Details
Stereochemistry | RACEMIC |
Molecular Formula | C6H11NO2 |
Molecular Weight | 129.157 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
NC(CCC(O)=O)C=C
InChI
InChIKey=PJDFLNIOAUIZSL-UHFFFAOYSA-N
InChI=1S/C6H11NO2/c1-2-5(7)3-4-6(8)9/h2,5H,1,3-4,7H2,(H,8,9)
DescriptionSources: https://www.drugbank.ca/drugs/DB01080Curator's Comment: Description was created based on several sources, including http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/020427s010s011s012,022006s011s012s013lbl.pdf | https://www.ncbi.nlm.nih.gov/pubmed/22061175
Sources: https://www.drugbank.ca/drugs/DB01080
Curator's Comment: Description was created based on several sources, including http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/020427s010s011s012,022006s011s012s013lbl.pdf | https://www.ncbi.nlm.nih.gov/pubmed/22061175
Vigabatrin is an anticonvulsant chemically unrelated to other anticonvulsants. Vigabatrin prevents the catabolism of GABA by irreversibly inhibiting the enzyme GABA transaminase. It is an analog of GABA, but it is not a receptor agonist. However, vigabatrin is not a potent inhibitor of GABA-T with a Ki of 10 mM. Vigabatrin increases brain concentrations of gamma-aminobutyric acid (GABA), an inhibitory neurotransmitter in the CNS, by irreversibly inhibiting enzymes that catabolize GABA (gamma-aminobutyric acid transaminase, GABA-T). Duration of action is determined by rate of GABA-T re-synthesis. Vigabatrin may also work by suppressing repetitive neuronal firing through inhibition of voltage-sensitive sodium channels. Although administered as a racemic mixture, only the S(+) enantiomer is pharmacologically active. Vigabatrin is sold under the trade name SABRIL, it is indicated as adjunctive therapy for adults and pediatric patients 10 years of age and older with refractory complex partial seizures who have inadequately responded to several alternative treatments and for whom the potential benefits outweigh the risk of vision loss.
CNS Activity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
0.85 mM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | SABRIL Approved UseSABRIL is an antiepileptic drug (AED) indicated for:
• Refractory Complex Partial Seizures in Adults
(1.1). It should be used as adjunctive therapy in
patients who have responded inadequately to
several alternative treatments. Launch Date2009 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
18.4 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8331204/ |
2 g single, oral dose: 2 g route of administration: Oral experiment type: SINGLE co-administered: |
VIGABATRIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
73 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8331204/ |
2 g single, oral dose: 2 g route of administration: Oral experiment type: SINGLE co-administered: |
VIGABATRIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
7 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8331204/ |
2 g single, oral dose: 2 g route of administration: Oral experiment type: SINGLE co-administered: |
VIGABATRIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
100% |
2 g single, oral dose: 2 g route of administration: Oral experiment type: SINGLE co-administered: |
VIGABATRIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
2 g 1 times / day multiple, oral Highest studied dose Dose: 2 g, 1 times / day Route: oral Route: multiple Dose: 2 g, 1 times / day Sources: |
unhealthy, 16-63 |
Disc. AE: Sedation, Seizures... Other AEs: Weight gain, Depression... AEs leading to discontinuation/dose reduction: Sedation (9%) Other AEs:Seizures (2%) Status epilepticus (1%) Weight gain (6%) Sources: Depression (1%) Excitability (1%) Itching (1%) Headache (1%) Irritability (1%) Muscle pain (1%) Libido decreased (1%) |
2 g 2 times / day multiple, oral Highest studied dose Dose: 2 g, 2 times / day Route: oral Route: multiple Dose: 2 g, 2 times / day Sources: |
healthy, 25.8 ± 8.2 |
|
4 g single, oral Highest studied dose |
healthy, 27.0 ± 8.2 |
|
