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Ampicillin
Last updated: 07/04/2021
(Also known as: alpha-aminobenzylpenicillin)

GENERAL INFORMATION
Description
A common and extensively used antibiotic used to treat both Gram-positive and Gram-negative bacterial infections
Availability status
-
Introduction & key dates
1961
Examples of species treated
Dogs, Cats, Rabbits, Cattle, Sheep, Pigs
Chemical structure
Isomerism
Isomeric
Chemical formula
C₁₆H₁₉N₃O₄S
Canonical SMILES
CC1(C(N2C(S1)C(C2=O)NC(=O)C(C3=CC=CC=C3)N)C(=O)O)C
Isomeric 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
International Chemical Identifier key (InChIKey)
AVKUERGKIZMTKX-NJBDSQKTSA-N
International Chemical Identifier (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
2D structure diagram/image available?
Yes
Cambridge Crystallographic Data Centre diagrams
Common Name Relationship Link
ampicillin -
General status
Veterinary substance type
Antibacterial, Antibiotic
Substance group
Aminopenicillin
Minimum active substance purity
-
Known relevant impurities
-
Substance origin
Semi-synthetic
Mode of action
Broad-spectrum, inhibts bacterial cell-wall synthesis
Molecular targets
[Penicillin-binding protein 2a, antagonist], [Penicillin-binding protein 1b, antagonist], [Penicillin-binding protein 3, antagonist], [Penicillin-binding protein 1A, antagonist], [Penicillin-binding protein 2B, antagonist]
CAS RN
69-53-4
EC number
200-709-7
CIPAC number
-
US EPA chemical code
-
PubChem CID
-
ATCvet Code
QJ51CA01
Therapeutic Class
Antiinfectants for systemic use: Antibacterials for intramammary
Controlled Drug?
No
Regulation 37/2010 MRL Classification
Allowed substance (Table 1: All food producing species)
Molecular mass
349.41
PIN (Preferred Identification Name)
-
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
CAS name
6-(D(-)-α-aminophenylacetamido)penicillanic acid
Other status information
-
Relevant Environmental Water Quality Standards
-
Physical state
White to off-white powder
Formulations
Property
Product
Manufacturer
Authorisation Route
UK Legal Class
Example products using this active
Amfipen LA, 100 mg/ml suspension for injection Intervet UK Ltd UK National authorisation (IC) Prescription only medicine to be authorised by a veterinarian (POM-V)
Bovaclox DC Xtra Intramammary Suspension Norbrook Laboratories UK National authorisation Prescription only medicine to be authorised by a veterinarian (POM-V)
Lactaclox Intramammary Infusion Norbrook Laboratories UK National authorisation Prescription only medicine to be authorised by a veterinarian (POM-V)
Sheptaclox DC Intramammary Suspension Norbrook Laboratories UK National authorisation (IC) Prescription only medicine to be authorised by a veterinarian (POM-V)
Formulation and application details
Available in a variety of formulations including intramammary suspension and infusions
ENVIRONMENTAL FATE
Property
Value
Source; quality score; and other information
Interpretation
Solubility - In water at 20 °C (mg l⁻¹)
10100
V3 V = ChemID online databases / IPCS INCHEM (ChemID; IPCS INCHEM )
3 = Unverified data of known source
High
Solubility - In organic solvents at 20 °C (mg l⁻¹)
50000
CA3 CA = Medical and toxicological databases and information systems e.g. TOXNET (click here )
3 = Unverified data of known source
Methanol
-
4000
CA3 CA = Medical and toxicological databases and information systems e.g. TOXNET (click here )
3 = Unverified data of known source
Ethanol
-
77000
CA3 CA = Medical and toxicological databases and information systems e.g. TOXNET (click here )
3 = Unverified data of known source
Dimethylacetamide
-
Melting point (°C)
208
