Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C14H17N3O |
Molecular Weight | 243.3043 |
Optical Activity | ( + ) |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CN[C@@H]1CCC2=C(C1)C3=C(N2)C=CC(=C3)C(N)=O
InChI
InChIKey=XPSQPHWEGNHMSK-SECBINFHSA-N
InChI=1S/C14H17N3O/c1-16-9-3-5-13-11(7-9)10-6-8(14(15)18)2-4-12(10)17-13/h2,4,6,9,16-17H,3,5,7H2,1H3,(H2,15,18)/t9-/m1/s1
Molecular Formula | C14H17N3O |
Molecular Weight | 243.3043 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
Frovatriptan succinate (trade name Frova) is a selective 5-hydroxytryptamine1 (5-HT1B/1D) receptor subtype agonist, and is used for the treatment of migraine attacks with or without aura in adults. Frovatriptan has no significant effects on GABAA mediated channel activity and has no significant affinity for benzodiazepine binding sites. Frovatriptan is believed to act on extracerebral, intracranial arteries and to inhibit excessive dilation of these vessels in migraine. Serious but rare cardiac events have been reported in patients with risk factors predictive of coronary artery disease (CAD). These include coronary artery vasospasm, transient myocardial ischemia, myocardial infarction, ventricular tachycardia and ventricular fibrillation.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
62.0 nM [Ki] | |||
10.3 nM [Ki] | |||
4.4 nM [Ki] | |||
Target ID: CHEMBL1983 |
|||
Target ID: CHEMBL1898 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | FROVA Approved UseFROVA is indicated for the acute treatment of migraine attacks with or without aura in adults. FROVA is not intended for the prophylactic therapy of migraine or for use in the management of hemiplegic or basilar migraine (see CONTRAINDICATIONS). The safety and effectiveness of FROVA have not been established for cluster headache, which is present in an older, predominately male, population. Launch Date2001 |
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Primary | FROVA Approved UseFROVA is indicated for the acute treatment of migraine attacks with or without aura in adults. FROVA is not intended for the prophylactic therapy of migraine or for use in the management of hemiplegic or basilar migraine (see CONTRAINDICATIONS). The safety and effectiveness of FROVA have not been established for cluster headache, which is present in an older, predominately male, population. Launch Date2001 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
2.44 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25092964 |
2.5 mg single, oral dose: 2.5 mg route of administration: Oral experiment type: SINGLE co-administered: |
FROVATRIPTAN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
50.7 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25092964 |
2.5 mg single, oral dose: 2.5 mg route of administration: Oral experiment type: SINGLE co-administered: |
FROVATRIPTAN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
29.3 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25092964 |
2.5 mg single, oral dose: 2.5 mg route of administration: Oral experiment type: SINGLE co-administered: |
FROVATRIPTAN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
85% |
FROVATRIPTAN serum | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
0.8 mg single, intravenous Highest studied dose Dose: 0.8 mg Route: intravenous Route: single Dose: 0.8 mg Sources: |
healthy, 21 - 37 |
|
40 mg single, oral Highest studied dose |
healthy, 21 - 37 |
|
40 mg single, oral Highest studied dose |
unhealthy, 40.4 |
|
7.5 mg 3 times / day multiple, oral Recommended Dose: 7.5 mg, 3 times / day Route: oral Route: multiple Dose: 7.5 mg, 3 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Disc. AE: Arrhythmia, Cerebral hemorrhage... Other AEs: Myocardial ischemia, Myocardial infarction... AEs leading to discontinuation/dose reduction: Arrhythmia Other AEs:Cerebral hemorrhage Subarachnoid hemorrhage Stroke Gastrointestinal ischemia Peripheral vasoconstriction Serotonin syndrome Myocardial ischemia Sources: Myocardial infarction Prinzmetal angina Chest pain Throat pain Neck pain Jaw pain Chest tightness Throat tightness Pressure |
7.5 mg 3 times / day multiple, oral Recommended Dose: 7.5 mg, 3 times / day Route: oral Route: multiple Dose: 7.5 mg, 3 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Disc. AE: Splenic infarction, Raynaud's syndrome... AEs leading to discontinuation/dose reduction: Splenic infarction Sources: Raynaud's syndrome Blood pressure high (grade 3) Hypertensive crisis Anaphylactic reaction (grade 4-5) Anaphylactoid reaction (grade 4-5) Angioedema (grade 4-5) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Chest pain | 7.5 mg 3 times / day multiple, oral Recommended Dose: 7.5 mg, 3 times / day Route: oral Route: multiple Dose: 7.5 mg, 3 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