3 g 2 times / day multiple, oral Highest studied dose Dose: 3 g, 2 times / day Route: oral Route: multiple Dose: 3 g, 2 times / day Sources: |
unhealthy, 35 ± 11 |
|
90 g single, oral Overdose Dose: 90 g Route: oral Route: single Dose: 90 g Sources: |
unhealthy Health Status: unhealthy Sources: |
Other AEs: Coma, Unconsciousness... Other AEs: Coma (common) Sources: Unconsciousness (common) Drowsiness (common) Vertigo (uncommon) Psychosis (uncommon) Apnea (uncommon) Respiratory depression (uncommon) Bradycardia (uncommon) Agitation (uncommon) Irritability (uncommon) Confusion (uncommon) Headache (uncommon) Hypotension (uncommon) Abnormal behavior (uncommon) Seizures (uncommon) Status epilepticus (uncommon) Speech disorder (uncommon) |
1500 mg 2 times / day multiple, oral Recommended Dose: 1500 mg, 2 times / day Route: oral Route: multiple Dose: 1500 mg, 2 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Other AEs: Vision loss, Brain MRI signal changes... Other AEs: Vision loss Sources: Brain MRI signal changes Suicidal behavior Suicidal ideation Anemia Somnolence Fatigue |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Depression | 1% | 2 g 1 times / day multiple, oral Highest studied dose Dose: 2 g, 1 times / day Route: oral Route: multiple Dose: 2 g, 1 times / day Sources: |
unhealthy, 16-63 |
Excitability | 1% | 2 g 1 times / day multiple, oral Highest studied dose Dose: 2 g, 1 times / day Route: oral Route: multiple Dose: 2 g, 1 times / day Sources: |
unhealthy, 16-63 |
Headache | 1% | 2 g 1 times / day multiple, oral Highest studied dose Dose: 2 g, 1 times / day Route: oral Route: multiple Dose: 2 g, 1 times / day Sources: |
unhealthy, 16-63 |
Irritability | 1% | 2 g 1 times / day multiple, oral Highest studied dose Dose: 2 g, 1 times / day Route: oral Route: multiple Dose: 2 g, 1 times / day Sources: |
unhealthy, 16-63 |
Itching | 1% | 2 g 1 times / day multiple, oral Highest studied dose Dose: 2 g, 1 times / day Route: oral Route: multiple Dose: 2 g, 1 times / day Sources: |
unhealthy, 16-63 |
Libido decreased | 1% | 2 g 1 times / day multiple, oral Highest studied dose Dose: 2 g, 1 times / day Route: oral Route: multiple Dose: 2 g, 1 times / day Sources: |
unhealthy, 16-63 |
Muscle pain | 1% | 2 g 1 times / day multiple, oral Highest studied dose Dose: 2 g, 1 times / day Route: oral Route: multiple Dose: 2 g, 1 times / day Sources: |
unhealthy, 16-63 |
Status epilepticus | 1% Disc. AE |
2 g 1 times / day multiple, oral Highest studied dose Dose: 2 g, 1 times / day Route: oral Route: multiple Dose: 2 g, 1 times / day Sources: |
unhealthy, 16-63 |
Seizures | 2% Disc. AE |
2 g 1 times / day multiple, oral Highest studied dose Dose: 2 g, 1 times / day Route: oral Route: multiple Dose: 2 g, 1 times / day Sources: |
unhealthy, 16-63 |
Weight gain | 6% | 2 g 1 times / day multiple, oral Highest studied dose Dose: 2 g, 1 times / day Route: oral Route: multiple Dose: 2 g, 1 times / day Sources: |
unhealthy, 16-63 |
Sedation | 9% Disc. AE |
2 g 1 times / day multiple, oral Highest studied dose Dose: 2 g, 1 times / day Route: oral Route: multiple Dose: 2 g, 1 times / day Sources: |
unhealthy, 16-63 |
Coma | common | 90 g single, oral Overdose Dose: 90 g Route: oral Route: single Dose: 90 g Sources: |
unhealthy Health Status: unhealthy Sources: |
Drowsiness | common | 90 g single, oral Overdose Dose: 90 g Route: oral Route: single Dose: 90 g Sources: |
unhealthy Health Status: unhealthy Sources: |
Unconsciousness | common | 90 g single, oral Overdose Dose: 90 g Route: oral Route: single Dose: 90 g Sources: |
unhealthy Health Status: unhealthy Sources: |
Abnormal behavior | uncommon | 90 g single, oral Overdose Dose: 90 g Route: oral Route: single Dose: 90 g Sources: |
unhealthy Health Status: unhealthy Sources: |
Agitation | uncommon | 90 g single, oral Overdose Dose: 90 g Route: oral Route: single Dose: 90 g Sources: |
unhealthy Health Status: unhealthy Sources: |
Apnea | uncommon | 90 g single, oral Overdose Dose: 90 g Route: oral Route: single Dose: 90 g Sources: |
