PREGABALIN

Search structure
Trade Names:
Synonyms:
Status: Approved (2004)
Entry Type: Small molecule
Molecule Category: Parent
ATC: N03AX16
UNII: 55JG375S6M

Structure
InChI Key AYXYPKUFHZROOJ-ZETCQYMHSA-N
Smile CC(C)C[C@H](CN)CC(=O)O
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

Physicochemical Descriptors

Property Name Value
Molecular Formula C8H17NO2
Molecular Weight 159.23
AlogP 1.08
Hydrogen Bond Acceptor 2.0
Hydrogen Bond Donor 2.0
Number of Rotational Bond 5.0
Polar Surface Area 63.32
Molecular species ZWITTERION
Aromatic Rings 0.0
Heavy Atoms 11.0

Pharmacology

Action Mechanism of Action Reference
MODULATOR Voltage-gated calcium channel modulator FDA PubMed
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Auxiliary transport protein Calcium channel auxiliary subunit alpha2delta family
- 73-80 - 19 -
Ion channel Ligand-gated ion channel P2X receptor
- - - - 31
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 101

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Epilepsy 4 D004827 ClinicalTrials
Neuralgia 4 D009437 ClinicalTrials
Neuralgia, Postherpetic 3 D051474 ClinicalTrials
Peripheral Nervous System Diseases 3 D010523 ClinicalTrials
Pain 3 D010146 ClinicalTrials
Epilepsies, Partial 3 D004828 ClinicalTrials
Restless Legs Syndrome 3 D012148 ClinicalTrials
Anxiety 3 D001007 ClinicalTrials
Migraine Disorders 3 D008881 ClinicalTrials
Neurotic Disorders 3 D009497 ClinicalTrials
Dementia 3 D003704 ClinicalTrials
Peripheral Nervous System Diseases 3 D010523 ClinicalTrials
Mononeuropathies 3 D020422 ClinicalTrials
Chronic Pain 3 D059350 ClinicalTrials
Sleep Initiation and Maintenance Disorders 3 D007319 ClinicalTrials
Opioid-Related Disorders 3 D009293 ClinicalTrials
Muscle Cramp 3 D009120 ClinicalTrials
Epilepsy, Tonic-Clonic 3 D004830 ClinicalTrials
Intervertebral Disc Degeneration 3 D055959 ClinicalTrials
Radiculopathy 3 D011843 ClinicalTrials
Breast Neoplasms 3 D001943 ClinicalTrials
Prostatitis 3 D011472 ClinicalTrials
Herpes Zoster 3 D006562 ClinicalTrials
Depressive Disorder 3 D003866 ClinicalTrials
Anxiety Disorders 3 D001008 ClinicalTrials
Fractures, Bone 3 D050723 ClinicalTrials
Epilepsy, Complex Partial 3 D017029 ClinicalTrials
Schizophrenia 3 D012559 ClinicalTrials
Diabetic Neuropathies 3 D003929 ClinicalTrials
Osteoarthritis 3 D010003 ClinicalTrials
Nausea 2 D009325 ClinicalTrials
Pancreatitis, Chronic 2 D050500 ClinicalTrials
Dry Eye Syndromes 2 D015352 ClinicalTrials
Irritable Bowel Syndrome 2 D043183 ClinicalTrials
Urinary Bladder, Overactive 2 D053201 ClinicalTrials
Diabetes Mellitus 2 D003920 ClinicalTrials
Alcoholism 2 D000437 ClinicalTrials
Pruritus 2 D011537 ClinicalTrials
Complex Regional Pain Syndromes 2 D020918 ClinicalTrials
Refractive Errors 1 D012030 ClinicalTrials
Pregnancy 1 D011247 ClinicalTrials
Carcinoma, Squamous Cell 1 D002294 ClinicalTrials
Cough 1 D003371 ClinicalTrials
Oropharyngeal Neoplasms 1 D009959 ClinicalTrials
Tobacco Use Disorder 0 D014029 ClinicalTrials
Essential Tremor 0 D020329 ClinicalTrials
Marijuana Abuse 0 D002189 ClinicalTrials

