AMPICILLIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C16H19N3O4S
Molecular Weight	349.405
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC1(C)S[C@@H]2[C@H](NC(=O)[C@H](N)C3=CC=CC=C3)C(=O)N2[C@H]1C(O)=O

InChI

InChIKey=AVKUERGKIZMTKX-NJBDSQKTSA-N

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

HIDE SMILES / InChI

Molecular Formula	C16H19N3O4S
Molecular Weight	349.405
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	4 / 4
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/13859205 | https://www.drugs.com/pro/ampicillin.html

Ampicillin is a penicillin beta-lactam antibiotic. The following gram-negative and gram-positive bacteria have been shown in in vitro studies to be susceptible to ampicillin: Hemolytic and nonhemolytic streptococci, Streptococcus pneumoniae, Nonpenicillinase-producing staphylococci, Clostridium spp., B. anthracis, Listeria monocytogenes, most strains of enterococci, H. influenzae, N. gonorrhoeae, N. meningitidis, Proteus mirabilis, many strains of Salmonella, Shigella, and E. coli. Ampicillin is indicated in the treatment of bacterial meningitis, septicemia, endocarditis, urinary tract, gastrointestinal, respiratory tract infections caused by susceptible strains of the designated organisms.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Bacterial penicillin-binding protein 234 Target ID: CHEMBL2354204 Sources: http://biotechlab.fudan.edu.cn/database/bctd/search_drug.php?search=pivampicillin	Inhibitor 8504
Bacterial penicillin-binding protein 234 Target ID: CHEMBL2354204 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15761956 \| https://www.ncbi.nlm.nih.gov/pubmed/6774958 \| https://www.ncbi.nlm.nih.gov/pubmed/6373702	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Bacterial Infections 63 Sources: https://www.drugs.com/pro/ampicillin.html	Curative		Approved 8583	AMPICILLIN SODIUM Approved Use Ampicillin is indicated in the treatment of bacterial meningitis, septicemia, endocarditis, urinary tract, gastrointestinal, respiratory tracti nfections caused by susceptible strains of bacteria (Hemolytic and nonhemolytic streptococci, Streptococcus pneumoniae, Nonpenicillinase-producing staphylococci, Clostridium spp., B. anthracis, Listeria monocytogenes, most strains of enterococci, H. influenzae, N. gonorrhoeae, N. meningitidis, Proteus mirabilis, many strains of Salmonella, Shigella, and E. coli.)

