Ampicillin - DrugBank

ID Pharmacology Interactions References Trials Economics Properties Spectra Taxonomy

Targets (8)Carriers (1)Transporters (4)

Targets (8)Carriers (1)Transporters (4)Biointeractions (8)

Identification

Name

Ampicillin

Accession Number

DB00415 (APRD00320)

Type

Small Molecule

Groups

Approved, Vet Approved

Description

Ampicillin is a semi-synthetic derivative of penicillin that functions as an orally active broad-spectrum antibiotic.

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

(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

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	Details
Ampicillin sodium	JFN36L5S8K	69-52-3	KLOHDWPABZXLGI-YWUHCJSESA-M	Details
Ampicillin trihydrate	HXQ6A1N7R6	7177-48-2	RXDALBZNGVATNY-CWLIKTDRSA-N	Details

Approved Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Ampicillin for Injection	Powder, for solution	1 g	Intramuscular; Intravenous	Fresenius Kabi	1998-08-14	Not applicable	Canada
Ampicillin for Injection	Powder, for solution	500 mg	Intramuscular; Intravenous	Fresenius Kabi	1998-08-14	Not applicable	Canada
Ampicillin for Injection	Powder, for solution	250 mg	Intramuscular; Intravenous	Fresenius Kabi	1998-08-14	Not applicable	Canada
Ampicillin for Injection	Powder, for solution	125 mg	Intramuscular; Intravenous	Fresenius Kabi	Not applicable	Not applicable	Canada
Ampicillin for Injection	Powder, for solution	2 g	Intravenous	Fresenius Kabi	1998-07-27	Not applicable	Canada
Ampicillin for Injection, USP	Powder, for solution	250 mg	Intramuscular; Intravenous	Sterimax Inc	Not applicable	Not applicable	Canada
Ampicillin for Injection, USP	Powder, for solution	10 g	Intramuscular; Intravenous	Sterimax Inc	Not applicable	Not applicable	Canada
Ampicillin for Injection, USP	Powder, for solution	2 g	Intramuscular; Intravenous	Sterimax Inc	Not applicable	Not applicable	Canada
Ampicillin for Injection, USP	Powder, for solution	500 mg	Intramuscular; Intravenous	Sterimax Inc	Not applicable	Not applicable	Canada
Ampicillin for Injection, USP	Powder, for solution	1 g	Intramuscular; Intravenous	Sterimax Inc	Not applicable	Not applicable	Canada
Ampicillin Sodium for Injection, USP	Powder, for solution	250 mg	Intramuscular; Intravenous	Teva	1992-12-31	Not applicable	Canada
Ampicillin Sodium for Injection, USP	Powder, for solution	2000 mg	Intramuscular; Intravenous	Teva	1992-12-31	Not applicable	Canada
Ampicillin Sodium for Injection, USP	Powder, for solution	500 mg	Intramuscular; Intravenous	Teva	1992-12-31	Not applicable	Canada
Ampicillin Sodium for Injection, USP	Powder, for solution	1000 mg	Intramuscular; Intravenous	Teva	1992-12-31	Not applicable	Canada
Ampicin for Injection 250mg	Powder, for solution	250 mg	Intramuscular; Intravenous	Bristol Labs Division Of Bristol Myers Squibb	1963-12-31	2002-07-11	Canada
Ampicin Inj 125mg/vial	Powder, for solution	125 mg	Intramuscular; Intravenous	Bristol Labs Division Of Bristol Myers Squibb	1984-12-31	2002-07-11	Canada