Related Entries

MCS

Side Effects from Label

Side effects Relative Frequency (%) Labels
Cardiac disorders Dizziness 38.0
Nervous system disorders Somnolence 35.7
Cardiac disorders Dizziness 32.0
Cardiac disorders Dizziness 29.0
Cardiac disorders Dizziness 26.0
Cardiac disorders Dizziness 23.0
Nervous system disorders Somnolence 22.0
Cardiac disorders Dizziness 21.9
Cardiac disorders Dizziness 21.0
Cardiac disorders Dizziness 20.9
Nervous system disorders Somnolence 20.0
Nervous system disorders Somnolence 18.4
Cardiac disorders Dizziness 16.5
Nervous system disorders Somnolence 16.0
Nervous system disorders Ataxia 15.0
Nervous system disorders Somnolence 13.2
Nervous system disorders Somnolence 13.0
General disorders and administration site conditions Asthenia 12.6
Nervous system disorders Headache
Nervous system disorders Headache 12.0
Cardiac disorders Oedema peripheral 12.0
Nervous system disorders Somnolence 12.0
Investigations Weight increased 12.0
Gastrointestinal disorders Nausea 11.7
Nervous system disorders Somnolence
General disorders and administration site conditions Asthenia 11.0
Cardiac disorders Dizziness
Gastrointestinal disorders Dry mouth 11.0
General disorders and administration site conditions Fatigue 11.0
Nervous system disorders Somnolence
Investigations Weight increased 11.0
Gastrointestinal disorders Constipation 10.7
Nervous system disorders Insomnia 10.7
Cardiac disorders Oedema peripheral 10.4
Eye disorders Vision blurred 10.0
Cardiac disorders Dizziness
Eye disorders Diplopia 9.0
Cardiac disorders Dizziness
Cardiac disorders Dizziness 9.0
Injury, poisoning and procedural complications Injury 9.0
Nervous system disorders Neuropathy peripheral 9.0
Cardiac disorders Oedema peripheral 9.0
Nervous system disorders Somnolence
Gastrointestinal disorders Constipation 8.2
Infections and infestations Nasopharyngitis 8.2
General disorders and administration site conditions Oedema 8.2
Cardiac disorders Dizziness 8.0
Gastrointestinal disorders Dry mouth 8.0
Social circumstances Mental disability 8.0
Nervous system disorders Thinking abnormal 8.0
Nervous system disorders Tremor 8.0
Eye disorders Vision blurred 8.0
General disorders and administration site conditions Asthenia 7.0
Gastrointestinal disorders Constipation 7.0
Gastrointestinal disorders Dry mouth 7.0
General disorders and administration site conditions Fatigue 7.0
Nervous system disorders Headache 7.0
Infections and infestations Infection 7.0
Cardiac disorders Dizziness
Cardiac disorders Dizziness
Eye disorders Vision blurred 6.6
General disorders and administration site conditions Asthenia
Nervous system disorders Ataxia 6.0
Gastrointestinal disorders Constipation
Gastrointestinal disorders Constipation 6.0
Cardiac disorders Dizziness 6.0
Psychiatric disorders Euphoric mood 6.0
Infections and infestations Infection
Injury, poisoning and procedural complications Injury 6.0
Cardiac disorders Oedema peripheral
Cardiac disorders Oedema peripheral 6.0
Nervous system disorders Somnolence 6.0
Eye disorders Vision blurred 6.0
Investigations Weight increased 6.0
Gastrointestinal disorders Constipation
Eye disorders Vision blurred 5.5
General disorders and administration site conditions Asthenia 5.3
General disorders and administration site conditions Fatigue 5.3
Nervous system disorders Somnolence
Investigations Weight increased 5.3
Cardiac disorders Oedema peripheral
Gastrointestinal disorders Dry mouth 5.1
Nervous system disorders Headache
Nervous system disorders Amnesia 5.0
General disorders and administration site conditions Asthenia 5.0
Nervous system disorders Ataxia 5.0
General disorders and administration site conditions Balance disorder 5.0
Gastrointestinal disorders Constipation 5.0
Nervous system disorders Disturbance in attention 5.0
Cardiac disorders Dizziness
Gastrointestinal disorders Dry mouth 5.0
Nervous system disorders Headache
General disorders and administration site conditions Increased appetite 5.0
Injury, poisoning and procedural complications Injury
Injury, poisoning and procedural complications Injury 5.0
Nervous system disorders Neuropathy peripheral 5.0
Cardiac disorders Oedema peripheral 5.0
General disorders and administration site conditions Pain 5.0
Infections and infestations Sinusitis 5.0
Nervous system disorders Somnolence
Nervous system disorders Speech disorder 5.0
Eye disorders Vision blurred 5.0
Nervous system disorders Muscular weakness 4.9
Gastrointestinal disorders Nausea 4.9
Cardiac disorders Dizziness
Infections and infestations Nasopharyngitis
Nervous system disorders Somnolence
