Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C8H17NO2.ClH |
| Molecular Weight | 195.687 |
| Optical Activity | ( + ) |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.CC(C)C[C@H](CN)CC(O)=O
InChI
InChIKey=LMPTVIKQDISIBX-FJXQXJEOSA-N
InChI=1S/C8H17NO2.ClH/c1-6(2)3-7(5-9)4-8(10)11;/h6-7H,3-5,9H2,1-2H3,(H,10,11);1H/t7-;/m0./s1
| Molecular Formula | C8H17NO2 |
| Molecular Weight | 159.2261 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
| Molecular Formula | ClH |
| Molecular Weight | 36.461 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
DescriptionCurator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/17126531
Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/17126531
Pregabalin, marketed under the brand name Lyrica among others. LYRICA is indicated for: Neuropathic pain associated with diabetic peripheral neuropathy (DPN) Postherpetic neuralgia (PHN); Adjunctive therapy for adult patients with partial onset seizures; Fibromyalgia; Neuropathic pain associated with spinal cord injury. It has been shown the clinical effects of pregabalin are likely due to direct and selective interactions with α(2)δ-1 and α(2)δ-2 subunits of voltage-gated calcium channels. While pregabalin is a structural derivative of the inhibitory neurotransmitter gamma aminobutyric acid (GABA), it does not bind directly to GABAA, GABAB, or benzodiazepine receptors, does not augment GABAA responses in cultured neurons, does not alter rat brain GABA concentration or have acute effects on GABA uptake or degradation. However, in cultured neurons prolonged application of pregabalin increases the density of GABA transporter protein and increases the rate of functional GABA transport. Pregabalin does not block sodium channels, is not active at opiate receptors, and does not alter cyclooxygenase enzyme activity. It is inactive at serotonin and dopamine receptors and does not inhibit dopamine, serotonin, or noradrenaline reuptake.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL3896 |
|||
Target ID: CHEMBL1919 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Palliative | LYRICA Approved UseLYRICA is indicated for: Management of neuropathic pain associated with diabetic peripheral neuropathy Management of postherpetic neuralgia Adjunctive therapy for adult patients with partial onset seizures Management of fibromyalgia Management of neuropathic pain associated with spinal cord injury LYRICA is indicated for: Neuropathic pain associated with diabetic peripheral neuropathy (DPN) (1) Postherpetic neuralgia (PHN) (1) Adjunctive therapy for adult patients with partial onset seizures (1) Fibromyalgia (1) Neuropathic pain associated with spinal cord injury (1) Launch Date2004 |
|||
| Palliative | LYRICA Approved UseLYRICA is indicated for: Management of neuropathic pain associated with diabetic peripheral neuropathy Management of postherpetic neuralgia Adjunctive therapy for adult patients with partial onset seizures Management of fibromyalgia Management of neuropathic pain associated with spinal cord injury LYRICA is indicated for: Neuropathic pain associated with diabetic peripheral neuropathy (DPN) (1) Postherpetic neuralgia (PHN) (1) Adjunctive therapy for adult patients with partial onset seizures (1) Fibromyalgia (1) Neuropathic pain associated with spinal cord injury (1) Launch Date2004 |
|||
| Palliative | LYRICA Approved UseLYRICA is indicated for: Management of neuropathic pain associated with diabetic peripheral neuropathy Management of postherpetic neuralgia Adjunctive therapy for adult patients with partial onset seizures Management of fibromyalgia Management of neuropathic pain associated with spinal cord injury LYRICA is indicated for: Neuropathic pain associated with diabetic peripheral neuropathy (DPN) (1) Postherpetic neuralgia (PHN) (1) Adjunctive therapy for adult patients with partial onset seizures (1) Fibromyalgia (1) Neuropathic pain associated with spinal cord injury (1) Launch Date2004 |