Ampicin Inj 1gm	Powder, for solution	1 g	Intramuscular; Intravenous	Bristol Labs Division Of Bristol Myers Squibb	1965-12-31	2002-07-11	Canada
Ampicin Inj 2000mg	Powder, for solution	2 g	Intravenous	Bristol Labs Division Of Bristol Myers Squibb	1968-12-31	2002-07-11	Canada
Ampicin Inj 500mg	Powder, for solution	500 mg	Intramuscular; Intravenous	Bristol Labs Division Of Bristol Myers Squibb	1964-12-31	2002-07-11	Canada
Jaa Amp Tab 125mg	Tablet	125 mg	Oral	Jaapharm Canada Inc.	1989-12-31	2010-08-06	Canada
Novo-ampicillin Pws 500mg/5ml	Powder, for solution	500 mg	Oral	Novopharm Limited	1972-12-31	2015-10-26	Canada
Novo-ampicillin Sus 125mg/5ml	Powder, for solution	125 mg	Oral	Novopharm Limited	1971-12-31	2005-08-10	Canada
Novo-ampicillin Sus 250mg/5ml	Powder, for solution	250 mg	Oral	Novopharm Limited	1971-12-31	2005-08-10	Canada
Nu-ampi Capsules 250mg	Capsule	250 mg	Oral	Nu Pharm Inc	1990-12-31	2012-09-04	Canada
Nu-ampi Capsules 500mg	Capsule	500 mg	Oral	Nu Pharm Inc	1990-12-31	2012-09-04	Canada
Nu-ampi Sus 125mg/5ml	Suspension	125 mg	Oral	Nu Pharm Inc	1990-12-31	2012-09-04	Canada
Nu-ampi Suspension 250mg/5ml	Suspension	250 mg	Oral	Nu Pharm Inc	1990-12-31	2012-09-04	Canada
Penbritin Cap 250mg	Capsule	250 mg	Oral	Ayerst Laboratories	1962-12-31	1996-09-10	Canada
Penbritin Cap 500mg	Capsule	500 mg	Oral	Ayerst Laboratories	1964-12-31	1996-09-10	Canada
Penbritin Inj 1000mg	Powder, for solution	1 g	Intramuscular; Intravenous	Ayerst Laboratories	1965-12-31	1996-09-10	Canada
Penbritin Inj 2000mg	Liquid	2 g	Intramuscular; Intravenous	Ayerst Laboratories	1963-12-31	1999-04-12	Canada
Penbritin Inj 250mg	Powder, for solution	250 mg	Intramuscular; Intravenous	Ayerst Laboratories	1964-12-31	1996-09-10	Canada
Penbritin Inj 500mg	Powder, for solution	500 mg	Intramuscular; Intravenous	Ayerst Laboratories	1964-12-31	1996-09-10	Canada
Penbritin Pws 250mg/5ml	Powder, for solution	250 mg	Oral	Ayerst Laboratories	1965-12-31	1996-09-10	Canada
Penbritin-1000 Pws 1000mg/vial	Powder, for solution	1 g	Intravenous	Wyeth Ayerst Canada Inc.	1995-12-31	1999-04-12	Canada
Penbritin-125 Pws 125mg/vial	Powder, for solution	125 mg	Intramuscular; Intravenous	Wyeth Ayerst Canada Inc.	1995-12-31	1996-09-10	Canada
Penbritin-250 Pws Im/iv 250mg/vial	Powder, for solution	250 mg	Intramuscular; Intravenous	Wyeth Ayerst Canada Inc.	1994-12-31	1996-09-10	Canada
Pro Ampi 250 Cap 250mg	Capsule	250 mg	Oral	Pro Doc Limitee	1985-12-31	2003-07-31	Canada
Pro Ampi 500 Cap 500mg	Capsule	500 mg	Oral	Pro Doc Limitee	1985-12-31	2003-07-31	Canada
Sterile Ampicillin Sodium 250mg USP	Powder, for solution	250 mg	Intramuscular; Intravenous	Bioniche Pharma (Canada) Ltd	1994-12-31	2014-11-24	Canada
Taro-ampicillin Cap 250mg	Capsule	250 mg	Oral	Taro Pharmaceuticals, Inc.	1993-12-31	2000-08-31	Canada
Taro-ampicillin Cap 500mg	Capsule	500 mg	Oral	Taro Pharmaceuticals, Inc.	1993-12-31	2000-08-31	Canada
Teva-ampicillin	Capsule	500 mg	Oral	Teva	1971-12-31	Not applicable	Canada
Teva-ampicillin	Capsule	250 mg	Oral	Teva	1971-12-31	Not applicable	Canada