|
Chest tightness | 7.5 mg 3 times / day multiple, oral Recommended Dose: 7.5 mg, 3 times / day Route: oral Route: multiple Dose: 7.5 mg, 3 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
|
Jaw pain | 7.5 mg 3 times / day multiple, oral Recommended Dose: 7.5 mg, 3 times / day Route: oral Route: multiple Dose: 7.5 mg, 3 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
|
Myocardial infarction | 7.5 mg 3 times / day multiple, oral Recommended Dose: 7.5 mg, 3 times / day Route: oral Route: multiple Dose: 7.5 mg, 3 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
|
Myocardial ischemia | 7.5 mg 3 times / day multiple, oral Recommended Dose: 7.5 mg, 3 times / day Route: oral Route: multiple Dose: 7.5 mg, 3 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
|
Neck pain | 7.5 mg 3 times / day multiple, oral Recommended Dose: 7.5 mg, 3 times / day Route: oral Route: multiple Dose: 7.5 mg, 3 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
|
Pressure | 7.5 mg 3 times / day multiple, oral Recommended Dose: 7.5 mg, 3 times / day Route: oral Route: multiple Dose: 7.5 mg, 3 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
|
Prinzmetal angina | 7.5 mg 3 times / day multiple, oral Recommended Dose: 7.5 mg, 3 times / day Route: oral Route: multiple Dose: 7.5 mg, 3 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
|
Throat pain | 7.5 mg 3 times / day multiple, oral Recommended Dose: 7.5 mg, 3 times / day Route: oral Route: multiple Dose: 7.5 mg, 3 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
|
Throat tightness | 7.5 mg 3 times / day multiple, oral Recommended Dose: 7.5 mg, 3 times / day Route: oral Route: multiple Dose: 7.5 mg, 3 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
|
Arrhythmia | Disc. AE | 7.5 mg 3 times / day multiple, oral Recommended Dose: 7.5 mg, 3 times / day Route: oral Route: multiple Dose: 7.5 mg, 3 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Cerebral hemorrhage | Disc. AE | 7.5 mg 3 times / day multiple, oral Recommended Dose: 7.5 mg, 3 times / day Route: oral Route: multiple Dose: 7.5 mg, 3 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Gastrointestinal ischemia | Disc. AE | 7.5 mg 3 times / day multiple, oral Recommended Dose: 7.5 mg, 3 times / day Route: oral Route: multiple Dose: 7.5 mg, 3 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Peripheral vasoconstriction | Disc. AE | 7.5 mg 3 times / day multiple, oral Recommended Dose: 7.5 mg, 3 times / day Route: oral Route: multiple Dose: 7.5 mg, 3 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Serotonin syndrome | Disc. AE | 7.5 mg 3 times / day multiple, oral Recommended Dose: 7.5 mg, 3 times / day Route: oral Route: multiple Dose: 7.5 mg, 3 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Stroke | Disc. AE | 7.5 mg 3 times / day multiple, oral Recommended Dose: 7.5 mg, 3 times / day Route: oral Route: multiple Dose: 7.5 mg, 3 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Subarachnoid hemorrhage | Disc. AE | 7.5 mg 3 times / day multiple, oral Recommended Dose: 7.5 mg, 3 times / day Route: oral Route: multiple Dose: 7.5 mg, 3 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Hypertensive crisis | Disc. AE | 7.5 mg 3 times / day multiple, oral Recommended Dose: 7.5 mg, 3 times / day Route: oral Route: multiple Dose: 7.5 mg, 3 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Raynaud's syndrome | Disc. AE | 7.5 mg 3 times / day multiple, oral Recommended Dose: 7.5 mg, 3 times / day Route: oral Route: multiple Dose: 7.5 mg, 3 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Splenic infarction | Disc. AE | 7.5 mg 3 times / day multiple, oral Recommended Dose: 7.5 mg, 3 times / day Route: oral Route: multiple Dose: 7.5 mg, 3 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Blood pressure high | grade 3 Disc. AE |
7.5 mg 3 times / day multiple, oral Recommended Dose: 7.5 mg, 3 times / day Route: oral Route: multiple Dose: 7.5 mg, 3 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Anaphylactic reaction | grade 4-5 Disc. AE |
7.5 mg 3 times / day multiple, oral Recommended Dose: 7.5 mg, 3 times / day Route: oral Route: multiple Dose: 7.5 mg, 3 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Anaphylactoid reaction | grade 4-5 Disc. AE |
7.5 mg 3 times / day multiple, oral Recommended Dose: 7.5 mg, 3 times / day Route: oral Route: multiple Dose: 7.5 mg, 3 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Angioedema | grade 4-5 Disc. AE |