|||
| Palliative | LYRICA Approved UseLYRICA is indicated for: Management of neuropathic pain associated with diabetic peripheral neuropathy Management of postherpetic neuralgia Adjunctive therapy for adult patients with partial onset seizures Management of fibromyalgia Management of neuropathic pain associated with spinal cord injury LYRICA is indicated for: Neuropathic pain associated with diabetic peripheral neuropathy (DPN) (1) Postherpetic neuralgia (PHN) (1) Adjunctive therapy for adult patients with partial onset seizures (1) Fibromyalgia (1) Neuropathic pain associated with spinal cord injury (1) Launch Date2004 |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
4568.68 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/28513426 |
150 mg single, oral dose: 150 mg route of administration: Oral experiment type: SINGLE co-administered: |
PREGABALIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
29831.454 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/28513426 |
150 mg single, oral dose: 150 mg route of administration: Oral experiment type: SINGLE co-administered: |
PREGABALIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
6.3 h |
unknown, oral |
PREGABALIN plasma | Homo sapiens population: UNKNOWN age: ADULT sex: UNKNOWN food status: UNKNOWN |
Doses
| Dose | Population | Adverse events |
|---|---|---|
600 mg single, oral Highest studied dose |
healthy, 24.8 years n = 10 Health Status: healthy Age Group: 24.8 years Sex: M Population Size: 10 Sources: |
Other AEs: Vision blurred, Nausea... Other AEs: Vision blurred (moderate, 1 patient) Sources: Nausea (moderate, 1 patient) Dizziness (mild, 4 patients) Dysarthria (moderate, 1 patient) Headache (mild, 2 patients) |
600 mg 1 times / day multiple, oral Highest studied dose Dose: 600 mg, 1 times / day Route: oral Route: multiple Dose: 600 mg, 1 times / day Sources: |
unhealthy, 53.91 years n = 22 Health Status: unhealthy Condition: Essential Tremor Age Group: 53.91 years Sex: M+F Population Size: 22 Sources: |
|
150 mg 1 times / day steady, oral Dose: 150 mg, 1 times / day Route: oral Route: steady Dose: 150 mg, 1 times / day Sources: |
unhealthy, adult n = 979 Health Status: unhealthy Age Group: adult Population Size: 979 Sources: |
Disc. AE: Dizziness, Somnolence... AEs leading to discontinuation/dose reduction: Dizziness (3.47%) Sources: Somnolence (2.76%) Asthenia (0.82%) Confusion (0.72%) Peripheral edema (0.61%) Headache (1.12%) Amblyopia (0.82%) Dry mouth (0.72%) Nausea (0.72%) Infection (0.41%) Ataxia (0.41%) Neuropathy (0.41%) Tremor (0.41%) Constipation (0.31%) Diarrhea (0.31%) Incoordination (0.31%) Abnormal thinking (0.31%) |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Headache | mild, 2 patients | 600 mg single, oral Highest studied dose |
healthy, 24.8 years n = 10 Health Status: healthy Age Group: 24.8 years Sex: M Population Size: 10 Sources: |
| Dizziness | mild, 4 patients | 600 mg single, oral Highest studied dose |
healthy, 24.8 years n = 10 Health Status: healthy Age Group: 24.8 years Sex: M Population Size: 10 Sources: |
| Dysarthria | moderate, 1 patient | 600 mg single, oral Highest studied dose |
healthy, 24.8 years n = 10 Health Status: healthy Age Group: 24.8 years Sex: M Population Size: 10 Sources: |
| Nausea | moderate, 1 patient | 600 mg single, oral Highest studied dose |
healthy, 24.8 years n = 10 Health Status: healthy Age Group: 24.8 years Sex: M Population Size: 10 Sources: |
| Vision blurred | moderate, 1 patient | 600 mg single, oral Highest studied dose |
healthy, 24.8 years n = 10 Health Status: healthy Age Group: 24.8 years Sex: M Population Size: 10 Sources: |
| Abnormal thinking | 0.31% Disc. AE |
150 mg 1 times / day steady, oral Dose: 150 mg, 1 times / day Route: oral Route: steady Dose: 150 mg, 1 times / day Sources: |