Approved Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Ampicillin	Injection, powder, for solution	250 mg/1	Intramuscular; Intravenous	Cardinal Health	1971-03-03	Not applicable	US
Ampicillin	Injection, powder, for solution	1 g/mL	Intramuscular; Intravenous	AGILA SPECIALTIES PRIVATE LIMITED	2014-04-10	Not applicable	US
Ampicillin	Injection, powder, for solution	1 g/1	Intramuscular; Intravenous	WG Critical Care, LLC	2012-05-10	Not applicable	US
Ampicillin	Capsule	500 mg/1	Oral	Physicians Total Care, Inc.	2011-03-22	Not applicable	US
Ampicillin	Injection, powder, for solution	2 g/1	Intravenous	Sandoz	1971-03-03	Not applicable	US
Ampicillin	Injection, powder, for solution	1 g/1	Intramuscular; Intravenous	Hospira, Inc.	2015-09-04	Not applicable	US
Ampicillin	Injection, powder, for solution	250 mg/1	Intramuscular; Intravenous	WG Critical Care, LLC	2012-05-10	2016-10-13	US
Ampicillin	Injection, powder, for solution	2 g/1	Intravenous	Sandoz	1987-02-19	Not applicable	US
Ampicillin	Injection, powder, for solution	10 g/1	Intravenous	APP Pharmaceuticals, Inc.	2013-12-20	Not applicable	US
Ampicillin	Capsule	250 mg/1	Oral	Sandoz	1995-08-29	Not applicable	US
Ampicillin	Injection, powder, for solution	250 mg/1	Intramuscular; Intravenous	Fresenius Kabi	1971-03-03	Not applicable	US
Ampicillin	Suspension	50 mg/mL	Oral	DAVA Pharmaceuticals, Inc.	1989-02-10	Not applicable	US
Ampicillin	Injection, powder, for solution	2 g/1	Intravenous	Sandoz	1987-02-19	Not applicable	US
Ampicillin	Injection, powder, for solution	500 mg/1	Intramuscular; Intravenous	GC Hanford Manufacturing Company	2008-02-15	Not applicable	US
Ampicillin	Injection, powder, for solution	500 mg/1	Intramuscular; Intravenous	Auro Medics Pharma Llc	2012-02-01	Not applicable	US
Ampicillin	Injection, powder, for solution	250 mg/1	Intramuscular; Intravenous	Claris Lifesciences, Inc.	2010-04-25	Not applicable	US
Ampicillin	Injection, powder, for solution	1 g/1	Intramuscular; Intravenous	C.O. Truxton, Inc.	2009-12-28	Not applicable	US
Ampicillin	Injection, powder, for solution	500 mg/1	Intramuscular; Intravenous	Hospira, Inc.	2015-09-04	Not applicable	US
Ampicillin	Injection, powder, for solution	250 mg/1	Intramuscular; Intravenous	GC Hanford Manufacturing Company	2010-09-17	Not applicable	US
Ampicillin	Injection, powder, for solution	500 mg/1	Intramuscular; Intravenous	Sagent Pharmaceuticals	2014-07-01	Not applicable	US
Ampicillin	Injection, powder, for solution	10 g/100mL	Intravenous	Auro Medics Pharma Llc	2012-02-01	Not applicable	US
Ampicillin	Injection, powder, for solution	2 g/1	Intravenous	Claris Lifesciences, Inc.	2010-04-25	Not applicable	US
Ampicillin	Injection, powder, for solution	1 g/1	Intramuscular; Intravenous	Sandoz	1971-03-03	Not applicable	US
Ampicillin	Injection, powder, for solution	1 g/1	Intramuscular; Intravenous	Cardinal Health	1987-05-12	Not applicable	US
Ampicillin	Injection, powder, for solution	1 g/1	Intramuscular; Intravenous	Mylan Institutional	2014-04-10	Not applicable	US
Ampicillin	Injection, powder, for solution	1 g/1	Intramuscular; Intravenous	Sandoz	1971-03-03	Not applicable	US
Ampicillin	Capsule	500 mg/1	Oral	Nucare Pharmaceuticals, Inc.	1995-08-29	Not applicable	US
Ampicillin	Injection, powder, for solution	1 g/g	Intramuscular; Intravenous	General Injectables & Vaccines	2011-09-07	2017-02-03	US
Ampicillin	Injection, powder, for solution	1 g/1	Intramuscular; Intravenous	Sandoz	1971-03-03	Not applicable	US
Ampicillin	Injection, powder, for solution	500 mg/mL	Intramuscular; Intravenous	AGILA SPECIALTIES PRIVATE LIMITED	2014-04-10	Not applicable	US
Ampicillin	Injection, powder, for solution	500 mg/1	Intramuscular; Intravenous	WG Critical Care, LLC	2012-05-10	Not applicable	US
Ampicillin	Capsule	500 mg/1	Oral	A S Medication Solutions	1988-02-25	2017-06-20	US
Ampicillin	Injection, powder, for solution	1 g/1	Intramuscular; Intravenous	APP Pharmaceuticals, Inc.	1987-05-12	Not applicable	US
