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Apramycin sulphate
Last updated: 13/09/2025
(Also known as: apramycin sulphate)
GENERAL INFORMATION
Description
An antibiotic and antibacterial compound used in veterinary medicine
Examples of veterinary uses
Typically used for the treatment of colibacillosis and salmonella in calves and bacterial enteritis in pigs and lambs
Examples of species treated
Pigs; Lambs; Cattle; Chickens; Rabbits
Approval status
VMR 2013/2033 approval status (GB/UK)
Approved - usually supplied as aprescription only medicine to be authorised by a veterinarian (POM-V)
EU Regulatory approval status
Approved
Chemical structure
Isomerism
Apramycin sulphate exhibits complex stereoisomerism due to its highly branched and polycyclic structure, which includes multiple chiral centres. As an aminoglycoside antibiotic, it contains a central aminocyclitol ring linked to several sugar-like moieties, each contributing to the molecule’s stereochemical complexity. Only one stereoisomer of apramycin is biologically active.
Chemical formula
C₂₁H₄₃N₅O₁₅S
Canonical SMILES
CNC1C(C2C(CC(C(O2)OC3C(CC(C(C3O)O)N)N)N)OC1OC4C(C(C(C(O4)CO)N)O)O)O.OS(=O)(=O)O
Isomeric SMILES
CN[C@H]1[C@H]([C@@H]2[C@H](C[C@H]([C@H](O2)O[C@@H]3[C@H](C[C@H]([C@@H]([C@H]3O)O)N)N)N)O[C@@H]1O[C@@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)N)O)O)O.OS(=O)(=O)O
International Chemical Identifier key (InChIKey)
WGLYHYWDYPSNPF-RQFIXDHTSA-N
International Chemical Identifier (InChI)
InChI=1S/C21H41N5O11.H2O4S/c1-26-11-14(30)18-8(33-20(11)37-21-16(32)13(29)10(25)9(4-27)34-21)3-7(24)19(36-18)35-17-6(23)2-5(22)12(28)15(17)31;1-5(2,3)4/h5-21,26-32H,2-4,22-25H2,1H3;(H2,1,2,3,4)/t5-,6+,7-,8+,9-,10-,11+,12+,13+,14-,15-,16-,17-,18+,19+,20-,21-;/m1./s1
2D structure diagram/image available?
Yes
General status
Veterinary substance type
Antibiotic, Antimicrobial, Antibacterial
Substance groups
Aminoglycoside
Minimum active substance purity
-
Known relevant impurities
-
Substance origin
Synthetic
Mode of action
Inhibitor of protein synthesis in bacteria both in vivo and in vitro
Molecular targets
[16S rRNA]
CAS RN
65710-07-8
EC number
265-890-7
CIPAC number
-
US EPA chemical code
-
PubChem CID
3081544
Therapeutic Class
Antiinfectants for systemic use: Antibacterials for intramammary use; Alimentary tract & metabolism: Intestinal antiinfectants; Antiinfectants for systemic use: Antibacterials for systemic use
ATCvet Code
QJ51GB90; QA07AA92; QJ01GB90
Controlled Drug?
No
Regulation 37/2010 MRL Classification
Allowed substance (Table 1: Bovine, Ovine, Pocine, Chicken, Rabbit)
Molecular mass
637.7
PIN (Preferred Identification Name)
-
IUPAC name
(2R,3R,4S,5S,6S)-2-[[(2R,3S,4R,4aR,6S,7R,8aS)-7-amino-6-[(1R,2R,3S,4R,6S)-4,6-diamino-2,3-dihydroxycyclohexyl]oxy-4-hydroxy-3-(methylamino)-2,3,4,4a,6,7,8,8a-octahydropyrano[3,2-b]pyran-2-yl]oxy]-5-amino-6-(hydroxymethyl)oxane-3,4-diol;sulfuric acid
CAS name
-
Global Governance status: Listed (✓) under
UK Poisons List Order 1972 Rotterdam Convention Montreal Protocol
XNo
The Poisons List Order 1972
XNo
Rotterdam Convention
XNo
Montreal Protocol
Stockholm Convention OSPAR EU Water Framework Directive
XNo
Stockholm Convention
XNo
OSPAR
XNo
EU Water Framework Directive
Relevant Environmental Water Quality Standards
-
Forever chemical
-
Other status information
-
Physical state
-
Related substances & organisms
Commercial
Property
Value
Availability status
Current
Introduction & key dates
1980s, first clinical use
Example manufacturers & suppliers of products using this active now or historically
  • Elanco Animal Health
  • Sigma-Aldrich
  • Huvepharma N.V.
