||