7.5 mg 3 times / day multiple, oral Recommended Dose: 7.5 mg, 3 times / day Route: oral Route: multiple Dose: 7.5 mg, 3 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 |
---|---|---|---|---|
Page: 29, 35 |
no | |||
Page: 35.0 |
no | |||
Page: 35.0 |
no | |||
Page: 35.0 |
no | |||
Page: 35.0 |
no | |||
Page: 35.0 |
no | |||
Page: 29, 35 |
no | |||
Page: 35.0 |
no | |||
Page: 29, 35 |
no |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 35.0 |
no | |||
Page: 35.0 |
no | |||
Page: 35.0 |
no | |||
Page: 29.0 |
yes |
PubMed
Title | Date | PubMed |
---|---|---|
Comparative aspects of triptans in treating migraine. | 2001 |
|
Newer formulations of the triptans: advances in migraine management. | 2003 |
|
Migraine headache recurrence: relationship to clinical, pharmacological, and pharmacokinetic properties of triptans. | 2003 Apr |
|
Patent news. | 2003 Dec |
|
[Migraine therapy. new specific triptan frovatriptan--long acting]. | 2003 Jan |
|
Meta-analysis of oral triptan therapy for migraine: number needed to treat and relative cost to achieve relief within 2 hours. | 2003 Jan-Feb |
|
The evolving management of migraine. | 2003 Jun |
|
Gateways to clinical trials. | 2003 Jun |
|
The truth about frovatriptan. | 2003 Jun |
|
Gateways to clinical trials. | 2003 Oct |
|
[After the numerous ergotamine preparations are on the way out. Migraine patients to change over to triptans]. | 2003 Oct 16 |
|
Gateways to clinical trials. | 2004 Apr |
|
Evaluation of Frova, single-use intubation introducer, in a manikin. Comparison with Eschmann multiple-use introducer and Portex single-use introducer. | 2004 Aug |
|
Involvement of 5-HT1B receptors in triptan-induced contractile responses in guinea-pig isolated iliac artery. | 2004 Jul |
|
Cost considerations of acute migraine treatment. | 2004 Mar |
|
Gateways to clinical trials. | 2004 May |
|
Frovatriptan use in migraineurs with or at high risk of coronary artery disease. | 2004 May |
|
[PercuTwist dilational tracheostomy. Prospective evaluation of 54 consecutive patients]. | 2004 May |
|
Gateways to clinical trials. | 2004 Sep |
|
Regulatory and functional interactions of plant growth regulators and plant glutathione S-transferases (GSTs). | 2005 |
|
The use of triptans in the management of menstrual migraine. | 2005 |
|
Efficacy and tolerability of frovatriptan in acute migraine treatment: systematic review of randomized controlled trials. | 2005 Dec |
|
Frovatriptan-induced hypomania. | 2005 Summer |
|
[Clinical use of triptans in the management of migraine]. | 2006 |
|
Tracheal intubation using a classic laryngeal mask airway, Frova introducer, and pediatric bronchoscope. | 2006 Dec |
|
A comparative study on the cost of new antibiotics and drugs of other therapeutic categories. | 2006 Dec 20 |
|
Shearing of a Frova Intubating Introducer by a Bronchocath double lumen tube. | 2006 Feb |
|
Clinical review: percutaneous dilatational tracheostomy. | 2006 Feb |
|
A validated chiral CE method for Frovatriptan, using cyclodextrin as chiral selector. | 2006 Jun 16 |
|
Gateways to clinical trials. | 2006 Nov |
|
Tailoring management strategies for the patient with menstrual migraine: focus on prevention and treatment. | 2006 Oct |
|
Frovatriptan: a review of pharmacology, pharmacokinetics and clinical potential in the treatment of menstrual migraine. | 2006 Sep |
|
Editorial foreword. | 2006 Sep |
|
Airway management during microlaryngoscopic surgery with a Frova airway intubation catheter. | 2006 Sep |
|
Use of the sustained pain-free plus no adverse events endpoint in clinical trials of triptans in acute migraine. | 2007 |
|
Frovatriptan review. | 2007 Dec |
|
Chiral separation of Frovatriptan isomers by HPLC using amylose based chiral stationary phase. | 2007 Feb 1 |
|
Latest pain relief a combination of new and old. | 2007 Jan |
|
New pain management options: drugs. | 2007 Jan |
|
In silico prediction of pregnane X receptor activators by machine learning approaches. | 2007 Jan |
|
Frovatriptan for the prevention of postdural puncture headache. | 2007 Jul |
|
Times to pain relief and pain freedom with rizatriptan 10 mg and other oral triptans. | 2007 Jul |
|
Efficacy of frovatriptan. | 2007 Jun |
|
Frova intubating catheter position can be determined with aspirating oesophageal detection device. | 2007 Jun |
|
Menstrually related migraine: breaking the cycle in your clinical practice. | 2007 Oct |
|
Frovatriptan vs. transdermal oestrogens or naproxen sodium for the prophylaxis of menstrual migraine. | 2007 Oct |
|
Efficacy of frovatriptan. | 2007 Sep |
|
Acute treatment and prevention of menstrually related migraine headache: evidence-based review. | 2008 Apr 22 |
|
Triptans in pregnancy. | 2008 Feb |
|
