(2S,6R)-6-{[(2R)-2-amino-2-phenylethanoyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
6-(D-(2-amino-2-phenylacetamido))-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid
ABPC
Aminobenzylpenicillin
Ampicilina
Ampicillin
Ampicillin (anhydrous)
Ampicillin Acid
Ampicillin Anhydrous
Ampicillin, anhydrous
Ampicilline
Ampicillinum
Anhydrous ampicillin
AP
D-(−)-6-(α-aminophenylacetamido)penicillanic acid
D-(−)-ampicillin

External IDs

AY-6108 / Bayer 5427 / BRL-1341 / NSC-528986 / P-50 / WY 5103

Product Ingredients

Ingredient	UNII	CAS	InChI Key
Ampicillin sodium	JFN36L5S8K	69-52-3	KLOHDWPABZXLGI-UHFFFAOYSA-M
Ampicillin trihydrate	HXQ6A1N7R6	7177-48-2	RXDALBZNGVATNY-CWLIKTDRSA-N

Product Images

Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Ampicillin for Injection	Powder, for solution	250 mg	Intramuscular; Intravenous	Fresenius Kabi	1998-08-14	Not applicable
Ampicillin for Injection	Powder, for solution	1 g	Intramuscular; Intravenous	Fresenius Kabi	1998-08-14	Not applicable
Ampicillin for Injection	Powder, for solution	125 mg	Intramuscular; Intravenous	Fresenius Kabi	Not applicable	Not applicable
Ampicillin for Injection	Powder, for solution	2 g	Intravenous	Fresenius Kabi	1998-07-27	Not applicable
Ampicillin for Injection	Powder, for solution	500 mg	Intramuscular; Intravenous	Fresenius Kabi	1998-08-14	Not applicable
Ampicillin for Injection, USP	Powder, for solution	1 g	Intramuscular; Intravenous	Sterimax Inc	Not applicable	Not applicable
Ampicillin for Injection, USP	Powder, for solution	10 g	Intramuscular; Intravenous	Sterimax Inc	Not applicable	Not applicable
Ampicillin for Injection, USP	Powder, for solution	250 mg	Intramuscular; Intravenous	Sterimax Inc	Not applicable	Not applicable
Ampicillin for Injection, USP	Powder, for solution	2 g	Intramuscular; Intravenous	Sterimax Inc	Not applicable	Not applicable
Ampicillin for Injection, USP	Powder, for solution	500 mg	Intramuscular; Intravenous	Sterimax Inc	Not applicable	Not applicable

Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Ampicillin	Injection, powder, for solution	1 g/1	Intramuscular; Intravenous	Sandoz	1971-03-03	Not applicable
Ampicillin	Injection, powder, for solution	1 g/1	Intravenous	Sandoz GmbH	1987-02-19	Not applicable
Ampicillin	Injection, powder, for solution	500 mg/1	Intramuscular; Intravenous	Hospira, Inc.	2015-09-04	2015-09-04
Ampicillin	Injection, powder, for solution	2 g/1	Intravenous	Sandoz GmbH	1971-03-03	Not applicable
Ampicillin	Injection, powder, for solution	1 g/1	Intramuscular; Intravenous	Hospira, Inc.	1971-03-03	Not applicable
Ampicillin	Injection, powder, for solution	2 g/1mL	Intravenous	Mylan Laboratories Limited	2014-04-10	2017-12-31
Ampicillin	Injection, powder, for solution	250 mg/1	Intramuscular; Intravenous	Claris Lifesciences, Inc.	2010-04-25	Not applicable
Ampicillin	Capsule	500 mg/1	Oral	Pd Rx Pharmaceuticals, Inc.	1988-02-25	2018-06-18
Ampicillin	Injection, powder, for solution	10 g/1	Intravenous	Hospira, Inc.	1971-03-03	Not applicable
Ampicillin	Injection, powder, for solution	250 mg/1	Intramuscular; Intravenous	Putney Inc	1971-03-03	2011-03-18