Nervous system disorders Muscular weakness
Nervous system disorders Headache 4.2
Musculoskeletal and connective tissue disorders Arthralgia 4.0
General disorders and administration site conditions Asthenia
General disorders and administration site conditions Asthenia 4.0
Nervous system disorders Ataxia
Nervous system disorders Ataxia 4.0
Cardiac disorders Chest pain 4.0
Nervous system disorders Confusional state 4.0
Gastrointestinal disorders Constipation 4.0
Nervous system disorders Coordination abnormal 4.0
Eye disorders Diplopia
Cardiac disorders Dizziness 4.0
Gastrointestinal disorders Dry mouth 4.0
General disorders and administration site conditions Fatigue
General disorders and administration site conditions Feeling abnormal 4.0
General disorders and administration site conditions Gait disturbance 4.0
Infections and infestations Infection
Injury, poisoning and procedural complications Injury 4.0
Musculoskeletal and connective tissue disorders Muscle spasms 4.0
Musculoskeletal and connective tissue disorders Muscle twitching 4.0
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 4.0
Gastrointestinal disorders Nausea
Nervous system disorders Neuropathy peripheral 4.0
General disorders and administration site conditions Oedema 4.0
Cardiac disorders Oedema peripheral
Cardiac disorders Oedema peripheral 4.0
General disorders and administration site conditions Pain
General disorders and administration site conditions Pain 4.0
Infections and infestations Sinusitis
Nervous system disorders Somnolence
Nervous system disorders Somnolence 4.0
Nervous system disorders Tremor
Ear and labyrinth disorders Vertigo 4.0
Eye disorders Vision blurred
Eye disorders Vision blurred 4.0
Eye disorders Visual impairment 4.0
Investigations Weight increased 4.0
Nervous system disorders Disturbance in attention 3.8
Nervous system disorders Insomnia 3.8
Cardiac disorders Oedema peripheral 3.8
Cardiac disorders Oedema peripheral
Nervous system disorders Memory impairment 3.3
General disorders and administration site conditions Pain 3.3
Musculoskeletal and connective tissue disorders Pain in extremity 3.3
Investigations Weight increased 3.3
General disorders and administration site conditions Asthenia
Eye disorders Diplopia 3.2
General disorders and administration site conditions Fatigue
Nervous system disorders Amnesia
Nervous system disorders Amnesia 3.0
Nervous system disorders Ataxia 3.0
Musculoskeletal and connective tissue disorders Back pain
Musculoskeletal and connective tissue disorders Back pain 3.0
Nervous system disorders Confusional state 3.0
Cardiac disorders Dizziness 3.0
Gastrointestinal disorders Dry mouth
Gastrointestinal disorders Dry mouth 3.0
Cardiac disorders Dyspnoea 3.0
Psychiatric disorders Euphoric mood 3.0
General disorders and administration site conditions Feeling abnormal 3.0
Gastrointestinal disorders Flatulence 3.0
General disorders and administration site conditions Gait disturbance 3.0
Endocrine disorders Hypoglycaemia 3.0
Injury, poisoning and procedural complications Injury
Injury, poisoning and procedural complications Injury 3.0
Nervous system disorders Memory impairment 3.0
Social circumstances Mental disability 3.0
Nervous system disorders Neuropathy peripheral
General disorders and administration site conditions Pain
Nervous system disorders Somnolence
Nervous system disorders Somnolence 3.0
Nervous system disorders Thinking abnormal 3.0
Nervous system disorders Urinary incontinence
Ear and labyrinth disorders Vertigo 3.0
Eye disorders Vision blurred
Eye disorders Vision blurred 3.0
Gastrointestinal disorders Vomiting 3.0
Gastrointestinal disorders Dry mouth
Nervous system disorders Insomnia
Nervous system disorders Tremor 2.9
Gastrointestinal disorders Dry mouth
Investigations Blood creatine phosphokinase increased 2.7
Gastrointestinal disorders Constipation 2.7
Skin and subcutaneous tissue disorders Decubitus ulcer 2.7
Musculoskeletal and connective tissue disorders Neck pain 2.7
Nervous system disorders Urinary incontinence 2.7
Gastrointestinal disorders Vomiting 2.7
Nervous system disorders Somnolence
Eye disorders Vision blurred
General disorders and administration site conditions Asthenia
Cardiac disorders Oedema peripheral
General disorders and administration site conditions Gait disturbance 2.3
Musculoskeletal and connective tissue disorders Pain in extremity
Musculoskeletal and connective tissue disorders Back pain 2.2
Psychiatric disorders Euphoric mood 2.2
Vascular disorders Hypertension 2.2
Vascular disorders Hypotension 2.2
