Frovatriptan

From Wikipedia, the free encyclopedia
Jump to navigation Jump to search

Template:Short description Template:Use dmy dates Template:Cs1 config Template:Main other <templatestyles src="Infobox drug/styles.css"/> {{#invoke:Infobox|infobox}}Template:Template other{{#invoke:TemplatePar |check |template=Template:Infobox_drug |all= |opt= pronounce= pronounce_ref= pronounce_comment= ATC_prefix= ATC_suffix= ATC_supplemental= ATCvet= biosimilars= CAS_number_Ref= CAS_number= CAS_supplemental= ChEBI= ChEBI_Ref= ChEMBL_Ref= ChEMBL= ChemSpiderID= ChemSpiderID_Ref= chirality= class= container_only= DailyMedID= data_page= DrugBank_Ref= DrugBank= Drugs.com= duration_of_action= INN= INN_EMA= IUPAC_name= IUPHAR_ligand= KEGG_Ref= KEGG= MedlinePlus= NIAID_ChemDB= PDB_ligand= PubChemSubstance= PubChem= StdInChIKey_Ref= StdInChIKey= StdInChI_Ref= StdInChI_comment= StdInChI= UNII_Ref= UNII= DTXSID= Verifiedfields= Watchedfields= addiction_liability= alt2= altL= altR= alt= bioavailability= boiling_high= boiling_notes= boiling_point= captionLR= caption= caption2= charge= chemical_formula= chemical_formula_ref= chemical_formula_comment= class1= class2= class3= class4= class5= class6= component1= component2= component3= component4= component5= component6= density= density_notes= dependency_liability= drug_name= elimination_half-life= engvar= excretion= image2= imageL= imageR= image= image_class= image_class2= image_classL= image_classR= Jmol= legal_AU= legal_BR= legal_CA= legal_DE= legal_EU= legal_NZ= legal_UK= legal_UN= legal_US= legal_AU_comment= legal_BR_comment= legal_CA_comment= legal_DE_comment= legal_UK_comment= legal_NZ_comment= legal_US_comment= legal_UN_comment= legal_EU_comment= legal_status= licence_CA= licence_EU= licence_US= license_CA= license_EU= license_US= mab_type= melting_high= melting_notes= melting_point= metabolism= metabolites= molecular_weight= molecular_weight_round= molecular_weight_unit= molecular_weight_ref= molecular_weight_comment= onset= pregnancy_AU= pregnancy_AU_comment= pregnancy_category= protein_bound= routes_of_administration= SMILES= smiles= solubility= sol_units= source= specific_rotation= synonyms= target= tradename= type= vaccine_type= verifiedrevid= width2= widthL= widthR= width= AAN= BAN= JAN= USAN= source_tissues= target_tissues= receptors= agonists= antagonists= precursor= biosynthesis= gt_target_gene= gt_vector= gt_nucleic_acid_type= gt_editing_method= gt_delivery_method= sec_combustion= Ac=Ag=Al=Am=Ar=As=At=Au=B=Ba=Be=Bh=Bi=Bk=Br=C=Ca=Cd=Ce=Cf=Cl=Cm=Cn=Co=Cr=Cs=Cu= D=Db=Ds=Dy=Er=Es=Eu=F=Fe=Fl=Fm=Fr=Ga=Gd=Ge=H=He=Hf=Hg=Ho=Hs=I=In=Ir=K=Kr=La=Li=Lr=Lu=Lv= Mc=Md=Mg=Mn=Mo=Mt=N=Na=Nb=Nd=Ne=Nh=Ni=No=Np=O=Og=Os=P=Pa=Pb=Pd=Pm=Po=Pr=Pt=Pu=Ra=Rb=Re=Rf=Rg=Rh=Rn=Ru=S=Sb=Sc=Se=Sg=Si=Sm=Sn=Sr=Ta=Tb=Tc=Te=Th=Ti=Tl=Tm=Ts=U=V=W=Xe=Y=Yb=Zn=Zr= index_label= index2_label= index_comment= index2_comment= CAS_number2= CAS_supplemental2= ATC_prefix2= ATC_suffix2= ATC_supplemental2= PubChem2= PubChemSubstance2= IUPHAR_ligand2= DrugBank2= ChemSpiderID2= UNII2= KEGG2= ChEBI2= ChEMBL2= PDB_ligand2= NIAID_ChemDB2= SMILES2= smiles2= StdInChI2= StdInChIKey2= CAS_number2_Ref= ChEBI2_Ref= ChEMBL2_Ref= ChemSpiderID2_Ref= DrugBank2_Ref= KEGG2_Ref= StdInChI2_Ref= StdInChIKey2_Ref= UNII2_Ref= DTXSID2= QID= QID2=PLLR= pregnancy_US= pregnancy_US_comment= |cat=Pages using infobox drug with unknown parameters |format=0|errNS=0

|preview=

@@@ (See parameter list). This message only shows in Preview, it will not show after you do Template:Button.