Mixture Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End
Ampicillin and Sulbactam	Ampicillin sodium (100 mg/1mL) + Sulbactam sodium (50 mg/1mL)	Injection, powder, for solution	Intramuscular; Intravenous	Baxter Laboratories	2010-04-15	2013-02-27
Ampicillin and Sulbactam	Ampicillin sodium (250 mg/1mL) + Sulbactam sodium (125 mg/1mL)	Injection, powder, for suspension	Intramuscular; Intravenous	Mylan Institutional	2012-11-27	2014-03-31
Ampicillin and Sulbactam	Ampicillin sodium (250 mg/1mL) + Sulbactam sodium (125 mg/1mL)	Injection, powder, for solution	Intravenous	West Ward Pharmaceutical	2009-12-22	Not applicable
Ampicillin and Sulbactam	Ampicillin sodium (2 g/1) + Sulbactam sodium (1 g/1)	Injection, powder, for solution	Intramuscular; Intravenous	AuroMedics Pharma LLC	2012-02-10	Not applicable
Ampicillin and Sulbactam	Ampicillin sodium (2 g/1) + Sulbactam sodium (1 g/1)	Injection, powder, for solution	Intravenous	Hospira, Inc.	2012-03-19	2012-03-19
Ampicillin and Sulbactam	Ampicillin sodium (100 mg/1mL) + Sulbactam sodium (50 mg/1mL)	Injection, powder, for solution	Intramuscular; Intravenous	Baxter Laboratories	2010-04-15	2013-10-31
Ampicillin and Sulbactam	Ampicillin sodium (1 g/1) + Sulbactam sodium (0.5 g/1)	Injection, powder, for solution	Intravenous	Hospira, Inc	2006-07-25	Not applicable
Ampicillin and Sulbactam	Ampicillin sodium (1 g/1) + Sulbactam sodium (0.5 g/1)	Injection, powder, for solution	Intramuscular; Intravenous	Claris Lifesciences, Inc.	2015-12-14	Not applicable
Ampicillin and Sulbactam	Ampicillin sodium (2 g/1) + Sulbactam sodium (1 g/1)	Injection, powder, for solution	Intravenous	Aurobindo Pharma	2010-09-20	2012-09-12
Ampicillin and Sulbactam	Ampicillin sodium (2 g/20mL) + Sulbactam sodium (1 g/20mL)	Injection, powder, for solution	Intramuscular; Intravenous	WG Critical Care, LLC	2005-11-30	Not applicable

Unapproved/Other Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End
Ampicillin and Sulbactam	Ampicillin sodium (2 g/1) + Sulbactam sodium (1 g/1)	Injection, powder, for suspension	Intramuscular; Intravenous	Cardinal Health	2011-05-20	2014-02-28

International/Other Brands

Austrapen (Lennon Healthcare) / Binotal (Bayer) / Penbritin (GlaxoSmithKline) / Principen / Redicilin / Semicillin / Tokiocillin / Ultrabion / Viccillin (Meiji)

Categories

UNII

7C782967RD

CAS number

69-53-4

Weight

Average: 349.405
Monoisotopic: 349.109626801

Chemical Formula

C₁₆H₁₉N₃O₄S

InChI Key

AVKUERGKIZMTKX-NJBDSQKTSA-N

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

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

SMILES

[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)[C@H](N)C1=CC=CC=C1)C(O)=O

Pharmacology

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

Associated Conditions

Pharmacodynamics

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.

Mechanism of action

By binding to specific penicillin-binding proteins (PBPs) located inside the bacterial cell wall, Ampicillin inhibits the third and last stage of bacterial cell wall synthesis. Cell lysis is then mediated by bacterial cell wall autolytic enzymes such as autolysins; it is possible that Ampicillin interferes with an autolysin inhibitor.

Target	Actions	Organism
APenicillin-binding protein 2a	inhibitor	Streptococcus pneumoniae (strain ATCC BAA-255 / R6)
APenicillin-binding protein 1b	inhibitor	Streptococcus pneumoniae (strain ATCC BAA-255 / R6)
APenicillin-binding protein 3	inhibitor	Streptococcus pneumoniae
APenicillin-binding protein 1A	inhibitor	Streptococcus pneumoniae (strain ATCC BAA-255 / R6)
APenicillin-binding protein 2B	inhibitor	Streptococcus pneumoniae (strain ATCC BAA-255 / R6)
USolute carrier family 15 member 1	Not Available	Human
USolute carrier family 15 member 2	Not Available	Human
UAngiopoietin-1 receptor	Not Available	Human

Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism

Not Available

Route of elimination

Ampicillin is excreted largely unchanged in the urine.

Half life

Not Available

Clearance

Not Available

Toxicity

Not Available

Affected organisms

Enteric bacteria and other eubacteria
Gram-negative Bacteria
Gram-positive Bacteria
Streptococcus pyogenes
Streptococcus pneumoniae
Neisseria meningitidis
Listeria monocytogenes
Haemophilus influenzae

