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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2022-03-07 02:51:51 UTC
HMDB IDHMDB0015087
Secondary Accession Numbers
  • HMDB15087
Metabolite Identification
Common NameNaratriptan
DescriptionNaratriptan, also known as naramig or amerge, belongs to the class of organic compounds known as 3-alkylindoles. 3-alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 3-position. It was covered by U.S. Patent no. 4997841; the FDA lists the patent as expiring on July 7, 2010. Naratriptan is a drug which is used for the acute treatment of migraine attacks with or without aura in adults. Side-effects which are unlikely and which should be promptly reported include: chest pain/pressure, throat pain/pressure, unusually fast/slow/irregular pulse, one-sided muscle weakness, vision problems, cold/bluish hands or feet, stomach pain, bloody diarrhea, mental/mood changes, and fainting. Because Teva and Sandoz are the only approved suppliers of generic Naratriptan in Canada, the quarantine resulted in Naratriptan being placed on the Canadian drug shortage list. Naratriptan is a very strong basic compound (based on its pKa). Naratriptan is a potentially toxic compound. Naratriptan is used for the treatment of the acute migraine attacks and the symptoms of migraine, including severe, throbbing headaches that sometimes are accompanied by nausea and sensitivity to sound or light. Symptoms of a serious allergic reaction include: rash, itching, swelling, severe dizziness, trouble breathing (swelling of the throat). In July 2010, in the wake of the patent expiration, several drug manufacturers, including Roxane Labs, Sandoz and Teva Pharmaceuticals, announced that they were launching generic Naratriptan medications. A meta-analysis of 53 clinical trials has shown that all triptans are effective for treating migraine at marketed doses and that naratriptan, although less effective than sumatriptan and rizatriptan was more effective than placebo in reducing migraine symptoms at two hours and efficacy was demonstrated in almost two thirds of subjects after four hours of treatment. Naratriptan (trade names include Amerge) is a triptan drug marketed by GlaxoSmithKline and is used for the treatment of migraine headaches. It had previously been covered by Canadian patent 1210968; but both Sandoz and Teva (formerly Novopharm) have offered generic equivalents in Canada since that patent's expiration December 1, 2009.
Structure
Data?1582753257
Synonyms
ValueSource
N-Methyl-2-(3-(1-methylpiperiden-4-yl)indole-5-yl)ethanesulfonamideChEBI
N-Methyl-2-[3-(1-methyl-4-piperidyl)-1H-indol-5-yl]-ethanesulfonamideChEBI
NaratriptanumChEBI
NaramigKegg
N-Methyl-2-(3-(1-methylpiperiden-4-yl)indole-5-yl)ethanesulphonamideGenerator
N-Methyl-2-[3-(1-methyl-4-piperidyl)-1H-indol-5-yl]-ethanesulphonamideGenerator
Faes brand OF naratriptan hydrochlorideHMDB
AmergeHMDB
ColatanHMDB
Glaxo wellcome brand OF naratriptan hydrochlorideHMDB
GlaxoSmithKline brand OF naratriptan hydrochlorideHMDB
Schwarz brand OF naratriptan hydrochlorideHMDB
Naratriptan hydrochlorideHMDB
N-Methyl-3-(1-methyl-4-piperidinyl)-1H-indole-5-ethanesulfonamideHMDB
N-Methyl-3-(1-methyl-4-piperidyl)indole-5-ethanesulfonamide monohydrochlorideHMDB
1H-Indole-5-ethanesulfonamide, N-methyl-3-(1-methyl-4-piperidinyl)-, monohydrochlorideHMDB
Chemical FormulaC17H25N3O2S
Average Molecular Weight335.464
Monoisotopic Molecular Weight335.166747749
IUPAC NameN-methyl-2-[3-(1-methylpiperidin-4-yl)-1H-indol-5-yl]ethane-1-sulfonamide
Traditional Namenaratriptan
CAS Registry Number121679-13-8
SMILES
CNS(=O)(=O)CCC1=CC2=C(NC=C2C2CCN(C)CC2)C=C1
InChI Identifier
