CAS 69-53-4|Ampicillin|氨苄西林|(2S,5R,6R)-6-[(2R)-2-amino-2-phenylacetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid|Ampicillin Base|Ampicillin Sodium|Synpenin|Pfizer...

General Information

Structure

Molecular Formula

C₁₆H₁₉N₃O₄S

Molecular Mass

349.40476

Exact Mass

349.1096271

Charge

InChI

InChI=1S/C16H19N3O4S/c1-16(2)11(15(22)23)19-13(21)10(14(19)24-16)18-12(20)9(17)8-6-4-3-5-7-8/h3-7,9-11,14H,17H2,1-2H3,(H,18,20)(H,22,23)/t9-,10-,11+,14-/m1/s1

InChIKey

AVKUERGKIZMTKX-NJBDSQKTSA-N

Canonic Smiles

N[C@H](c1ccccc1)C(=O)N[C@@H]1C(=O)N2[C@@H]1SC([C@@H]2C(=O)O)(C)C

Isomeric Smiles

S1[C@H]2N([C@H](C1(C)C)C(=O)O)C(=O)[C@H]2NC(=O)[C@H](N)c1ccccc1

Calculated Properties

JChem

LogD (pH = 7.4)

-2.36

LogD (pH = 5.5)

-2.01

Log P

-2.00

Rotatable Bonds

H Donor

H Acceptors

Lipinski's Rule of Five

true

Acid pKa

3.24

Polar Surface Area

112.73

Polarizability

35.18

Molar Refractivity

87.52

LOG S

-4.79

Data Source

Academic Data

Commercial Catalog

Data Source

Names and Identifiers

Synonyms

Ampicillin氨苄西林Ampicillin BaseAmpicillin SodiumAmpicillin AnhydrateAmpicillinAmpicillina [Dcit]Bayer 5427D-AmpicillinAmpicillin TrihydrateAmpicillin [Usan:Ban:Inn:Jan]Ampicillin AnhydrousAminobenzylpenicillinAmpicilline [INN-French]Anhydrous AmpicillinAmpicilina [INN-Spanish]Ampicillinum [INN-Latin]AmpicillineAmpicillin AcidAMPICILLIN ANHYDROUS氨苄青霉素Amfipen-d5(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 AcidAlbipenAmpicillin-d5(Mixture of Diastereomers)Albipen-d5AY 6108-d5Amplital-d5Penicline-d5PeniclineAmfipen(2S,5R,6R)-6-[[(2RS)-2-Amino-2-(phenyl-d5)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic AcidAY 6108AmplitalD-(-)-α-Aminobenzylpenicillin(2S,6R)-6-{[(2R)-2-amino-2-phenylethanoyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acidaminobenzylpenicillin6-(D-(2-amino-2-phenylacetamido))-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acidampicillin anhydrousABPC(2S,5R,6R)-6-{[(2R)-2-AMINO-2-PHENYLETHANOYL]AMINO}-3,3-DIMETHYL-7-OXO-4-THIA-1-AZABICYCLO[3.2.0]HEPTANE-2-CARBOXYLIC ACIDAMPD-(-)-ampicillin(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 acidAnhydrous ampicillinAmpicillinampicillin acidampicillinD-(-)-6-(alpha-aminophenylacetamido)penicillanic acidAP

IUPAC name

(2S,5R,6R)-6-[(2R)-2-amino-2-phenylacetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

Brand Name

SynpeninPfizerpen ANorobrittinRacenacillinPen AmpilAmpichelAmpicilAmpicinAmplinGuicitrinaBonapicillinBinotalAmpi-BolAustrapenAmcillAmipenix SNovo-AmpicillinRo-AmpenRosamplineTolomolOlin KidVampenDuphacillinOmnipen-NPeniclineSumipantoServicillinPensynGuicitrineLifeampilAB-PCAdobacillinViccillinGeocillinDeripen