Musculoskeletal and connective tissue disorders Joint swelling 2.2
Gastrointestinal disorders Nausea 2.2
Nervous system disorders Paraesthesia 2.2
Eye disorders Vision blurred
Gastrointestinal disorders Abdominal distension 2.0
Nervous system disorders Amnesia
Nervous system disorders Amnesia 2.0
Psychiatric disorders Anxiety 2.0
Musculoskeletal and connective tissue disorders Arthralgia
General disorders and administration site conditions Asthenia
General disorders and administration site conditions Asthenia 2.0
Nervous system disorders Ataxia 2.0
Musculoskeletal and connective tissue disorders Back pain 2.0
Cardiac disorders Chest pain 2.0
Nervous system disorders Confusional state
Nervous system disorders Confusional state 2.0
Gastrointestinal disorders Constipation
Gastrointestinal disorders Constipation 2.0
Nervous system disorders Coordination abnormal 2.0
Psychiatric disorders Depression
Psychiatric disorders Depression 2.0
Eye disorders Diplopia 2.0
Nervous system disorders Disorientation 2.0
Gastrointestinal disorders Dry mouth
Gastrointestinal disorders Dry mouth 2.0
Cardiac disorders Dyspnoea 2.0
Psychiatric disorders Euphoric mood 2.0
General disorders and administration site conditions Face oedema 2.0
General disorders and administration site conditions Feeling abnormal
General disorders and administration site conditions Feeling abnormal 2.0
General disorders and administration site conditions Feeling drunk 2.0
Gastrointestinal disorders Flatulence 2.0
Metabolism and nutrition disorders Fluid retention 2.0
Nervous system disorders Hypoaesthesia 2.0
Endocrine disorders Hypoglycaemia 2.0
Infections and infestations Influenza 2.0
Injury, poisoning and procedural complications Injury
Injury, poisoning and procedural complications Injury 2.0
Respiratory, thoracic and mediastinal disorders Laryngeal pain
Respiratory, thoracic and mediastinal disorders Laryngeal pain 2.0
General disorders and administration site conditions Lethargy 2.0
Social circumstances Mental disability
Social circumstances Mental disability 2.0
Musculoskeletal and connective tissue disorders Muscle spasms
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort
Nervous system disorders Myoclonus 2.0
Nervous system disorders Neuropathy peripheral 2.0
General disorders and administration site conditions Oedema 2.0
Cardiac disorders Oedema peripheral
Nervous system disorders Somnolence 2.0
Nervous system disorders Thinking abnormal
Nervous system disorders Thinking abnormal 2.0
Nervous system disorders Tremor 2.0
Ear and labyrinth disorders Vertigo 2.0
Eye disorders Vision blurred
Eye disorders Visual impairment 2.0
Gastrointestinal disorders Vomiting
Gastrointestinal disorders Vomiting 2.0
Investigations Weight increased
Nervous system disorders Confusional state 1.9
General disorders and administration site conditions Feeling abnormal 1.9
Musculoskeletal and connective tissue disorders Back pain
Nervous system disorders Dysarthria 1.7
General disorders and administration site conditions Lethargy 1.7
Nervous system disorders Muscular weakness
Musculoskeletal and connective tissue disorders Osteoarthritis 1.7
Musculoskeletal and connective tissue disorders Back pain
Gastrointestinal disorders Constipation
Eye disorders Diplopia
Infections and infestations Influenza
Nervous system disorders Memory impairment 1.5
Social circumstances Mental disability
Musculoskeletal and connective tissue disorders Neck pain
General disorders and administration site conditions Pain
Nervous system disorders Paraesthesia
Skin and subcutaneous tissue disorders Skin ulcer
Nervous system disorders Speech disorder
Nervous system disorders Thinking abnormal
Eye disorders Vision blurred
Gastrointestinal disorders Diarrhoea
Nervous system disorders Disturbance in attention 1.4
Gastrointestinal disorders Dry mouth
General disorders and administration site conditions Increased appetite 1.4
General disorders and administration site conditions Oedema 1.4
Gastrointestinal disorders Constipation
Ear and labyrinth disorders Vertigo 1.3
Cardiac disorders Oedema peripheral
Nervous system disorders Coordination abnormal 1.1
Skin and subcutaneous tissue disorders Decubitus ulcer
Gastrointestinal disorders Diarrhoea 1.1
Gastrointestinal disorders Dry mouth
Vascular disorders Hypertension
Nervous system disorders Memory impairment
Musculoskeletal and connective tissue disorders Neck pain
General disorders and administration site conditions Oedema
General disorders and administration site conditions Pain
Nervous system disorders Urinary incontinence
Eye disorders Vision blurred