Pathways

Not Available

Pharmacogenomic Effects/ADRs

Not Available

Interactions

Drug Interactions

Drug	Interaction
(R)-warfarin	Ampicillin may increase the anticoagulant activities of (R)-warfarin.
(S)-Warfarin	Ampicillin may increase the anticoagulant activities of (S)-Warfarin.
4-hydroxycoumarin	Ampicillin may increase the anticoagulant activities of 4-hydroxycoumarin.
Abacavir	Ampicillin may decrease the excretion rate of Abacavir which could result in a higher serum level.
Acarbose	Acarbose may decrease the excretion rate of Ampicillin which could result in a higher serum level.
Aceclofenac	Aceclofenac may decrease the excretion rate of Ampicillin which could result in a higher serum level.
Acemetacin	Acemetacin may decrease the excretion rate of Ampicillin which could result in a higher serum level.
Acenocoumarol	Ampicillin may increase the anticoagulant activities of Acenocoumarol.
Acetaminophen	Acetaminophen may decrease the excretion rate of Ampicillin which could result in a higher serum level.
Acetazolamide	Acetazolamide may increase the excretion rate of Ampicillin which could result in a lower serum level and potentially a reduction in efficacy.

Food Interactions

Take on an empty stomach.

References

Synthesis Reference

Jean Bouchaudon, Pierre Le Roy, Mayer Naoum Messer, "Process for the preparation of ampicillin." U.S. Patent US3978078, issued December, 1974.

US3978078

General References

Not Available

External Links

Human Metabolome Database: HMDB0014559
KEGG Drug: D00204
KEGG Compound: C06574
PubChem Compound: 6249
PubChem Substance: 46505346
ChemSpider: 6013
BindingDB: 50350465
ChEBI: 28971
ChEMBL: CHEMBL174
Therapeutic Targets Database: DAP000432
PharmGKB: PA448419
HET: AIC
RxList: RxList Drug Page
Drugs.com: Drugs.com Drug Page
Wikipedia: Ampicillin

ATC Codes

J01CR50 — Combinations of penicillins

S01AA19 — Ampicillin

J01CR01 — Ampicillin and enzyme inhibitor

J01CA01 — Ampicillin

J01CA51 — Ampicillin, combinations

AHFS Codes

08:12.16.08 — Aminopenicillins

PDB Entries

1h8s / 1nx9 / 2rdd / 3ita / 3kp3 / 3ndv / 4gcp / 4kr4

MSDS

Download (71.8 KB)

Clinical Trials

Clinical Trials

Phase	Status	Purpose	Conditions	Count
0	Recruiting	Treatment	Osteomyelitis	1
1	Completed	Not Available	Infection NOS	1
1	Completed	Treatment	Castrate Resistant Prostate Cancer (CRPC)	1
1	Completed	Treatment	Dystonias / DYT-1	1
2	Completed	Treatment	Adult T-cell lymphomas/leukaemias	1
2	Completed	Treatment	Cleft Palates	1
2	Completed	Treatment	Multiple Organ Dysfunction Syndrome / Sepsis	1
2	Completed	Treatment	Ulcerative Colitis (UC)	1
2	Terminated	Treatment	Bacterial Infections and Mycoses / Sepsis	1
2	Terminated	Treatment	Late-onset Sepsis	1
2, 3	Completed	Prevention	Chorioamnionitis / Neonatal Early Onset Sepsis / Neonatal Meningitis / Neonatal Pneumonia / Puerperal Endometritis	1
2, 3	Completed	Treatment	Chorioamnionitis	1
2, 3	Completed	Treatment	Complicated Intra Abdominal Infections	1
2, 3	Completed	Treatment	Human Immunodeficiency Virus (HIV) Infections	1
3	Completed	Prevention	Herpes Zoster / Shingles	1
3	Completed	Prevention	Human Immunodeficiency Virus (HIV) Infections	1
3	Completed	Prevention	Mumps / Rubella / Rubeola / Varicella	1
3	Completed	Treatment	Infection During Hemodialysis	1
3	Completed	Treatment	Lung Abscess / Pneumonia, Aspiration	1
3	Completed	Treatment	Sepsis	1
3	Recruiting	Treatment	Enterobacteriaceae Infections	1
3	Recruiting	Treatment	Preterm Premature Rupture of Membranes (PPROM)	1
3	Withdrawn	Prevention	Preterm Premature Ruptured Membranes	1
4	Active Not Recruiting	Prevention	Calcium Nephrolithiasis / Urinary Tract Infections (UTIs)	1
4	Completed	Not Available	Perforated Appendicitis	1
4	Completed	Prevention	Cancer, Breast	1
4	Completed	Treatment	Intra-Abdominal Infections	1
4	Completed	Treatment	Pneumonia	1
4	Enrolling by Invitation	Prevention	Renal Stones	1
4	Recruiting	Prevention	Fractures, Open / Post-Op Wound Infection	1
4	Terminated	Treatment	Community Acquired Pneumonia (CAP)	1
4	Withdrawn	Prevention	Ventilator-associated Bacterial Pneumonia	1
Not Available	Completed	Not Available	Drug Metabolism During Pregnancy	1
Not Available	Completed	Basic Science	Healthy Volunteers	1
Not Available	Completed	Treatment	Human Immunodeficiency Virus (HIV) Infections / Salmonella Infections	1
Not Available	Recruiting	Not Available	Children; Infection / Newborn; Infection	1
Not Available	Recruiting	Other	Colic / Gastrointestinal Diseases	1
Not Available	Recruiting	Prevention	Calcium Nephrolithiasis / Sepsis / Urinary Tract Infections (UTIs)	1
Not Available	Recruiting	Prevention	Necrotizing Enterocolitis / Premature Birth of Newborn	1
Not Available	Suspended	Not Available	Transient ischemia attacks	1
Not Available	Unknown Status	Not Available	Asymptomatic Infections / Bacteriuria / Transplantation Infection / Urinary Tract Infections (UTIs)	1
Not Available	Unknown Status	Treatment	Endometritis	1

