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Pregabalin
Last updated: 22/05/2024
(Not known by any other names)

GENERAL INFORMATION
Description
A neuroactive veterinary drug used for dedation and as an anticonvulsant
Availability status
Current
Introduction & key dates
-
Examples of veterinary uses
Used to assist with acute anxiety and fear associated with transportation and veterinary visits as well as treating epilepsy, chronic pain and seizures
Examples of species treated
Cats
Approval status
VMR 2013/2033 approval status (GB/UK)
Approved
EU Regulatory approval status
Approved
Chemical structure
Isomerism
Substance is isomeric existing in the (R)- and (S)-forms. Pregabalin is the (S)-isomer and the potent of the two.
Chemical formula
C₈H₁₇NO₂
Canonical SMILES
CC(C)CC(CC(=O)O)CN
Isomeric SMILES
CC(C)C[C@@H](CC(=O)O)CN
International Chemical Identifier key (InChIKey)
AYXYPKUFHZROOJ-ZETCQYMHSA-N
International Chemical Identifier (InChI)
InChI=1S/C8H17NO2/c1-6(2)3-7(5-9)4-8(10)11/h6-7H,3-5,9H2,1-2H3,(H,10,11)/t7-/m0/s1
2D structure diagram/image available?
Yes
Cambridge Crystallographic Data Centre diagrams
Common Name Relationship Link
(R)-pregabalin Isomer
pregabalin -
(S)-pregabalin Isomer
General status
Veterinary substance type
Sedative
Substance groups
Alkylated analog of GABA
Minimum active substance purity
-
Known relevant impurities
-
Substance origin
Synthetic
Mode of action
Binds to the auxiliary subunit (alpha2-delta protein) of voltage-gated calcium channels in the CNS thereby reducing the release of various neurotransmitters and producing its anxiolytic effect.
Molecular targets
[Alpha2-delta subunits, Binder]
CAS RN
148553-50-8
EC number
604-639-1
CIPAC number
-
US EPA chemical code
-
PubChem CID
5486971
Therapeutic Class
Nervous system, other antiepileptics
ATCvet Code
QN03AX16
Controlled Drug?
UK: Class C, Schedule 3
Regulation 37/2010 MRL Classification
-
Molecular mass
159.23
PIN (Preferred Identification Name)
(3S)-3-(aminomethyl)-5-methylhexanoic acid
IUPAC name
(3S)-3-(aminomethyl)-5-methylhexanoic acid
CAS name
-
Other status information
-
Relevant Environmental Water Quality Standards
-
Physical state
Off-white coloured crystalline solid
Formulations
Property
Product
Manufacturer
Authorisation Route
Legal Class (GB/UK)
Example products (past and present) using this active
Bonqat 50 mg/ml oral solution for cats Orion Corp GB National authorisation Prescription only medicine to be authorised by a veterinarian (POM-V)
Formulation and application details
Usually supplied as an oral solution
ENVIRONMENTAL FATE
Property
Value
Source; quality score; and other information
Interpretation
Solubility - In water at 20 °C (mg l⁻¹)
11300
Q3 Q = Miscellaneous data from online sources
3 = Unverified data of known source
High
Solubility - In organic solvents at 20 °C (mg l⁻¹)
- - -
Melting point (°C)
176
Q3 Q = Miscellaneous data from online sources
3 = Unverified data of known source
-
Boiling point (°C)
145
Q3 Q = Miscellaneous data from online sources
3 = Unverified data of known source
-
Degradation point (°C)
- - -
Flashpoint (°C)
- - -
Octanol-water partition coefficient at pH 7, 20 °C
P
2.00 X 1001 Calculated -
Log P
1.3
Q3 Q = Miscellaneous data from online sources
3 = Unverified data of known source
Low
Fat solubility of residues
Solubility
- - -
Data type
- - -
Density (g ml⁻¹)
- - -
Dissociation constant pKa) at 25 °C
4.2
Q3 Q = Miscellaneous data from online sources
3 = Unverified data of known source
-
pKa(2) = 10.6
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
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)
- - -
CT₅₀ (days)
- -
Known metabolites

None

ECOTOXICOLOGY
Terrestrial ecotoxicology
Property
Value
Source; quality score; and other information
Interpretation
Mammals - Acute oral LD₅₀ (mg kg⁻¹)
> 5000
E4 E = Manufacturers safety data sheets
4 = Verified data
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)
- - -
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)
> 1000
E4 E = Manufacturers safety data sheets
4 = Verified data
Oncorhynchus mykiss
Low
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)
> 1000
E4 E = Manufacturers safety data sheets
4 = Verified data
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 - 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)
> 300
E4 E = Manufacturers safety data sheets
4 = Verified data
Scenedesmus quadricauda
Low
Mesocosm study data
NOEAEC mg l⁻¹
- - -
NOEAEC mg l⁻¹
- - -
HUMAN HEALTH AND PROTECTION
General
Property
Value
Source; quality score; and other information
Interpretation
Threshold of Toxicological Concern (Cramer Class)
- - -
Mammals - Acute oral LD₅₀ (mg kg⁻¹)
> 5000
E4 E = Manufacturers safety data sheets
4 = Verified data
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
Pattern of use is unlikely to result in toxicological relevant exposure
Occupational
Pattern of use is unlikely to result in toxicological relevant exposure
Mammalian dose elimination route and rate
Elimination is primarily as an unchanged drug by renal excretion usually within 7 hrs
E4 E = Manufacturers safety data sheets
4 = Verified data
-
Health issues
Specific human health issues
Carcinogen
Genotoxic
Endocrine disruptor
No data found
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
No data found
Yes, known to cause a problem
Respiratory tract irritant Skin irritant Skin sensitiser
No data found No data found
XNo, known not to cause a problem
Eye irritant Phototoxicant  
Yes, known to cause a problem
No data found  
General human health issues
Originally approved in US as an anti-epileptic & anticonvulsant drug
May cause severe allergic reaction
Possible liver toxin
Handling issues
Property
Value and interpretation
General
Corrosive
Incompatible with strong oxidising agents
CLP classification 2013
Health: H373, H361, H318
WHO Classification
Not listed (Not listed)
UN Number
Not registered
Waste disposal & packaging
-
Shelf-life, storage, stability and reactivity
Shelf-life for sale is 2 years but once package is opened shelf-life reduces to 6 months. Store in a refrigerator (2-8 DegC).
TRANSLATIONS
Language
Name
English
pregabalin
French
-
German
-
Danish
-
Italian
-
Spanish
-
Greek
-
Polish
-
Swedish
-
Hungarian
-
Dutch
-
Norwegian
-

Record last updated: 22/05/2024
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