BACAMPICILLIN

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 Search

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
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
Bacterial penicillin-binding protein 233 Target ID: CHEMBL2354204 Sources: http://www.antimicrobe.org/drugpopup/Bacampicillin.pdf \| http://edudrugs.com/S/Spectrobid.html	Inhibitor 8297

Conditions

Condition	Modality	Highest Phase	Product
Tonsillitis 36 Sources: https://www.drugs.com/mtm/bacampicillin.html https://www.ncbi.nlm.nih.gov/pubmed/6762528	Curative	Approved 8429	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 3.46291208E11
Pneumonia 90 Sources: https://www.drugs.com/mtm/bacampicillin.html https://www.ncbi.nlm.nih.gov/pubmed/6762528	Curative	Approved 8429	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 3.46291208E11
Bronchitis 51 Sources: https://www.drugs.com/mtm/bacampicillin.html https://www.ncbi.nlm.nih.gov/pubmed/6762528	Curative	Approved 8429	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 3.46291208E11
Urinary tract infections 205 Sources: https://www.drugs.com/mtm/bacampicillin.html https://www.ncbi.nlm.nih.gov/pubmed/6762528	Curative	Approved 8429	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 3.46291208E11
Gonorrhea 30 Sources: https://www.drugs.com/mtm/bacampicillin.html https://www.ncbi.nlm.nih.gov/pubmed/6762528	Curative	Approved 8429	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 3.46291208E11
Infections of the skin 2 Sources: https://www.drugs.com/mtm/bacampicillin.html https://www.ncbi.nlm.nih.gov/pubmed/6762528	Curative	Approved 8429	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 3.46291208E11

C_max

Value	Dose	Co-administered	Analyte	Population
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 Dose: 3200 mg Route: oral Route: single Dose: 3200 mg Sources: https://pubmed.ncbi.nlm.nih.gov/4028617	healthy, 22-41 years n = 12 Health Status: healthy Age Group: 22-41 years Sex: M+F Population Size: 12 Sources: https://pubmed.ncbi.nlm.nih.gov/4028617	Sources: https://pubmed.ncbi.nlm.nih.gov/4028617
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: https://pubmed.ncbi.nlm.nih.gov/32615	unhealthy n = 16 Health Status: unhealthy Condition: chronic bronchitis Population Size: 16 Sources: https://pubmed.ncbi.nlm.nih.gov/32615	Sources: https://pubmed.ncbi.nlm.nih.gov/32615

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:2968	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:2968
ChemicalBook	CB1343108	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB1343108

PubMed

Title	Date	PubMed
Clinical trial of bacampicillin in acute bacterial infections.	1983	6352033
beta-Lactam drug allergens: fine structural recognition patterns of cephalosporin-reactive IgE antibodies.	1996 Jul-Aug	9131470
Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients.	2001 Nov	11792017

Patents

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 Created by `admin` on `Sat Dec 16 15:49:49 UTC 2023` Edited by `admin` on `Sat Dec 16 15:49:49 UTC 2023`
Record UNII	8GM2J22278
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

BACAMPICILLIN

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