Pharmacoeconomics

Manufacturers

Acic fine chemicals inc
Apothecon inc div bristol myers squibb
Baxter healthcare corp anesthesia and critical care
Consolidated pharmaceutical group inc
Gc hanford manufacturing co
Istituto biochimico italiano spa
Instituto biochemico italiano spa
International medication systems ltd
Eli lilly and co
Marsam pharmaceuticals llc
Sandoz inc
Wyeth ayerst laboratories
Bristol laboratories inc div bristol myers co
Glaxosmithkline
Parke davis div warner lambert co
American antibiotics llc
Dava pharmaceuticals inc
Ivax pharmaceuticals inc sub teva pharmaceuticals usa
Lederle laboratories div american cyanamid co
Mylan pharmaceuticals inc
Purepac pharmaceutical co
Teva pharmaceuticals usa inc
Vitarine pharmaceuticals inc
Pfizer laboratories div pfizer inc
Bristol myers squibb co
Apothecon sub bristol myers squibb co

Packagers

American Antibiotics LLC
Apotheca Inc.
APP Pharmaceuticals
A-S Medication Solutions LLC
Bryant Ranch Prepack
C.O. Truxton Inc.
Cardinal Health
Carlisle Laboratories Inc.
Central Texas Community Health Centers
Claris Lifesciences Inc.
Clonmel Healthcare Ltd.
Comprehensive Consultant Services Inc.
Comptoir Francaise De Productores
Cura Pharmaceutical Co. Inc.
Darby Dental Supply Co. Inc.
DAVA Pharmaceuticals
Dispensing Solutions
Diversified Healthcare Services Inc.
E.R. Squibb and Sons LLC
GC Hanford Manufacturing Co.
H and H Laboratories
H.J. Harkins Co. Inc.
Ibi Istituto Biochimico Italiano Giovanni Lorenzini SPA
Major Pharmaceuticals
Marnel Pharmaceuticals Inc.
Mead Johnson and Co.
Medpharm Inc.
Nucare Pharmaceuticals Inc.
Palmetto Pharmaceuticals Inc.
Par Pharmaceuticals
PCA LLC
PD-Rx Pharmaceuticals Inc.
Pharmedix
Physicians Total Care Inc.
Preferred Pharmaceuticals Inc.
Prepackage Specialists
Prescript Pharmaceuticals
Putney Inc.
Sagent Pharmaceuticals
Sandhills Packaging Inc.
Sandoz
SC Antibiotice SA
Signal Health Ltd.
Southwood Pharmaceuticals
Teva Pharmaceutical Industries Ltd.
WG Critical Care LLC