InChI=1S/C17H25N3O2S/c1-18-23(21,22)10-7-13-3-4-17-15(11-13)16(12-19-17)14-5-8-20(2)9-6-14/h3-4,11-12,14,18-19H,5-10H2,1-2H3
InChI KeyAMKVXSZCKVJAGH-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 3-alkylindoles. 3-Alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 3-position.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassIndoles
Direct Parent3-alkylindoles
Alternative Parents
Substituents
  • 3-alkylindole
  • Aralkylamine
  • Piperidine
  • Substituted pyrrole
  • Organic sulfonic acid amide
  • Benzenoid
  • Organosulfonic acid amide
  • Pyrrole
  • Organic sulfonic acid or derivatives
  • Heteroaromatic compound
  • Organosulfonic acid or derivatives
  • Aminosulfonyl compound
  • Sulfonyl
  • Tertiary aliphatic amine
  • Tertiary amine
  • Azacycle
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organosulfur compound
  • Organonitrogen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point246 °C (hydrochloride salt)Not Available
Boiling PointNot AvailableNot Available
Water Solubility0.11 g/LNot Available
LogP1.6Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+CBM174.330932474
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.11 g/LALOGPS
logP2.16ALOGPS
logP1.44ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)11.55ChemAxon
pKa (Strongest Basic)9.18ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area65.2 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity94.26 m³·mol⁻¹ChemAxon
Polarizability38 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+180.40431661259
DarkChem[M-H]-179.63431661259
DeepCCS[M+H]+172.69530932474
DeepCCS[M-H]-170.33730932474
DeepCCS[M-2H]-203.63230932474
DeepCCS[M+Na]+178.85830932474
AllCCS[M+H]+180.032859911
AllCCS[M+H-H2O]+177.032859911
AllCCS[M+NH4]+182.832859911
AllCCS[M+Na]+183.632859911
AllCCS[M-H]-181.632859911
AllCCS[M+Na-2H]-181.932859911
AllCCS[M+HCOO]-182.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
NaratriptanCNS(=O)(=O)CCC1=CC2=C(NC=C2C2CCN(C)CC2)C=C14530.2Standard polar33892256
NaratriptanCNS(=O)(=O)CCC1=CC2=C(NC=C2C2CCN(C)CC2)C=C13193.2Standard non polar33892256
NaratriptanCNS(=O)(=O)CCC1=CC2=C(NC=C2C2CCN(C)CC2)C=C13217.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Naratriptan,1TMS,isomer #1CN1CCC(C2=C[NH]C3=CC=C(CCS(=O)(=O)N(C)[Si](C)(C)C)C=C23)CC13126.2Semi standard non polar33892256
Naratriptan,1TMS,isomer #1CN1CCC(C2=C[NH]C3=CC=C(CCS(=O)(=O)N(C)[Si](C)(C)C)C=C23)CC12973.1Standard non polar33892256
Naratriptan,1TMS,isomer #1CN1CCC(C2=C[NH]C3=CC=C(CCS(=O)(=O)N(C)[Si](C)(C)C)C=C23)CC13881.8Standard polar33892256
Naratriptan,1TMS,isomer #2CNS(=O)(=O)CCC1=CC=C2C(=C1)C(C1CCN(C)CC1)=CN2[Si](C)(C)C3027.5Semi standard non polar33892256
Naratriptan,1TMS,isomer #2CNS(=O)(=O)CCC1=CC=C2C(=C1)C(C1CCN(C)CC1)=CN2[Si](C)(C)C2926.4Standard non polar33892256
Naratriptan,1TMS,isomer #2CNS(=O)(=O)CCC1=CC=C2C(=C1)C(C1CCN(C)CC1)=CN2[Si](C)(C)C4002.1Standard polar33892256
Naratriptan,2TMS,isomer #1CN1CCC(C2=CN([Si](C)(C)C)C3=CC=C(CCS(=O)(=O)N(C)[Si](C)(C)C)C=C23)CC13118.1Semi standard non polar33892256
Naratriptan,2TMS,isomer #1CN1CCC(C2=CN([Si](C)(C)C)C3=CC=C(CCS(=O)(=O)N(C)[Si](C)(C)C)C=C23)CC13105.9Standard non polar33892256
Naratriptan,2TMS,isomer #1CN1CCC(C2=CN([Si](C)(C)C)C3=CC=C(CCS(=O)(=O)N(C)[Si](C)(C)C)C=C23)CC13737.6Standard polar33892256
Naratriptan,1TBDMS,isomer #1CN1CCC(C2=C[NH]C3=CC=C(CCS(=O)(=O)N(C)[Si](C)(C)C(C)(C)C)C=C23)CC13304.5Semi standard non polar33892256
Naratriptan,1TBDMS,isomer #1CN1CCC(C2=C[NH]C3=CC=C(CCS(=O)(=O)N(C)[Si](C)(C)C(C)(C)C)C=C23)CC13251.9Standard non polar33892256
Naratriptan,1TBDMS,isomer #1CN1CCC(C2=C[NH]C3=CC=C(CCS(=O)(=O)N(C)[Si](C)(C)C(C)(C)C)C=C23)CC13938.6Standard polar33892256