unhealthy, adult n = 979 Health Status: unhealthy Age Group: adult Population Size: 979 Sources: |
| Constipation | 0.31% Disc. AE |
150 mg 1 times / day steady, oral Dose: 150 mg, 1 times / day Route: oral Route: steady Dose: 150 mg, 1 times / day Sources: |
unhealthy, adult n = 979 Health Status: unhealthy Age Group: adult Population Size: 979 Sources: |
| Diarrhea | 0.31% Disc. AE |
150 mg 1 times / day steady, oral Dose: 150 mg, 1 times / day Route: oral Route: steady Dose: 150 mg, 1 times / day Sources: |
unhealthy, adult n = 979 Health Status: unhealthy Age Group: adult Population Size: 979 Sources: |
| Incoordination | 0.31% Disc. AE |
150 mg 1 times / day steady, oral Dose: 150 mg, 1 times / day Route: oral Route: steady Dose: 150 mg, 1 times / day Sources: |
unhealthy, adult n = 979 Health Status: unhealthy Age Group: adult Population Size: 979 Sources: |
| Ataxia | 0.41% Disc. AE |
150 mg 1 times / day steady, oral Dose: 150 mg, 1 times / day Route: oral Route: steady Dose: 150 mg, 1 times / day Sources: |
unhealthy, adult n = 979 Health Status: unhealthy Age Group: adult Population Size: 979 Sources: |
| Infection | 0.41% Disc. AE |
150 mg 1 times / day steady, oral Dose: 150 mg, 1 times / day Route: oral Route: steady Dose: 150 mg, 1 times / day Sources: |
unhealthy, adult n = 979 Health Status: unhealthy Age Group: adult Population Size: 979 Sources: |
| Neuropathy | 0.41% Disc. AE |
150 mg 1 times / day steady, oral Dose: 150 mg, 1 times / day Route: oral Route: steady Dose: 150 mg, 1 times / day Sources: |
unhealthy, adult n = 979 Health Status: unhealthy Age Group: adult Population Size: 979 Sources: |
| Tremor | 0.41% Disc. AE |
150 mg 1 times / day steady, oral Dose: 150 mg, 1 times / day Route: oral Route: steady Dose: 150 mg, 1 times / day Sources: |
unhealthy, adult n = 979 Health Status: unhealthy Age Group: adult Population Size: 979 Sources: |
| Peripheral edema | 0.61% Disc. AE |
150 mg 1 times / day steady, oral Dose: 150 mg, 1 times / day Route: oral Route: steady Dose: 150 mg, 1 times / day Sources: |
unhealthy, adult n = 979 Health Status: unhealthy Age Group: adult Population Size: 979 Sources: |
| Confusion | 0.72% Disc. AE |
150 mg 1 times / day steady, oral Dose: 150 mg, 1 times / day Route: oral Route: steady Dose: 150 mg, 1 times / day Sources: |
unhealthy, adult n = 979 Health Status: unhealthy Age Group: adult Population Size: 979 Sources: |
| Dry mouth | 0.72% Disc. AE |
150 mg 1 times / day steady, oral Dose: 150 mg, 1 times / day Route: oral Route: steady Dose: 150 mg, 1 times / day Sources: |
unhealthy, adult n = 979 Health Status: unhealthy Age Group: adult Population Size: 979 Sources: |
| Nausea | 0.72% Disc. AE |
150 mg 1 times / day steady, oral Dose: 150 mg, 1 times / day Route: oral Route: steady Dose: 150 mg, 1 times / day Sources: |
unhealthy, adult n = 979 Health Status: unhealthy Age Group: adult Population Size: 979 Sources: |
| Amblyopia | 0.82% Disc. AE |
150 mg 1 times / day steady, oral Dose: 150 mg, 1 times / day Route: oral Route: steady Dose: 150 mg, 1 times / day Sources: |
unhealthy, adult n = 979 Health Status: unhealthy Age Group: adult Population Size: 979 Sources: |
| Asthenia | 0.82% Disc. AE |
150 mg 1 times / day steady, oral Dose: 150 mg, 1 times / day Route: oral Route: steady Dose: 150 mg, 1 times / day Sources: |
unhealthy, adult n = 979 Health Status: unhealthy Age Group: adult Population Size: 979 Sources: |
| Headache | 1.12% Disc. AE |
150 mg 1 times / day steady, oral Dose: 150 mg, 1 times / day Route: oral Route: steady Dose: 150 mg, 1 times / day Sources: |
unhealthy, adult n = 979 Health Status: unhealthy Age Group: adult Population Size: 979 Sources: |
| Somnolence | 2.76% Disc. AE |
150 mg 1 times / day steady, oral Dose: 150 mg, 1 times / day Route: oral Route: steady Dose: 150 mg, 1 times / day Sources: |
