Ketoprofen

Ketoprofen	Last updated: 06/09/2025
(Also known as: m-benzoylhydratropic acid )

GENERAL INFORMATION

Description

A veterinary non-steroidal anti-inflammatory drug (NSAID) used to treat pain and inflammation

Examples of veterinary uses

Most commonly prescribed for musculoskeletal pain from soft-tissue injury, osteoarthritis or other bone and joint problems. Also used to reduce or control fevers due to viral or bacterial infections.

Examples of species treated

Dogs; Cats; Horses; Goats; Sheep; Pigs

Approval status

VMR 2013/2033 approval status (GB/UK)

Approved - usually available as a prescription only medicine to be authorised by a veterinarian (POM-V)

EU Regulatory approval status

Approved

Chemical structure

Isomerism

Ketoprofen exhibits enantiomeric isomerism, meaning it exists as the (R)-ketoprofen and (S)-ketoprofen enantiomers. These arise due to the presence of a chiral centre in its 2-arylpropionic acid structure. Although ketoprofen is typically administered as a racemic mixture (equal parts R and S), only the S-enantiomer is primarily responsible for its anti-inflammatory effects, as it inhibits cyclooxygenase (COX) enzymes and prostaglandin synthesis. The R-enantiomer, while less active in COX inhibition, contributes to analgesic effects and does not amplify inflammatory cytokine production, which may reduce gastrointestinal side effects. Moreover, in mammals, chiral inversion can occur where the R-form partially converts to the S-form, especially in the gastrointestinal tract, influencing the drug’s overall pharmacokinetics and therapeutic profile.

Chemical formula

C₁₆H₁₄O₃

Canonical SMILES

CC(C1=CC=CC(=C1)C(=O)C2=CC=CC=C2)C(=O)O

Isomeric SMILES

C[C@H](C1=CC=CC(=C1)C(=O)C2=CC=CC=C2)C(=O)O

International Chemical Identifier key (InChIKey)

DKYWVDODHFEZIM-LLVKDONJSA-N

International Chemical Identifier (InChI)

InChI=1S/C16H14O3/c1-11(16(18)19)13-8-5-9-14(10-13)15(17)12-6-3-2-4-7-12/h2-11H,1H3,(H,18,19)/t11-/m1/s1

2D structure diagram/image available?

Yes

Cambridge Crystallographic Data Centre diagrams

Common Name	Relationship	Link
ketoprofen	-

General status

Veterinary substance type

Anti-inflammatory, Analgesic, Medicinal drug

Substance groups

Propionic acid based substance

Minimum active substance purity

Known relevant impurities

Substance origin

Synthetic

Mode of action

Works by inhibiting the body's production of prostaglandins, thromboxane and other inflammatory mediators

Molecular targets

[Prostaglandin G/H synthase 1, Inhibitor], [Prostaglandin G/H synthase 2, inhibitor], [High affinity interleukin-8 receptor A]

CAS RN

56105-81-8

EC number

CIPAC number

US EPA chemical code

PubChem CID

Therapeutic Class

Musculo-skeletal system: Anti-inflammatory & antirheumatic products

ATCvet Code

QM01AE03

Controlled Drug?

Regulation 37/2010 MRL Classification

Allowed substance (Table 1: Bovine, Porcine, Equidae)

Molecular mass

254.28

PIN (Preferred Identification Name)

IUPAC name

(RS)2-(3-benzoylphenyl)-propionic acid

CAS name

(2R)-2-(3-phenylcarbonylphenyl)propanoic acid

Forever chemical

Other status information

Relevant Environmental Water Quality Standards

Physical state

White crystalline solid

Commercial

Property

Value

Availability status

Current

Introduction & key dates

Circa 1990, introduced

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

Virbac Ltd
Ecuphar Veterinaria S.L.U.
Ceval Animal Health Ltd

Example products using this active

Curacef Duo Suspension for Injection
Dinalgen Solution for Injection
Ketofen solution for injection

Formulation and application details

Available in a variety of formulations including tablets for oral administration and solutions for injection

Commercial production

Ketoprofen is synthesised through a multi-step chemical process that typically begins with 3-methylbenzophenone as the key starting material. In one industrial route, this compound undergoes bromination to form 3-bromo-methylbenzophenone, which is then subjected to a Friedel–Crafts acylation and benzylic oxidation to yield the final ketoprofen structure. A more environmentally friendly method starts from cyclohexanone, which is transformed via Stork enamine alkylation, followed by aldol addition, enol-lactonization, and pyrolytic aromatization, ultimately producing the arylpropionic acid backbone of ketoprofen.

Impact on climate of production and use

Published GHG data is not available for most pharmaceuticals. However, according to industry, global averages suggest producing 1 kg of a typical active pharmaceutical ingredient can range from 10 to 100 kg CO₂e for small molecule drugs and potentially up to 1000 kg CO₂e for complex biologicals such as vaccines, depending on the drug type, its formulation, complexity of synthesis, solvent recovery, and energy sources used.

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

500

Moderate

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

Max at 255nm

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)

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 soil and groundwater metabolites

None

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

glucuronic acid

ECOTOXICOLOGY

Terrestrial ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

62.4

Rat

High

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

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)

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 (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 II)

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

62.4

Rat

High

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

Extensively metabolised and around 90% of metabolites eliminated in the urine

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

General human health issues

Possible blood, kidneys, liver and gastrointestinal tract toxicant

Handling issues

Property

Value and interpretation

General

IMDG Transport Hazard Class 6.1

CLP classification 2013

WHO Classification

Not listed (Not listed)

UN Number

UN2811

Waste disposal & packaging

Packaging Group III (minor danger)

Shelf-life, storage, stability and reactivity

TRANSLATIONS

Language

Name

English

ketoprofen

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Polish

Swedish

Hungarian

Dutch

Norwegian

Record last updated:	06/09/2025
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