F4 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents (US EPA Databases Related to Pesticide Risk Assessment )
4 = Verified data
-
Boiling point (°C)
- - -
Degradation point (°C)
- - -
Flashpoint (°C)
- - -
Octanol-water partition coefficient at pH 7, 20 °C
P
2.24 X 1001 Calculated -
Log P
1.35
R4 R = Peer reviewed scientific publications
4 = Verified data
Low
Bulk density (g ml⁻¹)
- - -
Dissociation constant pKa) at 25 °C
2.61
R4 R = Peer reviewed scientific publications
4 = Verified data
-
-
Vapour pressure at 20 °C (mPa)
1.61 X 10-14
R4 R = Peer reviewed scientific publications
4 = Verified data
Low volatility
Henry's law constant at 25 °C (Pa m³ mol⁻¹)
- - -
Maximum UV-vis absorption L mol⁻¹ cm⁻¹
- - -
Surface tension (mN m⁻¹)
- - -
Refractive Index
- - -
Degradation
Property
Value
Source; quality score; and other information
Interpretation
Soil degradation (days) (aerobic)
DT₅₀ (typical)
- - -
DT₅₀ (lab at 20 °C)
- - -
DT₅₀ (field)
- - -
DT₉₀ (lab at 20 °C)
- - -
DT₉₀ (field)
- - -
Note
-
Manure DT₅₀ (days)
- - -
Aqueous photolysis DT₅₀ (days) at pH 7
Value
- - -
Note
-
Aqueous hydrolysis DT₅₀ (days) at 20 °C and pH 7
Value
- - -
Note
-
Water-sediment DT₅₀ (days)
- - -
Water phase only DT₅₀ (days)
- - -
Soil adsorption and mobility
Property
Value
Source; quality score; and other information
Interpretation
Linear
Kd
- - -
Koc
-
Notes and range
-
Freundlich
Kf
- - -
Kfoc
-
1/n
-
Notes and range
-
pH sensitivity
-
Fate indices
Property
Value
Source; quality score; and other information
Interpretation
GUS leaching potential index
- - -
Other known metabolites
Metabolite name and reference
Aliases
Formation medium / Rate
Estimated maximum occurrence fraction
Metabolising enzymes
5R,6R-penicilloic acid - Animal (Urine) - -
5S,6R-penicilloic acid - Animal (Urine) - -
piperazine-2,5-dione - Animal (Urine) - -
ECOTOXICOLOGY
Property
Value
Source; quality score; and other information
Interpretation
Bio-concentration factor
BCF (l kg⁻¹)
- - -
CT₅₀ (days)
- -
Mammals - Acute oral LD₅₀ (mg kg⁻¹)
> 5000
V3 V = ChemID online databases / IPCS INCHEM (ChemID; IPCS INCHEM )
3 = Unverified data of known source
Rat
Low
Mammals - Short term dietary NOEL
(mg kg⁻¹)
- - -
(ppm diet)
- -
Mammals - Chronic 21d NOAEL (mg kg⁻¹ bw d⁻¹)
- - -
Birds - Acute LD₅₀ (mg kg⁻¹)
- - -
Birds - Short term dietary (LC₅₀/LD₅₀)
- - -
Birds - Chronic 21d NOEL (mg kg⁻¹ bw d⁻¹)
- - -
Fish - Acute 96 hour LC₅₀ (mg l⁻¹)
- - -
Fish - Chronic 21 day NOEC (mg l⁻¹)
- - -
Aquatic invertebrates - Acute 48 hour EC₅₀ (mg l⁻¹)
- - -
Aquatic invertebrates - Chronic 21 day NOEC (mg l⁻¹)
- - -
Aquatic crustaceans - Acute 96 hour LC₅₀ (mg l⁻¹)
- - -
Sediment dwelling organisms - Acute 96 hour LC₅₀ (mg l⁻¹)
- - -
Sediment dwelling organisms - Chronic 28 day NOEC, static, water (mg l⁻¹)
- - -
Sediment dwelling organisms - Chronic 28 day NOEC, sediment (mg kg⁻¹)
- - -
Aquatic plants - Acute 7 day EC₅₀, biomass (mg l⁻¹)
- - -
Non-target plants
- - -
- - -
Algae - Acute 72 hour EC₅₀, growth (mg l⁻¹)
> 1000
R4 R = Peer reviewed scientific publications
4 = Verified data
Selenastrum capricornutum
Low
Algae - Chronic 96 hour NOEC, growth (mg l⁻¹)
> 1000
R4 R = Peer reviewed scientific publications
4 = Verified data
Selanstrum capricornutum
Low
Honeybees (Apis spp.)
Contact acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)
- - -
Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)
- - -
Unknown mode acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)
- - -
Bumblebees (Bombus spp.)
Contact acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)
- - -
-
Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)
- - -
-
Mason bees (Osmia spp.)