Evaluation of clinical effectiveness of the Frova single-use tracheal tube introducer. | 2008 Feb |
Sample Use Guides
The recommended dose is a single tablet of FROVA (frovatriptan 2.5 mg) taken orally with fluids. If the headache recurs after initial relief, a second tablet may be taken, providing there is an interval of at least 2 hours between doses. The total daily dose of frovatriptan should not exceed 3 tablets (3 x 2.5 mg per day). The safety of treating an average of more than 4 migraine attacks in a 30-day period has not been established.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/9700983
Curator's Comment: Frovatriptan was investigated in human isolated basilar and coronary arteries in which the endothelium had been removed. Basilar arteries were obtained post mortem, and coronary arteries were obtained from patients undergoing heart transplant (recipient) or from donor hearts that were not suitable for transplant. Frovatriptan was a potent contractile agent in isolated basilar artery with a -log mean effective concentration (EC50) value of 7.86 +/- 0.07 and intrinsic activity of 1.25 +/- 0.10 relative to 5-HT (n = 4). In coronary arteries, frovatriptan produced contraction with -log EC50 values of 7.38 +/- 0.12 and 7.81 +/- 0.2 in recipient (n = 7) and donor (n = 3) arteries, respectively. The relative degree of contraction of frovatriptan was lower than that of 5-HT, with relative intrinsic activities of 0.42 +/- 0.06 and 0.40 +/- 0.09, respectively.
Unknown
Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 18:15:34 GMT 2025
by
admin
on
Mon Mar 31 18:15:34 GMT 2025
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Record UNII |
H82Q2D5WA7
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Record Status |
Validated (UNII)
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Record Version |
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Common Name | English | ||
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Common Name | English | ||
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Common Name | English | ||
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Systematic Name | English |
Classification Tree | Code System | Code | ||
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NDF-RT |
N0000175763
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WHO-ATC |
N02CC07
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NDF-RT |
N0000175765
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WHO-VATC |
QN02CC07
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NCI_THESAURUS |
C47794
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NDF-RT |
N0000175764
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LIVERTOX |
443
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m5571
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PRIMARY | Merck Index | ||
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C65772
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100000080448
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H82Q2D5WA7
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Frovatriptan
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7191
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DB00998
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SUB07817MIG
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1251
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CHEMBL1279
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FROVATRIPTAN
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DTXSID0023080
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C108128
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Related Record | Type | Details | ||
---|---|---|---|---|
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SALT/SOLVATE -> PARENT |
|
||
|
TARGET -> AGONIST |
pKi
|
||
|
BINDER->LIGAND |
BINDING
|
||
|
EXCRETED UNCHANGED |
oral administration
AMOUNT EXCRETED
FECAL
|
||
|
METABOLIC ENZYME -> SUBSTRATE |
MAJOR
|
||
|
EXCRETED UNCHANGED |
oral administration
AMOUNT EXCRETED
URINE
|
||
|
EXCRETED UNCHANGED |
intravenous administration
AMOUNT EXCRETED
URINE
|
||
|
RACEMATE -> ENANTIOMER |
|
Related Record | Type | Details | ||
---|---|---|---|---|
|
METABOLITE -> PARENT |
URINE
|
||
|
METABOLITE -> PARENT |
MAJOR
FECAL
|
||
|
METABOLITE -> PARENT |
URINE
|
Related Record | Type | Details | ||
---|---|---|---|---|
|
ACTIVE MOIETY |
|
Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
---|---|---|---|---|---|---|
Tmax | PHARMACOKINETIC |
|
ORAL ADMINISTRATION |
|
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Biological Half-life | PHARMACOKINETIC |
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