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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 IDHMDB0015088
Secondary Accession Numbers
  • HMDB15088
Metabolite Identification
Common NameRizatriptan
DescriptionRizatriptan is only found in individuals that have used or taken this drug. It is a triptan drug used for the treatment of migraine headaches. It is a selective 5-hydroxytryptamine1 receptor subtype agonist.Three distinct pharmacological actions have been implicated in the antimigraine effect of the triptans: (1) stimulation of presynaptic 5-HT1D receptors, which serves to inhibit both dural vasodilation and inflammation; (2) direct inhibition of trigeminal nuclei cell excitability via 5-HT1B/1D receptor agonism in the brainstem and (3) vasoconstriction of meningeal, dural, cerebral or pial vessels as a result of vascular 5-HT1B receptor agonism.
Structure
Data?1582753257
Synonyms
ValueSource
MK 462 Free baseChEBI
N,N-Dimethyl-2-[5-(1,2,4-triazol-1-ylmethyl)-1H-indol-3-yl]-ethanamineChEBI
N,N-Dimethyl-5-(1H-1,2,4-triazol-1-ylmethyl)-1H-indole-3-ethanamineChEBI
RisatriptanChEBI
RizatriptanumChEBI
MaxaltKegg
Rizatriptan benzoatHMDB
Rizatriptan benzoateHMDB
N,N-Dimethyl-2-(5-(1,2,4-triazol-1-ylmethyl)-1H-indole-3-yl)ethylamineHMDB
Chemical FormulaC15H19N5
Average Molecular Weight269.3449
Monoisotopic Molecular Weight269.164045633
IUPAC Namedimethyl({2-[5-(1H-1,2,4-triazol-1-ylmethyl)-1H-indol-3-yl]ethyl})amine
Traditional Namemaxalt
CAS Registry Number145202-66-0
SMILES
CN(C)CCC1=CNC2=C1C=C(CN1C=NC=N1)C=C2
InChI Identifier
InChI=1S/C15H19N5/c1-19(2)6-5-13-8-17-15-4-3-12(7-14(13)15)9-20-11-16-10-18-20/h3-4,7-8,10-11,17H,5-6,9H2,1-2H3
InChI KeyULFRLSNUDGIQQP-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as tryptamines and derivatives. Tryptamines and derivatives are compounds containing the tryptamine backbone, which is structurally characterized by an indole ring substituted at the 3-position by an ethanamine.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassTryptamines and derivatives
Direct ParentTryptamines and derivatives
Alternative Parents
Substituents
  • Tryptamine
  • 3-alkylindole
  • Indole
  • Aralkylamine
  • Substituted pyrrole
  • Benzenoid
  • Azole
  • Pyrrole
  • 1,2,4-triazole
  • Heteroaromatic compound
  • Tertiary aliphatic amine
  • Tertiary amine
  • Azacycle
  • Organopnictogen compound
  • Organonitrogen compound
  • Amine
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Not AvailableNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point178 - 180 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.34 g/LNot Available
LogP1.4Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+CBM160.330932474
[M+H]+Not Available160.642http://allccs.zhulab.cn/database/detail?ID=AllCCS00001039
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.34 g/LALOGPS
logP1.67ALOGPS
logP1.77ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)17.24ChemAxon
pKa (Strongest Basic)9.56ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area49.74 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity93.13 m³·mol⁻¹ChemAxon
Polarizability30 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]+164.63331661259
DarkChem[M-H]-163.79631661259
DeepCCS[M+H]+159.0830932474
DeepCCS[M-H]-156.72230932474
DeepCCS[M-2H]-189.60730932474
DeepCCS[M+Na]+165.17330932474
AllCCS[M+H]+164.332859911
AllCCS[M+H-H2O]+160.732859911
AllCCS[M+NH4]+167.632859911
AllCCS[M+Na]+168.632859911
AllCCS[M-H]-170.332859911
AllCCS[M+Na-2H]-170.132859911
AllCCS[M+HCOO]-170.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
RizatriptanCN(C)CCC1=CNC2=C1C=C(CN1C=NC=N1)C=C23665.0Standard polar33892256
RizatriptanCN(C)CCC1=CNC2=C1C=C(CN1C=NC=N1)C=C22718.3Standard non polar33892256
RizatriptanCN(C)CCC1=CNC2=C1C=C(CN1C=NC=N1)C=C22695.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Rizatriptan,1TMS,isomer #1CN(C)CCC1=CN([Si](C)(C)C)C2=CC=C(CN3C=NC=N3)C=C122562.1Semi standard non polar33892256
Rizatriptan,1TMS,isomer #1CN(C)CCC1=CN([Si](C)(C)C)C2=CC=C(CN3C=NC=N3)C=C122745.8Standard non polar33892256
Rizatriptan,1TMS,isomer #1CN(C)CCC1=CN([Si](C)(C)C)C2=CC=C(CN3C=NC=N3)C=C123326.5Standard polar33892256