Example products using this active
  • Apralan Soluble Powder
  • Apravet Premix Medicated Feed
Formulation and application details
Often supplied as a powder which is added to livestock's drinking water. Also available as premix and pour-on formulations
Commercial production
Apramycin sulphate is produced through a fermentation-based process using the actinomycete bacterium Streptomyces tenebrarius, which naturally synthesises apramycin as a secondary metabolite. The production begins by culturing this microorganism in a nutrient-rich medium under carefully controlled conditions of temperature, pH, aeration, and agitation to optimsze yield. After fermentation, the broth is subjected to filtration and centrifugation to remove biomass, followed by extraction and purification steps that often involve ion-exchange resins or membrane separation to isolate apramycin. The purified compound is then reacted with sulfuric acid to form the sulphate salt.
Impact on climate of production and use
As microbial-based products tend to use fermentation-based production processes rather than chemical synthesis, they typically have a lower fossil fuel input in formulation and active ingredient creation, and also have reduced downstream emissions due to biodegradability and minimal soil disruption, their life-cycle GHG emissions are expected to be low. Whilst hard and precise data is not available, broad estimates suggest that typically emissions are likely to be below 5 kg CO₂e/kg.
ENVIRONMENTAL FATE
Property
Value
Source; quality score; and other information
Interpretation
Solubility - In water at 20 °C at pH 7 (mg l⁻¹)
300000
F3 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents / FAO data, IPCS INCHEM data (US EPA Databases Related to Pesticide Risk Assessment )
3 = Unverified data of known source
 High
Solubility - In organic solvents at 20 °C (mg l⁻¹)
- - -
Melting point (°C)
245
F3 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents / FAO data, IPCS INCHEM data (US EPA Databases Related to Pesticide Risk Assessment )
3 = Unverified data of known source
 -
Boiling point (°C)
- - -
Degradation point (°C)
- - -
Flashpoint (°C)
- - -
Octanol-water partition coefficient at pH 7, 20 °C
P
3.48 X 1000 Calculated -
Log P
0.542
F3 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents / FAO data, IPCS INCHEM data (US EPA Databases Related to Pesticide Risk Assessment )
3 = Unverified data of known source
 Low
Fat solubility of residues
Solubility
- - -
Data type
- - -
Density (g ml⁻¹)
- - -
Dissociation constant pKa) at 25 °C
- - -
-
Vapour pressure at 20 °C (mPa)
- - -
Henry's law constant at 25 °C (Pa m³ mol⁻¹)
- - -
Volatilisation as max % of applied dose lost
From plant surface
- - -
From soil surface
- - -
Maximum UV-vis absorption L mol⁻¹ cm⁻¹
- - -
Surface tension (mN m⁻¹)
- - -
Refractive Index
- - -
Environmental release
Main route into the environment from treated pigs is via animal urine and faeces.
Degradation
Property
Value
Source; quality score; and other information
Interpretation
Soil degradation (days) (aerobic)
DT₅₀ (typical)
365
F3 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents / FAO data, IPCS INCHEM data (US EPA Databases Related to Pesticide Risk Assessment )
3 = Unverified data of known source
 Very persistent
DT₅₀ (lab at 20 °C)
- - -
DT₅₀ (field)
- - -
DT₉₀ (lab at 20 °C)
- - -
DT₉₀ (field)
- - -
Note
DT₅₀ in soil is reported to be >1 year. Greenhouse studies suggest > 3 years (F3)
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)
- - -
Sediment phase only DT₅₀ (days)
- - -
Air degradation
As this parameter is not normally measured directly, a surrogate measure is used: ‘Photochemical oxidative DT₅₀’. Where data is available, this can be found in the Fate Indices section below.
Decay in stored produce DT₅₀
-
Soil adsorption and mobility
Property
Value
Source; quality score; and other information
Interpretation
Linear
Kd (mL g⁻¹)
- - -
Koc (mL g⁻¹)
-
Notes and range
-
Freundlich
Kf (mL g⁻¹)
- - -
Kfoc (mL g⁻¹)
-
1/n
-
Notes and range
-
pH sensitivity
-
Fate indices
Property
Value
Source; quality score; and other information
Interpretation
GUS leaching potential index
- - -
Bio-concentration factor
BCF (l kg⁻¹)
0.26
F3 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents / FAO data, IPCS INCHEM data (US EPA Databases Related to Pesticide Risk Assessment )
3 = Unverified data of known source
 Low potential
CT₅₀ (days)
ND -
Known metabolites

None

ECOTOXICOLOGY
Terrestrial ecotoxicology
Property
Value
Source; quality score; and other information
Interpretation
Mammals - Acute oral LD₅₀ (mg kg⁻¹)
> 4160
F3 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents / FAO data, IPCS INCHEM data (US EPA Databases Related to Pesticide Risk Assessment )
