bacampicillin

Trade name: spectrobid

Small moleculeapproved

Approved

Dec 22, 1980

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. — NCATS

Clinical trial activity

2 trials · 4 clinical orgs · 1 marketing orgs

Phase 1

Phase 2

Phase 3

Phase 4

Earliest trial started Aug 1, 2013 (NCT01931150)

Timeline

1980s

Dec 22, 1980
Pfizer — Earliest FDA Approval
Dec 22, 1980
Pfizer — NDA Organization

2010s

Jan 1, 2013
Earliest Phase 3 Sponsor(trial)
Jan 1, 2014
Earliest Phase 1 Sponsor(trial)

Indications

Approved for

Studied for

Mechanism of action

Bacterial penicillin-binding proteinINHIBITOR
Bacterial penicillin-binding protein inhibitor

Approval history

approvedDec 22, 1980

Chemistry & pharmacology

Loading structure…

SMILES

CCOC(=O)OC(C)OC(=O)[C@@H]1N2C(=O)[C@@H](NC(=O)[C@H](N)c3ccccc3)[C@H]2SC1(C)C

Mol. weight: 465.53 g/mol
Lipinski Ro5: Pass
Rule of 3: No
Chirality: Racemic Mixture
Inorganic: No
Polymer: No
Delivery: Oral
Availability: Discontinued

Oral

Yes

Parenteral

Topical

Prodrug

Sources

Also known as

1-[(ethoxycarbonyl)oxy]ethyl (2s,5r,6r)-6-{[(2r)-2-amino-2-phenylacetyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
1-[(ethoxycarbonyl)oxy]ethyl (2s,5r,6r)-6-{[(2r)-2-amino-2-phenylacetyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
1'-ethoxycarbonyloxyethyl-(6-d-alpha-aminophenylacetamido)penicillanate
1'-ethoxycarbonyloxyethyl-(6-d-alpha-aminophenylacetamido)penicillanate
1'-ethoxycarbonyloxyethyl-(6-d-alpha-aminophenylacetamido)penicillanate
ambaxin
ambaxin
bacampicilina
bacampicilina
bacampicillin
bacampicillin
bacampicillin
bacampicillin
bacampicillin
bacampicillin
bacampicillin
bacampicillin
bacampicillin
bacampicillin
bacampicillin
bacampicilline
bacampicilline
bacampicillin hcl
bacampicillin hcl
bacampicillin hcl
bacampicillin hydrochloride
bacampicillin hydrochloride
bacampicillin hydrochloride
bacampicillin hydrochloride
bacampicillin hydrochloride
bacampicillin monohydrochloride
bacampicillinum
bacampicillinum
bacampicine
carampicillin
carampicillin
ethoxycarbonyloxyethyl ester of ampicillin
penglobe
spectrobid
spectrobid
spectrobid

Clinical trials

NCT ID	Phase	Start date	Sponsor(s)
NCT02099240	Early Phase 1 (Phase 1)	Apr 1, 2014	James Graham Brown Cancer Center, University of Louisville
NCT01931150	Phase 3	Aug 1, 2013	Bristol-Myers Squibb, Cornell University

Showing 2 of 2 trials

Page 1 / 1

Organizations

Research & Development (4)

Organization	Org type	Trials	As lead sponsor	Phases	Earliest year
Bristol-Myers Squibb	For profit	1	0	1	2013
Cornell University	Academic/Hospital	1	1	1	2013
James Graham Brown Cancer Center	Academic/Hospital	1	0	1	2014
University of Louisville	Academic/Hospital	1	1	1	2014

4 organizations

Page 1 / 1

Marketing (1)

Organization	Org type	Relationship	Date
Pfizer	For profit	NDA	Dec 22, 1980