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
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- Synthesis
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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.