sumatriptan   Click here for help

GtoPdb Ligand ID: 54

Synonyms: GR-43175C | Imigran® | Tosymra® (nasal spray)
Approved drug
sumatriptan is an approved drug (FDA (1992))
Compound class: Synthetic organic
Comment: Sumatriptan is a selective serotonin 5-HT1B/ID receptor agonist.
Marketed formulations contain sumatriptan succinate (PubChem CID 59772).
Click here for help
IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: sumatriptan

2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
Hydrogen bond acceptors 4
Hydrogen bond donors 2
Rotatable bonds 6
Topological polar surface area 73.58
Molecular weight 295.14
XLogP 0.88
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Click here for help
Canonical SMILES CNS(=O)(=O)Cc1ccc2c(c1)c(CCN(C)C)c[nH]2
Isomeric SMILES CNS(=O)(=O)Cc1ccc2c(c1)c(CCN(C)C)c[nH]2
InChI InChI=1S/C14H21N3O2S/c1-15-20(18,19)10-11-4-5-14-13(8-11)12(9-16-14)6-7-17(2)3/h4-5,8-9,15-16H,6-7,10H2,1-3H3
InChI Key KQKPFRSPSRPDEB-UHFFFAOYSA-N
References
1. Adham N, Bard JA, Zgombick JM, Durkin MM, Kucharewicz S, Weinshank RL, Branchek TA. (1997)
Cloning and characterization of the guinea pig 5-HT1F receptor subtype: a comparison of the pharmacological profile to the human species homolog.
Neuropharmacology, 36 (4-5): 569-76. [PMID:9225282]
2. Adham N, Kao HT, Schecter LE, Bard J, Olsen M, Urquhart D, Durkin M, Hartig PR, Weinshank RL, Branchek TA. (1993)
Cloning of another human serotonin receptor (5-HT1F): a fifth 5-HT1 receptor subtype coupled to the inhibition of adenylate cyclase.
Proc Natl Acad Sci USA, 90 (2): 408-12. [PMID:8380639]
3. Bai F, Yin T, Johnstone EM, Su C, Varga G, Little SP, Nelson DL. (2004)
Molecular cloning and pharmacological characterization of the guinea pig 5-HT1E receptor.
Eur J Pharmacol, 484 (2-3): 127-39. [PMID:14744596]
4. Bard JA, Zgombick J, Adham N, Vaysse P, Branchek TA, Weinshank RL. (1993)
Cloning of a novel human serotonin receptor (5-HT7) positively linked to adenylate cyclase.
J Biol Chem, 268 (31): 23422-6. [PMID:8226867]
5. Boess FG, Monsma Jr FJ, Sleight AJ. (1998)
Identification of residues in transmembrane regions III and VI that contribute to the ligand binding site of the serotonin 5-HT6 receptor.
J Neurochem, 71 (5): 2169-77. [PMID:9798944]
6. Grånäs C, Larhammar D. (1999)
Identification of an amino acid residue important for binding of methiothepin and sumatriptan to the human 5-HT(1B) receptor.
Eur J Pharmacol, 380 (2-3): 171-81. [PMID:10513577]
7. Grailhe R, Grabtree GW, Hen R. (2001)
Human 5-HT(5) receptors: the 5-HT(5A) receptor is functional but the 5-HT(5B) receptor was lost during mammalian evolution.
Eur J Pharmacol, 418 (3): 157-67. [PMID:11343685]
8. Hamblin MW, Metcalf MA. (1991)
Primary structure and functional characterization of a human 5-HT1D-type serotonin receptor.
Mol Pharmacol, 40 (2): 143-8. [PMID:1652050]
9. Jasper JR, Kosaka A, To ZP, Chang DJ, Eglen RM. (1997)
Cloning, expression and pharmacology of a truncated splice variant of the human 5-HT7 receptor (h5-HT7b).
Br J Pharmacol, 122 (1): 126-32. [PMID:9298538]
10. Kohen R, Metcalf MA, Khan N, Druck T, Huebner K, Lachowicz JE, Meltzer HY, Sibley DR, Roth BL, Hamblin MW. (1996)
Cloning, characterization, and chromosomal localization of a human 5-HT6 serotonin receptor.
J Neurochem, 66 (1): 47-56. [PMID:8522988]
11. Leysen JE, Gommeren W, Heylen L, Luyten WH, Van de Weyer I, Vanhoenacker P, Haegeman G, Schotte A, Van Gompel P, Wouters R et al.. (1996)
Alniditan, a new 5-hydroxytryptamine1D agonist and migraine-abortive agent: ligand-binding properties of human 5-hydroxytryptamine1D alpha, human 5-hydroxytryptamine1D beta, and calf 5-hydroxytryptamine1D receptors investigated with [3H]5-hydroxytryptamine and [3H]alniditan.