}}{{Infobox drug/maintenance categoriesTemplate:Yesno | drug_name = | INN = | _drugtype =

| _has_physiological_data= | _has_gene_therapy=

| vaccine_type= | mab_type= | _number_of_combo_chemicals={{#invoke:ParameterCount |main |component1 |component2 |component3 |component4|component5|component6 }} | _vaccine_data= | _mab_data= | _mab_vaccine_data= | _mab_other_data=141731CN[C@@H]3CCc2[nH]c1ccc(C(N)=O)cc1c2C31S/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/s1XPSQPHWEGNHMSK-SECBINFHSA-NTemplate:StdinchiciteTemplate:Stdinchicite | _combo_data= | _physiological_data= | _clinical_data=Template:Drugs.coma604013Frovatriptan B3OralFrovaSerotonin 5-HT1B, 5-HT1D, 5-HT1F, and 5-HT7 receptor agonistN02 | _legal_data=Rx-onlyRx-only

| _other_data=(+)-(R)-3-Methylamino-6-carboxamido-1,2,3,4-tetrahydrocarbazole

| _image_0_or_2 = Frovatriptan structure.svgFrovatriptan 3D BS.png | _image_LR =

| _datapage = Frovatriptan (data page) | _vaccine_target={{#ifeq: | vaccine | | _type_not_vaccine }} | _legal_all=Rx-onlyRx-only | _ATC_prefix_supplemental=N02 | _has_EMA_link = | CAS_number=158747-02-5 | PubChem=77992 | ChemSpiderID=70378 | ChEBI= | ChEMBL=1279 | DrugBank=DB00998 | KEGG=D07997 | _hasInChI_or_Key={{#if: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/s1XPSQPHWEGNHMSK-SECBINFHSA-N |yes}} | UNII=H82Q2D5WA7 | _hasJmol02 = |_hasMultipleCASnumbers = 158930-17-7 |_hasMultiplePubChemCIDs = |_hasMultipleChEBIs =

| _countSecondIDs={{#invoke:ParameterCount |main |CAS_number2 |ATC_prefix2 |PubChem2 |PubChemStructure2 |IUPHAR_ligand2 |DrugBank2 |ChemSpiderID2 |UNII2 |KEGG2 |ChEBI2 |ChEMBL2 |PDB_ligand2 |NIAID_ChemDB2 |SMILES2 |smiles2 |StdInChI2 |StdInChIKey2 |DTXCID2}} | _countIndexlabels={{#invoke:ParameterCount |main |index_label |index2_label}} | _trackListSortletter= |QID = |QID2 = |Verifiedfields=verified |Watchedfields=verified |verifiedrevid=461114004}}

Frovatriptan, sold under the brand name Frova among others, is a triptan medication developed by Vernalis for the treatment of migraine headaches<ref name="pmid27757013">Template:Cite journal</ref> and for short term prevention of menstrual migraine.<ref name="pmid24904224">Template:Cite journal</ref><ref name="ColeRabasseda2002">Template:Cite journal</ref> The product is licensed to Endo Pharmaceuticals in North America and Menarini in Europe.<ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref>

Medical uses

Frovatriptan is used in the treatment of migraine.

Available forms

It is available as 2.5 mg tablets.

Contraindications

Frovatriptan should not be given to patients with:

  • Ischemic heart disease
  • Cerebrovascular syndrome
  • Peripheral vascular disease
  • Uncontrolled hypertension
  • Hemiplegic or basilar migraine

Side effects

Rare, but serious cardiac events have been reported in patients with risk factors predictive of CAD. These include: coronary artery vasospasm, transient myocardial ischemia, myocardial infarction, ventricular tachycardia and ventricular fibrillation.