Ampicillin	Injection, powder, for solution	1 g/1	Intramuscular; Intravenous	Fresenius Kabi	1971-03-03	Not applicable	US
Ampicillin	Capsule	500 mg/1	Oral	DAVA Pharmaceuticals, Inc.	1988-02-25	Not applicable	US
Ampicillin	Injection, powder, for solution	10 g/1	Intravenous	Sandoz	1971-03-03	Not applicable	US
Ampicillin	Injection, powder, for solution	1 g/g	Intravenous	General Injectables & Vaccines	2010-04-01	2017-02-03	US
Ampicillin	Injection, powder, for solution	10 g/100mL	Intravenous	Sagent Pharmaceuticals	2010-07-07	Not applicable	US
Ampicillin	Injection, powder, for solution	10 g/1	Intravenous	Sandoz	1971-03-03	Not applicable	US
Ampicillin	Injection, powder, for solution	500 mg/1	Intramuscular; Intravenous	Claris Lifesciences, Inc.	2010-04-25	Not applicable	US
Ampicillin	Injection, powder, for solution	125 mg/1	Intramuscular; Intravenous	Sandoz	1971-03-03	Not applicable	US
Ampicillin	Injection, powder, for solution	250 mg/1	Intramuscular; Intravenous	Cardinal Health	1987-05-12	Not applicable	US
Ampicillin	Injection, powder, for solution	2 g/mL	Intravenous	AGILA SPECIALTIES PRIVATE LIMITED	2014-04-10	Not applicable	US
Ampicillin	Injection, powder, for solution	2 g/1	Intramuscular; Intravenous	WG Critical Care, LLC	2012-05-10	Not applicable	US
Ampicillin	Capsule	250 mg/1	Oral	Pd Rx Pharmaceuticals, Inc.	1995-08-29	Not applicable	US
Ampicillin	Injection, powder, for solution	125 mg/1	Intramuscular; Intravenous	Sandoz	1971-03-03	Not applicable	US
Ampicillin	Injection, powder, for solution	2 g/1	Intramuscular; Intravenous	Hospira, Inc.	2015-09-04	Not applicable	US
Ampicillin	Injection, powder, for solution	10 g/100mL	Intravenous	WG Critical Care, LLC	2012-05-10	Not applicable	US
Ampicillin	Injection, powder, for solution	250 mg/1	Intramuscular; Intravenous	Sandoz	1971-03-03	Not applicable	US
Ampicillin	Capsule	500 mg/1	Oral	Sandoz	1995-08-29	Not applicable	US
Ampicillin	Injection, powder, for solution	500 mg/1	Intramuscular; Intravenous	Fresenius Kabi	1971-03-03	Not applicable	US
Ampicillin	Capsule	500 mg/1	Oral	Nucare Pharmaceuticals, Inc.	1988-02-25	Not applicable	US
Ampicillin	Injection, powder, for solution	2 g/1	Intramuscular; Intravenous	GC Hanford Manufacturing Company	2008-02-15	Not applicable	US
Ampicillin	Injection, powder, for solution	1 g/1	Intramuscular; Intravenous	GC Hanford Manufacturing Company	2008-02-15	Not applicable	US
Ampicillin	Injection, powder, for solution	1 g/1	Intramuscular; Intravenous	Auro Medics Pharma Llc	2012-02-01	Not applicable	US
Ampicillin	Injection, powder, for solution	1 g/1	Intramuscular; Intravenous	Sagent Pharmaceuticals	2014-07-01	Not applicable	US
Ampicillin	Injection, powder, for solution	500 mg/1	Intramuscular; Intravenous	Sandoz	1971-03-03	Not applicable	US
Ampicillin	Injection, powder, for solution	250 mg/1	Intramuscular; Intravenous	APP Pharmaceuticals, Inc.	1987-05-12	Not applicable	US
Ampicillin	Injection, powder, for solution	2 g/1	Intravenous	Mylan Institutional	2014-04-10	Not applicable	US
Ampicillin	Injection, powder, for solution	500 mg/1	Intramuscular; Intravenous	Sandoz	1971-03-03	Not applicable	US
Ampicillin	Capsule	250 mg/1	Oral	Avera Mc Kennan Hospital	2015-07-15	Not applicable	US
Ampicillin	Injection, powder, for solution	500 mg/500mg	Intramuscular; Intravenous	General Injectables & Vaccines	2013-03-13	Not applicable	US
Ampicillin	Injection, powder, for solution	1 g/1	Intravenous	Sandoz	1987-02-19	Not applicable	US
Ampicillin	Injection, powder, for solution	2 g/1	Intramuscular; Intravenous	APP Pharmaceuticals, Inc.	1993-07-12	Not applicable	US
Ampicillin	Capsule	500 mg/1	Oral	Remedy Repack	2016-02-10	2017-03-02	US
Ampicillin	Injection, powder, for solution	2 g/1	Intravenous	Fresenius Kabi	1971-03-03	Not applicable	US
Ampicillin	Suspension	25 mg/mL	Oral	DAVA Pharmaceuticals, Inc.	1989-02-10	Not applicable	US