unhealthy Health Status: unhealthy Sources: |
Bradycardia | uncommon | 90 g single, oral Overdose Dose: 90 g Route: oral Route: single Dose: 90 g Sources: |
unhealthy Health Status: unhealthy Sources: |
Confusion | uncommon | 90 g single, oral Overdose Dose: 90 g Route: oral Route: single Dose: 90 g Sources: |
unhealthy Health Status: unhealthy Sources: |
Headache | uncommon | 90 g single, oral Overdose Dose: 90 g Route: oral Route: single Dose: 90 g Sources: |
unhealthy Health Status: unhealthy Sources: |
Hypotension | uncommon | 90 g single, oral Overdose Dose: 90 g Route: oral Route: single Dose: 90 g Sources: |
unhealthy Health Status: unhealthy Sources: |
Irritability | uncommon | 90 g single, oral Overdose Dose: 90 g Route: oral Route: single Dose: 90 g Sources: |
unhealthy Health Status: unhealthy Sources: |
Psychosis | uncommon | 90 g single, oral Overdose Dose: 90 g Route: oral Route: single Dose: 90 g Sources: |
unhealthy Health Status: unhealthy Sources: |
Respiratory depression | uncommon | 90 g single, oral Overdose Dose: 90 g Route: oral Route: single Dose: 90 g Sources: |
unhealthy Health Status: unhealthy Sources: |
Seizures | uncommon | 90 g single, oral Overdose Dose: 90 g Route: oral Route: single Dose: 90 g Sources: |
unhealthy Health Status: unhealthy Sources: |
Speech disorder | uncommon | 90 g single, oral Overdose Dose: 90 g Route: oral Route: single Dose: 90 g Sources: |
unhealthy Health Status: unhealthy Sources: |
Status epilepticus | uncommon | 90 g single, oral Overdose Dose: 90 g Route: oral Route: single Dose: 90 g Sources: |
unhealthy Health Status: unhealthy Sources: |
Vertigo | uncommon | 90 g single, oral Overdose Dose: 90 g Route: oral Route: single Dose: 90 g Sources: |
unhealthy Health Status: unhealthy Sources: |
Anemia | 1500 mg 2 times / day multiple, oral Recommended Dose: 1500 mg, 2 times / day Route: oral Route: multiple Dose: 1500 mg, 2 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
|
Brain MRI signal changes | 1500 mg 2 times / day multiple, oral Recommended Dose: 1500 mg, 2 times / day Route: oral Route: multiple Dose: 1500 mg, 2 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
|
Fatigue | 1500 mg 2 times / day multiple, oral Recommended Dose: 1500 mg, 2 times / day Route: oral Route: multiple Dose: 1500 mg, 2 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
|
Somnolence | 1500 mg 2 times / day multiple, oral Recommended Dose: 1500 mg, 2 times / day Route: oral Route: multiple Dose: 1500 mg, 2 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
|
Suicidal behavior | 1500 mg 2 times / day multiple, oral Recommended Dose: 1500 mg, 2 times / day Route: oral Route: multiple Dose: 1500 mg, 2 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
|
Suicidal ideation | 1500 mg 2 times / day multiple, oral Recommended Dose: 1500 mg, 2 times / day Route: oral Route: multiple Dose: 1500 mg, 2 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
|
Vision loss | 1500 mg 2 times / day multiple, oral Recommended Dose: 1500 mg, 2 times / day Route: oral Route: multiple Dose: 1500 mg, 2 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/020427s000_ClinPharmR_P1.pdf#page=70 Page: 70.0 |
likely | weak (co-administration study) Comment: A 16% to 20% average reduction in total phenytoin plasma levels was reported (see label page 21) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/020427s000_ClinPharmR_P1.pdf#page=70 Page: 70.0 |
||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/020427s000_ClinPharmR_P1.pdf#page=70 Page: 70.0 |
likely | weak (co-administration study) Comment: A 16% to 20% average reduction in total phenytoin plasma levels was reported (see label page 21) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/020427s000_ClinPharmR_P1.pdf#page=70 Page: 70.0 |
||
Page: 22.0 |
no | no (co-administration study) Comment: No significant difference in pharmacokinetic parameters of vigabatrin were found after treatment with ethinyl estradiol and levonorgestrel; vigabatrin did not interfere significantly with the cytochrome P450 isoenzyme (CYP3A)-mediated metabolism of the contraceptive tested Page: 22.0 |