Contact acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)
- - -
Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)
- - -
Other pollinators (1)
Acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg insect⁻¹)
- - -
Mode of exposure
-
Other pollinators (2)
Acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg insect⁻¹)
- - -
Mode of exposure
-
Earthworms - Acute 14 day LC₅₀ (mg kg⁻¹)
- - -
Earthworms - Chronic NOEC, reproduction (mg kg⁻¹)
- - -
Other soil macro-organisms
Acute LC₅₀ (mg kg⁻¹)
- - -
Chronic NOEC (mg kg⁻¹)
- - -
Other arthropod (1)
LR₅₀ g ha⁻¹
- - -
% Effect
- - -
Other arthropod (2)
LR₅₀ g ha⁻¹
- - -
% Effect
- - -
Soil micro-organisms
- - -
Mesocosm study data
NOEAEC mg l⁻¹
- - -
NOEAEC mg l⁻¹
- - -
HUMAN HEALTH AND PROTECTION
General
Property
Value
Source; quality score; and other information
Interpretation
Threshold of Toxicological Concern (Cramer Class)
High (class III) - -
Mammals - Acute oral LD₅₀ (mg kg⁻¹)
> 5000
V3 V = ChemID online databases / IPCS INCHEM (ChemID; IPCS INCHEM )
3 = Unverified data of known source
Rat
Low
Mammals - Dermal LD₅₀ (mg kg⁻¹ body weight)
- - -
Mammals - Inhalation LC₅₀ (mg l⁻¹)
- - -
Other Mammal toxicity endpoints
Subcutaneous LD₅₀ > 5000 mg kg⁻¹
V3 V = ChemID online databases / IPCS INCHEM (ChemID; IPCS INCHEM )
3 = Unverified data of known source
Rat
-
Intraperitoneal LD₅₀ = 4500 mg kg⁻¹
V3 V = ChemID online databases / IPCS INCHEM (ChemID; IPCS INCHEM )
3 = Unverified data of known source
Rat
-
ADI - Acceptable Daily Intake (mg kg⁻¹ bw day⁻¹)
- - -
ARfD - Acute Reference Dose (mg kg⁻¹ bw day⁻¹)
- - -
AAOEL - Acute Acceptable Operator Exposure Level (mg kg⁻¹ bw day⁻¹)
- - -
AOEL - Acceptable Operator Exposure Level - Systemic (mg kg⁻¹ bw day⁻¹)
- - -
Dermal penetration studies (%)
- - -
Dangerous Substances Directive 76/464
- - -
Exposure Routes
Public
-
Occupational
-
Elimination route and rate
Excreted, largely unchanged, in the urine and to a lesser extent in faeces and bile
CA3 CA = Medical and toxicological databases and information systems e.g. TOXNET (click here )
3 = Unverified data of known source
-
Health issues
Specific human health issues
Carcinogen
Genotoxic
Endocrine disruptor
?Possibly, status not identified
A0 A = Chromosome aberration (EFSA database)
0 = No data
;
B0 B = DNA damage/repair (EFSA database)
0 = No data
;
C0 C = Gene mutation (EFSA database)
0 = No data
;
D0 D = Genome mutation (EFSA database)
0 = No data
;
E0 E = Unspecified genotoxicity type (miscellaneous data source)
0 = No data
No data found
Reproduction / development effects Acetyl cholinesterase inhibitor Neurotoxicant
Yes, known to cause a problem
No data found No data found
Respiratory tract irritant Skin irritant Skin sensitiser
XNo, known not to cause a problem
XNo, known not to cause a problem
?Possibly, status not identified
Eye irritant Phototoxicant  
XNo, known not to cause a problem
No data found  
General human health issues
May induce asthma, diarrhea, nausea, vomiting, epigastric and abdominal pain
May cause skin rashes and sensitisation
Handling issues
Property
Value and interpretation
General
No information available
CLP classification 2013
-
EC Risk Classification
Xn - Harmful: R42, R43
Xi - Irritant: R36/37/38
EC Safety Classification
S22, S26, S36/37
WHO Classification
None - not a ppp
UN Number
-
Waste disposal & packaging
-
TRANSLATIONS
Language
Name
English
ampicillin
French
ampicilline
German
-
Danish
-
Italian
-
Spanish
ampicilina
Greek
-
Polish
-
Swedish
-
Hungarian
-
Dutch
-

Record last updated: 07/04/2021
Contact: aeru@herts.ac.uk
Please cite as: Lewis, K.A., Tzilivakis, J., Warner, D. and Green, A. (2016) An international database for pesticide risk assessments and management. Human and Ecological Risk Assessment: An International Journal, 22(4), 1050-1064. DOI: 10.1080/10807039.2015.1133242