C_max

Value	Dose	Co-administered	Analyte	Population
15.04 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/20399996	1500 mg single, oral dose: 1500 mg route of administration: Oral experiment type: SINGLE co-administered: PROBENECID	PROBENECID	AMPICILLIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
129.5 μg/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/050608s040lbl.pdf	2000 mg single, intravenous dose: 2000 mg route of administration: Intravenous experiment type: SINGLE co-administered: SULBACTAM	SULBACTAM	AMPICILLIN plasma	Homo sapiens population: UNKNOWN age: ADULT sex: UNKNOWN food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
58.74 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/20399996	1500 mg single, oral dose: 1500 mg route of administration: Oral experiment type: SINGLE co-administered: PROBENECID	PROBENECID	AMPICILLIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
1.82 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/20399996	1500 mg single, oral dose: 1500 mg route of administration: Oral experiment type: SINGLE co-administered: PROBENECID	PROBENECID	AMPICILLIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
1 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/050608s040lbl.pdf	2000 mg single, intravenous dose: 2000 mg route of administration: Intravenous experiment type: SINGLE co-administered: SULBACTAM	SULBACTAM	AMPICILLIN plasma	Homo sapiens population: UNKNOWN age: ADULT sex: UNKNOWN food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
72% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/050608s040lbl.pdf			AMPICILLIN serum	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
650 mg 3 times / day multiple, intravenous Studied dose Dose: 650 mg, 3 times / day Route: intravenous Route: multiple Dose: 650 mg, 3 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/pre96/050608Orig1s000rev.pdf	unhealthy, 11 to 18 months Health Status: unhealthy Age Group: 11 to 18 months Sex: M+F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/pre96/050608Orig1s000rev.pdf	Disc. AE: Skin rash... AEs leading to discontinuation/dose reduction: Skin rash (25%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/pre96/050608Orig1s000rev.pdf
5 g 3 times / day multiple, intravenous Highest studied dose Dose: 5 g, 3 times / day Route: intravenous Route: multiple Dose: 5 g, 3 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/pre96/050608Orig1s000rev.pdf	unhealthy, adult Health Status: unhealthy Age Group: adult Sex: M+F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/pre96/050608Orig1s000rev.pdf	Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/pre96/050608Orig1s000rev.pdf
0.5 g 1 times / day single, intramuscular Recommended Dose: 0.5 g, 1 times / day Route: intramuscular Route: single Dose: 0.5 g, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/pre96/050608Orig1s000rev.pdf	healthy, adult Health Status: healthy Age Group: adult Sex: M Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/pre96/050608Orig1s000rev.pdf	Other AEs: Injection site pain... Other AEs: Injection site pain Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/pre96/050608Orig1s000rev.pdf
1 g 1 times / day single, intramuscular Studied dose Dose: 1 g, 1 times / day Route: intramuscular Route: single Dose: 1 g, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/pre96/050608Orig1s000rev.pdf	healthy, adult Health Status: healthy Age Group: adult Sex: M Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/pre96/050608Orig1s000rev.pdf	Other AEs: Injection site pain, Creatine phosphokinase increased... Other AEs: Injection site pain (grade 3-4, 100%) Creatine phosphokinase increased (100%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/pre96/050608Orig1s000rev.pdf
2 g 1 times / day single, intramuscular Studied dose Dose: 2 g, 1 times / day Route: intramuscular Route: single Dose: 2 g, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/pre96/050608Orig1s000rev.pdf	unhealthy, mean age 25.8 years Health Status: unhealthy Age Group: mean age 25.8 years Sex: M+F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/pre96/050608Orig1s000rev.pdf	Other AEs: Injection site pain, Rash... Other AEs: Injection site pain (1%) Rash (1%) Diarrhea (5%) Fatigue (3%) Chills (1%) Headache (1%) AST increased (3%) Bilirubin increased (1%) Creatinine increased (1%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/pre96/050608Orig1s000rev.pdf
2 g 3 times / day multiple, intravenous Studied dose Dose: 2 g, 3 times / day Route: intravenous Route: multiple Dose: 2 g, 3 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/pre96/050608Orig1s000rev.pdf	unhealthy, mean age 27.1 years Health Status: unhealthy Age Group: mean age 27.1 years Sex: F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/pre96/050608Orig1s000rev.pdf	Other AEs: Chest pain, Flatulence... Other AEs: Chest pain (5%) Flatulence (5%) Diarrhea (10%) Injection site pain (5%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/pre96/050608Orig1s000rev.pdf
2 g 3 times / day multiple, intravenous Studied dose Dose: 2 g, 3 times / day Route: intravenous Route: multiple Dose: 2 g, 3 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/pre96/050608Orig1s000rev.pdf	unhealthy, mean age 27.4 years Health Status: unhealthy Age Group: mean age 27.4 years Sex: M+F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/pre96/050608Orig1s000rev.pdf	Other AEs: Injection site pain, Phlebitis... Other AEs: Injection site pain (0.8%) Phlebitis (5.3%) Chest pain (0.8%) Diarrhea (6.8%) Vomiting (0.8%) Retention of urine (0.8%) Rash (0.8%) Epistaxis (0.8%) Edema (0.8%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/pre96/050608Orig1s000rev.pdf
2 g 3 times / day multiple, intravenous Studied dose Dose: 2 g, 3 times / day Route: intravenous Route: multiple Dose: 2 g, 3 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/pre96/050608Orig1s000rev.pdf	unhealthy, mean age 60.1 years Health Status: unhealthy Age Group: mean age 60.1 years Sex: M+F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/pre96/050608Orig1s000rev.pdf	Other AEs: Thrombophlebitis, Nausea... Other AEs: Thrombophlebitis (6.7%) Nausea (6.7%) Diarrhea (6.7%) Rash (6.7%) Blood eosinophils increased (6.7%) AST increased (6.7%) ALT increased (13.3%) GGT increased (13.3%) Alkaline phosphatase increased (6.7%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/pre96/050608Orig1s000rev.pdf

AEs

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2252 inducer 1087	inhibitor 2438 inducer 440	inhibitor 2507 inducer 109

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP3A5 136 CYP2C8 1057		CYP3A5 92

