Ampicillin
drugOn this page
Also known as AmcillAmfipenAminobenzylpenicillinAminobenzylpenicillin trihydrateAmpicilinaAmpicillin (anhydrous)Ampicillin anhydrousAmpicillin hydrateAmpicillin trihydrateanhydrousAmpicillin/ampicillin trihydrateAmpicillineAmpicillinumAmpilarAnhydrous ampicillinAY-6108Alpha-aminobenzylpenicillinBritcinBRL-1341
Summary
Ampicillin (CHEMBL174) is an approved small-molecule antibacterial drug (ATC J01CA01); indicated across 12 conditions including bacterial infectious disease and eye infectious disorder.
At a glance
- Status: Approved (max clinical phase 4)
- Modality: Small molecule
- ATC class: J01CA01 (+2 more)
- Indications: 12 conditions
- Clinical trials: 39
- Chemistry: 349.4 Da · C16H19N3O4S
Identifiers
Drug identity and classification
| Field | Value |
|---|---|
| ChEMBL ID | CHEMBL174 |
| Name | Ampicillin |
| Type | Small molecule |
| Max phase | 4 |
| FDA approved | yes |
| PubChem CID | 6249 |
| ChEBI | CHEBI:28971 |
| ATC | J01CA01, J01CA51, S01AA19 |
| Molecular formula | C16H19N3O4S |
| Molecular weight | 349.4 |
| InChIKey | AVKUERGKIZMTKX-NJBDSQKTSA-N |
SMILES: CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)[C@@H](C3=CC=CC=C3)N)C(=O)O)C
IUPAC name: (2S,5R,6R)-6-[[(2R)-2-amino-2-phenylacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
ChEBI definition: A penicillin in which the substituent at position 6 of the penam ring is a 2-amino-2-phenylacetamido group.
Pharmacological roles (ChEBI): antibacterial drug.
Also known as: Amcill, Amfipen, Aminobenzylpenicillin, Aminobenzylpenicillin trihydrate, Ampicilina, Ampicillin, Ampicillin (anhydrous), Ampicillin anhydrous, Ampicillin hydrate, Ampicillin trihydrate, anhydrous, Ampicillin/ampicillin trihydrate
Parent form; salt/anhydrous children: CHEMBL453388, CHEMBL1078033, CHEMBL1200758
Patent coverage: 109,733 distinct patent families (334,414 SureChEMBL compound mentions), from 1 matched compound structure(s). Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.
Targets
Targets
Broader ChEMBL bioactivity targets: 8 (assay-derived). Sample: Lysine-specific demethylase 4E, ATP-dependent DNA helicase Q1, 15-hydroxyprostaglandin dehydrogenase [NAD(+)], Solute carrier family 15 member 2, Beta-lactamase, DNA polymerase beta, Cruzipain, Angiopoietin-1 receptor.
Bioactivity
ChEMBL activities: 1 potent at pChembl ≥ 5 of 9 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):
| Target | pChembl | Type | Value | Unit | Activity ID |
|---|---|---|---|---|---|
| P00811 | 6.25 | Potency | 562.3 | nM | CHEMBL_ACT_4662933 |
Target pathways
No target-pathway data for this drug (no mapped target genes).
Indications & clinical
Indications
12 indications (5 at ChEMBL trial phase 4). Phase below is the highest clinical-trial phase recorded for this drug against each disease — not the molecule’s overall approval status (that is in the Summary).
| Indication | Trial phase | MONDO | EFO |
|---|---|---|---|
| bacterial infectious disease | 4 | MONDO:0005113 | EFO:0000771 |
| eye infectious disorder | 4 | MONDO:0043885 | EFO:1001888 |
| gonorrhea | 4 | MONDO:0004277 | DOID:7551 |
| infectious meningitis | 4 | MONDO:0004796 | EFO:0000584 |
| nephrolithiasis | 3 | MONDO:0008171 | EFO:0004253 |
| cleft palate | 2 | MONDO:0016064 | HP:0000175 |
| chorioamnionitis | 2 | MONDO:0000409 | EFO:0009948 |
| dystonic disorder | 1 | MONDO:0003441 | MONDO:0003441 |
| osteomyelitis | 0 | MONDO:0005246 | EFO:0003102 |
3 further indication records had no mapped disease name (EFO/MeSH-only) or were duplicates, and are omitted.
Clinical trials
Total trials: 39.
