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.

In the Vinony graph

Within Vinony's link graph, bacampicillin is referenced by 189 other articles, and connects out to antibiotic, ceftolozane/tazobactam and penicillin.

It sits within the topics Carboxylate esters, Chemical articles with multiple CAS registry numbers and Chemicals using indexlabels.

Its subject is documented across 15 Wikipedia language editions.

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

Chemical data

Formula: C21H27N3O7S
Molecular weight: 465.5 g/mol
IUPAC name: 1-ethoxycarbonyloxyethyl (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
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
InChIKey: PFOLLRNADZZWEX-FFGRCDKISA-N
XLogP: 2.7
Polar surface area: 163 Å²
H-bond donors: 2
H-bond acceptors: 9
Formal charge: 0

via PubChem

Drug data · ChEMBL

Max clinical phase: Approved
Molecule type: Small molecule
First approval: 1980
Admin. routes: oral
Indications: osteomyelitis, bacterial disease

via ChEMBL · EBI

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

Subclass of: chemical compound
Mass: 465.156971
Has use: medication

Show 8 more facts

medical condition treated: gonorrhea
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
subject has role: antibiotic
Commons category: Bacampicillin

Sources (3)

via Wikidata · CC0

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Encyclopedic overview

2 sections

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.

Excerpted from Wikipedia’s “bacampicillin” article, available under the CC BY-SA 4.0 licence.