Sulphanilamide

Sulphanilamide	Last updated: 23/02/2024
(Also known as: 4-aminobenzenesulphonamide; bacteramid; 4-sulfamoylaniline; PABS; sulphonamide; sulfanilamide)

GENERAL INFORMATION

Description

A Sulphonamide antibiotic drug once used in veterinary medicine

Availability status

Current

Introduction & key dates

1935, active parent introduced

Examples of veterinary uses

Used to manage bacterial infections notably streptococcal septicaemia, equine pneumonia, strangles, joint-ill and metritis

Examples of species treated

Cattle; Sheep

Approval status

VMR 2013/2033 approval status (GB/UK)

Not approved

EU Regulatory approval status

Not approved

Chemical structure

Isomerism

Chemical formula

C₆H₈N₂O₂S

Canonical SMILES

C1=CC(=CC=C1N)S(=O)(=O)N

Isomeric SMILES

International Chemical Identifier key (InChIKey)

FDDDEECHVMSUSB-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C6H8N2O2S/c7-5-1-3-6(4-2-5)11(8,9)10/h1-4H,7H2,(H2,8,9,10)

2D structure diagram/image available?

Yes

Cambridge Crystallographic Data Centre diagrams

Common Name	Relationship	Link
sulphanilamide	-

General status

Veterinary substance type

Antibiotic, Antibacterial, Antimicrobial, Medicinal drug

Metabolite Type

Soil, Animal, Surface water, Sediment

Substance groups

Sulphonamide substance

Minimum active substance purity

Known relevant impurities

Substance origin

Natural

Mode of action

A competitive inhibitor of bacterial enzyme dihydropteroate synthetase

Molecular targets

[Dihydropteroate synthase, Antagonist]

CAS RN

63-74-1

EC number

200-563-4

CIPAC number

US EPA chemical code

077902

PubChem CID

Therapeutic Class

Antiinfectants for systemic use: Antibacterials for system use

ATCvet Code

QJ01EQ06

Controlled Drug?

Regulation 37/2010 MRL Classification

Molecular mass

172.20

PIN (Preferred Identification Name)

IUPAC name

4-aminobenzene-1-sulfonamide

CAS name

4-aminobenzenesulfonamide

Other status information

Possible groundwater pollutant

Relevant Environmental Water Quality Standards

Physical state

Yellow-white coloured solid

Can be a metabolite of:

Parent

Formation medium

Estimated maximum occurrence fraction

1107/2009 relevancy

asulam

Soil

Major fraction

asulam sodium

Soil

0.139

Major fraction

Formulations

Property

Product

Manufacturer

Authorisation Route

Legal Class (GB/UK)

Example products (past and present) using this active

Formulation and application details

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

7500

High

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

Melting point (°C)

165.5

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

Flashpoint (°C)

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

2.40 X 10^-01

Calculated

Log P

-0.62

Low

Fat solubility of residues

Solubility

Data type

Density (g ml⁻¹)

Dissociation constant pKa) at 25 °C

10.58

Vapour pressure at 20 °C (mPa)

0.973

at 25 °C

Low volatility. If applied directly to plants, drift is a concern & mitigation is advisable

Henry's law constant at 25 °C (Pa m³ mol⁻¹)

1.52 X 10^-05

at 25 °C

Non-volatile

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

Degradation

Property

Value

Source; quality score; and other information

Interpretation

Soil degradation (days) (aerobic)

DT₅₀ (typical)

13.4

Non-persistent

DT₅₀ (lab at 20 °C)

13.4

Non-persistent

DT₅₀ (field)

DT₉₀ (lab at 20 °C)

DT₉₀ (field)

Note

EU dossier Aerobic lab studies DT₅₀ range 3.1-76.3 days, Soils=6

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)

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.

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

K_oc

Notes and range

Freundlich

K_f

2.90

Moderately mobile

K_foc

166

¹/_n

0.708

Notes and range

EU dossier K_f range 1.45-4.07 mL g⁻¹, K_foc range 96-278 mL g⁻¹, ¹/_n range 0.673-0.748, Soils=8

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

2.01

Calculated

Transition state

Bio-concentration factor

BCF (l kg⁻¹)

Low risk

Based on LogP < 3

Low risk

CT₅₀ (days)

Known metabolites

None

ECOTOXICOLOGY

Terrestrial ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

3700

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)

Earthworms - Acute 14 day LC₅₀ (mg kg⁻¹)

> 1000

Eisenia foetida

Low

Earthworms - Chronic NOEC, reproduction (mg kg⁻¹)

3.75

Eisenia foetida

Moderate

Soil micro-organisms

Nitrogen mineralisation: No significant adverse eff

Dose: 3.3 mg kg⁻¹ soil 28 Day

Collembola

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

Non-target plants

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

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)

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)

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 - Acute 7 day EC₅₀, biomass (mg l⁻¹)

2.3

Lemna minor

Moderate

Algae - Acute 72 hour EC₅₀, growth (mg l⁻¹)

> 21.15

Pseudokirchneriella subcapitata 120 hr

Low

Algae - Chronic 96 hour NOEC, growth (mg l⁻¹)

Mesocosm study data

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)

3700

Rat

Low

Mammals - Dermal LD₅₀ (mg kg⁻¹ body weight)

Mammals - Inhalation LC₅₀ (mg l⁻¹)

255

Rat 4 hr

Other Mammal toxicity endpoints

Intravenous LD₅₀ = 1400 mg kg⁻¹

Rat

Subcutaneous LD₅₀ = 2900 mg kg⁻¹

Mouse

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

Excreted mainly in the urine but can also be found in most dody fluids including breast milk

Health issues

Specific human health issues

Carcinogen

Genotoxic

Endocrine disruptor

; ; ; ;

No data found

Reproduction / development effects

Acetyl cholinesterase inhibitor

Neurotoxicant

No data found

Respiratory tract irritant

Skin irritant

Skin sensitiser

No data found

Eye irritant

Phototoxicant

No data found

General human health issues

Ingestion may cause allergic reactions
Long-term use may cause cancer of the thyroid gland
Published studies suggest substance is carcinogenic

Handling issues

Property

Value and interpretation

General

IMDG Transport Hazard Class 8
Corrosive solid

CLP classification 2013

WHO Classification

Not listed (Not listed)

UN Number

UN1759

Waste disposal & packaging

Shelf-life, storage, stability and reactivity

TRANSLATIONS

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Record last updated:	23/02/2024
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