||
Page: 22.0 |
no | no (co-administration study) Comment: No significant difference in pharmacokinetic parameters of vigabatrin were found after treatment with ethinyl estradiol and levonorgestrel; vigabatrin did not interfere significantly with the cytochrome P450 isoenzyme (CYP3A)-mediated metabolism of the contraceptive tested Page: 22.0 |
||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/020427s000_ClinPharmR_P1.pdf#page=70 Page: 70.0 |
not significant | |||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/020427s000_ClinPharmR_P1.pdf#page=70 Page: 70.0 |
not significant |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/022006s000_ClinPharm.pdf#page=4 Page: 4.0 |
PubMed
Title | Date | PubMed |
---|---|---|
GABA changes with vigabatrin in the developing human brain. | 1999 Apr |
|
Visual dysfunction in patients receiving vigabatrin: clinical and electrophysiologic findings. | 1999 Dec 10 |
|
Elimination of oxcarbazepine-induced oculogyric crisis following vagus nerve stimulation. | 1999 Jun 10 |
|
Preclinical evaluation of newly approved and potential antiepileptic drugs against cocaine-induced seizures. | 1999 Sep |
|
[Visual field changes secondary to vigabatrin treatment]. | 2000 Dec 16-31 |
|
Synergistic neurotoxicity by human immunodeficiency virus proteins Tat and gp120: protection by memantine. | 2000 Feb |
|
Another case of reversibility of visual-field defect induced by vigabatrin monotherapy: is young age a favorable factor? | 2000 Jun |
|
Vigabatrin-associated visual field defects in children. | 2000 Jun |
|
Electro-oculography, electroretinography, visual evoked potentials, and multifocal electroretinography in patients with vigabatrin-attributed visual field constriction. | 2000 Nov |
|
Visual field defects in patients taking vigabatrin. | 2000 Oct |
|
Anti-spasticity agents for multiple sclerosis. | 2001 |
|
GABAergic mechanisms in epilepsy. | 2001 |
|
The new generation of GABA enhancers. Potential in the treatment of epilepsy. | 2001 |
|
Visual field defects with vigabatrin: epidemiology and therapeutic implications. | 2001 |
|
Behavioural effects of the new anticonvulsants. | 2001 |
|
New developments in the pharmacotherapy of alcohol dependence. | 2001 |
|
Update on anticonvulsants for the treatment of alcohol withdrawal. | 2001 |
|
Visual function is stable in patients who continue long-term vigabatrin therapy: implications for clinical decision making. | 2001 Apr |
|
Newer antiepileptic drugs: advantages and disadvantages. | 2001 Aug |
|
Paradoxical reduction of synaptic inhibition by vigabatrin. | 2001 Aug |
|
Infantile spasms. | 2001 Feb |
|
Increased vigabatrin entry into the brain by polysorbate 80 and sodium caprate. | 2001 Feb |
|
The effect of gamma-vinyl-GABA on the consumption of concurrently available oral cocaine and ethanol in the rat. | 2001 Feb |
|
Determination of the antiepileptics vigabatrin and gabapentin in dosage forms and biological fluids using Hantzsch reaction. | 2001 Feb |
|
Nicotine-conditioned locomotor activity in rats: dopaminergic and GABAergic influences on conditioned expression. | 2001 Jan |
|
The use of vigabatrin in infantile spasms in Asian children. | 2001 Jan |
|
[Evaluation of extensive visual field defects with computer-assisted kinetic perimetry]. | 2001 Jan |
|
Effects of vigabatrin on brain GABA+/CR signals in patients with epilepsy monitored by 1H-NMR-spectroscopy: responder characteristics. | 2001 Jan |
|
Revised guideline for prescribing vigabatrin in children. Guideline's claim about infantile spasms is not based on appropriate evidence. | 2001 Jan 27 |
|
Changes in color vision after a single dose of vigabatrin or carbamazepine in healthy volunteers. | 2001 Jan-Feb |
|
Gabapentin but not vigabatrin is effective in the treatment of acquired nystagmus in multiple sclerosis: How valid is the GABAergic hypothesis? | 2001 Jul |