Drug as perpetrator

Target	Modality	Activity
CYP2C9 2497	inducer 1966 Sources: https://www.jstage.jst.go.jp/article/jts/41/1/41_143/_article/-char/ja/ Page: 1.0	no
CYP2C9 2497	inhibitor 4027 Sources: https://www.jstage.jst.go.jp/article/jts/41/1/41_143/_article/-char/ja/ Page: 1.0	no
CYP2D6 2546	inducer 1966 Sources: https://www.jstage.jst.go.jp/article/jts/41/1/41_143/_article/-char/ja/ Page: 1.0	no
CYP2D6 2546	inhibitor 4027 Sources: https://www.jstage.jst.go.jp/article/jts/41/1/41_143/_article/-char/ja/ Page: 1.0	no
CYP3A4 2633	inducer 1966 Sources: https://www.jstage.jst.go.jp/article/jts/41/1/41_143/_article/-char/ja/ Page: 1.0	no
CYP3A4 2633	inhibitor 4027 Sources: https://www.jstage.jst.go.jp/article/jts/41/1/41_143/_article/-char/ja/ Page: 1.0	no
CYP3A5 201	inducer 1966 Sources: https://www.jstage.jst.go.jp/article/jts/41/1/41_143/_article/-char/ja/ Page: 1.0	no
CYP3A5 201	inhibitor 4027 Sources: https://www.jstage.jst.go.jp/article/jts/41/1/41_143/_article/-char/ja/ Page: 1.0	no
CYP2C8 1117	inhibitor 4027 Sources: https://www.jstage.jst.go.jp/article/jts/41/1/41_143/_article/-char/ja/ Page: 2.0	yes [Inhibition 1000 uM]

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:28971	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:28971
ChemicalBook	CB2247346	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB2247346
eMolecules	30487994	https://www.emolecules.com/cgi-bin/more?vid=30487994
eMolecules	477641	https://www.emolecules.com/cgi-bin/more?vid=477641
MolPort	MolPort-001-794-635	https://www.molport.com/shop/molecule-link/MolPort-001-794-635
ZINC	ZINC000003830218	http://zinc15.docking.org/substances/ZINC000003830218

PubMed

Title	Date	PubMed
Fresh vs aged benzylpenicillin on non-IgE responses in mice.	1998 Jan	10375765
A simple classification method for residual antibiotics using E. coli cells transformed by the calcium chloride method and drug resistance plasmid DNA.	2001	11327109
Superantigen antagonist peptides.	2001	11299061
Antibiotic susceptibility, serum response and surface properties of Klebsiella species.	2001	11297012
Enterobacter spp. infections complicating the course of HIV disease.	2001 Apr	11330368
[Clinical characteristics of beta-lactamase negative ampicillin resistant Haemophilus influenzae (BLNAR) in respiratory tract].	2001 Apr	11305000
Use of antibiotics to treat bacteriuria of pregnancy in the Nordic countries. Which antibiotics are appropriate to treat bacteriuria of pregnancy?	2001 Apr	11295409
Multicenter evaluation of resistance patterns of Klebsiella pneumoniae, Escherichia coli, Salmonella spp and Shigella spp isolated from clinical specimens in Brazil: RESISTNET Surveillance Program.	2001 Feb	11290309
Illegal abortions in Addis Ababa, Ethiopia.	2001 Jan	11320760
Antibiotic susceptibilities among recent clinical isolates of Haemophilus influenzae and Moraxella catarrhalis from fifteen countries.	2001 Jan	11245326
Meropenem in neonatal severe infections due to multiresistant gram-negative bacteria.	2001 Jan	11237230
Fetal and neonatal death from maternally acquired infection.	2001 Jan	11237116
Carboxydobrachium pacificum gen. nov., sp. nov., a new anaerobic, thermophilic, CO-utilizing marine bacterium from Okinawa Trough.	2001 Jan	11211251
Salmonella typhimurium-endocarditis secondary to an acquired environmental infection: a case report.	2001 Jan	11209847
Adhesion to a polymeric biomaterial affects the antibiotic resistance of Staphylococcus epidermidis.	2001 Jan	11209844
In vitro Gram-positive antimicrobial activity of evernimicin (SCH 27899), a novel oligosaccharide, compared with other antimicrobials: a multicentre international trial.	2001 Jan	11152427
Chryseobacterium (Flavobacterium) meningosepticum outbreak associated with colonization of water taps in a neonatal intensive care unit.	2001 Mar	11247678
Factors associated with antibiotic resistance in coliform organisms from community urinary tract infection in Wales.	2001 Mar	11222563
A multicenter study of the antimicrobial susceptibility of Haemophilus influenzae, Streptococcus pneumoniae, and Moraxella catarrhalis isolated from patients with community-acquired lower respiratory tract infections in 1999 in Portugal.	2001 Spring	11310801