Dosage forms

Form	Route	Strength
Capsule	Oral	250 mg/1
Capsule	Oral	500 mg/1
Injection, powder, for solution	Intramuscular; Intravenous	1 g/1
Injection, powder, for solution	Intramuscular; Intravenous	1 g/1mL
Injection, powder, for solution	Intramuscular; Intravenous	1 g/1g
Injection, powder, for solution	Intramuscular; Intravenous	125 mg/1
Injection, powder, for solution	Intramuscular; Intravenous	2 g/1
Injection, powder, for solution	Intramuscular; Intravenous	250 mg/1mL
Injection, powder, for solution	Intramuscular; Intravenous	250 mg/1
Injection, powder, for solution	Intramuscular; Intravenous	500 mg/1mL
Injection, powder, for solution	Intramuscular; Intravenous	500 mg/500mg
Injection, powder, for solution	Intramuscular; Intravenous	500 mg/1
Injection, powder, for solution	Intravenous	1 g/1
Injection, powder, for solution	Intravenous	10 g/1
Injection, powder, for solution	Intravenous	10 g/100mL
Injection, powder, for solution	Intravenous	2 g/1mL
Injection, powder, for solution	Intravenous	2 g/1
Suspension	Oral	125 mg/5mL
Suspension	Oral	25 mg/1mL
Suspension	Oral	250 mg/5mL
Suspension	Oral	50 mg/1mL
Injection, powder, for solution	Intramuscular; Intravenous
Injection, powder, for solution	Intravenous
Injection, powder, for suspension	Intramuscular; Intravenous
Powder, for solution	Intramuscular; Intravenous	10 g
Powder, for solution	Intramuscular; Intravenous	2 g
Powder, for solution	Intramuscular; Intravenous	250 mg
Powder, for solution	Intramuscular; Intravenous	500 mg
Powder, for solution	Intravenous	2 g
Liquid	Oral	125 mg
Liquid	Oral	250 mg
Tablet	Oral	125 mg
Powder, for solution	Oral	500 mg
Powder, for solution	Oral	125 mg
Powder, for solution	Oral	250 mg
Capsule	Oral	250 mg
Capsule	Oral	500 mg
Suspension	Oral	125 mg
Suspension	Oral	250 mg
Powder, for solution	Intramuscular; Intravenous	1 g
Liquid	Intramuscular; Intravenous	2 g
Powder, for solution	Intravenous	1 g
Powder, for solution	Intramuscular; Intravenous	125 mg
Capsule; tablet	Oral

Prices

Unit description	Cost	Unit
Ampicillin 10 gm vial	107.77USD	vial
Ampicillin 2 gm vial	16.75USD	vial
Principen 250 mg/5ml Suspension 200ml Bottle	16.27USD	bottle
Ampicillin 1 gm vial	8.64USD	vial
Principen 250 mg/5ml Suspension 100ml Bottle	7.99USD	bottle
Ampicillin Sodium 2 g/vial	7.56USD	vial
Ampicillin Sodium 1 g/vial	3.78USD	vial
Ampicillin tr 250 mg capsule	3.53USD	capsule
Ampicillin Sodium 500 mg/vial	2.26USD	vial
Ampicillin Sodium 250 mg/vial	2.15USD	vial
Ampicillin tr 500 mg capsule	0.61USD	capsule
Ampicillin 500 mg capsule	0.5USD	capsule
Ampicillin 250 mg capsule	0.44USD	capsule

DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.

Patents

Not Available

Properties

State

Solid

Experimental Properties

Property	Value	Source
melting point (°C)	208 dec °C	PhysProp
water solubility	1.01E+004 mg/L (at 21 °C)	YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP	1.35	SANGSTER (1994)

Predicted Properties

Property	Value	Source
Water Solubility	0.605 mg/mL	ALOGPS
logP	0.88	ALOGPS
logP	-2	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	3.24	ChemAxon
pKa (Strongest Basic)	7.44	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	112.73 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	87.52 m³·mol^-1	ChemAxon
Polarizability	34.54 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted ADMET features

Property	Value	Probability
Human Intestinal Absorption	-	0.927
Blood Brain Barrier	-	0.9961
Caco-2 permeable	-	0.8956
P-glycoprotein substrate	Substrate	0.5603
P-glycoprotein inhibitor I	Non-inhibitor	0.9626
P-glycoprotein inhibitor II	Non-inhibitor	0.9971
Renal organic cation transporter	Non-inhibitor	0.9689
CYP450 2C9 substrate	Non-substrate	0.8297
CYP450 2D6 substrate	Non-substrate	0.8447
CYP450 3A4 substrate	Non-substrate	0.5825
CYP450 1A2 substrate	Non-inhibitor	0.9253
CYP450 2C9 inhibitor	Non-inhibitor	0.9402
CYP450 2D6 inhibitor	Non-inhibitor	0.9401
CYP450 2C19 inhibitor	Non-inhibitor	0.9399
CYP450 3A4 inhibitor	Non-inhibitor	0.8309
CYP450 inhibitory promiscuity	Low CYP Inhibitory Promiscuity	0.9884
Ames test	Non AMES toxic	0.9132
Carcinogenicity	Non-carcinogens	0.5363
Biodegradation	Not ready biodegradable	0.9844
Rat acute toxicity	1.5620 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.9998
hERG inhibition (predictor II)	Non-inhibitor	0.9031