Rizatriptan,1TBDMS,isomer #1CN(C)CCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(CN3C=NC=N3)C=C122764.2Semi standard non polar33892256
Rizatriptan,1TBDMS,isomer #1CN(C)CCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(CN3C=NC=N3)C=C122924.5Standard non polar33892256
Rizatriptan,1TBDMS,isomer #1CN(C)CCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(CN3C=NC=N3)C=C123400.0Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Rizatriptan GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9130000000-5d4f05bf987cb9fd7f282017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Rizatriptan GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Rizatriptan LC-ESI-qTof , Positive-QTOFsplash10-0udi-0590000000-de0b61f549c5a86c98df2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Rizatriptan , positive-QTOFsplash10-0udi-0590000000-de0b61f549c5a86c98df2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Rizatriptan 35V, Negative-QTOFsplash10-014i-9000000000-2ee19b9378ec57dc6f432021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Rizatriptan 35V, Positive-QTOFsplash10-0a4i-3940000000-fea36e233d8f7992136d2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rizatriptan 10V, Positive-QTOFsplash10-00di-0090000000-ec16b67adaf4329a82c32016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rizatriptan 20V, Positive-QTOFsplash10-0fb9-0390000000-142ab3615bb7e088f8902016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rizatriptan 40V, Positive-QTOFsplash10-05fr-5920000000-27bd73d39b069bbb22322016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rizatriptan 10V, Negative-QTOFsplash10-014i-9070000000-08285abbdf6e069d27752016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rizatriptan 20V, Negative-QTOFsplash10-014i-9060000000-4bb5daacabdae76b4c332016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rizatriptan 40V, Negative-QTOFsplash10-00kf-9000000000-308c89a78f967378d5542016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rizatriptan 10V, Positive-QTOFsplash10-0uk9-0290000000-c3ca4cb34ec759f725f92021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rizatriptan 20V, Positive-QTOFsplash10-004i-1190000000-6aedfe651c028f506d3d2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rizatriptan 40V, Positive-QTOFsplash10-00di-9300000000-0f35fc5e2bd4d164a0512021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rizatriptan 10V, Negative-QTOFsplash10-014i-7090000000-43c2efadf3b9b7e5b6dd2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rizatriptan 20V, Negative-QTOFsplash10-014i-9010000000-a3f5fa7f89b227f2c0a32021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rizatriptan 40V, Negative-QTOFsplash10-014i-9200000000-74919258163afaab32512021-10-11Wishart 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 DB00953 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00953 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 IDDB00953
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4900
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkRizatriptan
METLIN IDNot Available
PubChem Compound5078
PDB IDNot Available
ChEBI ID48273
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. 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 ]
  2. 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 ]
  3. Wellington K, Plosker GL: Rizatriptan: an update of its use in the management of migraine. Drugs. 2002;62(10):1539-74. [PubMed:12093318 ]
  4. Wellington K, Jarvis B: Spotlight on rizatriptan in migraine. CNS Drugs. 2002;16(10):715-20. [PubMed:12269863 ]
  5. Ikemoto F, Toru T, Aijima H, Natsumeda Y: [Rizatriptan (Maxalt), a new entity of triptan for migraine: pharmacology and therapeutic relevance]. Nihon Yakurigaku Zasshi. 2004 Apr;123(4):295-302. [PubMed:15056946 ]

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. Iwasa T, Sano H, Sugiura A, Uchiyama N, Hara K, Okochi H, Nakagawa K, Yasumori T, Ishizaki T: An in vitro interethnic comparison of monoamine oxidase activities between Japanese and Caucasian livers using rizatriptan, a serotonin receptor 1B/1D agonist, as a model drug. Br J Clin Pharmacol. 2003 Nov;56(5):537-44. [PubMed:14651728 ]