Patents

Sample Use Guides

In Vivo Use Guide

Ampicillin Dosage and Administration This insert is for a Pharmacy Bulk Package and is intended for preparing IV admixtures only. Dosage recommendations for intramuscular or direct intravenous injection are for informational purposes only. Infections of the respiratory tract and soft tissues. Patients weighing 40 kg (88 lbs) or more: 250 to 500 mg every 6 hours. Patients weighing less than 40 kg (88 lbs): 25 to 50 mg/kg/day in equally divided doses at 6- to 8- hour intervals. Infections of the gastrointestinal and genitourinary tracts (including those caused by Neisseria gonorrhoeae in females). Patients weighing 40 kg (88 lbs) or more: 500 mg every 6 hours. Patients weighing less than 40 kg (88 lbs): 50 mg/kg/day in equally divided doses at 6- to 8- hour intervals. In the treatment of chronic urinary tract and intestinal infections, frequent bacteriological and clinical appraisal is necessary. Smaller doses than those recommended above should not be used. Higher doses should be used for stubborn or severe infections. In stubborn infections, therapy may be required for several weeks. It may be necessary to continue clinical and/or bacteriological follow-up for several months after cessation of therapy. Urethritis in males due to N. gonorrhoeae. Adults – Two doses of 500 mg each at an interval of 8 to 12 hours. Treatment may be repeated if necessary or extended if required. In the treatment of complications of gonorrheal urethritis, such as prostatitis and epididymitis, prolonged and intensive therapy is recommended. Cases of gonorrhea with a suspected primary lesion of syphilis should have darkfield examinations before receiving treatment. In all other cases where concomitant syphilis is suspected, monthly serological tests should be made for a minimum of four months. The doses for the preceding infections may be given by either the intramuscular or intravenous route. A change to oral Ampicillin may be made when appropriate. Bacterial Meningitis Adults and children – 150 to 200 mg/kg/day in equally divided doses every 3 to 4 hours. (Treatment may be initiated with intravenous drip therapy and continued with intramuscular injections.) The doses for other infections may be given by either the intravenous or intramuscular route. Septicemia Adults and children – 150 to 200 mg/kg/day. Start with intravenous administration for at least three days and continue with the intramuscular route every 3 to 4 hours. Treatment of all infections should be continued for a minimum of 48 to 72 hours beyond the time that the patient becomes asymptomatic or evidence of bacterial eradication has been obtained. A minimum of 10-days treatment is recommended for any infection caused by Group A beta-hemolytic streptococci to help prevent the occurrence of acute rheumatic fever or acute glomerulonephritis.

Route of Administration: Other

In Vitro Use Guide

Ampicillin was tested in vitro for antibacterial activity against 673 clinical isolates of Gram-negative bacilli and Streptococcus faecalis. Taking the group of 673 isolates tested as a whole, 448 (67 %) were inhibited by ampicillin at a concentration of 5 ug/ml.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:49:25 GMT 2025` Edited by `admin` on `Mon Mar 31 17:49:25 GMT 2025`
Record UNII	7C782967RD
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

AMPICILLIN ANHYDROUS

Preferred Name

English

AMPICILLIN

Official Name

English

AMPICILLIN [MART.]

Common Name

English

AMPICILLIN [EP MONOGRAPH]

Common Name

English

4-THIA-1-AZABICYCLO(3.2.0)HEPTANE-2-CARBOXYLIC ACID, 6-((AMINOPHENYLACETYL)AMINO)-3,3-DIMETHYL-7-OXO-, (2S-(2.ALPHA.,5.ALPHA.,6.BETA.(S*)))-

Systematic Name

English

BRL-1341

Code

English

AMINOBENZYLPENICILLIN

Common Name

English

PIPERACILLIN SODIUM IMPURITY A [EP IMPURITY]

Common Name

English

AMPICILLIN [MI]

Common Name

English

AMPICILLIN ANHYDROUS [WHO-IP]

Common Name

English

WY 5103

Code

English

REDICILIN

Common Name

English

ULTRABION

Common Name

English

AMPICILLIN [USP MONOGRAPH]

Common Name

English

Ampicillin [WHO-DD]

Common Name

English

P-50

Code

English

AMPICILLIN (ANHYDROUS)

Common Name

English

AMPICILLIN [WHO-IP]

Common Name

English

SEMICILLIN

Common Name

English

AMPICILLIN [USAN]

Common Name

English

ANHYDROUS AMPICILLIN [JAN]

Common Name

English

AMPICILLIN ANHYDROUS [GREEN BOOK]

Common Name

English

AMPICILLIN, ANHYDROUS

Common Name

English

SULTAMICILLIN IMPURITY C [EP IMPURITY]

Common Name

English

ANHYDROUS AMPICILLIN

Common Name

English

AMPICILLIN [HSDB]

Common Name

English

TOKIOCILLIN

Common Name

English

AMPICILLIN [USP-RS]

Common Name

English

ampicillin [INN]

Common Name

English

AMPICILLINUM [WHO-IP LATIN]

Common Name

English

AMPICILLIN [IARC]

Common Name

English

AY-6108

Code

English

AMPICILLIN [VANDF]

Common Name

English

NSC-528986

Code

English

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

Systematic Name

English

Classification Tree Code System Code

NDF-RT

N0000011281