|
Visual field constriction: accumulation of vigabatrin but not tiagabine in the retina. | 2001 Jul 24 |
|
Placental transfer of vigabatrin (gamma-vinyl GABA) and its effect on concentration of amino acids in the embryo of TO mice. | 2001 Mar |
|
Chronic elevation of brain GABA levels beginning two days after status epilepticus does not prevent epileptogenesis in rats. | 2001 Mar |
|
Development of a stable-isotope dilution assay for gamma-aminobutyric acid (GABA) transaminase in isolated leukocytes and evidence that GABA and beta-alanine transaminases are identical. | 2001 Mar |
|
[Social and economic aspects of administration of new antiepileptic drugs]. | 2001 Mar-Apr |
|
Vigabatrin visual toxicity: evolution and dose dependence. | 2001 May |
|
West syndrome and other infantile epileptic encephalopathies--Indian hospital experience. | 2001 Nov |
|
West syndrome: a university hospital based study from Oman. | 2001 Nov |
|
Gamma vinyl-GABA differentially modulates NMDA antagonist-induced increases in mesocortical versus mesolimbic DA transmission. | 2001 Nov |
|
Anxiolytic effects of vigabatrin in panic disorder. | 2001 Oct |
|
Plasticity of rat central inhibitory synapses through GABA metabolism. | 2001 Sep 1 |
|
Determination of vigabatrin in human plasma and urine by high-performance liquid chromatography with fluorescence detection. | 2001 Sep 5 |
Patents
Sample Use Guides
Refractory Complex Partial Seizures
Adults >16 years of age: Initiate therapy at 500 mg twice daily, increasing total daily dose per instructions. The recommended dose is 1500 mg twice daily (2.2).
Pediatrics 10 to 16 years of age: Treatment is based on body weight. Initiate therapy at 250 mg twice daily, increasing total daily dose per instructions.
The recommended maintenance dose is 1000 mg twice daily. Patients weighing more than 60 kg should be dosed according to adult recommendations (2.2).
Infantile Spasms
Initiate therapy at 50 mg/kg/day given in 2 divided doses increasing total daily dose per instructions to a maximum of 150 mg/kg/day given in 2 divided doses (2.3).
Given orally with or without food.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25062867
Vigabatrin inhibits the uptake of taurine in Caco-2 and MDCK cells to 34 ± 3 and 53 ± 2%, respectively, at a concentration of 30 mM.
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Classification Tree | Code System | Code | ||
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FDA ORPHAN DRUG |
609817
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NCI_THESAURUS |
C264
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FDA ORPHAN DRUG |
135100
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WHO-ATC |
N03AG04
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LIVERTOX |
NBK548253
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NDF-RT |
N0000175753
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FDA ORPHAN DRUG |
905322
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WHO-VATC |
QN03AG04
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5665
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1712001
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14851
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DB01080
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D020888
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Vigabatrin
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VIGABATRIN
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GR120KRT6K
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C87611
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SUB00048MIG
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U-75
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m11445
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68506-86-5
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CHEMBL89598
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63638
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ACTIVE MOIETY