Bacampicillin

HCID 441397
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Substructure searchFind similar structures

Basic information

CAS
50972-17-3
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
Molecular formula
C21H27N3O7S
Average molar mass
465.5 g/mol
Monoisotopic mass
465.1569712

Overview

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.

Names & identifiers

Preferred 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
English name
BACAMPICILLIN
Molecular formula
C21H27N3O7S
Molecular weight
465.52

Names & synonyms

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
Show more names
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

Database identifiers

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

Properties

Computed structural properties

XLogP
2.7
Topological polar surface area
163 Ų
Hydrogen bond donors
2
Hydrogen bond acceptors
9
Rotatable bonds
10
Heavy atoms
32

Experimental & physicochemical properties

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

Physicochemical properties

Boiling point
678.4 · 678.4±55.0 °C(Predicted)
Density
1.37 · 1.37±0.1 g/cm3(Predicted)
storage temp.
-20 °C · Store at -20°C
solubility
Soluble in DMSO
pka
6.8 · pKa 6.8 (Uncertain)
CAS DataBase Reference
50972 · 50972-17-3

Safety & regulation

Toxicology

Drug Induced Liver Injury · 4 items

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

Chemistry & industry

Pharmacology

ATC Code · 2 items

J - Antiinfectives for systemic use

QJ - Antiinfectives for systemic use

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

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
Applications · 1 item

UsesBACAMPICILLIN is ampicillin-methyl ester, which has no antibacterial activity in vitro. During in vivo absorption, it is hydrolyzed to ampicillin by non-specific esterases in the intestinal wall, thus exerting its antibacterial effect. Ampicillin sodium is a broad-spectrum semi-synthetic penicillin. This product is effective against a variety of Gram-positive and Gram-negative bacteria.

Upstream & downstream products

Suppliers18 total

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]

Additional notes

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

Related reactions

3 records
New reaction record

Compound notes

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