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	Not Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
LC-MS/MS Spectrum - LC-ESI-QQ , positive	LC-MS/MS	splash10-0udi-1349000000-51be76a1d965184221c8
LC-MS/MS Spectrum - LC-ESI-QQ , positive	LC-MS/MS	splash10-0006-9810000000-75530784e97a116633e5
LC-MS/MS Spectrum - LC-ESI-QQ , positive	LC-MS/MS	splash10-0006-9600000000-0f235a2c675944bd7f8a
LC-MS/MS Spectrum - LC-ESI-QQ , positive	LC-MS/MS	splash10-006x-9300000000-766d3a6fea596a3f18a8
LC-MS/MS Spectrum - LC-ESI-QQ , positive	LC-MS/MS	splash10-00di-9100000000-147bdc3aaa0be3d0b419

Taxonomy

Description: This compound belongs to the class of organic compounds known as penicillins. These are organic compounds containing the penicillin core structure, which is structurally characterized by a penam ring bearing two methyl groups at position 2, and an amide group at position 6 [starting from the sulfur atom at position 1].
Kingdom: Organic compounds
Super Class: Organoheterocyclic compounds
Class: Lactams
Sub Class: Beta lactams
Direct Parent: Penicillins
Alternative Parents: N-acyl-alpha amino acids and derivatives / Alpha amino acid amides / Phenylacetamides / Aralkylamines / Thiazolidines / Tertiary carboxylic acid amides / Secondary carboxylic acid amides / Amino acids / Azetidines / Thiohemiaminal derivatives
show 9 more
Substituents: Penicillin / N-acyl-alpha amino acid or derivatives / Alpha-amino acid amide / Alpha-amino acid or derivatives / Phenylacetamide / Aralkylamine / Monocyclic benzene moiety / Benzenoid / Thiazolidine / Tertiary carboxylic acid amide
show 24 more
Molecular Framework: Aromatic heteropolycyclic compounds
External Descriptors: penicillin, beta-lactam antibiotic (CHEBI:28971) / penams (C06574)

Targets

Details1. Penicillin-binding protein 2a

Kind: Protein
Organism: Streptococcus pneumoniae (strain ATCC BAA-255 / R6)
Pharmacological action: Yes
Actions: Inhibitor

General Function: Transferase activity, transferring acyl groups
Specific Function: Not Available
Gene Name: pbp2a
Uniprot ID: Q8DNB6
Uniprot Name: Penicillin-binding protein 2a
Molecular Weight: 80797.94 Da

References

Williamson R, Hakenbeck R, Tomasz A: In vivo interaction of beta-lactam antibiotics with the penicillin-binding proteins of Streptococcus pneumoniae. Antimicrob Agents Chemother. 1980 Oct;18(4):629-37. [PubMed:7447421]

Details2. Penicillin-binding protein 1b

Kind: Protein
Organism: Streptococcus pneumoniae (strain ATCC BAA-255 / R6)
Pharmacological action: Yes
Actions: Inhibitor

General Function: Transferase activity, transferring acyl groups
Specific Function: Not Available
Gene Name: pbp1b
Uniprot ID: Q7CRA4
Uniprot Name: Penicillin-binding protein 1b
Molecular Weight: 89479.92 Da

References

Williamson R, Hakenbeck R, Tomasz A: In vivo interaction of beta-lactam antibiotics with the penicillin-binding proteins of Streptococcus pneumoniae. Antimicrob Agents Chemother. 1980 Oct;18(4):629-37. [PubMed:7447421]
Sala-Rabanal M, Loo DD, Hirayama BA, Turk E, Wright EM: Molecular interactions between dipeptides, drugs and the human intestinal H+ -oligopeptide cotransporter hPEPT1. J Physiol. 2006 Jul 1;574(Pt 1):149-66. Epub 2006 Apr 20. [PubMed:16627568]

Details3. Penicillin-binding protein 3

Kind: Protein
Organism: Streptococcus pneumoniae
Pharmacological action: Yes
Actions: Inhibitor

General Function: Serine-type d-ala-d-ala carboxypeptidase activity
Specific Function: Not Available
Gene Name: pbp3
Uniprot ID: Q75Y35
Uniprot Name: Penicillin-binding protein 3
Molecular Weight: 45209.84 Da

References

Williamson R, Hakenbeck R, Tomasz A: In vivo interaction of beta-lactam antibiotics with the penicillin-binding proteins of Streptococcus pneumoniae. Antimicrob Agents Chemother. 1980 Oct;18(4):629-37. [PubMed:7447421]
Li YH, Tanno M, Itoh T, Yamada H: Role of the monocarboxylic acid transport system in the intestinal absorption of an orally active beta-lactam prodrug: carindacillin as a model. Int J Pharm. 1999 Nov 30;191(2):151-9. [PubMed:10564841]

Details4. Penicillin-binding protein 1A

Kind: Protein
Organism: Streptococcus pneumoniae (strain ATCC BAA-255 / R6)
Pharmacological action: Yes
Actions: Inhibitor