Ampicillin	Injection, powder, for solution	1 g/1	Intravenous	Sandoz	1987-02-19	Not applicable	US
Ampicillin	Injection, powder, for solution	250 mg/1	Intramuscular; Intravenous	Auro Medics Pharma Llc	2012-02-01	Not applicable	US
Ampicillin	Injection, powder, for solution	1 g/1	Intramuscular; Intravenous	Putney, Inc.	1971-03-03	Not applicable	US
Ampicillin	Injection, powder, for solution	1 g/1	Intramuscular; Intravenous	Claris Lifesciences, Inc.	2010-04-25	Not applicable	US
Ampicillin	Injection, powder, for solution	250 mg/1	Intramuscular; Intravenous	Sandoz	1971-03-03	Not applicable	US
Ampicillin	Injection, powder, for solution	2 g/1	Intramuscular; Intravenous	Cardinal Health	1993-07-12	Not applicable	US
Ampicillin	Injection, powder, for solution	500 mg/1	Intramuscular; Intravenous	Mylan Institutional	2014-04-10	Not applicable	US
Ampicillin	Capsule	500 mg/1	Oral	Pd Rx Pharmaceuticals, Inc.	1988-02-25	Not applicable	US
Ampicillin	Injection, powder, for solution	250 mg/1	Intramuscular; Intravenous	Sandoz	1971-03-03	Not applicable	US
Ampicillin	Injection, powder, for solution	10 g/1	Intravenous	Hospira, Inc.	2015-09-04	Not applicable	US
Ampicillin	Injection, powder, for solution	500 mg/500mg	Intramuscular; Intravenous	General Injectables & Vaccines	2011-09-02	2017-02-07	US
Ampicillin	Injection, powder, for solution	500 mg/1	Intramuscular; Intravenous	Sandoz	1971-03-03	Not applicable	US
Ampicillin	Injection, powder, for solution	250 mg/mL	Intramuscular; Intravenous	AGILA SPECIALTIES PRIVATE LIMITED	2014-04-10	Not applicable	US
Ampicillin	Capsule	500 mg/1	Oral	Blenheim Pharmacal, Inc.	2010-03-30	Not applicable	US
Ampicillin	Capsule	500 mg/1	Oral	H.J. Harkins Company	1988-02-25	Not applicable	US
Ampicillin	Injection, powder, for solution	250 mg/1	Intramuscular; Intravenous	Hospira, Inc.	2015-09-04	Not applicable	US
Ampicillin	Injection, powder, for solution	10 g/1	Intravenous	GC Hanford Manufacturing Company	2008-02-15	Not applicable	US
Ampicillin	Injection, powder, for solution	250 mg/1	Intramuscular; Intravenous	Sagent Pharmaceuticals	2014-07-01	Not applicable	US
Ampicillin	Injection, powder, for solution	2 g/1	Intravenous	Auro Medics Pharma Llc	2012-02-01	Not applicable	US
Ampicillin	Capsule	250 mg/1	Oral	DAVA Pharmaceuticals, Inc.	1988-02-25	Not applicable	US
Ampicillin	Injection, powder, for solution	2 g/1	Intravenous	Sandoz	1971-03-03	Not applicable	US
Ampicillin	Injection, powder, for solution	1 g/g	Intramuscular; Intravenous	General Injectables & Vaccines	2013-03-14	Not applicable	US
Ampicillin	Injection, powder, for solution	2 g/1	Intravenous	Sagent Pharmaceuticals	2014-07-01	Not applicable	US
Ampicillin	Injection, powder, for solution	2 g/1	Intravenous	Sandoz	1971-03-03	Not applicable	US
Ampicillin	Injection, powder, for solution	500 mg/1	Intramuscular; Intravenous	APP Pharmaceuticals, Inc.	1987-05-12	Not applicable	US
Ampicillin	Injection, powder, for solution	250 mg/1	Intramuscular; Intravenous	Mylan Institutional	2014-04-10	Not applicable	US
Ampicillin Sodium	Injection, powder, for solution	10 g/100mL	Intravenous	Mylan Institutional	2014-04-08	Not applicable	US
Ampicillin Sodium	Injection, powder, for solution	10 g/100mL	Intravenous	AGILA SPECIALTIES PRIVATE LIMITED	2014-04-08	Not applicable	US
Ampicillin Trihydrate	Capsule	250 mg/1	Oral	Golden State Medical Supply	1988-02-25	Not applicable	US
Ampicillin Trihydrate	Capsule	500 mg/1	Oral	Golden State Medical Supply	1988-02-25	Not applicable	US
Apo Ampi Capsules 250mg	Capsule	250 mg	Oral	Apotex Corporation	1984-12-31	Not applicable	Canada
Apo Ampi Capsules 500mg	Capsule	500 mg	Oral	Apotex Corporation	1984-12-31	Not applicable	Canada
Apo Ampi Liq 125mg/5ml	Liquid	125 mg	Oral	Apotex Corporation	1984-12-31	Not applicable	Canada
Apo Ampi Liq 250mg/5ml	Liquid	250 mg	Oral	Apotex Corporation	1984-12-31	Not applicable	Canada