Naratriptan,1TBDMS,isomer #2CNS(=O)(=O)CCC1=CC=C2C(=C1)C(C1CCN(C)CC1)=CN2[Si](C)(C)C(C)(C)C3211.5Semi standard non polar33892256
Naratriptan,1TBDMS,isomer #2CNS(=O)(=O)CCC1=CC=C2C(=C1)C(C1CCN(C)CC1)=CN2[Si](C)(C)C(C)(C)C3167.4Standard non polar33892256
Naratriptan,1TBDMS,isomer #2CNS(=O)(=O)CCC1=CC=C2C(=C1)C(C1CCN(C)CC1)=CN2[Si](C)(C)C(C)(C)C4064.5Standard polar33892256
Naratriptan,2TBDMS,isomer #1CN1CCC(C2=CN([Si](C)(C)C(C)(C)C)C3=CC=C(CCS(=O)(=O)N(C)[Si](C)(C)C(C)(C)C)C=C23)CC13476.7Semi standard non polar33892256
Naratriptan,2TBDMS,isomer #1CN1CCC(C2=CN([Si](C)(C)C(C)(C)C)C3=CC=C(CCS(=O)(=O)N(C)[Si](C)(C)C(C)(C)C)C=C23)CC13609.4Standard non polar33892256
Naratriptan,2TBDMS,isomer #1CN1CCC(C2=CN([Si](C)(C)C(C)(C)C)C3=CC=C(CCS(=O)(=O)N(C)[Si](C)(C)C(C)(C)C)C=C23)CC13814.3Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Naratriptan GC-MS (Non-derivatized) - 70eV, Positivesplash10-0563-6592000000-ddbcdc8fb1564ab679542017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Naratriptan GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Naratriptan GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Naratriptan 10V, Positive-QTOFsplash10-0079-0019000000-6a6e24b9a465404217cb2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Naratriptan 20V, Positive-QTOFsplash10-052f-5196000000-d65d77c315f42655bc942016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Naratriptan 40V, Positive-QTOFsplash10-00dj-9181000000-5426adb0583eefe0387d2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Naratriptan 10V, Negative-QTOFsplash10-001i-2009000000-94e23cf10a35640e16652016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Naratriptan 20V, Negative-QTOFsplash10-056r-9047000000-e204b450ea7d673673772016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Naratriptan 40V, Negative-QTOFsplash10-03fu-9010000000-4168e596b68161b1f5642016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Naratriptan 10V, Positive-QTOFsplash10-000i-0009000000-eb77fa3eb994fd4f881e2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Naratriptan 20V, Positive-QTOFsplash10-03di-0091000000-3e0656c2932e260310872021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Naratriptan 40V, Positive-QTOFsplash10-001j-8974000000-f06f269baa785ea29ed42021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Naratriptan 10V, Negative-QTOFsplash10-001i-0009000000-0fe6fb135327a243d85b2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Naratriptan 20V, Negative-QTOFsplash10-001l-1096000000-9e82cb949d18ff9c097d2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Naratriptan 40V, Negative-QTOFsplash10-0200-2091000000-28483e9f079277138f812021-10-11Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00952 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00952 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00952
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4287
KEGG Compound IDC07792
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNaratriptan
METLIN IDNot Available
PubChem Compound4440
PDB IDNot Available
ChEBI ID7478
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Villalon CM, Centurion D, Valdivia LF, de Vries P, Saxena PR: Migraine: pathophysiology, pharmacology, treatment and future trends. Curr Vasc Pharmacol. 2003 Mar;1(1):71-84. [PubMed:15320857 ]
  2. Massiou H: Naratriptan. Curr Med Res Opin. 2001;17 Suppl 1:s51-3. [PubMed:12463278 ]
  3. Lambert GA: Preclinical neuropharmacology of naratriptan. CNS Drug Rev. 2005 Autumn;11(3):289-316. [PubMed:16389295 ]

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOA preferentially oxidizes biogenic amines such as 5-hydroxytryptamine (5-HT), norepinephrine and epinephrine.