General Function: Penicillin binding
Specific Function: Cell wall formation.
Gene Name: pbpA
Uniprot ID: Q8DR59
Uniprot Name: Penicillin-binding protein 1A
Molecular Weight: 79700.9 Da

References

Williamson R, Hakenbeck R, Tomasz A: In vivo interaction of beta-lactam antibiotics with the penicillin-binding proteins of Streptococcus pneumoniae. Antimicrob Agents Chemother. 1980 Oct;18(4):629-37. [PubMed:7447421]

Details5. Penicillin-binding protein 2B

Kind: Protein
Organism: Streptococcus pneumoniae (strain ATCC BAA-255 / R6)
Pharmacological action: Yes
Actions: Inhibitor

General Function: Not Available
Specific Function: Penicillin binding
Gene Name: penA
Uniprot ID: P0A3M6
Uniprot Name: Penicillin-binding protein 2B
Molecular Weight: 73872.305 Da

References

Williamson R, Hakenbeck R, Tomasz A: In vivo interaction of beta-lactam antibiotics with the penicillin-binding proteins of Streptococcus pneumoniae. Antimicrob Agents Chemother. 1980 Oct;18(4):629-37. [PubMed:7447421]

Details6. Solute carrier family 15 member 1

Kind: Protein
Organism: Human
Pharmacological action: Unknown

General Function: Proton-dependent oligopeptide secondary active transmembrane transporter activity
Specific Function: Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides. May constitute a major route for the absorption of protein digestion end-products.
Gene Name: SLC15A1
Uniprot ID: P46059
Uniprot Name: Solute carrier family 15 member 1
Molecular Weight: 78805.265 Da

References

Luckner P, Brandsch M: Interaction of 31 beta-lactam antibiotics with the H+/peptide symporter PEPT2: analysis of affinity constants and comparison with PEPT1. Eur J Pharm Biopharm. 2005 Jan;59(1):17-24. [PubMed:15567297]

Details7. Solute carrier family 15 member 2

Kind: Protein
Organism: Human
Pharmacological action: Unknown

General Function: Peptide:proton symporter activity
Specific Function: Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides.
Gene Name: SLC15A2
Uniprot ID: Q16348
Uniprot Name: Solute carrier family 15 member 2
Molecular Weight: 81782.77 Da

References

Pedretti A, De Luca L, Marconi C, Regazzoni L, Aldini G, Vistoli G: Fragmental modeling of hPepT2 and analysis of its binding features by docking studies and pharmacophore mapping. Bioorg Med Chem. 2011 Aug 1;19(15):4544-51. doi: 10.1016/j.bmc.2011.06.027. Epub 2011 Jun 16. [PubMed:21741846]

Property	Measurement	pH	Temperature (°C)	References
Kd (nM)	82000	N/A	N/A	22406116

Details8. Angiopoietin-1 receptor

Kind: Protein
Organism: Human
Pharmacological action: Unknown

General Function: Transmembrane receptor protein tyrosine kinase activity
Specific Function: Tyrosine-protein kinase that acts as cell-surface receptor for ANGPT1, ANGPT2 and ANGPT4 and regulates angiogenesis, endothelial cell survival, proliferation, migration, adhesion and cell spreading...
Gene Name: TEK
Uniprot ID: Q02763
Uniprot Name: Angiopoietin-1 receptor
Molecular Weight: 125829.005 Da

References

Gong XW, Mai JH, Xu YH: Discovery of loperamide as an antagonist of angiopoietin1 and angiopoietin2 by virtual screening. Bioorg Med Chem Lett. 2012 Apr 1;22(7):2388-92. doi: 10.1016/j.bmcl.2012.02.036. Epub 2012 Feb 22. [PubMed:22406116]

Carriers

Details1. Serum albumin

Kind: Protein
Organism: Human
Pharmacological action: No
Actions: Other/unknown

General Function: Toxic substance binding
Specific Function: Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name: ALB
Uniprot ID: P02768
Uniprot Name: Serum albumin
Molecular Weight: 69365.94 Da

References

Bratlid D, Bergan T: Displacement of albumin-bound antimicrobial agents by bilirubin. Pharmacology. 1976;14(5):464-72. [PubMed:1031216]

Transporters

Details1. Solute carrier family 22 member 5

Kind: Protein
Organism: Human
Pharmacological action: Unknown
Actions: Inhibitor

General Function: Symporter activity
Specific Function: Sodium-ion dependent, high affinity carnitine transporter. Involved in the active cellular uptake of carnitine. Transports one sodium ion with one molecule of carnitine. Also transports organic cat...
Gene Name: SLC22A5
Uniprot ID: O76082
Uniprot Name: Solute carrier family 22 member 5
Molecular Weight: 62751.08 Da