Approved Over the Counter Products

Not Available

Unapproved/Other Products

Not Available

International Brands

Name	Company
Austrapen	Lennon Healthcare
Binotal	Bayer
Penbritin	GlaxoSmithKline
Principen	Not Available
Redicilin	Not Available
Semicillin	Not Available
Tokiocillin	Not Available
Ultrabion	Not Available
Viccillin	Meiji

Brand mixtures

Name	Labeller	Ingredients
Ampicillin and Sulbactam	Hospira, Inc.	Ampicillin Sulbactam
Ampicillin Sodium and Sulbactam Sodium	Mylan Institutional	Ampicillin Sulbactam
Pro Biosan Kit	Icn Pharmaceuticals	Ampicillin Probenecid
Unasyn	Roerig	Ampicillin Sulbactam

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)[[email protected]]2NC(=O)[[email protected]](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

Structured Indications

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	Kind	Pharmacological action	Actions	Organism	UniProt ID
Penicillin-binding protein 2a	Protein	yes	inhibitor	Streptococcus pneumoniae (strain ATCC BAA-255 / R6)	Q8DNB6	details
Penicillin-binding protein 1b	Protein	yes	inhibitor	Streptococcus pneumoniae (strain ATCC BAA-255 / R6)	Q7CRA4	details
Penicillin-binding protein 3	Protein	yes	inhibitor	Streptococcus pneumoniae	Q75Y35	details
Penicillin-binding protein 1A	Protein	yes	inhibitor	Streptococcus pneumoniae (strain ATCC BAA-255 / R6)	Q8DR59	details
Penicillin-binding protein 2B	Protein	yes	inhibitor	Streptococcus pneumoniae (strain ATCC BAA-255 / R6)	P0A3M6	details
Solute carrier family 15 member 1	Protein	unknown	Not Available	Human	P46059	details
Solute carrier family 15 member 2	Protein	unknown	Not Available	Human	Q16348	details
Angiopoietin-1 receptor	Protein	unknown	Not Available	Human	Q02763	details