3 = Unverified data of known source
Rat		 Low
Mammals - Short Term Oral NOAEL (mg kg⁻¹ bw d⁻¹)
- - -
Mammals - Long Term (Chronic) Oral NOAEL (mg kg⁻¹ bw d⁻¹)
- - -
Birds - Acute LD₅₀ (mg kg⁻¹)
> 1838
F3 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents / FAO data, IPCS INCHEM data (US EPA Databases Related to Pesticide Risk Assessment )
3 = Unverified data of known source
Anas platyrhynchos		 Moderate
Birds - Short term dietary (LC₅₀/LD₅₀)
- - -
Birds - Chronic 21d NOEL (mg kg⁻¹ bw d⁻¹)
- - -
Earthworms - Acute 14 day LC₅₀ (mg kg⁻¹ dw soil)
- - -
Earthworms - Chronic NOEC, reproduction (mg kg⁻¹ dw soil)
- - -
Soil micro-organisms
- - -
Collembola
Acute LC₅₀ (mg kg⁻¹)
- - -
Chronic NOEC (mg kg⁻¹)
- - -
Non-target plants
Vegetative vigour ER₅₀ (g ha⁻¹)
- - -
Seedling emergence ER₅₀ (g ha⁻¹)
- - -
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)
- - -
Chronic
- - -
Notes
-
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 bee species (1)
Acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg insect⁻¹)
- - -
Mode of exposure
-
Other bee species (2)
Acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg insect⁻¹)
- - -
Mode of exposure
-
Beneficial insects (Ladybirds)
- - -
Beneficial insects (Lacewings)
- - -
Beneficial insects (Parasitic wasps)
- - -
Beneficial insects (Predatory mites)
- - -
Beneficial insects (Ground beetles)
- - -
Beneficial insects (Butterflies)
Contact
- - -
Notes
-
Oral
- - -
Notes
-
Aquatic ecotoxicology
Property
Value
Source; quality score; and other information
Interpretation
Temperate Freshwater Fish - Acute 96 hour LC₅₀ (mg l⁻¹)
- - -
Temperate Freshwater Fish - Chronic 21 day NOEC (mg l⁻¹)
- - -
Tropical Freshwater Fish - Acute 96 hour LC₅₀ (mg l⁻¹)
- - -
Temperate Freshwater Aquatic invertebrates - Acute 48 hour EC₅₀ (mg l⁻¹)
191.6
F3 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents / FAO data, IPCS INCHEM data (US EPA Databases Related to Pesticide Risk Assessment )
3 = Unverified data of known source
Daphnia magna		 Low
Temperate Freshwater Aquatic invertebrates - Chronic 21 day NOEC (mg l⁻¹)
- - -
Tropical Freshwater Aquatic invertebrates - Acute 48 hour EC₅₀ (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 (free-floating, fonds growth, fresh) - 7 day (mg l⁻¹)
- - -
Aquatic plants (rooted, growth rate, fresh) - 14 day (mg l⁻¹)
- - -
Algae - Acute (growth rate, fresh; mg l⁻¹)
- - -
Algae - Chronic (growth rate, fresh; mg l⁻¹)
- - -
Mesocosm study data
NOEAEC mg l⁻¹
- - -
NOEAEC mg l⁻¹
- - -
Marine bivalves
- - -
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)
> 4160
F3 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents / FAO data, IPCS INCHEM data (US EPA Databases Related to Pesticide Risk Assessment )
3 = Unverified data of known source
Rat		 Low
Mammals - Short Term Oral NOAEL (mg kg⁻¹ bw d⁻¹)
- - -
Mammals - Long Term (Chronic) Oral NOAEL (mg kg⁻¹ bw d⁻¹)
- - -
Mammals - Dermal LD₅₀ (mg kg⁻¹ body weight)
- - -
Mammals - Inhalation LC₅₀ (mg l⁻¹)
- - -
Other Mammal toxicity endpoints
- - -
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
-
Mammalian dose elimination route and rate
Apramycin is rapidly absorbed when administered orally and is excreted via the kidneys without metabolisation.
Q3 Q = Miscellaneous data from online sources
3 = Unverified data of known source
 -
Health issues
Specific human health issues (hazard-based)
Carcinogen
Genotoxic
Endocrine disruptor
XNo, known not to cause a problem
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
;
E3 E = Unspecified genotoxicity type (miscellaneous data source)
3 = Negative
XNo, known not to cause a problem
Reproduction / development effects Acetyl cholinesterase inhibitor Neurotoxicant
?Possibly, status not identified
XNo, known not to cause a problem
XNo, known not to cause a problem
Respiratory tract irritant Skin irritant Skin sensitiser
✓Yes, known to cause a problem
✓Yes, known to cause a problem
 No data found
Eye irritant Phototoxicant  
✓Yes, known to cause a problem
 No data found  
General human health issues
Possible kidney toxicant
Handling issues
Property
Value and interpretation
General
When heated to decomposition it emits acrid smoke and irritating fumes
Corrosive
CLP classification 2013
-
WHO Classification
Not listed (Not listed)
UN Number
-
Waste disposal & packaging
-
Shelf-life, storage, stability and reactivity
-
TRANSLATIONS
Language
Name
English
apramycin sulphate
French
-
German
-
Danish
-
Italian
-
Spanish
-
Greek
-
Polish
-
Swedish
-
Hungarian
-
Dutch
-
Norwegian
-
Record last updated: 13/09/2025
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

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