Ampicillin

Penicillin-class Antibacterial — ANTIINFECTIVES FOR SYSTEMIC USE

Key facts

Ampicillin is an ofp drug in the Penicillin-class Antibacterial class catalogued in DrugCentral. It was first approved by the FDA in 1965. DrugCentral lists 4 molecular targets, including TRPM4, TEK and pbpA. Recorded indications include Acute bacterial epiglottitis, Acute bacterial sinusitis, Acute epiglottitis and Acute exacerbation of chronic bronchitis.

• Approval status: ofp (first approved 1965 by the FDA).
• Drug class: Penicillin-class Antibacterial.
• Molecular targets: TRPM4, TEK, pbpA and mrcA|mrcB|dacC|mrdA|ftsI|dacA|dacB (4 listed in DrugCentral).
• Indications: Acute bacterial epiglottitis, Acute bacterial sinusitis, Acute epiglottitis, Acute exacerbation of chronic bronchitis and Acute gonococcal cervicitis and others.
• ATC code: J01CA01 (Penicillins with extended spectrum).
• Molecular formula: C16H19N3O4S; molecular weight 349.41 g/mol.

Indications & contraindications

Drug–disease relationships curated by DrugCentral (OMOP / SNOMED concepts).

Indications (73)

• Acute bacterial epiglottitis
• Acute bacterial sinusitis
• Acute epiglottitis
• Acute exacerbation of chronic bronchitis
• Acute gonococcal cervicitis
• Acute gonococcal endometritis
• Acute gonococcal urethritis
• Acute otitis media
• Bacterial endocarditis
• Bacterial meningitis
• Bacterial peritonitis
• Bacterial pneumonia
• Bacterial septicemia
• Bacterial urinary infection
• Bacteroides Gynecological Infections
• Bacteroides Peritonitis
• Cesarean Section Infection Prevention
• Cholangitis
• Dysentery
• E. Coli Gynecological Infections
• E. Coli Peritonitis
• Enterococcus Urinary Tract Infection
• Escherichia coli meningitis
• Female genital tract infection
• Gastroenteritis due to Salmonella
• Genitourinary Tract Infections
• Gonorrhea
• Gonorrhea of rectum
• Haemophilus Influenzae Acute Otitis Media
• Haemophilus Influenzae Chronic Bronchitis
• + 43 more

Off-label uses (21)

• Anthrax
• Cat bite - wound
• Cutaneous listeriosis
• Diabetic Foot Infection
• Diverticulitis of gastrointestinal tract
• Dog bite - wound
• Enterocolitis
• Gastrointestinal anthrax
• Granulomatosis Infantiseptica
• H. Influenzae Meningitis
• Haemophilus Parainfluenzae Acute Otitis Media
• Haemophilus Parainfluenzae Chronic Bronchitis
• Haemophilus Parainfluenzae Pneumonia
• Human bite - wound
• Infection by Campylobacter fetus
• Infection of bone
• Inhalational anthrax
• Listeria meningitis
• Listeria Monocytogenes Septicemia
• Listeria Osteomyelitis
• Listeria Septic Arthritis

Contraindications (6)

• Acute nephropathy
• Anemia due to enzyme deficiency
• Disease of blood AND/OR blood-forming organ
• Impaired renal function disorder
• Infectious mononucleosis
• Kidney disease

Mechanism & targets

• Established pharmacologic class: Penicillin-class Antibacterial

Molecular targets (4)

Target	Gene	Action	Activity
Transient receptor potential cation channel subfamily M member 4	TRPM4	unknown	IC50 4.72
Angiopoietin-1 receptor	TEK	unknown	Kd 4.09
Penicillin-binding protein 1A	pbpA	unknown	—
Bacterial penicillin-binding protein	mrcA|mrcB|dacC|mrdA|ftsI|dacA|dacB	inhibitor	—

Regulatory approvals (1)

Date	Agency	Marketed as	Applicant	Orphan
1965-12-17	FDA	—	WYETH AYERST

ATC classification

ATC code	Therapeutic hierarchy
J01CA01	ANTIINFECTIVES FOR SYSTEMIC USE › ANTIBACTERIALS FOR SYSTEMIC USE › BETA-LACTAM ANTIBACTERIALS, PENICILLINS › Penicillins with extended spectrum
J01CA51	ANTIINFECTIVES FOR SYSTEMIC USE › ANTIBACTERIALS FOR SYSTEMIC USE › BETA-LACTAM ANTIBACTERIALS, PENICILLINS › Penicillins with extended spectrum
J01CR01	ANTIINFECTIVES FOR SYSTEMIC USE › ANTIBACTERIALS FOR SYSTEMIC USE › BETA-LACTAM ANTIBACTERIALS, PENICILLINS › Combinations of penicillins, incl. beta-lactamase inhibitors
S01AA19	SENSORY ORGANS › OPHTHALMOLOGICALS › ANTIINFECTIVES › Antibiotics

Reported adverse-event signals

Strongest FDA FAERS disproportionality signals (log-likelihood ratio). A signal is a statistical association in spontaneous reports, not proof that the drug causes the event.

MedDRA term	LLR
Premature baby	1196.2
Premature delivery	858.6
Foetal exposure during pregnancy	637.2
Normal labour	622.9
Delivery	520.4
Maternal exposure during pregnancy	491.3
Low birth weight baby	384.5
Type IV hypersensitivity reaction	333.6
Drug hypersensitivity	328.4
Cross sensitivity reaction	219.6
Pathogen resistance	185.0
Neonatal respiratory distress syndrome	158.7

Chemical structure

Full physicochemical, ADMET and 3D-structure analysis of Ampicillin is on its molecule page.

• Molecular formula: C₁₆H₁₉N₃O₄S
• Molecular weight: 349.41 g/mol
• CAS number: 69-53-4
• InChIKey: AVKUERGKIZMTKX-NJBDSQKTSA-N
• PubChem CID: 6249

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

Frequently asked questions

Answers are generated from the structured data on this page, not written by hand.

What is Ampicillin used for?

DrugCentral lists the following indications for Ampicillin: Acute bacterial epiglottitis, Acute bacterial sinusitis, Acute epiglottitis, Acute exacerbation of chronic bronchitis, Acute gonococcal cervicitis, Acute gonococcal endometritis, Acute gonococcal urethritis and Acute otitis media and others.

How does Ampicillin work?

Its molecular targets in DrugCentral include TRPM4, TEK, pbpA and mrcA|mrcB|dacC|mrdA|ftsI|dacA|dacB (inhibitor).

When was Ampicillin first approved?

Ampicillin was first approved by the FDA in 1965.

What drug class does Ampicillin belong to?

Ampicillin is in the Penicillin-class Antibacterial class.

What is the chemical formula of Ampicillin?

Ampicillin has the molecular formula C16H19N3O4S and a molecular weight of 349.41 g/mol.

Sources

• DrugCentral drug card 198 — structure, indications, targets, approvals, pharmacologic classes (CC BY-SA 4.0)
• ChEMBL CHEMBL1200758 — compound record and bioactivity
• PubChem CID 6249 — chemical identifiers
• DrugBank DB00415 — drug record
• FDA UNII 7C782967RD — substance identity
• DailyMed: FDA labels for Ampicillin — current prescribing information (label search)
• UniProt Q8TD43 (TRPM4) — target protein
• UniProt Q02763 (TEK) — target protein
• FDA Adverse Event Reporting System (openFDA FAERS) — adverse-event signals, as aggregated by DrugCentral

How this page is built: methodology · editorial policy & corrections.