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	Drug group
Acenocoumarol	Ampicillin may increase the anticoagulant activities of Acenocoumarol.	Approved
Aclarubicin	The serum concentration of Aclarubicin can be decreased when it is combined with Ampicillin.	Investigational
Allopurinol	The risk of a hypersensitivity reaction to Ampicillin is increased when it is combined with Allopurinol.	Approved
Amikacin	The serum concentration of Amikacin can be decreased when it is combined with Ampicillin.	Approved, Vet Approved
Amrubicin	The serum concentration of Amrubicin can be decreased when it is combined with Ampicillin.	Approved, Investigational
Apramycin	The serum concentration of Apramycin can be decreased when it is combined with Ampicillin.	Experimental, Vet Approved
Arbekacin	The serum concentration of Arbekacin can be decreased when it is combined with Ampicillin.	Approved
Atenolol	The bioavailability of Atenolol can be decreased when combined with Ampicillin.	Approved
Chloroquine	The serum concentration of Ampicillin can be decreased when it is combined with Chloroquine.	Approved, Vet Approved
Chlortetracycline	The therapeutic efficacy of Ampicillin can be decreased when used in combination with Chlortetracycline.	Approved, Vet Approved
Daunorubicin	The serum concentration of Daunorubicin can be decreased when it is combined with Ampicillin.	Approved
Demeclocycline	The therapeutic efficacy of Ampicillin can be decreased when used in combination with Demeclocycline.	Approved
Dicoumarol	Ampicillin may increase the anticoagulant activities of Dicoumarol.	Approved
Doxorubicin	The serum concentration of Doxorubicin can be decreased when it is combined with Ampicillin.	Approved, Investigational
Doxycycline	The therapeutic efficacy of Ampicillin can be decreased when used in combination with Doxycycline.	Approved, Investigational, Vet Approved
Epirubicin	The serum concentration of Epirubicin can be decreased when it is combined with Ampicillin.	Approved
Ethyl biscoumacetate	Ampicillin may increase the anticoagulant activities of Ethyl biscoumacetate.	Withdrawn
Framycetin	The serum concentration of Framycetin can be decreased when it is combined with Ampicillin.	Approved
Geneticin	The serum concentration of Geneticin can be decreased when it is combined with Ampicillin.	Experimental
Gentamicin	The serum concentration of Gentamicin can be decreased when it is combined with Ampicillin.	Approved, Vet Approved
GENTAMICIN C1A	The serum concentration of GENTAMICIN C1A can be decreased when it is combined with Ampicillin.	Experimental
Idarubicin	The serum concentration of Idarubicin can be decreased when it is combined with Ampicillin.	Approved
Kanamycin	The serum concentration of Kanamycin can be decreased when it is combined with Ampicillin.	Approved, Vet Approved
Lanthanum carbonate	The serum concentration of Ampicillin can be decreased when it is combined with Lanthanum carbonate.	Approved
Methotrexate	The serum concentration of Methotrexate can be increased when it is combined with Ampicillin.	Approved
Metrizamide	The serum concentration of Metrizamide can be decreased when it is combined with Ampicillin.	Approved
Minocycline	The therapeutic efficacy of Ampicillin can be decreased when used in combination with Minocycline.	Approved, Investigational
Mycophenolic acid	The serum concentration of the active metabolites of Mycophenolic acid can be reduced when Mycophenolic acid is used in combination with Ampicillin resulting in a loss in efficacy.	Approved
Neamine	The serum concentration of Neamine can be decreased when it is combined with Ampicillin.	Experimental
Neomycin	The serum concentration of Neomycin can be decreased when it is combined with Ampicillin.	Approved, Vet Approved
Netilmicin	The serum concentration of Netilmicin can be decreased when it is combined with Ampicillin.	Approved
Oxytetracycline	The therapeutic efficacy of Ampicillin can be decreased when used in combination with Oxytetracycline.	Approved, Vet Approved
Paromomycin	The serum concentration of Paromomycin can be decreased when it is combined with Ampicillin.	Approved, Investigational
Phenindione	Ampicillin may increase the anticoagulant activities of Phenindione.	Approved
Phenprocoumon	Ampicillin may increase the anticoagulant activities of Phenprocoumon.	Approved
Picosulfuric acid	The therapeutic efficacy of Picosulfuric acid can be decreased when used in combination with Ampicillin.	Approved
Pirarubicin	The serum concentration of Pirarubicin can be decreased when it is combined with Ampicillin.	Investigational
Plicamycin	The serum concentration of Plicamycin can be decreased when it is combined with Ampicillin.	Approved, Withdrawn
Probenecid	The serum concentration of Ampicillin can be increased when it is combined with Probenecid.	Approved
Puromycin	The serum concentration of Puromycin can be decreased when it is combined with Ampicillin.	Experimental
Ribostamycin	The serum concentration of Ribostamycin can be decreased when it is combined with Ampicillin.	Approved
SP1049C	The serum concentration of SP1049C can be decreased when it is combined with Ampicillin.	Investigational
Spectinomycin	The serum concentration of Spectinomycin can be decreased when it is combined with Ampicillin.	Approved, Vet Approved
Streptomycin	The serum concentration of Streptomycin can be decreased when it is combined with Ampicillin.	Approved, Vet Approved
Streptozocin	The serum concentration of Streptozocin can be decreased when it is combined with Ampicillin.	Approved
Tetracycline	The therapeutic efficacy of Ampicillin can be decreased when used in combination with Tetracycline.	Approved, Vet Approved
Tobramycin	The serum concentration of Tobramycin can be decreased when it is combined with Ampicillin.	Approved, Investigational
Valrubicin	The serum concentration of Valrubicin can be decreased when it is combined with Ampicillin.	Approved
Warfarin	Ampicillin may increase the anticoagulant activities of Warfarin.	Approved
Zorubicin	The serum concentration of Zorubicin can be decreased when it is combined with Ampicillin.	Experimental

