Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C15H27NO6 |
Molecular Weight | 317.378 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(C)C[C@H](CNC(=O)O[C@H](C)OC(=O)C(C)C)CC(O)=O
InChI
InChIKey=YDHZNJWFIYERIF-NEPJUHHUSA-N
InChI=1S/C15H27NO6/c1-9(2)6-12(7-13(17)18)8-16-15(20)22-11(5)21-14(19)10(3)4/h9-12H,6-8H2,1-5H3,(H,16,20)(H,17,18)/t11-,12+/m1/s1
Molecular Formula | C15H27NO6 |
Molecular Weight | 317.378 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
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.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL3896 Sources: https://www.ncbi.nlm.nih.gov/pubmed/?term=21651903 |
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Target ID: CHEMBL1919 Sources: https://www.ncbi.nlm.nih.gov/pubmed/?term=21651903 |
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 |
---|---|---|---|---|
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/021446s040,%20022488s017lbl.pdf#page=34 Page: 34.0 |
no | |||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/021446s040,%20022488s017lbl.pdf#page=34 Page: 34.0 |
no | |||
no |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://www.iqpc.com/media/8156/15859.pdf#page=6 Page: 6.0 |
no | |||
Sources: https://www.iqpc.com/media/8156/15859.pdf#page=6 Page: 6.0 |
no | |||
Sources: https://www.iqpc.com/media/8156/15859.pdf#page=6 Page: 6.0 |
no | |||
no | ||||
Sources: https://www.iqpc.com/media/8156/15859.pdf#page=5 Page: 5.0 |
yes | |||
Sources: https://www.iqpc.com/media/8156/15859.pdf#page=5 Page: 5.0 |
yes |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
PubMed
Title | Date | PubMed |
---|---|---|
New single-isomer compounds on the horizon. | 2002 Apr |
|
The role of GABA in the pathophysiology and treatment of anxiety disorders. | 2003 |
|
Gateways to clinical trials. | 2003 Dec |
|
Genotype-dependence of gabapentin and pregabalin sensitivity: the pharmacogenetic mediation of analgesia is specific to the type of pain being inhibited. | 2003 Dec |
|
Evaluation of mixture modeling with count data using NONMEM. | 2003 Jun |
|
Future Pain Drugs - Europe 2003. 15-16 September 2003, London, UK. | 2003 Nov |
|
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 |
|
Antiepileptic drugs in the treatment of anxiety disorders: role in therapy. | 2004 |
|
Selecting pharmacotherapy for generalized anxiety disorder. | 2004 |
|
Pregabalin as adjunctive therapy for partial seizures. | 2004 |
|
Pregabalin pharmacology and its relevance to clinical practice. | 2004 |
|
Newer anticonvulsants in the treatment of bipolar disorder. | 2004 |
|
Efficacy of the novel anxiolytic pregabalin in social anxiety disorder: a placebo-controlled, multicenter study. | 2004 Apr |
|
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 for the treatment of painful diabetic peripheral neuropathy: a double-blind, placebo-controlled trial. | 2004 Aug |
|
Pharmaceutical treatment options for fibromyalgia. | 2004 Aug |
|
A study comparing the actions of gabapentin and pregabalin on the electrophysiological properties of cultured DRG neurones from neonatal rats. | 2004 Aug 4 |
|
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 |
|
Gateways to clinical trials. | 2004 Jul-Aug |
|
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 |
|
Anticonvulsants and the relief of chronic pain: pregabalin and gabapentin as alpha(2)delta ligands at voltage-gated calcium channels. | 2004 May |
|
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 |
|
[How neuropathic is sciatica? The mixed pain concept]. | 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 |
|
[New options in the treatment of various forms of diabetic neuropathy]. | 2004 May 20 |
|
Gateways to clinical trials. | 2004 Nov |
|
Gateways to clinical trials. | 2004 Oct |
|
Efficacy and tolerability of the new antiepileptic drugs: comparison of two recent guidelines. | 2004 Oct |
|
'Protective premedication': an option with gabapentin and related drugs? A review of gabapentin and pregabalin in in the treatment of post-operative pain. | 2004 Oct |
|
Simultaneous high-performance liquid chromatographic analysis of pregabalin, gabapentin and vigabatrin in human serum by precolumn derivatization with o-phtaldialdehyde and fluorescence detection. | 2004 Oct 25 |
|
Dual effects of gabapentin and pregabalin on glutamate release at rat entorhinal synapses in vitro. | 2004 Sep |
|
Practice parameter: treatment of postherpetic neuralgia: an evidence-based report of the Quality Standards Subcommittee of the American Academy of Neurology. | 2004 Sep 28 |
|
Progress report on new antiepileptic drugs: a summary of the Seventh Eilat Conference (EILAT VII). | 2004 Sep-Oct |
|
The biology and pharmacology of calcium channel alpha2-delta proteins Pfizer Satellite Symposium to the 2003 Society for Neuroscience Meeting. Sheraton New Orleans Hotel, New Orleans, LA November 10, 2003. | 2004 Summer |
|
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/21196706
Curator's Comment: Pregabalin antagonizes the neurotoxic effects of copper
Unknown
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 10:08:33 GMT 2023
by
admin
on
Sat Dec 16 10:08:33 GMT 2023
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Record UNII |
JNY093NZ79
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Record Status |
Validated (UNII)
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Record Version |
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1174748-30-1
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300000018840
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44138069
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C175848
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11118
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