Pharmacology

Pharmacodynamics

Template:Further

Template:Nowrap
Target Affinity (Ki, nM)
5-HT1A 50–62 (Ki)
759–>10,000 (Template:Abbrlink)
38% (Template:Abbrlink)
5-HT1B 2.5–46 (Ki)
6.3–20 (Template:Abbr)
92% (Template:Abbr)
5-HT1D 1.7–10 (Ki)
2–5 (Template:Abbr)
98% (Template:Abbr)
5-HT1E >1,000 (Ki)
6,610–>10,000 (Template:Abbr)
44% (Template:Abbr)
5-HT1F 63–120 (Ki)
79–447 (Template:Abbr)
46% (Template:Abbr)
5-HT2A >10,000 (Ki)
>10,000 (Template:Abbr)
5-HT2B >10,000 (Ki)
>10,000 (Template:Abbr)
5-HT2C >5,000 (Ki)
Template:Abbr (Template:Abbr)
5-HT3 >1,000 (mouse/rat)
5-HT4 Template:Abbr
5-HT5A Template:Abbr
5-HT6 Template:Abbr
5-HT7 107–200 (Ki)
38 (Template:Abbr)
α1 >10,000 (rat)
α1A–α1D Template:Abbr
α2A–α2C Template:Abbr
β1–β3 Template:Abbr
D1 >10,000
D2 >10,000
D3 >10,000
D4–D5 Template:Abbr
H1 >10,000 (guinea pig)
H2–H4 Template:Abbr
M1–M5 Template:Abbr
I1, I2 Template:Abbr
σ1, σ2 Template:Abbr
Template:Abbrlink Template:Abbr
Template:Abbrlink Template:Abbr
Template:Abbrlink Template:Abbr
Template:Abbrlink Template:Abbr
Notes: The smaller the value, the more avidly the drug binds to the site. All proteins are human unless otherwise specified. Refs: <ref name="BindingDB">{{#invoke:citation/CS1|citation CitationClass=web

}}</ref><ref name="DeVriesVillalónSaxena1999">Template:Cite journal</ref><ref name="Tfelt-HansenDeVriesSaxena2000">Template:Cite journal</ref><ref name="SaxenaTfelt-Hansen2001">Template:Cite journal</ref><ref name="ColeRabasseda2002" /><ref name="Brink1999">{{#invoke:citation/CS1|citation

CitationClass=web

}}</ref><ref name="Broek2002">{{#invoke:citation/CS1|citation

CitationClass=web

}}</ref>
<ref name="NelsonPhebusJohnson2010">Template:Cite journal</ref><ref name="Rubio-BeltránLabastida-RamírezHaanes2019">Template:Cite journal</ref><ref name="ReuterNeeb2012">Template:Cite journal</ref><ref name="MitsikostasWard2024">Template:Cite book</ref><ref name="Comer2002">Template:Cite journal</ref>

Frovatriptan is a serotonin receptor agonist, with high affinity for the serotonin 5-HT1B and 5-HT1D receptors and with weaker activity at the serotonin 5-HT1F receptor.<ref name="Rubio-BeltránLabastida-RamírezHaanes2019" /> It has no significant effects on the GABAA mediated channel activity and benzodiazepine binding sites.Template:Citation needed Frovatriptan inhibits excessive dilation of arteries that supply blood to the head.Template:Citation needed Uniquely among most triptans, frovatriptan is also a relatively potent serotonin 5-HT7 receptor agonist.<ref name="Rubio-BeltránLabastida-RamírezHaanes2019" /> It is inactive at the serotonin 5-HT2A and 5-HT2B receptors.<ref name="Rubio-BeltránLabastida-RamírezHaanes2019" />

Pharmacokinetics

Frovatriptan has a terminal elimination half-life of approximately 26 hours, making it the longest within its class.<ref>Template:Cite journal</ref>

Chemistry

Frovatriptan's chemical structure is unusual among triptans, with other triptans being simple tryptamines or closely related compounds but frovatriptan instead being a tricyclic cyclized tryptamine and tetrahydrocarbazolamine derivative.<ref name="DeleuHanssens2000">Template:Cite journal</ref> It can be thought of as a 5-substituted and side chain-cyclized derivative of N-methyltryptamine (NMT).<ref name="DeleuHanssens2000" />

The experimental log P of frovatriptan is 0.9 and its predicted log P is 1.2.<ref name="PubChem">{{#invoke:citation/CS1|citation |CitationClass=web }}</ref>

History

Frovatriptan was first described in the scientific literature by 1997.<ref name="BrownParsonsRaval1996">Brown, A. M., Parsons, A. A., Raval, P., Porter, R., Tilford, N. S., Gager, T. L., ... & King, F. D. (1996, October). SB 209509 (VML 251), a potent constrictor of rabbit basilar artery with high affinity and selectivity for human 5-HT1D receptors. In BRITISH JOURNAL OF PHARMACOLOGY (Vol. 119, pp. P110-P110).</ref><ref name="ParsonsParkerRaval1997">Template:Cite journal</ref><ref name="ParsonsRavalSmith1998">Template:Cite journal</ref> It was approved for medical use in the United States in 2001.<ref name="FDA2001">{{#invoke:citation/CS1|citation |CitationClass=web }}</ref>

Society and culture

Frovatriptan is available only by prescription in the United States and Canada.<ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref>

See also

References

Template:Reflist

{{#invoke:Navbox|navbox}} Template:Serotonin receptor modulators {{#invoke:Navbox|navbox}} Template:Portal bar Template:Authority control

Retrieved from "https://wiki.sarg.dev/index.php?title=Frovatriptan&oldid=411551"