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

Resource	Link
Human Metabolome Database (HMDB)	HMDB14559
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
Drug Product Database	8450
RxList	http://www.rxlist.com/cgi/generic/ampicillin.htm
Drugs.com	http://www.drugs.com/cdi/ampicillin.html
Wikipedia	Ampicillin

ATC Codes

S01AA19

J01CA51

J01CR01

J01CA01

AHFS Codes

08:12.16.08

PDB Entries

Not Available

FDA label

Not Available

MSDS

Download (71.8 KB)

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	Recruiting	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	Recruiting	Treatment	Bacteremia / Chronic Lung Disease of Prematurity / Necrotizing Enterocolitis	1
2	Terminated	Treatment	Bacterial Infections and Mycoses / Sepsis	1
2, 3	Active Not Recruiting	Treatment	Chorioamnionitis	1
2, 3	Completed	Prevention	Chorioamnionitis / Neonatal Early Onset Sepsis / Neonatal Meningitis / Neonatal Pneumonia / Puerperal Endometritis	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	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	Calcium Nephrolithiasis / Urinary Tract Infections (UTIs)	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	Not Yet Recruiting	Not Available	Colic / Gastrointestinal Diseases	1
Not Available	Not Yet Recruiting	Not Available	Newborn; Infection	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/mL
Injection, powder, for solution	Intramuscular; Intravenous	1 g/g
Injection, powder, for solution	Intramuscular; Intravenous	1 g/1
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/mL
Injection, powder, for solution	Intramuscular; Intravenous	250 mg/1
Injection, powder, for solution	Intramuscular; Intravenous	500 mg/500mg
Injection, powder, for solution	Intramuscular; Intravenous	500 mg/1
Injection, powder, for solution	Intramuscular; Intravenous	500 mg/mL
Injection, powder, for solution	Intravenous	1 g/g
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/mL
Injection, powder, for solution	Intravenous	2 g/1
Suspension	Oral	25 mg/mL
Suspension	Oral	50 mg/mL
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	1000 mg
Powder, for solution	Intramuscular; Intravenous	2000 mg
Powder, for solution	Intramuscular; Intravenous	250 mg
Powder, for solution	Intramuscular; Intravenous	500 mg
Powder, for solution	Intravenous	2 g
Capsule	Oral	250 mg
Capsule	Oral	500 mg
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
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	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	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 Type	Description	Splash Key
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0udi-1349000000-51be76a1d965184221c8	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0006-9810000000-75530784e97a116633e5	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0006-9600000000-0f235a2c675944bd7f8a	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-006x-9300000000-766d3a6fea596a3f18a8	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-00di-9100000000-147bdc3aaa0be3d0b419	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	Not Available

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

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

penicillin, beta-lactam antibiotic (CHEBI:28971 ) / penams (C06574 )

Targets

Details

1. 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
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 ]

Details

2. 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
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 ]

Details

3. 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
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 ]

Details

4. 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
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 ]

Details

5. Penicillin-binding protein 2B

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

General Function:: Penicillin binding
Specific Function:: Not Available
Gene Name:: penA
Uniprot ID:: P0A3M6
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 ]

Details

6. 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
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 ]

Details

7. 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
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 ]

Details

8. 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, reorganization of the actin cytoskeleton, but also maintenance of vascular quiescence. Has anti-inflammatory effects by preventing the leakage of proinflammatory plasma proteins and leukocytes from ...
Gene Name:: TEK
Uniprot ID:: Q02763
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

Details

1. 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 colloidal osmotic pressure of blood. Major zinc transporter in plasma, typically binds about 80% of all plasma zinc.
Gene Name:: ALB
Uniprot ID:: P02768
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

Details

1. 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 cations such as tetraethylammonium (TEA) without the involvement of sodium. Also relative uptake activity ratio of carnitine to TEA is 11.3.
Gene Name:: SLC22A5
Uniprot ID:: O76082
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 ]

Details

2. 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
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 ]

Details

3. 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
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 ]

Details

4. 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 leucine, valine and isoleucine, and the ketone bodies acetoacetate, beta-hydroxybutyrate and acetate. Depending on the tissue and on cicumstances, mediates the import or export of lactic acid and ketone bod...
Gene Name:: SLC16A1
Uniprot ID:: P53985
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 June 11, 2017 15:37

Get DrugBank to go!

Structure for DB00415 (Ampicillin)

Targets

References

References

References

References

References

References

References

References

Carriers

References

Transporters

References

References

References

References