IUPAC Traditional name

ampicillin

API Name

Ampicillin

International Nonproprietary Name (INN)

ampicillinampicillinumampicillineampicilina

Names and Identifiers

Registration numbers

Beilstein Number

CAS Number

EC Number

MDL Number

Unique Ingredient Identifier

Wikipedia Title

CHEMBL

PubChem CID

KEGG ID

DrugBank ID

Chemspider ID

ATC CODE

J01CA01QJ51CA01S01AA19

CHEBI ID

28971CHEBI:2683CHEBI:45042CHEBI:22536CHEBI:28971CHEBI:40648

Medline Plus

a685002

PubChem SID

248914424650534616096376153801116

CompTox Database

DTXSID4022602

SABIO-RK Database

7628121100466491716765306602963971697168108

UniProt Database

Q6G8T5P15419Q896N5Q8TVD2B5XZG7A1W0F9P57000A4QDE1A8GQM8C0R1U9Q7NC67Q164C1A6VFH1Q8I5P7P0AG22

BKMS React Database

6654229159229160191

BRENDA Database

3.1.1.433.4.11.193.4.24.752.5.1.153.1.1.13.4.16.42.3.1.1802.3.2.121.8.1.71.14.11.263.5.1.23.4.17.86.3.1.53.5.1.11

SureChEMBL Database

SCHEMBL3526

PubMed Citation Links

15768449943393824666465208397880200882599894924474427238612681256998710930630141391192901783319967069285433951445582012562703

MetaboLights Database

MTBLS1918MTBLS2291MTBLS2384MTBLS1041MTBLS1906MTBLS4012MTBLS3487MTBLS417

LINCS Database

LSM-5761

BRENDA Ligand Database

2291602291596654191

Protein Data Bank

3ita4gcp3kp34kr42rdd3ndv1h8s1nx9

Reaxys Registry

4300240

ACToR Database

69-53-433604-21-6

Patent number

EP1754712GB2157565GB2321455WO2007103555EP1829963US2005070552WO2005018635EP0826776US2007248666US2007253973US2007196504US2007248677WO2007100902EP1514877

EnzymePortal Database

A3PRU3Q9ZBA9Q3IX78Q8YD27B2SD81A6WYS5A9MCM7B9KTA6A5VVL2Q5FRJ7Q579G4A9WVV8P39045Q8FV99C0RM93

Drug Central Database

IEDB Database

HMDB Database

KEGG DRUG Database

PDBeChem Database

VSDB Database

Registration numbers

Properties

Related Proteins

Related Proteins

Molecular Spectra

No Data Available

Click here to submit data

Molecule Details

DrugBank

DB00415

Drug Groups

approved

Description

Semi-synthetic derivative of penicillin that functions as an orally active broad-spectrum antibiotic. [PubChem]

Indication

For treatment of infection (Respiratory, GI, UTI and meningitis) due to E. coli, P. mirabilis, enterococci, Shigella, S. typhosa and other Salmonella, nonpenicillinase-producing N. gononhoeae, H. influenzae, staphylococci, streptococci including streptoc

Pharmacology

Ampicillin is a penicillin beta-lactam antibiotic used in the treatment of bacterial infections caused by susceptible, usually gram-positive, organisms. The name "penicillin" can either refer to several variants of penicillin available, or to the group of antibiotics derived from the penicillins. Ampicillin has in vitro activity against gram-positive and gram-negative aerobic and anaerobic bacteria. The bactericidal activity of Ampicillin results from the inhibition of cell wall synthesis and is mediated through Ampicillin binding to penicillin binding proteins (PBPs). Ampicillin is stable against hydrolysis by a variety of beta-lactamases, including penicillinases, and cephalosporinases and extended spectrum beta-lactamases.

Affected Organisms

Enteric bacteria and other eubacteria

Elimination

Ampicillin is excreted largely unchanged in the urine.

External Links

• [Wikipedia]

• [RxList]

• [Drugs.com]

Molecule Details

References

PubChem Literature

From Data Sources

• Campoli-Richards, D.M., et al.: Drugs, 33, 577 (1973)

• Sill, M. L., et al.: Antimicrob. Agents Chemother., 52, 1551 (1973)

• Ivashkiv, E., et al.: Anal. Profiles Drug Subs., 2, 1 (1973)

• Campoli-Richards, D.M., et al.: Drugs, 33, 577 (1973)

• Ivashkiv, E., et al.: Anal. Profiles Drug Subs., 2, 1 (1973)

• Sill, M. L., et al.: Antimicrob. Agents Chemother., 52, 1551 (1973)

References

Bioactivity

PubChem BioAssay

Bioactivity

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Calculated Properties

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• JChem

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• Commercial Catalog

Names and Identifiers

• Synonyms

• IUPAC name

• Brand Name

• IUPAC Traditional name

• API Name

• International Nonproprietary Name (INN)

