bacampicillin

Also known as Bacampicillinum, 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, Bacampicilina, Bacampicilline

Bacampicillin (INN) is a penicillin antibiotic. It is a prodrug of ampicillin with improved oral bioavailability.

Key facts

Drug.Verifiedfields: changed
Drug.verifiedrevid: 458983047
Drug.IUPAC_name: 1-Ethoxycarbonyloxyethyl (2S,5R)-6-[[(2R)-2-amino-2-phenylacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate | image = Bacampicillin Structural Formula V2.svg | image_class = skin-invert-image | class = aminopenicillin | tradename = | Drugs.com = | pregnancy_AU = | pregnancy_US = | pregnancy_category = | legal_AU = | legal_CA = | legal_UK = | legal_US = | legal_status = | routes_of_administration = Oral | bioavailability = | protein_bound = | metabolism = Rapidly hydrolyzed to ampicillin | elimination_half-life = | excretion = | index2_label = HCL | CAS_number_Ref = | CAS_number = 50972-17-3 | CAS_number2_Ref = | CAS_number2 = 37661-08-8 | UNII_Ref = | UNII = 8GM2J22278 | ATC_prefix = J01 | ATC_suffix = CA06 | ATC_supplemental = | ChEBI_Ref = | ChEBI = 2968 | StdInChI_Ref = | StdInChI = 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 | StdInChIKey_Ref = | StdInChIKey = PFOLLRNADZZWEX-FFGRCDKISA-N | PubChem = 39849 | DrugBank_Ref = | DrugBank = DB01602 | ChemSpiderID_Ref = | ChemSpiderID = 390135 | ChEMBL_Ref = | ChEMBL = 1583 | UNII2_Ref = | UNII2 = PM034U953T | chemical_formula = | C=21 | H=27 | N=3 | O=7 | S=1

via Wikipedia infobox

Research

258 papers

Bacampicillin.2006
[Bacampicillin].The Japanese journal of antibiotics · 1982
The pharmacokinetics of bacampicillin.Reviews of infectious diseases · 1981
Bacampicillin hydrochloride: chemistry, pharmacology, and clinical use.Pharmacotherapy · 1982
Bacampicillin uptake is shared with thiamine in Caco-2 cells.Biological & pharmaceutical bulletin · 2007

via PubMed

Wikidata facts

Mass: 465.156971

Show 6 more facts

chemical formula: C₂₁H₂₇N₃O₇S
isomeric SMILES: CCOC(=O)OC(C)OC(=O)[C@H]1C(S[C@H]2N1C(=O)[C@H]2NC(=O)[C@@H](C3=CC=CC=C3)N)(C)C
canonical SMILES: CCOC(=O)OC(C)OC(=O)C1C(SC2N1C(=O)C2NC(=O)C(C3=CC=CC=C3)N)(C)C
World Health Organisation international non-proprietary name: bacampicillin
defined daily dose: 1.2
Commons category: Bacampicillin

Sources (3)

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Article

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Contents

Synthesis
References

Bacampicillin (INN) is a penicillin antibiotic. It is a prodrug of ampicillin with improved oral bioavailability.

It was sold under the brand names Spectrobid (Pfizer) and Penglobe (AstraZeneca).In 2015, Pfizer discontinued Spectrobid, and no generic manufacturer has taken over production. Bacampicillin is thus unavailable in the United States, and is no longer FDA approved.