unhealthy, adult n = 979 Health Status: unhealthy Age Group: adult Population Size: 979 Sources: |
| Dizziness | 3.47% Disc. AE |
150 mg 1 times / day steady, oral Dose: 150 mg, 1 times / day Route: oral Route: steady Dose: 150 mg, 1 times / day Sources: |
unhealthy, adult n = 979 Health Status: unhealthy Age Group: adult Population Size: 979 Sources: |
Overview
| CYP3A4 | CYP2C9 | CYP2D6 | hERG |
|---|---|---|---|
Drug as perpetrator
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| no |
Drug as victim
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
Page: 6.0 |
no | |||
Page: 6.0 |
no | |||
Page: 6.0 |
no | |||
| no | ||||
Page: 5.0 |
yes | |||
Page: 5.0 |
yes |
Tox targets
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
PubMed
| Title | Date | PubMed |
|---|---|---|
| Gateways to clinical trials. | 2002 Dec |
|
| Gateways to clinical trials. | 2002 Nov |
|
| Pharmacotherapy of social phobia. | 2003 |
|
| Pregabalin: a new anxiolytic. | 2003 Apr |
|
| Highly enantioselective, catalytic conjugate addition of cyanide to alpha,beta-unsaturated imides. | 2003 Apr 16 |
|
| Patient pages. Treatment of postherpetic neuralgia. | 2003 Apr 22 |
|
| Pregabalin for the treatment of postherpetic neuralgia: a randomized, placebo-controlled trial. | 2003 Apr 22 |
|
| Synthesis of both enantiomers of a P-chirogenic 1,2-bisphospholanoethane ligand via convergent routes and application to rhodium-catalyzed asymmetric hydrogenation of CI-1008 (pregabalin). | 2003 Aug 27 |
|
| Genotype-dependence of gabapentin and pregabalin sensitivity: the pharmacogenetic mediation of analgesia is specific to the type of pain being inhibited. | 2003 Dec |
|
| Protein 4.1N is required for translocation of inositol 1,4,5-trisphosphate receptor type 1 to the basolateral membrane domain in polarized Madin-Darby canine kidney cells. | 2003 Feb 7 |
|
| Gateways to clinical trials. | 2003 Jan-Feb |
|
| Long-term pregabalin treatment protects basal cortices and delays the occurrence of spontaneous seizures in the lithium-pilocarpine model in the rat. | 2003 Jul |
|
| Acute effects of gabapentin and pregabalin on rat forebrain cellular GABA, glutamate, and glutamine concentrations. | 2003 Jul |
|
| An enantioselective synthesis of (S)-(+)-3-aminomethyl-5-methylhexanoic acid via asymmetric hydrogenation. | 2003 Jul 11 |
|
| Gateways to clinical trials. | 2003 Jul-Aug |
|
| Evaluation of mixture modeling with count data using NONMEM. | 2003 Jun |
|
| GABA-ergic drugs: exit stage left, enter stage right. | 2003 Jun |
|
| Gateways to clinical trials. | 2003 Jun |
|
| A randomized, double-blind, placebo-controlled, fixed-dose, multicenter study of pregabalin in patients with generalized anxiety disorder. | 2003 Jun |
|
| Exposure-response analysis of pregabalin add-on treatment of patients with refractory partial seizures. | 2003 Jun |
|
| Gateways to clinical trials. March 2003. | 2003 Mar |
|
| Pharmacokinetics of pregabalin in subjects with various degrees of renal function. | 2003 Mar |
|
| Pregabalin in generalized anxiety disorder: a placebo-controlled trial. | 2003 Mar |
|
| Gateways to clinical trials. | 2003 May |
|
| Dose-response trial of pregabalin adjunctive therapy in patients with partial seizures. | 2003 May 27 |
|
| The use of clinical trial simulation to support dose selection: application to development of a new treatment for chronic neuropathic pain. | 2003 Nov |
|
| Gateways to clinical trials. | 2003 Oct |
|
| Gateways to clinical trials. | 2003 Sep |
|
| Pregabalin and gabapentin reduce release of substance P and CGRP from rat spinal tissues only after inflammation or activation of protein kinase C. | 2003 Sep |
|
| Pregabalin: in the treatment of painful diabetic peripheral neuropathy. | 2004 |
|
| [New molecular targets in pharmacological treatment of anxiety disorders]. | 2004 |
|
| Gateways to clinical trials. | 2004 Apr |
|
