Acepromazine maleate

Acepromazine maleate	Last updated: 07/03/2024
(Also known as: acetylpromazine maleate; ACP; ACE; acepromazine hydrogen maleate)

GENERAL INFORMATION

Description

A veterinary phenothiazine neuroleptic drug used as a sedative

Availability status

Current

Introduction & key dates

1950's, first use in humans; late 1960's veterinary applications

Examples of veterinary uses

Used as a premedication for quietening and calming animals. It also has antihistamine effects.

Examples of species treated

Horses; Dogs; Cats; Elephants; Deer

Approval status

VMR 2013/2033 approval status (GB/UK)

Approved

EU Regulatory approval status

Approved

Chemical structure

Isomerism

None

Chemical formula

C₂₃H₂₆N₂O₅S

Canonical SMILES

CC(=O)C1=CC2=C(C=C1)SC3=CC=CC=C3N2CCCN(C)C.C(=CC(=O)O)C(=O)O

Isomeric SMILES

CC(=O)C1=CC2=C(C=C1)SC3=CC=CC=C3N2CCCN(C)C.C(=C/C(=O)O)\C(=O)O

International Chemical Identifier key (InChIKey)

FQRHOOHLUYHMGG-WLHGVMLRSA-N

International Chemical Identifier (InChI)

InChI=1S/C19H22N2OS.C4H4O4/c1-14(22)15-9-10-19-17(13-15)21(12-6-11-20(2)3)16-7-4-5-8-18(16)23-19;5-3(6)1-2-4(7)8/h4-5,7-10,13H,6,11-12H2,1-3H3;1-2H,(H,5,6)(H,7,8)/b;2-1-

2D structure diagram/image available?

Yes

General status

Veterinary substance type

Tranquiliser, Antihistamine

Substance groups

Phenothiazine neuroleptic

Minimum active substance purity

Known relevant impurities

Substance origin

Synthetic

Mode of action

Has a depressant effect on the central nervous system and therefore causes sedation. Dopamine antagonist.

Molecular targets

[D(2) dopamine receptor, Antagonist], [D(1A) dopamine receptor, Antagonist], [5-hydroxytryptamine 2A receptor, Antagonist], [5-hydroxytryptamine 1A receptor, Antagonist], [Alpha-1A adrenergic receptor, Antagonist], [Alpha-1B adrenergic receptor, Antagonist]

CAS RN

3598-37-6

EC number

222-748-9

CIPAC number

US EPA chemical code

PubChem CID

6420038

Therapeutic Class

Nervous system: Antipsychotics

ATCvet Code

QN05AA04

Controlled Drug?

Regulation 37/2010 MRL Classification

Molecular mass

442.50

PIN (Preferred Identification Name)

IUPAC name

(E)-but-2-enedioic acid;1-[10-[3-(dimethylamino)propyl]phenothiazin-2-yl]ethanone

CAS name

10-(3-dimethylaminopropyl)phenothiazine-2-yl methyl hydrogen maleate

Other status information

Relevant Environmental Water Quality Standards

Physical state

Yellow, crystalline powder

Formulations

Property

Product

Manufacturer

Authorisation Route

Legal Class (GB/UK)

Example products (past and present) using this active

Acecare Injection for dogs and cats

Ecuphar NV

GB National authorisation

Prescription only medicine to be authorised by a veterinarian (POM-V)

Large animal immobilion solution for injection

AbbeyVet Export LLP

UK National authorisation (IC)

Prescription only medicine to be authorised by a veterinarian (POM-V)

ACP Solution for Injection

Elanco Europe Ltd

UK National authorisation

Prescription only medicine to be authorised by a veterinarian (POM-V)

Tranquigel 35 for dogs and horses

Le Vet Beheer B.V.

Mutually recognised procedure

Prescription only medicine to be authorised by a veterinarian (POM-V)

Formulation and application details

Supplied as in a variety of formulations depending on intended application including solutions for injection, tablets and as an oral gel

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

37000

High

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

333000

Chloroform

77000

Methanol

Melting point (°C)

135

Boiling point (°C)

497

Degradation point (°C)

Flashpoint (°C)

254.4

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

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)

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 soil and groundwater metabolites

None

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

2-(1-hydroxyethyl)promazine sulfoxide
Note: C19H24N2O2S; Mwt = 344.47

Animal

ECOTOXICOLOGY

Terrestrial ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

400

Rat

Moderate

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)

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

Soil micro-organisms

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)

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

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)

400

Rat

Moderate

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

Mammals - Inhalation LC₅₀ (mg l⁻¹)

Other Mammal toxicity endpoints

Subcutaneous LD₅₀ = 65 mg kg⁻¹

Mouse

Intravenous LD₅₀ = 95 mg kg⁻¹

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

Mammalian dose elimination route and rate

Metabolised by liver, excreted in urine

Health issues

Specific human health issues

Carcinogen

Genotoxic

Endocrine disruptor

; ; ; ;

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 affect heart and respiratory rate leading to hypotension
Ingestion may cause gastrointestinal disturbances

Handling issues

Property

Value and interpretation

General

When heated to decomposition it emits highly toxic fumes of NOx and SOx

CLP classification 2013

Health: H302, H315, H317, H332, H335

WHO Classification

Not listed (Not listed)

UN Number

Waste disposal & packaging

Shelf-life, storage, stability and reactivity

TRANSLATIONS

Language

Name

English

acepromazine maleate

French

maléate d'acépromazine

German

Danish

Italian

Spanish

maleato de acepromazina

Greek

Polish

Swedish

Hungarian

Dutch

Norwegian

Record last updated:	07/03/2024
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