Details
Stereochemistry | EPIMERIC |
Molecular Formula | C21H27N3O7S |
Molecular Weight | 465.52 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 4 / 5 |
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)OC(C)OC(=O)OCC
InChI
InChIKey=PFOLLRNADZZWEX-FFGRCDKISA-N
InChI=1S/C21H27N3O7S/c1-5-29-20(28)31-11(2)30-19(27)15-21(3,4)32-18-14(17(26)24(15)18)23-16(25)13(22)12-9-7-6-8-10-12/h6-11,13-15,18H,5,22H2,1-4H3,(H,23,25)/t11?,13-,14-,15+,18-/m1/s1
DescriptionSources: https://www.drugs.com/mtm/bacampicillin.htmlCurator's Comment: description was created based on several sources, including:
https://www.ncbi.nlm.nih.gov/pubmed/6762528 | http://www.antimicrobe.org/drugpopup/Bacampicillin.pdf
Sources: https://www.drugs.com/mtm/bacampicillin.html
Curator's Comment: description was created based on several sources, including:
https://www.ncbi.nlm.nih.gov/pubmed/6762528 | http://www.antimicrobe.org/drugpopup/Bacampicillin.pdf
Bacampicillin is a penicillin antibiotic. It is a prodrug of ampicillin with improved oral bioavailability. It exerts bactericidal activity via inhibition of bacterial cell wall synthesis by binding one or more of the penicillin binding proteins (PBPs). Spectrobid is used to treat bacterial infections such as tonsillitis, pneumonia (lung infection), bronchitis (inflammation of airway), urinary tract infections, gonorrhea, and infections of the skin. Adverse effects are: anemia, thrombocytopenia, neutropenia, agranulocytosis, seizures, nephrotoxicity, Jarisch-Herxheimer Reaction (fever, chills, sweating, tachycardia, hyperventilation, flushing, and myalgia). Drug interactions: Contraceptives - decreased contraceptive effectiveness; Live Typhoid Vaccine - decreased immunological response to the typhoid vaccine; Probenecid - increased bacampicillin levels.
CNS Activity
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2354204 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Curative | SPECTROBID Approved UseBacampicillin is used to treat many different types of infections, such as tonsillitis, pneumonia, bronchitis, urinary tract infections, gonorrhea, and infections of the skin. Launch Date1980 |
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Curative | SPECTROBID Approved UseBacampicillin is used to treat many different types of infections, such as tonsillitis, pneumonia, bronchitis, urinary tract infections, gonorrhea, and infections of the skin. Launch Date1980 |
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Curative | SPECTROBID Approved UseBacampicillin is used to treat many different types of infections, such as tonsillitis, pneumonia, bronchitis, urinary tract infections, gonorrhea, and infections of the skin. Launch Date1980 |
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Curative | SPECTROBID Approved UseBacampicillin is used to treat many different types of infections, such as tonsillitis, pneumonia, bronchitis, urinary tract infections, gonorrhea, and infections of the skin Launch Date1980 |
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Curative | SPECTROBID Approved UseBacampicillin is used to treat many different types of infections, such as tonsillitis, pneumonia, bronchitis, urinary tract infections, gonorrhea, and infections of the skin. Launch Date1980 |
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Curative | SPECTROBID Approved UseBacampicillin is used to treat many different types of infections, such as tonsillitis, pneumonia, bronchitis, urinary tract infections, gonorrhea, and infections of the skin. Launch Date1980 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
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13.5 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/529016 |
808 mg single, oral dose: 808 mg route of administration: Oral experiment type: SINGLE co-administered: |
BACAMPICILLIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
3.09 μg × min/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/529016 |
808 mg single, oral dose: 808 mg route of administration: Oral experiment type: SINGLE co-administered: |
BACAMPICILLIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
3200 mg single, oral Highest studied dose |
healthy, 22-41 years n = 12 Health Status: healthy Age Group: 22-41 years Sex: M+F Population Size: 12 Sources: |
|
1600 mg 2 times / day multiple, oral Highest studied dose Dose: 1600 mg, 2 times / day Route: oral Route: multiple Dose: 1600 mg, 2 times / day Sources: |
unhealthy n = 16 Health Status: unhealthy Condition: chronic bronchitis Population Size: 16 Sources: |
PubMed
Title | Date | PubMed |
---|---|---|
Clinical trial of bacampicillin in acute bacterial infections. | 1983 |
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beta-Lactam drug allergens: fine structural recognition patterns of cephalosporin-reactive IgE antibodies. | 1996 Jul-Aug |
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Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients. | 2001 Nov |
Sample Use Guides
Upper respiratory tract infections, Urinary tract infections, skin infections: 400 mg q12h; treat for a minimum of 48-72 hours after the patient becomes asymptomatic.
Severe infections: 800 mg q12h; treat for a minimum of 48-72 hours after the patient
becomes asymptomatic.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/10998023
Bacampicillin-treated lymphocyte cultures (200 ug/ml) from the two retested patients with allergic contact dermatitis showed an IFN-gamma production that peaked at 96 h or later. The four retested patients with rhinitis showed no or low IFN-gamma production which peaked at 48 h or 72 h. Two of them responded with IL-4 production.
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Classification Tree | Code System | Code | ||
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WHO-ATC |
J01CA06
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WHO-VATC |
QJ01CA06
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LIVERTOX |
86
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NCI_THESAURUS |
C1500
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BACAMPICILLIN
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CHEMBL1583
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50972-17-3
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3630
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100000090507
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8GM2J22278
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DB01602
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DTXSID2048030
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2968
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280
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Bacampicillin
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441397
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18687
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SUB05666MIG
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C65245
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m2194
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PRIMARY | Merck Index |
METABOLITE ACTIVE (PRODRUG)
SALT/SOLVATE (PARENT)
SUBSTANCE RECORD