Bacampicillin

HCID 441397CAS 50972-17-3
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Grundinformationen

Standard-SMILES
CCOC(=O)OC(C)OC(=O)[C@@H]1N2C(=O)[C@@H](NC(=O)[C@H](N)c3ccccc3)[C@H]2SC1(C)C
InChIKey
PFOLLRNADZZWEX-FFGRCDKISA-N
Summenformel
C21H27N3O7S
Durchschnittliche Molmasse
465,5 g/mol
Monoisotopische Masse
465,1569712

Überblick

Bacampicillin is a penicillanic acid ester that is the 1-ethoxycarbonyloxyethyl ester of ampicillin. It is a semi-synthetic, microbiologically inactive prodrug of ampicillin. It has a role as a prodrug. It is functionally related to an ampicillin.

Namen und Bezeichner

Bevorzugter Name
Bacampicillin
IUPAC
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
Englischer Name
BACAMPICILLIN
Summenformel
C21H27N3O7S
Molmasse
465.52

Namen und Synonyme

bacampicillin50972-17-3BacampicillineBacampicilinaPenglobebacampicillinumCHEBI:29681-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-carboxylate8GM2J22278DTXSID20480301'-Ethoxycarbonyloxyethyl-(6-D-alpha-aminophenylacetamido)penicillanatecarampicillin
Weitere Namen anzeigen
BACAMPICILLIN USP/EP/BPBACAMPICILLIN HCL USP(CRM STANDARD)Bacampicillin (base and/or unspecified salts)6α-[[(R)-2-Amino-2-phenylacetyl]amino]penicillanic acid 1-[(ethoxycarbonyl)oxy]ethyl ester(2S,5R,6R)-6-[[(2R)-2-Amino-2-phenylacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 1-(ethoxycarbonyloxy)ethyl ester4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-[[(2R)-aminophenylacetyl]amino]-3,3-dimethyl-7-oxo-, 1-[(ethoxycarbonyl)oxy]ethyl ester, (2S,5R,6R)-(2S,5R,6R)-6-[[(2R)-2-amino-1-oxo-2-phenylethyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 1-ethoxycarbonyloxyethyl ester4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-[(aminophenylacetyl)amino]-3,3-dimethyl-7-oxo-, 1-[(ethoxycarbonyl)oxy]ethyl ester, [2S-[2α,5α,6β(S*)]]-
BAPC1-[(ethoxycarbonyl)oxy]ethyl (2S,5R,6R)-6-[(2R)-2-amino-2-phenylacetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate1-[(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-carboxylate4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-((aminophenylacetyl)amino)-3,3-dimethyl-7-oxo-, 1-((ethoxycarbonyl)oxy)ethyl ester, (2S-(2alpha,5alpha,6beta(S*)))-bacampicillina1-((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-carboxylate1-((ethoxycarbonyl)oxy)ethyl (2S,5R,6R)-6-((2R)-2-amino-2-phenylacetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylate1-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

Datenbank-Bezeichner

CAS
50972-17-3
PubChem CID
441397
DTXSID
DTXSID2048030
ChEMBL
CHEMBL1583
ChEBI
CHEBI:2968
UNII
8GM2J22278
Nikkaji
J14.626I

Eigenschaften

Berechnete Struktureigenschaften

XLogP
2,7
Polarare Oberfläche (TPSA)
163 Ų
H-Brücken-Donoren
2
H-Brücken-Akzeptoren
9
Frei drehbare Bindungen
10
Schwere Atome
32

Experimentelle und physikochemische Eigenschaften

DrugsPharmaceuticals -> Antibiotics
Solubility1.23e-01 g/L
Human DrugsBreast Feeding; Lactation; Milk, Human; Anti-Infective Agents; Antibacterial Agents; Penicillins
Melting Point171-176
Physical DescriptionSolid

Physikochemische Eigenschaften

Siedepunkt
678.4 · 678.4±55.0 °C(Predicted)
Dichte
1.37 · 1.37±0.1 g/cm3(Predicted)
storage temp.
-20 °C · Store at -20°C
Löslichkeit
Soluble in DMSO
pka
6.8 · pKa 6.8 (Uncertain)
CAS Datenbank
50972 · 50972-17-3

Sicherheit und Regulatorisches

Toxikologische Informationen

Drug Induced Liver Injury · 4 Einträge

Drug-Induced Liver Injury Severity and Toxicity (DILIst)

Bacampicillin

DILI Positive

DOI:10.1016/j.drudis.2019.09.022

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation

Chemie und Industrie

Pharmakologische Informationen

ATC Code · 2 Einträge

J - Antiinfectives for systemic use

QJ - Antiinfectives for systemic use

PharmacodynamicsBacampicillin is a prodrug of ampicillin and is microbiologically inactive.
Mechanism of Action · 1 Eintrag

During absorption from the gastrointestinal tract, bacampicillin is hydrolyzed by esterases present in the intestinal wall. It is microbiologically active as ampicillin, and exerts a bactericidal action through the inhibition of the biosynthesis of cell wall mucopeptides.

MeSH Pharmacological ClassificationSubstances that inhibit the growth or reproduction of BACTERIA.
Absorption, Distribution and ExcretionAbsorbed following oral administration.
Cellular LocationsCytoplasm

Vor- und nachgelagerte Produkte

Anbieter18 Anbieter

北京华美互利生物化工010-56205725 · [email protected]
Career Henan Chemica Co+86-0371-86658258 +86-13203830695 · [email protected]
江苏艾康生物医药研发有限公司025-025-66113011 15955137747 · [email protected]
广东元丰化学试剂有限公司0751-2829979 13318593351 · [email protected]
MedChemexpress LLC021-58955995 · [email protected]

Ergänzende Hinweise

DefinitionChEBI: A penicillanic acid ester that is the 1-ethoxycarbonyloxyethyl ester of ampicillin. It is a semi-synthetic, microbiologically inactive prodrug of ampicillin.

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