References

Ganapathy ME, Huang W, Rajan DP, Carter AL, Sugawara M, Iseki K, Leibach FH, Ganapathy V: beta-lactam antibiotics as substrates for OCTN2, an organic cation/carnitine transporter. J Biol Chem. 2000 Jan 21;275(3):1699-707. [PubMed:10636865]

Property	Measurement	pH	Temperature (°C)	References
Ki (nM)	14500000	N/A	N/A	15567297
Ki (nM)	15000000	N/A	N/A	15974593

Details2. Solute carrier family 15 member 1

Kind: Protein
Organism: Human
Pharmacological action: Unknown
Actions: Inhibitor

General Function: Proton-dependent oligopeptide secondary active transmembrane transporter activity
Specific Function: Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides. May constitute a major route for the absorption of protein digestion end-products.
Gene Name: SLC15A1
Uniprot ID: P46059
Uniprot Name: Solute carrier family 15 member 1
Molecular Weight: 78805.265 Da

References

Covitz KM, Amidon GL, Sadee W: Human dipeptide transporter, hPEPT1, stably transfected into Chinese hamster ovary cells. Pharm Res. 1996 Nov;13(11):1631-4. [PubMed:8956326]
Guo A, Hu P, Balimane PV, Leibach FH, Sinko PJ: Interactions of a nonpeptidic drug, valacyclovir, with the human intestinal peptide transporter (hPEPT1) expressed in a mammalian cell line. J Pharmacol Exp Ther. 1999 Apr;289(1):448-54. [PubMed:10087037]
Luckner P, Brandsch M: Interaction of 31 beta-lactam antibiotics with the H+/peptide symporter PEPT2: analysis of affinity constants and comparison with PEPT1. Eur J Pharm Biopharm. 2005 Jan;59(1):17-24. [PubMed:15567297]
Terada T, Saito H, Mukai M, Inui K: Recognition of beta-lactam antibiotics by rat peptide transporters, PEPT1 and PEPT2, in LLC-PK1 cells. Am J Physiol. 1997 Nov;273(5 Pt 2):F706-11. [PubMed:9374833]
Sala-Rabanal M, Loo DD, Hirayama BA, Turk E, Wright EM: Molecular interactions between dipeptides, drugs and the human intestinal H+ -oligopeptide cotransporter hPEPT1. J Physiol. 2006 Jul 1;574(Pt 1):149-66. Epub 2006 Apr 20. [PubMed:16627568]

Property	Measurement	pH	Temperature (°C)	References
Ki (nM)	1300000	N/A	N/A	21741846

Details3. Solute carrier family 15 member 2

Kind: Protein
Organism: Human
Pharmacological action: Unknown
Actions: Inhibitor

General Function: Peptide:proton symporter activity
Specific Function: Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides.
Gene Name: SLC15A2
Uniprot ID: Q16348
Uniprot Name: Solute carrier family 15 member 2
Molecular Weight: 81782.77 Da

References

Terada T, Saito H, Mukai M, Inui K: Recognition of beta-lactam antibiotics by rat peptide transporters, PEPT1 and PEPT2, in LLC-PK1 cells. Am J Physiol. 1997 Nov;273(5 Pt 2):F706-11. [PubMed:9374833]
Luckner P, Brandsch M: Interaction of 31 beta-lactam antibiotics with the H+/peptide symporter PEPT2: analysis of affinity constants and comparison with PEPT1. Eur J Pharm Biopharm. 2005 Jan;59(1):17-24. [PubMed:15567297]

Details4. Monocarboxylate transporter 1

Kind: Protein
Organism: Human
Pharmacological action: Unknown

General Function: Symporter activity
Specific Function: Proton-coupled monocarboxylate transporter. Catalyzes the rapid transport across the plasma membrane of many monocarboxylates such as lactate, pyruvate, branched-chain oxo acids derived from leucin...
Gene Name: SLC16A1
Uniprot ID: P53985
Uniprot Name: Monocarboxylate transporter 1
Molecular Weight: 53943.685 Da

References

Li YH, Tanno M, Itoh T, Yamada H: Role of the monocarboxylic acid transport system in the intestinal absorption of an orally active beta-lactam prodrug: carindacillin as a model. Int J Pharm. 1999 Nov 30;191(2):151-9. [PubMed:10564841]

Drug created on June 13, 2005 07:24 / Updated on December 18, 2018 09:07

Ampicillin

Identification

Structure for Ampicillin (DB00415)

Pharmacology

Interactions

References

Clinical Trials

Pharmacoeconomics

Properties

Spectra

Taxonomy

Targets

References

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References

References

References

References

Carriers

References

Transporters

References

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References