Gene Name:
MAOA
Uniprot ID:
P21397
Molecular weight:
59681.27
References
  1. Millson DS, Tepper SJ, Rapoport AM: Migraine pharmacotherapy with oral triptans: a rational approach to clinical management. Expert Opin Pharmacother. 2000 Mar;1(3):391-404. [PubMed:11249525 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. The activity of this receptor is mediated by G proteins that inhibit adenylate cyclase activity
Gene Name:
HTR1B
Uniprot ID:
P28222
Molecular weight:
43567.5
References
  1. Akin D, Onaran HO, Gurdal H: Agonist-directed trafficking explaining the difference between response pattern of naratriptan and sumatriptan in rabbit common carotid artery. Br J Pharmacol. 2002 May;136(2):171-6. [PubMed:12010764 ]
  2. Hoskin KL, Lambert GA, Donaldson C, Zagami AS: The 5-hydroxytryptamine1B/1D/1F receptor agonists eletriptan and naratriptan inhibit trigeminovascular input to the nucleus tractus solitarius in the cat. Brain Res. 2004 Feb 13;998(1):91-9. [PubMed:14725972 ]
  3. Boers PM, Donaldson C, Zagami AS, Lambert GA: Naratriptan has a selective inhibitory effect on trigeminovascular neurones at central 5-HT1A and 5-HT(1B/1D) receptors in the cat: implications for migraine therapy. Cephalalgia. 2004 Feb;24(2):99-109. [PubMed:14728705 ]
  4. Pauwels PJ, Palmier C, Dupuis DS, Colpaert FC: Interaction of 5-HT1B/D ligands with recombinant h 5-HT1A receptors: intrinsic activity and modulation by G-protein activation state. Naunyn Schmiedebergs Arch Pharmacol. 1998 May;357(5):490-9. [PubMed:9650800 ]
  5. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
  6. Johnston MM, Rapoport AM: Triptans for the management of migraine. Drugs. 2010 Aug 20;70(12):1505-18. doi: 10.2165/11537990-000000000-00000. [PubMed:20687618 ]
  7. Dulli DA: Naratriptan: an alternative for migraine. Ann Pharmacother. 1999 Jun;33(6):704-11. [PubMed:10410185 ]
  8. Tfelt-Hansen P, De Vries P, Saxena PR: Triptans in migraine: a comparative review of pharmacology, pharmacokinetics and efficacy. Drugs. 2000 Dec;60(6):1259-87. [PubMed:11152011 ]
  9. Massiou H: Naratriptan. Curr Med Res Opin. 2001;17 Suppl 1:s51-3. [PubMed:12463278 ]
  10. Lambert GA: Preclinical neuropharmacology of naratriptan. CNS Drug Rev. 2005 Autumn;11(3):289-316. [PubMed:16389295 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. The activity of this receptor is mediated by G proteins that inhibit adenylate cyclase activity
Gene Name:
HTR1F
Uniprot ID:
P30939
Molecular weight:
41708.5
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
  2. Hoskin KL, Lambert GA, Donaldson C, Zagami AS: The 5-hydroxytryptamine1B/1D/1F receptor agonists eletriptan and naratriptan inhibit trigeminovascular input to the nucleus tractus solitarius in the cat. Brain Res. 2004 Feb 13;998(1):91-9. [PubMed:14725972 ]
  3. Tfelt-Hansen P, De Vries P, Saxena PR: Triptans in migraine: a comparative review of pharmacology, pharmacokinetics and efficacy. Drugs. 2000 Dec;60(6):1259-87. [PubMed:11152011 ]
  4. Massiou H: Naratriptan. Curr Med Res Opin. 2001;17 Suppl 1:s51-3. [PubMed:12463278 ]
  5. Villalon CM, Centurion D, Valdivia LF, de Vries P, Saxena PR: Migraine: pathophysiology, pharmacology, treatment and future trends. Curr Vasc Pharmacol. 2003 Mar;1(1):71-84. [PubMed:15320857 ]