| Anticonvulsants as anxiolytics, part 2: Pregabalin and gabapentin as alpha(2)delta ligands at voltage-gated calcium channels. | 2004 Apr |
|
| Mechanism of action of alpha2delta ligands: voltage sensitive calcium channel (VSCC) modulators. | 2004 Aug |
|
| Pregabalin relieves symptoms of painful diabetic neuropathy: a randomized controlled trial. | 2004 Dec 14 |
|
| High dose pregabalin is effective for the treatment of generalised anxiety disorder. | 2004 Feb |
|
| Pregabalin (Pfizer). | 2004 Jan |
|
| Pregabalin add-on treatment: a randomized, double-blind, placebo-controlled, dose-response study in adults with partial seizures. | 2004 Jan |
|
| Gateways to clinical trials. | 2004 Jan-Feb |
|
| Neuromodulating drugs for the symptomatic treatment of neuropathic pain. | 2004 Jun |
|
| Gateways to clinical trials. | 2004 Mar |
|
| Pharmacologic management part 1: better-studied neuropathic pain diseases. | 2004 Mar |
|
| American Chemical Society--227th annual meeting. Neuroprotection. 28 March - 1 April 2004, Anaheim, CA, USA. | 2004 May |
|
| Pregabalin reduces pain and improves sleep and mood disturbances in patients with post-herpetic neuralgia: results of a randomised, placebo-controlled clinical trial. | 2004 May |
|
| Effect of gabapentin derivates on mechanical allodynia-like behaviour in a rat model of chronic sciatic constriction injury. | 2004 May 17 |
|
| Highly selective asymmetric hydrogenation using a three hindered quadrant bisphosphine rhodium catalyst. | 2004 May 19 |
|
| Gateways to clinical trials. | 2004 Nov |
|
| Gateways to clinical trials. | 2004 Oct |
|
| Progress report on new antiepileptic drugs: a summary of the Seventh Eilat Conference (EILAT VII). | 2004 Sep-Oct |
|
| Pregabalin: in the treatment of postherpetic neuralgia. | 2005 |
Patents
Sample Use Guides
Neuropathic Pain Associated with Diabetic Peripheral Neuropathy:
The maximum recommended dose is 100 mg three times a day (300 mg/day) in patients with creatinine clearance of at least 60 mL/min.
Postherpetic Neuralgia:
The recommended dose is 75 to 150 mg two times a day, or 50 to 100 mg three times a day (150 to 300 mg/day) in patients with creatinine clearance of at least 60 mL/min. Begin dosing at 75 mg two times a day, or 50 mg three times a day (150 mg/day). The dose may be increased to 300 mg/day within 1 week based on efficacy and tolerability.
Adjunctive Therapy for Adult Patients with Partial Onset Seizures:
LYRICA at doses of 150 to 600 mg/day has been shown to be effective as adjunctive therapy in
the treatment of partial onset seizures in adults. Both the efficacy and adverse event profiles of
In general, it is recommended that patients be started on a total daily dose no greater than 150 mg/day (75 mg two times a day, or 50 mg three times a day).
Management of Fibromyalgia:
The recommended dose is 300 to 450 mg/day. Begin dosing at
75 mg two times a day (150 mg/day). The dose may be increased to 150 mg two times a day (300 mg/day) within 1 week based on efficacy and tolerability.
Neuropathic Pain Associated with Spinal Cord Injury:
The recommended dose range is 150 to 600 mg/day. The recommended starting dose is 75 mg two times a day (150 mg/day). The dose may be increased to 150 mg two times a day (300 mg/day) within 1 week based on efficacy and tolerability.
Route of Administration:
Oral
| Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 19:11:55 GMT 2023
by
admin
on
Sat Dec 16 19:11:55 GMT 2023
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| Record UNII |
8348PZ4JYW
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| Record Status |
Validated (UNII)
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| Record Version |
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PARENT -> SALT/SOLVATE |
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ACTIVE MOIETY |
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