Names and Identifiers

Registration numbers

• Beilstein Number

• CAS Number

• EC Number

• MDL Number

• Unique Ingredient Identifier

• Wikipedia Title

• CHEMBL

• PubChem CID

• KEGG ID

• DrugBank ID

• Chemspider ID

• ATC CODE

• CHEBI ID

• Medline Plus

• PubChem SID

• CompTox Database

• SABIO-RK Database

• UniProt Database

• BKMS React Database

• BRENDA Database

• SureChEMBL Database

• PubMed Citation Links

• MetaboLights Database

• LINCS Database

• BRENDA Ligand Database

• Protein Data Bank

• Reaxys Registry

• ACToR Database

• Patent number

• EnzymePortal Database

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• Physical Property

• Safety Information

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• DrugBank

• MP Biomedicals

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• Sigma Aldrich

• TRC

• ChEBI

Molecule Details

References

• PubChem Literature

• From Data Sources

Bioactivity

• PubChem BioAssay

From Data Sources

• Campoli-Richards, D.M., et al.: Drugs, 33, 577 (1973)

• Sill, M. L., et al.: Antimicrob. Agents Chemother., 52, 1551 (1973)

• Ivashkiv, E., et al.: Anal. Profiles Drug Subs., 2, 1 (1973)

• Campoli-Richards, D.M., et al.: Drugs, 33, 577 (1973)

• Ivashkiv, E., et al.: Anal. Profiles Drug Subs., 2, 1 (1973)

• Sill, M. L., et al.: Antimicrob. Agents Chemother., 52, 1551 (1973)

Synonyms

IUPAC name

(2S,5R,6R)-6-[(2R)-2-amino-2-phenylacetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

Brand Name

IUPAC Traditional name

ampicillin

International Nonproprietary Name (INN)

ampicillinampicillinumampicillineampicilina

Physical Property

208 °C (dec.)(lit.)

196-198°C (dec.)

199-202°C (dec.)

Optical Rotation

[α]20/D +295±5°, c = 0.2% in H2O

Apperance

White Solid

Off-White to Pale Yellow Solid

Safety Information

Product Information

Pharmacology Properties

DrugBank

DB00415

Drug Groups

approved

Description

Semi-synthetic derivative of penicillin that functions as an orally active broad-spectrum antibiotic. [PubChem]

Indication

Pharmacology

Affected Organisms

Enteric bacteria and other eubacteria

Elimination

Ampicillin is excreted largely unchanged in the urine.

External Links

• [Wikipedia]

• [RxList]

• [Drugs.com]

Sigma Aldrich

A9393

Frequently Asked Questions
Live Chat and Frequently Asked Questions are available for this Product.
Biochem/physiol Actions
A β-lactam antibiotic with an amino group attached to the penicillin structure. Inhibits bacterial cell-wall synthesis (peptidoglycan cross-linking) by inactivating transpeptidases on the inner surface of the bacterial cell membrane. Bactericidal only to growing Escherichia coli. Mode of resistance: Cleavage of β-lactam ring of ampicillin by β-lactamase. Antimicrobial spectrum: Gram-negative and Gram-positive bacteria.
Application
Ampicillin is used to select bacteria cells with specific resistance during general microbiology studies. It is used to study antibiotic resistance and penetration limitations, the synergy between multiple antibiotics, certain bloodstream infections, and has been used to develop PCR assays to detect resistance genes in cerebrospinal fluid 1,2,3,4.

10047

Biochem/physiol Actions
A β-lactam antibiotic with an amino group attached to the penicillin structure. Inhibits bacterial cell-wall synthesis (peptidoglycan cross-linking) by inactivating transpeptidases on the inner surface of the bacterial cell membrane. Bactericidal only to growing Escherichia coli. Mode of resistance: Cleavage of β-lactam ring of ampicillin by β-lactamase. Antimicrobial spectrum: Gram-negative and Gram-positive bacteria.
Inhibits cell wall synthesis in Escherichia coli1; In the purification of penicillin acylase2; Enhances luminol chemiluminescence.3

TRC

A634302

Labelled Ampicillin. Orally active, semi-synthetic antibiotic; structurally related to penicillin. Antibacterial.

A634300

Orally active, semi-synthetic antibiotic; structurally related to penicillin. Antibacterial.

ChEBI

CHEBI:28971

A penicillin in which the substituent at position 6 of the penam ring is a 2-amino-2-phenylacetamido group.