NP-MRD: Showing NP-Card for Sumatriptan (NP0334576)

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Record Information

Version

2.0

Created at

2024-09-10 18:58:30 UTC

Updated at

2024-09-10 18:58:30 UTC

NP-MRD ID

NP0334576

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Sumatriptan

Description

Sumatriptan, also known as imigran or imitrex, 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. A sulfonamide that consists of N,N-dimethyltryptamine bearing an additional (N-methylsulfamoyl)methyl substituent at position 5. Sumatriptan is a very strong basic compound (based on its pKa). Sumatriptan is a potentially toxic compound. Used (in the form of its succinate salt) for the acute treatment of migraine with or without aura in adults. Sumatriptan was first documented in 1996 (PMID: 8869766). Selective agonist for a vascular 5-HT1 receptor subtype (probably a member of the 5-HT1D family) (PMID: 9225278) (PMID: 11045888) (PMID: 11401410) (PMID: 12172708).

Structure

MOL SDF PDB SMILES InChI

669
  Mrv0541 02231214552D          

 20 21  0  0  0  0            999 V2000
    3.0791   -0.5207    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.4916   -1.2351    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6665    0.1938    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7176   -1.5972    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0375    1.4693    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.9332    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7176   -0.2693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370   -0.5207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9739    0.5149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370   -1.3457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -0.5207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7812    0.6851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -0.1082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1991   -0.9332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.1082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -1.7582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -1.3457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8448    1.6394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4865    2.0833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.5207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  2  0  0  0  0
  1  6  1  0  0  0  0
  1 15  1  0  0  0  0
  4 10  1  0  0  0  0
  4 14  1  0  0  0  0
  5 12  1  0  0  0  0
  5 18  1  0  0  0  0
  5 19  1  0  0  0  0
  6 20  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  7 14  2  0  0  0  0
  8 10  2  0  0  0  0
  8 13  1  0  0  0  0
  9 12  1  0  0  0  0
 10 16  1  0  0  0  0
 11 13  2  0  0  0  0
 11 15  1  0  0  0  0
 11 17  1  0  0  0  0
 16 17  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0334576

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CNS(=O)(=O)CC1=CC2=C(NC=C2CCN(C)C)C=C1

> <INCHI_IDENTIFIER>
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

> <FORMULA>
C14H21N3O2S

> <MOLECULAR_WEIGHT>
295.4

> <EXACT_MASS>
295.135447621

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
32.30534147835603

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-{3-[2-(dimethylamino)ethyl]-1H-indol-5-yl}-N-methylmethanesulfonamide

> <ALOGPS_LOGP>
1.17

> <JCHEM_LOGP>
0.7419288613400098

> <ALOGPS_LOGS>
-3.37

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
17.140195724720275

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.244987975521886

> <JCHEM_PKA_STRONGEST_BASIC>
9.536988551879368

> <JCHEM_POLAR_SURFACE_AREA>
65.2

> <JCHEM_REFRACTIVITY>
82.08419999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.27e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
sumatriptan

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 669                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  S   UNK     0       5.748  -0.972   0.000  0.00  0.00           S+0
HETATM    2  O   UNK     0       6.518  -2.306   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       4.977   0.362   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0      12.540  -2.981   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0      15.003   2.743   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0       4.414  -1.742   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0      12.540  -0.503   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.082  -0.972   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      13.018   0.961   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.082  -2.512   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.415  -0.972   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      14.525   1.279   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.748  -0.202   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      13.438  -1.742   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.081  -0.202   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.748  -3.282   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.415  -2.512   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      16.510   3.060   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      13.975   3.889   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.080  -0.972   0.000  0.00  0.00           C+0
CONECT    1    2    3    6   15                                             
CONECT    2    1                                                            
CONECT    3    1                                                            
CONECT    4   10   14                                                       
CONECT    5   12   18   19                                                  
CONECT    6    1   20                                                       
CONECT    7    8    9   14                                                  
CONECT    8    7   10   13                                                  
CONECT    9    7   12                                                       
CONECT   10    4    8   16                                                  
CONECT   11   13   15   17                                                  
CONECT   12    5    9                                                       
CONECT   13    8   11                                                       
CONECT   14    4    7                                                       
CONECT   15    1   11                                                       
CONECT   16   10   17                                                       
CONECT   17   11   16                                                       
CONECT   18    5                                                            
CONECT   19    5                                                            
CONECT   20    6                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

