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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
Stereochemistry EPIMERIC
Additional Stereochemistry No
Defined Stereocenters 4 / 5
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
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.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
SPECTROBID

Approved Use

Bacampicillin is used to treat many different types of infections, such as tonsillitis, pneumonia, bronchitis, urinary tract infections, gonorrhea, and infections of the skin.

Launch Date

1980
Curative
SPECTROBID

Approved Use

Bacampicillin is used to treat many different types of infections, such as tonsillitis, pneumonia, bronchitis, urinary tract infections, gonorrhea, and infections of the skin.

Launch Date

1980
Curative
SPECTROBID

Approved Use

Bacampicillin is used to treat many different types of infections, such as tonsillitis, pneumonia, bronchitis, urinary tract infections, gonorrhea, and infections of the skin.

Launch Date

1980
Curative
SPECTROBID

Approved Use

Bacampicillin is used to treat many different types of infections, such as tonsillitis, pneumonia, bronchitis, urinary tract infections, gonorrhea, and infections of the skin

Launch Date

1980
Curative
SPECTROBID

Approved Use

Bacampicillin is used to treat many different types of infections, such as tonsillitis, pneumonia, bronchitis, urinary tract infections, gonorrhea, and infections of the skin.

Launch Date

1980
Curative
SPECTROBID

Approved Use

Bacampicillin is used to treat many different types of infections, such as tonsillitis, pneumonia, bronchitis, urinary tract infections, gonorrhea, and infections of the skin.

Launch Date

1980
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
13.5 μg/mL
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

AUC

ValueDoseCo-administeredAnalytePopulation
3.09 μg × min/mL
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

Doses

DosePopulationAdverse events​
3200 mg single, oral
Highest studied dose
Dose: 3200 mg
Route: oral
Route: single
Dose: 3200 mg
Sources:
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

PubMed

TitleDatePubMed
beta-Lactam drug allergens: fine structural recognition patterns of cephalosporin-reactive IgE antibodies.
1996 Jul-Aug
Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients.
2001 Nov
Patents

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
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
Created
by admin
on Sat Dec 16 15:49:49 GMT 2023
Edited
by admin
on Sat Dec 16 15:49:49 GMT 2023
Record UNII
8GM2J22278
Record Status Validated (UNII)
Record Version
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Name Type Language
BACAMPICILLIN
INN   MI   VANDF   WHO-DD  
INN  
Official Name English
BACAMPICILLIN [MI]
Common Name English
BACAMPICILLIN [VANDF]
Common Name English
4-THIA-1-AZABICYCLO(3.2.0)HEPTANE-2-CARBOXYLIC ACID, 6-((AMINOPHENYLACETYL)AMINO)-3,3-DIMETHYL-7-OXO-, 1-((ETHOXYCARBONYL)OXY)ETHYL ESTER, (2S-(2.ALPHA.,5.ALPHA.,6.BETA.(S*)))-
Common Name English
Bacampicillin [WHO-DD]
Common Name English
PENGLOBE
Brand Name English
bacampicillin [INN]
Common Name English
Classification Tree Code System Code
WHO-ATC J01CA06
Created by admin on Sat Dec 16 15:49:50 GMT 2023 , Edited by admin on Sat Dec 16 15:49:50 GMT 2023
WHO-VATC QJ01CA06
Created by admin on Sat Dec 16 15:49:50 GMT 2023 , Edited by admin on Sat Dec 16 15:49:50 GMT 2023
LIVERTOX 86
Created by admin on Sat Dec 16 15:49:50 GMT 2023 , Edited by admin on Sat Dec 16 15:49:50 GMT 2023
NCI_THESAURUS C1500
Created by admin on Sat Dec 16 15:49:50 GMT 2023 , Edited by admin on Sat Dec 16 15:49:50 GMT 2023
Code System Code Type Description
WIKIPEDIA
BACAMPICILLIN
Created by admin on Sat Dec 16 15:49:50 GMT 2023 , Edited by admin on Sat Dec 16 15:49:50 GMT 2023
PRIMARY
ChEMBL
CHEMBL1583
Created by admin on Sat Dec 16 15:49:50 GMT 2023 , Edited by admin on Sat Dec 16 15:49:50 GMT 2023
PRIMARY
CAS
50972-17-3
Created by admin on Sat Dec 16 15:49:50 GMT 2023 , Edited by admin on Sat Dec 16 15:49:50 GMT 2023
PRIMARY
INN
3630
Created by admin on Sat Dec 16 15:49:50 GMT 2023 , Edited by admin on Sat Dec 16 15:49:50 GMT 2023
PRIMARY
SMS_ID
100000090507
Created by admin on Sat Dec 16 15:49:50 GMT 2023 , Edited by admin on Sat Dec 16 15:49:50 GMT 2023
PRIMARY
FDA UNII
8GM2J22278
Created by admin on Sat Dec 16 15:49:50 GMT 2023 , Edited by admin on Sat Dec 16 15:49:50 GMT 2023
PRIMARY
DRUG BANK
DB01602
Created by admin on Sat Dec 16 15:49:50 GMT 2023 , Edited by admin on Sat Dec 16 15:49:50 GMT 2023
PRIMARY
EPA CompTox
DTXSID2048030
Created by admin on Sat Dec 16 15:49:50 GMT 2023 , Edited by admin on Sat Dec 16 15:49:50 GMT 2023
PRIMARY
CHEBI
2968
Created by admin on Sat Dec 16 15:49:50 GMT 2023 , Edited by admin on Sat Dec 16 15:49:50 GMT 2023
PRIMARY
DRUG CENTRAL
280
Created by admin on Sat Dec 16 15:49:50 GMT 2023 , Edited by admin on Sat Dec 16 15:49:50 GMT 2023
PRIMARY
LACTMED
Bacampicillin
Created by admin on Sat Dec 16 15:49:50 GMT 2023 , Edited by admin on Sat Dec 16 15:49:50 GMT 2023
PRIMARY
PUBCHEM
441397
Created by admin on Sat Dec 16 15:49:50 GMT 2023 , Edited by admin on Sat Dec 16 15:49:50 GMT 2023
PRIMARY
RXCUI
18687
Created by admin on Sat Dec 16 15:49:50 GMT 2023 , Edited by admin on Sat Dec 16 15:49:50 GMT 2023
PRIMARY RxNorm
EVMPD
SUB05666MIG
Created by admin on Sat Dec 16 15:49:50 GMT 2023 , Edited by admin on Sat Dec 16 15:49:50 GMT 2023
PRIMARY
NCI_THESAURUS
C65245
Created by admin on Sat Dec 16 15:49:50 GMT 2023 , Edited by admin on Sat Dec 16 15:49:50 GMT 2023
PRIMARY
MERCK INDEX
m2194
Created by admin on Sat Dec 16 15:49:50 GMT 2023 , Edited by admin on Sat Dec 16 15:49:50 GMT 2023
PRIMARY Merck Index
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