Phase distribution
| Phase | Trials |
|---|---|
| PHASE4 | 15 |
| Not specified | 11 |
| PHASE3 | 7 |
| PHASE2/PHASE3 | 4 |
| PHASE2 | 1 |
| PHASE1 | 1 |
Top trials by phase / activity
| NCT | Phase | Status | Title |
|---|---|---|---|
| NCT06396078 | PHASE4 | RECRUITING | Improvement of PPROM Management With Prophylactic Antimicrobial Therapy (iPROMPT) |
| NCT06440304 | PHASE4 | RECRUITING | Therapeutic Options for CRAB |
| NCT06494072 | PHASE4 | RECRUITING | Short Versus Standard of Care Antibiotic Duration for Children Hospitalized for CAP |
| NCT07183462 | PHASE4 | RECRUITING | Azithromycin and Ampicillin for Late PPROM |
| NCT07563504 | PHASE4 | NOT_YET_RECRUITING | PROMab Trial: Ampicillin With or Without Gentamicin for Term Prelabour Rupture of Membranes |
| NCT00137007 | PHASE4 | COMPLETED | Zithromax EV in Community-Acquired Pneumonia (CAP) |
| NCT00356148 | PHASE4 | COMPLETED | The Efficacy of Prophylactic Antibiotic Administration During Breast Cancer Surgery in Overweight Patients. |
| NCT00952796 | PHASE4 | COMPLETED | A Comparative Study of Ampicillin/Sulbactam Versus Moxifloxacin in the Treatment of Complicated Intra-abdominal Infections |
| NCT02384200 | PHASE4 | COMPLETED | A Randomized Trial of Preoperative Prophylactic Antibiotics Prior to Kidney Stone Surgery (Percutaneous Nephrolithotomy [PCNL]) |
| NCT03560232 | PHASE4 | TERMINATED | Noninferiority Comparison of Prophylactic Open Fracture Antimicrobial Regimens |
| NCT03795194 | PHASE4 | TERMINATED | Antibiotic Duration in Post-appendectomy Abscess |
| NCT03997266 | PHASE4 | COMPLETED | NICU Antibiotics and Outcomes Trial |
| NCT05156437 | PHASE4 | TERMINATED | Postoperative Antibiotic Management Duration Following Surgery for Intravenous Drug Abuse (IVDA) Endocarditis (OPTIMAL) |
| NCT05977868 | PHASE4 | TERMINATED | Comparing Oral Versus Parenteral Antimicrobial Therapy |
| NCT06368102 | PHASE4 | COMPLETED | Prophylactic Effects for Preventing Surgical Site Infection in Third Molar Surgery |
| NCT05977400 | PHASE3 | NOT_YET_RECRUITING | NICU Antibiotics and Outcomes (NANO) Follow-up Study |
| NCT00879190 | PHASE2/PHASE3 | COMPLETED | Ampicillin / Sulbactam vs. Ampicillin / Gentamicin for Treatment of Chorioamnionitis |
| NCT01045902 | PHASE3 | COMPLETED | BAY12-8039, iv/Oral Pulmonary Abscess/Aspiration Pneumonia |
| NCT01551394 | PHASE3 | COMPLETED | Efficacy, Pharmacokinetics and Safety of Meropenem in Infants Below 90 Days With Clinical or Confirmed Late-onset Sepsis |
| NCT01633294 | PHASE2/PHASE3 | COMPLETED | Antibiotic Prophylaxis in Prelabor Rupture of Membranes at Term |
| NCT01994993 | PHASE2/PHASE3 | COMPLETED | Antibiotic Safety (SCAMP) |
| NCT02007603 | PHASE3 | COMPLETED | Concentration of Ampicillin / Sulbactam and Amoxicillin / Clavulanic Acid in the Blood During Renal Replacement Therapy in Longterm Renal Replacement Therapy Patients |
| NCT02579161 | PHASE3 | COMPLETED | Trial of Randomized Antibiotic Administration in Percutaneous Nephrolithotomy |
| NCT03060473 | PHASE3 | TERMINATED | Treatment of ppROM With Erythromycin vs. Azithromycin Trial |
| NCT04041791 | PHASE3 | COMPLETED | A Study to Compare Different Antibiotics and Different Modes of Fluid Treatment for Children With Severe Pneumonia |
| NCT05051163 | PHASE2/PHASE3 | UNKNOWN | Strategies to Reduce Mortality Among HIV-infected and HIV-exposed Children Admitted With Severe Acute Malnutrition |
| NCT02424734 | PHASE2 | TERMINATED | Safety, Tolerability and Efficacy of Ceftaroline in Paediatrics With Late-Onset Sepsis |
| NCT01433757 | PHASE1 | COMPLETED | Ampicillin for DYT-1 Dystonia Motor Symptoms |
| NCT00195923 | Not specified | COMPLETED | Prospective Randomized Evaluation of Antibiotic Regimen Following Appendectomy for Perforated Appendicitis |
| NCT00491426 | Not specified | COMPLETED | Antimicrobial PK in Infants With Suspected or Confirmed Infection |
| NCT00814905 | Not specified | WITHDRAWN | Treatment of Chorioamnionitis After Delivery |
| NCT01945450 | Not specified | UNKNOWN | Prophylactic Antibiotics for Manual Removal of Retained Placenta in Vaginal Birth: a Randomized Controlled Trial |
| NCT02427932 | Not specified | COMPLETED | Pharmacokinetic (PK) and Pharmacodynamic (PD) Modeling of Ampicillin and Gentamicin in Peripartum Patients |
| NCT02477423 | Not specified | COMPLETED | A Randomized Controlled Trial Investigating if Antibiotic Use in the First 48 Hours of Life Adversely Impacts the Preterm Infant Microbiome |
| NCT02829060 | Not specified | COMPLETED | Endourology Disease Group Excellence (EDGE) Consortium: Antibiotics (Abx) for Percutaneous Nephrolithotomy (PCNL) Part 2 |
| NCT02865564 | Not specified | COMPLETED | Effect of Lactobacillus Reuteri DSM17938 in Neonates Treated With Antibiotics |
| NCT03248973 | Not specified | COMPLETED | Successful Treatment of Maternal Listeria Monocytogenes Bacteremia in the First Trimester |
| NCT04202380 | Not specified | COMPLETED | Azithromycin for Preterm Pre-labor Rupture of Membranes |
| NCT07148622 | Not specified | COMPLETED | Effects of Different Antibiotic Regimens in Preterm Premature Rupture of Membranes |
Clinical evidence (CIViC)
No CIViC predictive evidence (expected for non-precision-medicine drugs).
Pharmacology
Pharmacogenomics
No CPIC/DPWG dosing guideline, but PharmGKB curates 0 clinical and 1 variant annotation(s) for this drug (gene-keyed; see PharmGKB).
Related molecules
Related molecules
No competitor molecules sharing a primary target (ChEMBL phase ≥2 or PubChem drug-class).