View in JSmol

Synonyms

Value	Source
(3-[2-(Dimethylamino)ethyl]-1H-indol-5-yl)-N-methylmethanesulfonamide	ChEBI
1-[3-(2-Dimethylaminoethyl)-1H-indol-5-yl]-N-methyl-methanesulfonamide	ChEBI
3-(2-(Dimethylamino)ethyl)-N-methyl-1H-indole-5-methanesulfonamide	ChEBI
3-[2-(Dimethylamino)ethyl]-N-methylindole-5-methanesulfonamide	ChEBI
Imigran	ChEBI
Imitrex	ChEBI
Sumatran	ChEBI
Sumatriptanum	ChEBI
Sumax	ChEBI
(3-[2-(Dimethylamino)ethyl]-1H-indol-5-yl)-N-methylmethanesulphonamide	Generator
1-[3-(2-Dimethylaminoethyl)-1H-indol-5-yl]-N-methyl-methanesulphonamide	Generator
3-(2-(Dimethylamino)ethyl)-N-methyl-1H-indole-5-methanesulphonamide	Generator
3-[2-(Dimethylamino)ethyl]-N-methylindole-5-methanesulphonamide	Generator
Imigran recovery	HMDB
Glaxo wellcome brand OF sumatriptan	HMDB
Sumatriptan GSK brand	HMDB
GSK Brand OF sumatriptan	HMDB
Sumatriptan succinate	HMDB
Succinate, sumatriptan	HMDB

Chemical Formula

C₁₄H₂₁N₃O₂S

Average Mass

295.4000 Da

Monoisotopic Mass

295.13545 Da

IUPAC Name

1-{3-[2-(dimethylamino)ethyl]-1H-indol-5-yl}-N-methylmethanesulfonamide

Traditional Name

sumatriptan

CAS Registry Number

Not Available

SMILES

CNS(=O)(=O)CC1=CC2=C(NC=C2CCN(C)C)C=C1

InChI Identifier

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

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Tryptamines and derivatives

Direct Parent

Tryptamines and derivatives

Alternative Parents

Substituents

Tryptamine
3-alkylindole
Indole
Aralkylamine
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
Organosulfur compound
Organonitrogen compound
Organic nitrogen compound
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

sulfonamide (CHEBI:10650 )
tryptamines (CHEBI:10650 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	1.17	ALOGPS
logP	0.74	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	11.24	ChemAxon
pKa (Strongest Basic)	9.54	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	65.2 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	82.08 m³·mol⁻¹	ChemAxon
Polarizability	32.31 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0005037

DrugBank ID

DB00669

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB023604

KNApSAcK ID

Not Available

Chemspider ID

5165

KEGG Compound ID

C07319

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Sumatriptan

METLIN ID

2612

PubChem Compound

5358

PDB ID

Not Available

ChEBI ID

10650

Good Scents ID

Not Available

References

General References

Pascual J, del Arco C, Romon T, del Olmo E, Castro E, Pazos A: Autoradiographic distribution of [3H]sumatriptan-binding sites in post-mortem human brain. Cephalalgia. 1996 Aug;16(5):317-22. doi: 10.1046/j.1468-2982.1996.1605317.x. [PubMed:8869766 ]
Castro ME, Pascual J, Romon T, del Arco C, del Olmo E, Pazos A: Differential distribution of [3H]sumatriptan binding sites (5-HT1B, 5-HT1D and 5-HT1F receptors) in human brain: focus on brainstem and spinal cord. Neuropharmacology. 1997 Apr-May;36(4-5):535-42. doi: 10.1016/s0028-3908(97)00061-0. [PubMed:9225278 ]
Poondru S, Devaraj R, Boinpally RR, Yamasani MR: Chronopharmacokinetics of sumatriptan in healthy human subjects. J Pharm Pharmacol. 2000 Sep;52(9):1085-90. doi: 10.1211/0022357001775001. [PubMed:11045888 ]
Cipolla G, Sacco S, Crema F, Moro E, De Ponti F, Frigo G: Gastric motor effects of triptans: open questions and future perspectives. Pharmacol Res. 2001 Mar;43(3):205-10. doi: 10.1006/phrs.2000.0766. [PubMed:11401410 ]
Gul H, Yildiz O: Amplification of sumatriptan-induced contractions with phenylephrine, histamine and KCl in the isolated human mesenteric artery: in-vitro evidence for sumatriptan-induced mesenteric ischaemia. Naunyn Schmiedebergs Arch Pharmacol. 2002 Sep;366(3):254-61. doi: 10.1007/s00210-002-0587-1. Epub 2002 Jun 22. [PubMed:12172708 ]

Showing NP-Card for Sumatriptan (NP0334576)

MOL for NP0334576 (Sumatriptan)

3D MOL for NP0334576 (Sumatriptan)

3D SDF for NP0334576 (Sumatriptan)

3D-SDF for NP0334576 (Sumatriptan)

PDB for NP0334576 (Sumatriptan)

3D PDB for NP0334576 (Sumatriptan)

SMILES for NP0334576 (Sumatriptan)

INCHI for NP0334576 (Sumatriptan)

Structure for NP0334576 (Sumatriptan)

3D Structure for NP0334576 (Sumatriptan)