Mol Pharmacol, 50 (6): 1567-80. [PMID:8967979]
12. Lovenberg TW, Erlander MG, Baron BM, Racke M, Slone AL, Siegel BW, Craft CM, Burns JE, Danielson PE, Sutcliffe JG. (1993)
Molecular cloning and functional expression of 5-HT1E-like rat and human 5-hydroxytryptamine receptor genes.
Proc Natl Acad Sci USA, 90 (6): 2184-8. [PMID:8384716]
13. Matthaei J, Kuron D, Faltraco F, Knoch T, Dos Santos Pereira JN, Abu Abed M, Prukop T, Brockmöller J, Tzvetkov MV. (2016)
OCT1 mediates hepatic uptake of sumatriptan and loss-of-function OCT1 polymorphisms affect sumatriptan pharmacokinetics.
Clin Pharmacol Ther, 99 (6): 633-41. [PMID:26659468]
14. Matthes H, Boschert U, Amlaiky N, Grailhe R, Plassat JL, Muscatelli F, Mattei MG, Hen R. (1993)
Mouse 5-hydroxytryptamine5A and 5-hydroxytryptamine5B receptors define a new family of serotonin receptors: cloning, functional expression, and chromosomal localization.
Mol Pharmacol, 43 (3): 313-9. [PMID:8450829]
15. McAllister G, Charlesworth A, Snodin C, Beer MS, Noble AJ, Middlemiss DN, Iversen LL, Whiting P. (1992)
Molecular cloning of a serotonin receptor from human brain (5HT1E): a fifth 5HT1-like subtype.
Proc Natl Acad Sci USA, 89 (12): 5517-21. [PMID:1608964]
16. Millan MJ, Newman-Tancredi A, Audinot V, Cussac D, Lejeune F, Nicolas JP, Cogé F, Galizzi JP, Boutin JA, Rivet JM et al.. (2000)
Agonist and antagonist actions of yohimbine as compared to fluparoxan at alpha(2)-adrenergic receptors (AR)s, serotonin (5-HT)(1A), 5-HT(1B), 5-HT(1D) and dopamine D(2) and D(3) receptors. Significance for the modulation of frontocortical monoaminergic transmission and depressive states.
Synapse, 35 (2): 79-95. [PMID:10611634]
17. Napier C, Stewart M, Melrose H, Hopkins B, McHarg A, Wallis R. (1999)
Characterisation of the 5-HT receptor binding profile of eletriptan and kinetics of [3H]eletriptan binding at human 5-HT1B and 5-HT1D receptors.
Eur J Pharmacol, 368 (2-3): 259-68. [PMID:10193663]
18. Newman-Tancredi A, Audinot V, Moreira C, Verrièle L, Millan MJ. (2000)
Inverse agonism and constitutive activity as functional correlates of serotonin h5-HT(1B) receptor/G-protein stoichiometry.
Mol Pharmacol, 58 (5): 1042-9. [PMID:11040052]
19. Parker EM, Izzarelli DG, Lewis-Higgins L, Palmer D, Shapiro RA. (1996)
Two amino acid differences in the sixth transmembrane domain are partially responsible for the pharmacological differences between the 5-HT1D beta and 5-HT1E 5-hydroxytryptamine receptors.
J Neurochem, 67 (5): 2096-103. [PMID:8863519]
20. Rees S, den Daas I, Foord S, Goodson S, Bull D, Kilpatrick G, Lee M. (1994)
Cloning and characterisation of the human 5-HT5A serotonin receptor.
FEBS Lett, 355 (3): 242-6. [PMID:7988681]
21. Ruat M, Traiffort E, Leurs R, Tardivel-Lacombe J, Diaz J, Arrang JM, Schwartz JC. (1993)
Molecular cloning, characterization, and localization of a high-affinity serotonin receptor (5-HT7) activating cAMP formation.
Proc Natl Acad Sci USA, 90 (18): 8547-51. [PMID:8397408]
22. Shen Y, Monsma Jr FJ, Metcalf MA, Jose PA, Hamblin MW, Sibley DR. (1993)
Molecular cloning and expression of a 5-hydroxytryptamine7 serotonin receptor subtype.
J Biol Chem, 268 (24): 18200-4. [PMID:8394362]
23. Wainscott DB, Krushinski Jr JH, Audia JE, Schaus JM, Zgombick JM, Lucaites VL, Nelson DL. (2005)
[3H]LY334370, a novel radioligand for the 5-HT1F receptor. I. In vitro characterization of binding properties.
Naunyn Schmiedebergs Arch Pharmacol, 371 (3): 169-77. [PMID:15900510]
24. Weinshank RL, Zgombick JM, Macchi MJ, Branchek TA, Hartig PR. (1992)
Human serotonin 1D receptor is encoded by a subfamily of two distinct genes: 5-HT1D alpha and 5-HT1D beta.
Proc Natl Acad Sci USA, 89 (8): 3630-4. [PMID:1565658]