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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
Structure of BACAMPICILLIN

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

HIDE SMILES / InChI

Molecular Formula C21H27N3O7S
Molecular Weight 465.52
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry EPIMERIC
Additional Stereochemistry No
Defined Stereocenters 4 / 5
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

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 TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
SPECTROBID
Curative
SPECTROBID
Curative
SPECTROBID
Curative
SPECTROBID
Curative
SPECTROBID
Curative
SPECTROBID

Cmax

ValueDoseCo-administeredAnalytePopulation
13.5 μg/mL
808 mg single, oral
BACAMPICILLIN plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
3.09 μg × min/mL
808 mg single, oral
BACAMPICILLIN plasma
Homo sapiens

Doses

PubMed

Sample Use Guides

In Vivo Use Guide
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
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.
Substance Class Chemical
Record UNII
8GM2J22278
Record Status Validated (UNII)
Record Version