Gastrointestinal disorders Vomiting
Investigations Weight increased
Gastrointestinal disorders Abdominal distension
Nervous system disorders Amnesia 1.0
Psychiatric disorders Anxiety
Nervous system disorders Ataxia
Nervous system disorders Ataxia 1.0
Musculoskeletal and connective tissue disorders Back pain 1.0
Infections and infestations Bronchitis
Infections and infestations Bronchitis 1.0
Cardiac disorders Chest pain
Cardiac disorders Chest pain 1.0
Nervous system disorders Confusional state
Nervous system disorders Confusional state 1.0
Nervous system disorders Coordination abnormal
Nervous system disorders Coordination abnormal 1.0
Nervous system disorders Disturbance in attention
Gastrointestinal disorders Dry mouth
Cardiac disorders Dyspnoea
Psychiatric disorders Euphoric mood
Eye disorders Eye disorder 1.0
General disorders and administration site conditions Face oedema
General disorders and administration site conditions Face oedema 1.0
General disorders and administration site conditions Feeling abnormal
General disorders and administration site conditions Feeling abnormal 1.0
Gastrointestinal disorders Flatulence
Metabolism and nutrition disorders Fluid retention
General disorders and administration site conditions Gait disturbance
General disorders and administration site conditions Gait disturbance 1.0
Nervous system disorders Hypoaesthesia
Endocrine disorders Hypoglycaemia
Endocrine disorders Hypoglycaemia 1.0
General disorders and administration site conditions Increased appetite
Infections and infestations Influenza
Local swelling 1.0
Social circumstances Mental disability 1.0
Musculoskeletal and connective tissue disorders Muscle twitching
Nervous system disorders Muscular weakness 1.0
Psychiatric disorders Nervousness 1.0
General disorders and administration site conditions Oedema
Nervous system disorders Speech disorder
Nervous system disorders Speech disorder 1.0
Psychiatric disorders Tension 1.0
Nervous system disorders Thinking abnormal 1.0
Nervous system disorders Tremor
Nervous system disorders Tremor 1.0
Nervous system disorders Urinary incontinence 1.0
Ear and labyrinth disorders Vertigo
Ear and labyrinth disorders Vertigo 1.0
Eye disorders Vision blurred
Eye disorders Vision blurred 1.0
Eye disorders Visual impairment
Eye disorders Visual impairment 1.0
Gastrointestinal disorders Vomiting
Investigations Weight increased
Eye disorders Diplopia
Cardiac disorders Dizziness
Nervous system disorders Disturbance in attention
Nervous system disorders Ataxia
Nervous system disorders Confusional state
Psychiatric disorders Euphoric mood
General disorders and administration site conditions Feeling abnormal
Nervous system disorders Paraesthesia
Nervous system disorders Ataxia
General disorders and administration site conditions Gait disturbance
Nervous system disorders Memory impairment
Investigations Weight increased
Cardiac disorders Dizziness
Investigations Weight increased
General disorders and administration site conditions Increased appetite
Local swelling
General disorders and administration site conditions Oedema
Ear and labyrinth disorders Vertigo
Investigations Weight increased
Nervous system disorders Confusional state
Gastrointestinal disorders Dry mouth
General disorders and administration site conditions Feeling abnormal
Cardiac disorders Oedema peripheral
Nervous system disorders Somnolence
Nervous system disorders Coordination abnormal
Nervous system disorders Dysarthria
General disorders and administration site conditions Gait disturbance
Musculoskeletal and connective tissue disorders Osteoarthritis
General disorders and administration site conditions Lethargy

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
General disorders and administration site conditions
21.53
Nervous system disorders
16.34
Psychiatric disorders
11.07
Injury, poisoning and procedural complications
9.06
Musculoskeletal and connective tissue disorders
8.98
Gastrointestinal disorders
4.16
Skin and subcutaneous tissue disorders
3.88
Investigations
3.36
Cardiac disorders
3.35
Respiratory, thoracic and mediastinal disorders
3.31
Vascular disorders
3.23
Infections and infestations
2.12

Cross References

Resources Reference
CAS NUMBER 148553-50-8
ChEBI 64356
ChEMBL CHEMBL1059
DrugBank DB00230
DrugCentral 2255
EPA CompTox DTXSID1045950
FDA SRS 55JG375S6M
Human Metabolome Database HMDB0014375
Guide to Pharmacology 5484
KEGG D02716
PharmGKB PA164754814
PubChem 5486971
SureChEMBL SCHEMBL17510367
ZINC ZINC000000005152
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