  2. Van Haarst AD, Van Gerven JM, Cohen AF, De Smet M, Sterrett A, Birk KL, Fisher AL, De Puy ME, Goldberg MR, Musson DG: The effects of moclobemide on the pharmacokinetics of the 5-HT1B/1D agonist rizatriptan in healthy volunteers. Br J Clin Pharmacol. 1999 Aug;48(2):190-6. [PubMed:10417495 ]
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
Gene Name:
CYP1A2
Uniprot ID:
P05177
Molecular weight:
58406.915
References
  1. Sternieri E, Coccia CP, Pinetti D, Ferrari A: Pharmacokinetics and interactions of headache medications, part I: introduction, pharmacokinetics, metabolism and acute treatments. Expert Opin Drug Metab Toxicol. 2006 Dec;2(6):961-79. [PubMed:17125411 ]
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. Wellington K, Plosker GL: Rizatriptan: an update of its use in the management of migraine. Drugs. 2002;62(10):1539-74. [PubMed:12093318 ]
  2. Wellington K, Jarvis B: Spotlight on rizatriptan in migraine. CNS Drugs. 2002;16(10):715-20. [PubMed:12269863 ]
  3. Ikemoto F, Toru T, Aijima H, Natsumeda Y: [Rizatriptan (Maxalt), a new entity of triptan for migraine: pharmacology and therapeutic relevance]. Nihon Yakurigaku Zasshi. 2004 Apr;123(4):295-302. [PubMed:15056946 ]
  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. Williamson DJ, Hill RG, Shepheard SL, Hargreaves RJ: The anti-migraine 5-HT(1B/1D) agonist rizatriptan inhibits neurogenic dural vasodilation in anaesthetized guinea-pigs. Br J Pharmacol. 2001 Aug;133(7):1029-34. [PubMed:11487512 ]
  7. Wackenfors A, Jarvius M, Ingemansson R, Edvinsson L, Malmsjo M: Triptans induce vasoconstriction of human arteries and veins from the thoracic wall. J Cardiovasc Pharmacol. 2005 May;45(5):476-84. [PubMed:15821444 ]
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. 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 ]
  3. 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 ]
  4. Wainscott DB, Johnson KW, Phebus LA, Schaus JM, Nelson DL: Human 5-HT1F receptor-stimulated [35S]GTPgammaS binding: correlation with inhibition of guinea pig dural plasma protein extravasation. Eur J Pharmacol. 1998 Jul 3;352(1):117-24. [PubMed:9718276 ]
  5. 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 ]
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. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
  2. Longmore J, Hargreaves RJ, Boulanger CM, Brown MJ, Desta B, Ferro A, Schofield WN, Taylor AA, Hill RG: Comparison of the vasoconstrictor properties of the 5-HT1D-receptor agonists rizatriptan (MK-462) and sumatriptan in human isolated coronary artery: outcome of two independent studies using different experimental protocols. Funct Neurol. 1997 Jan-Feb;12(1):3-9. [PubMed:9127118 ]
  3. Longmore J, Boulanger CM, Desta B, Hill RG, Schofield WN, Taylor AA: 5-HT1D receptor agonists and human coronary artery reactivity in vitro: crossover comparisons of 5-HT and sumatriptan with rizatriptan and L-741,519. Br J Clin Pharmacol. 1996 Oct;42(4):431-41. [PubMed:8904614 ]
  4. Sciberras DG, Polvino WJ, Gertz BJ, Cheng H, Stepanavage M, Wittreich J, Olah T, Edwards M, Mant T: Initial human experience with MK-462 (rizatriptan): a novel 5-HT1D agonist. Br J Clin Pharmacol. 1997 Jan;43(1):49-54. [PubMed:9056052 ]
  5. Williamson DJ, Hill RG, Shepheard SL, Hargreaves RJ: The anti-migraine 5-HT(1B/1D) agonist rizatriptan inhibits neurogenic dural vasodilation in anaesthetized guinea-pigs. Br J Pharmacol. 2001 Aug;133(7):1029-34. [PubMed:11487512 ]
  6. Wackenfors A, Jarvius M, Ingemansson R, Edvinsson L, Malmsjo M: Triptans induce vasoconstriction of human arteries and veins from the thoracic wall. J Cardiovasc Pharmacol. 2005 May;45(5):476-84. [PubMed:15821444 ]
  7. Wellington K, Plosker GL: Rizatriptan: an update of its use in the management of migraine. Drugs. 2002;62(10):1539-74. [PubMed:12093318 ]
  8. Wellington K, Jarvis B: Spotlight on rizatriptan in migraine. CNS Drugs. 2002;16(10):715-20. [PubMed:12269863 ]
  9. Ikemoto F, Toru T, Aijima H, Natsumeda Y: [Rizatriptan (Maxalt), a new entity of triptan for migraine: pharmacology and therapeutic relevance]. Nihon Yakurigaku Zasshi. 2004 Apr;123(4):295-302. [PubMed:15056946 ]