Gentamicin sulphate

Gentamicin sulphate	Last updated: 15/09/2025
(Also known as: gentamicin sulfate)

GENERAL INFORMATION

Description

A veterinary aminoglycoside antibiotic drug used to treat a range of gram-negative bacterial infections. Gentamicin and so its variants are composed of a number of related components which have varying degrees of antimicrobial potency.

Examples of veterinary uses

Used to treat bacterial infections of the bloodstream, respiratory tract, skin, sinuses, ear canal and bladder

Examples of species treated

Cats; Dogs; Horses; Pigs; Poultry

Approval status

VMR 2013/2033 approval status (GB/UK)

Not approved

EU Regulatory approval status

Not approved

Chemical structure

Isomerism

Gentamicin sulphate is a complex mixture of diastereomers, primarily composed of several closely related aminoglycoside antibiotics produced by Micromonospora purpurea. The major components include gentamicin C1, C1a, C2, C2a, and C2b, each differing in the configuration and substitution of their sugar moieties and side chains. These variations arise from differences in stereochemistry at multiple chiral centres, particularly within the 2-deoxystreptamine ring and the attached amino sugars, which influence their antimicrobial potency and toxicity profiles.

Chemical formula

C₆₀H₁₂₅N₁₅O₂₅S

Canonical SMILES

CC(C1CCC(C(O1)OC2C(CC(C(C2O)OC3C(C(C(CO3)(C)O)NC)O)N)N)N)N.CC(C1CCC(C(O1)OC2C(CC(C(C2O)OC3C(C(C(CO3)(C)O)NC)O)N)N)N)NC.CC1(COC(C(C1NC)O)OC2C(CC(C(C2O)OC3C(CCC(O3)CN)N)N)N)O.OS(=O)(=O)O

Isomeric SMILES

C[C@H]([C@@H]1CC[C@H]([C@H](O1)O[C@@H]2[C@H](C[C@H]([C@@H]([C@H]2O)O[C@@H]3[C@@H]([C@H]([C@@](CO3)(C)O)NC)O)N)N)N)N.C[C@H]([C@@H]1CC[C@H]([C@H](O1)O[C@@H]2[C@H](C[C@H]([C@@H]([C@H]2O)O[C@@H]3[C@@H]([C@H]([C@@](CO3)(C)O)NC)O)N)N)N)NC.C[C@@]1(CO[C@@H]([C@@H]([C@H]1NC)O)O[C@H]2[C@@H](C[C@@H]([C@H]([C@@H]2O)O[C@@H]3[C@@H](CC[C@H](O3)CN)N)N)N)O.OS(=O)(=O)O

International Chemical Identifier key (InChIKey)

RDEIXVOBVLKYNT-HDZPSJEVSA-N

International Chemical Identifier (InChI)

InChI=1S/C21H43N5O7.C20H41N5O7.C19H39N5O7.H2O4S/c1-9(25-3)13-6-5-10(22)19(31-13)32-16-11(23)7-12(24)17(14(16)27)33-20-15(28)18(26-4)21(2,29)8-30-20;1-8(21)12-5-4-9(22)18(30-12)31-15-10(23)6-11(24)16(13(15)26)32-19-14(27)17(25-3)20(2,28)7-29-19;1-19(27)7-28-18(13(26)16(19)24-2)31-15-11(23)5-10(22)14(12(15)25)30-17-9(21)4-3-8(6-20)29-17;1-5(2,3)4/h9-20,25-29H,5-8,22-24H2,1-4H3;8-19,25-28H,4-7,21-24H2,1-3H3;8-18,24-27H,3-7,20-23H2,1-2H3;(H2,1,2,3,4)/t9-,10-,11+,12-,13+,14+,15-,16-,17+,18-,19-,20-,21+;8-,9-,10+,11-,12+,13+,14-,15-,16+,17-,18-,19-,20+;8-,9+,10-,11+,12-,13+,14+,15-,16+,17+,18+,19-;/m110./s1

2D structure diagram/image available?

Yes

General status

Veterinary substance type

Antibiotic, Antibacterial, Medicinal drug

Substance groups

Aminoglycoside substance; Micro-organism derived susbstance

Minimum active substance purity

Known relevant impurities

Substance origin

Semi-synthetic

Mode of action

Broad-spectrum, inhibits protein synthesis,

Molecular targets

[30S ribosomal protein S12, adduct], [16S rRNA, adduct], [Low-density lipoprotein receptor-related protein 2]

CAS RN

1405-41-0

EC number

215-778-9

CIPAC number

US EPA chemical code

PubChem CID

6419933

Therapeutic Class

Alimentary tract & metabolism; Genito urinary system & sex hormones; Antiinfectants for systemic use

ATCvet Code

QA07AA91; QG01AA91; QG51AA04; QJ51GB03

Controlled Drug?