  6. Goadsby PJ, Classey JD: Evidence for serotonin (5-HT)1B, 5-HT1D and 5-HT1F receptor inhibitory effects on trigeminal neurons with craniovascular input. Neuroscience. 2003;122(2):491-8. [PubMed:14614913 ]
  7. Villalon CM, Centurion D, Valdivia LF, De Vries P, Saxena PR: An introduction to migraine: from ancient treatment to functional pharmacology and antimigraine therapy. Proc West Pharmacol Soc. 2002;45:199-210. [PubMed:12434581 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. The activity of this receptor is mediated by G proteins that inhibit adenylate cyclase activity
Gene Name:
HTR1A
Uniprot ID:
P08908
Molecular weight:
46106.3
References
  1. Boers PM, Donaldson C, Zagami AS, Lambert GA: Naratriptan has a selective inhibitory effect on trigeminovascular neurones at central 5-HT1A and 5-HT(1B/1D) receptors in the cat: implications for migraine therapy. Cephalalgia. 2004 Feb;24(2):99-109. [PubMed:14728705 ]
  2. Tfelt-Hansen P, De Vries P, Saxena PR: Triptans in migraine: a comparative review of pharmacology, pharmacokinetics and efficacy. Drugs. 2000 Dec;60(6):1259-87. [PubMed:11152011 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. The activity of this receptor is mediated by G proteins that inhibit adenylate cyclase activity
Gene Name:
HTR1D
Uniprot ID:
P28221
Molecular weight:
41906.4
References
  1. Hargreaves RJ, Shepheard SL: Pathophysiology of migraine--new insights. Can J Neurol Sci. 1999 Nov;26 Suppl 3:S12-9. [PubMed:10563228 ]
  2. Donaldson C, Boers PM, Hoskin KL, Zagami AS, Lambert GA: The role of 5-HT1B and 5-HT1D receptors in the selective inhibitory effect of naratriptan on trigeminovascular neurons. Neuropharmacology. 2002 Mar;42(3):374-85. [PubMed:11897116 ]
  3. Pauwels PJ, Colpaert FC: Selective antagonism of human 5-HT1D and 5-HT1B receptor-mediated responses in stably transfected C6-glial cells by ketanserin and GR 127,935. Eur J Pharmacol. 1996 Apr 4;300(1-2):141-5. [PubMed:8741180 ]
  4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
  5. Akin D, Onaran HO, Gurdal H: Agonist-directed trafficking explaining the difference between response pattern of naratriptan and sumatriptan in rabbit common carotid artery. Br J Pharmacol. 2002 May;136(2):171-6. [PubMed:12010764 ]
  6. Hoskin KL, Lambert GA, Donaldson C, Zagami AS: The 5-hydroxytryptamine1B/1D/1F receptor agonists eletriptan and naratriptan inhibit trigeminovascular input to the nucleus tractus solitarius in the cat. Brain Res. 2004 Feb 13;998(1):91-9. [PubMed:14725972 ]
  7. Boers PM, Donaldson C, Zagami AS, Lambert GA: Naratriptan has a selective inhibitory effect on trigeminovascular neurones at central 5-HT1A and 5-HT(1B/1D) receptors in the cat: implications for migraine therapy. Cephalalgia. 2004 Feb;24(2):99-109. [PubMed:14728705 ]
  8. Johnston MM, Rapoport AM: Triptans for the management of migraine. Drugs. 2010 Aug 20;70(12):1505-18. doi: 10.2165/11537990-000000000-00000. [PubMed:20687618 ]
  9. Dulli DA: Naratriptan: an alternative for migraine. Ann Pharmacother. 1999 Jun;33(6):704-11. [PubMed:10410185 ]
  10. Tfelt-Hansen P, De Vries P, Saxena PR: Triptans in migraine: a comparative review of pharmacology, pharmacokinetics and efficacy. Drugs. 2000 Dec;60(6):1259-87. [PubMed:11152011 ]
  11. Massiou H: Naratriptan. Curr Med Res Opin. 2001;17 Suppl 1:s51-3. [PubMed:12463278 ]
  12. Lambert GA: Preclinical neuropharmacology of naratriptan. CNS Drug Rev. 2005 Autumn;11(3):289-316. [PubMed:16389295 ]