Regulation 37/2010 MRL Classification

Allowed substance (Table 1: Bovine, Porcine)

Molecular mass

1488.8 (typical)

PIN (Preferred Identification Name)

IUPAC name

(2R,3R,4R,5R)-2-[(1S,2S,3R,4S,6R)-4,6-diamino-3-[(2R,3R,6S)-3-amino-6-[(1R)-1-aminoethyl]oxan-2-yl]oxy-2-hydroxycyclohexyl]oxy-5-methyl-4-(methylamino)oxane-3,5-diol;(2R,3R,4R,5R)-2-[(1S,2S,3R,4S,6R)-4,6-diamino-3-[(2R,3R,6S)-3-amino-6-(aminomethyl)oxan-2-yl]oxy-2-hydroxycyclohexyl]oxy-5-methyl-4-(methylamino)oxane-3,5-diol;(2R,3R,4R,5R)-2-[(1S,2S,3R,4S,6R)-4,6-diamino-3-[(2R,3R,6S)-3-amino-6-[(1R)-1-(methylamino)ethyl]oxan-2-yl]oxy-2-hydroxycyclohexyl]oxy-5-methyl-4-(methylamino)oxane-3,5-diol;sulfuric acid

CAS name

Forever chemical

Other status information

Relevant Environmental Water Quality Standards

Physical state

White powdery solid

Related substances & organisms

gentamicin

Commercial

Property

Value

Availability status

Introduction & key dates

1963, first isolated; 1977, first veterinary registrations USA

Example manufacturers & suppliers of products using this active now or historically

AdvaCare Pharma
Biopharm

Example products using this active

GentaCare
Gentovitr-10

Formulation and application details

Usually supplied in either tablet form or as a cream or gel for topical application

Commercial production

Gentamicin sulphate is produced through a microbial fermentation process using the bacterium Micromonospora purpurea. The production begins with the cultivation of the organism in a carefully optimised fermentation medium containing carbon sources (like glucose), nitrogen sources (such as soybean meal), and mineral salts. After several days of aerobic fermentation under controlled temperature and pH, the broth contains a mixture of gentamicin components (C1, C1a, C2, etc.). The broth is then filtered to remove biomass, and the gentamicin is extracted using solvent partitioning or ion exchange resins to remove impurities and dyes. The purified gentamicin base is then reacted with sulphuric acid to form gentamicin sulphate.

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 (mg l⁻¹)

Solubility - In organic solvents at 20 °C (mg l⁻¹)

Melting point (°C)

Boiling point (°C)

Degradation point (°C)

Flashpoint (°C)

Octanol-water partition coefficient at pH 7, 20 °C

Log P

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

May be introduced into the environment via the faeces, urine and manure of treated animals

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)

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

K_d (mL g⁻¹)

K_oc (mL g⁻¹)

Notes and range

Freundlich

K_f (mL g⁻¹)

K_foc (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)

CT₅₀ (days)

Known metabolites

None

ECOTOXICOLOGY

Terrestrial ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 6600

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)

> 5366

Colinus virginians

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

Birds - Chronic 21d NOEL (mg kg⁻¹ bw d⁻¹)

912.8

Colinus virginians

Low

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)

Aquatic ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Temperate Freshwater Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

> 955

Oncorhychus mykiss

Low

Temperate Freshwater Fish - Chronic 21 day NOEC (mg l⁻¹)

955

Oncorhychus mykiss

Low

Tropical Freshwater Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

Temperate Freshwater Aquatic invertebrates - Acute 48 hour EC₅₀ (mg l⁻¹)

> 16.1

Daphnia magna

Moderate

Temperate Freshwater Aquatic invertebrates - Chronic 21 day NOEC (mg l⁻¹)

4.73

Daphnia magna

Moderate

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

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)

> 6600

Rat

Low

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

No metabolism and excreted unchanged in the urine. Can cross the placenta.

Health issues

Specific human health issues (hazard-based)

Carcinogen

Genotoxic

Endocrine disruptor

No data found

; ; ; ;

No data found

Reproduction / development effects

Acetyl cholinesterase inhibitor

Neurotoxicant

No data found

Respiratory tract irritant

Skin irritant

Skin sensitiser

Eye irritant

Phototoxicant

No data found

General human health issues

May cause anorexia, confusion, depression, disorientation and visual hallucinations
May damage hearing
Kidney toxicant

Handling issues

Property

Value and interpretation

General

When heated to decomposition it emits acrid smoke and fumes

CLP classification 2013

Health: H315, H317, H334, H361
Environment: H411

WHO Classification

Not listed (Not listed)

UN Number

Waste disposal & packaging

Shelf-life, storage, stability and reactivity

Chemically stable for around 2 years when stored as directed

TRANSLATIONS

Language

Name

English

gentamicin sulphate

French

German

Danish

Italian

Spanish

Greek

Polish

Swedish

Hungarian

Dutch

Norwegian

Record last updated:	15/09/2025
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