α-{3-[2-(Dimethylammonio)ethyl]-1<i>H</i>-indol-5-yl}-<i>N</i>-methylmethanesulfonamide succinate (sumatriptan succinate)

Ravikumar, K.; Swamy, G. Y. S. K.; Krishnan, H.

doi:10.1107/s1600536804005896

Cited by 7 publications

(12 citation statements)

References 6 publications

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“…In all essential details, the molecular geometry (Table 1) is in good agreement with that of sumatriptan succinate (Ravikumar et al, 2004). The O S O angle is widened from the regular tetrahedral value.…”

Section: Commentsupporting

confidence: 58%

“…The biological and pharmacological aspects of sumatriptan have been studied extensively (Evers et al, 2003;Dahlof, 2003;Diener, 2003). Recently, the crystal structure of sumatriptan succinate (Ravikumar et al, 2004) was published from our laboratory. The present report provides, for the first time, a precise structure determination of this pharmaceutically important compound in its parent form, (I) ( Fig.…”

Section: Commentmentioning

confidence: 99%

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Sumatriptan, an antimigraine drug

Ravikumar¹,

Sridhar²,

Krishnan³

2006

Acta Cryst E

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Section: Commentsupporting

confidence: 58%

Section: Commentmentioning

confidence: 99%

Sumatriptan, an antimigraine drug

Ravikumar¹,

Sridhar²,

Krishnan³

2006

Acta Cryst E

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“…Viewing the structural features in the light of the theoretical 5-HT 1B -like receptor model (Moloney et al, 1999), the N1Á Á ÁN2 distances are 5.603 (2), 5.564 (4)/4.682 (4) and 5.566 (3)/4.660 (3) Å for (I), (II) and (III), respectively. The corresponding distance is 5.998 (3) Å in sumatriptan succinate (Ravikumar et al, 2004) (Ravikumar et al, 2008b) and 6.322 (2) Å in naratriptan hydrochloride (Ravikumar et al, 2008b).…”

Section: Figurementioning

confidence: 99%

“…Frovatriptan is currently marketed as the monosuccinate salt monohydrate, Frova, by Vernalis partner Endo Pharmaceuticals Inc., USA. In continuation of our crystallographic studies on triptans (Ravikumar et al, 2004(Ravikumar et al, , 2006(Ravikumar et al, , 2007a(Ravikumar et al, ,b, 2008a, we describe herein the crystal structures of frovatriptan with acetic acid, (I), and succinic acid, (II) and (III).…”

Section: Commentmentioning

confidence: 99%

Frovatriptan salts of aliphatic carboxylic acids

Ravikumar¹,

Sridhar²,

Nanubolu³

et al. 2013

Acta Crystallogr C

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The interaction of the antimigraine pharmaceutical agent frovatriptan with acetic acid and succinic acid yields the salts (±)-6-carbamoyl-N-methyl-2,3,4,9-tetrahydro-1H-carbazol-3-aminium acetate, C14H18N3O(+)·C2H3O2(-), (I), (R)-(+)-6-carbamoyl-N-methyl-2,3,4,9-tetrahydro-1H-carbazol-3-aminium 3-carboxypropanoate monohydrate, C14H18N3O(+)·C4H5O4(-)·H2O, (II), and bis[(R)-(+)-6-carbamoyl-N-methyl-2,3,4,9-tetrahydro-1H-carbazol-3-aminium] succinate trihydrate, 2C14H18N3O(+)·C4H4O4(2-)·3H2O, (III). The methylazaniumyl substitutent is oriented differently in all three structures. Additionally, the amide group in (I) is in a different orientation. All the salts form three-dimensional hydrogen-bonded structures. In (I), the cations form head-to-head hydrogen-bonded amide-amide catemers through N-H···O interactions, while in (II) and (III) the cations form head-to-head amide-amide dimers. The cation catemers in (I) are extended into a three-dimensional network through further interactions with acetate anion acceptors. The presence of succinate anions and water molecules in (II) and (III) primarily governs the three-dimensional network through water-bridged cation-anion associations via O-H···O and N-H···O hydrogen bonds. The structures reported here shed some light on the possible mode of noncovalent interactions in the aggregation and interaction patterns of drug molecule adducts.

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“…Eletriptan and naratriptan, the second-generation drugs of Pfizer and Glaxo Wellcome, respectively, are more lipophilic and have higher oral bioavailability than sumatriptan (Tepper et al, 2002). We have been studying the structural characteristics of a series of triptans (Ravikumar et al, 2004(Ravikumar et al, , 2006(Ravikumar et al, , 2007a(Ravikumar et al, ,b, 2008, and the present study of eletriptan hydrobromide monohydrate, (I), and naratriptan hydrochloride, (II), is a continuation of our investigation into the threedimensional structural correlation of triptans.…”

Section: Commentmentioning

confidence: 99%

Halide salts of antimigraine agents eletriptan and naratriptan

Ravikumar

Sridhar

Krishnan³

et al. 2008

Acta Crystallogr C

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Molecules of eletriptan hydrobromide monohydrate (systematic name: (1S,2R)-1-methyl-2-{5-[2-(phenylsulfonyl)ethyl]-1H-indol-3-ylmethyl}pyrrolidinium bromide monohydrate), C(22)H(27)N(2)O(2)S(+) x Br(-) x H(2)O, (I), and naratriptan hydrochloride (systematic name: 1-methyl-4-{5-[2-(methylsulfamoyl)ethyl]-1H-indol-3-yl}piperidinium chloride), C(17)H(26)N(3)O(2)S(+) x Cl(-), (II), adopt conformations similar to other triptans. The C-2 and C-5 substituents of the indole ring, both of which are in a region of conformational flexibility, are found to be oriented on either side of the indole ring plane in (I), whilst they are on the same side in (II). The N atom in the C-2 side chain is protonated in both structures and is involved in the hydrogen-bonding networks. In (I), the water molecules create helical hydrogen-bonded chains along the c axis. In (II), the hydrogen bonding of the chloride ions results in macrocyclic R(4)(2)(20) and R(4)(2)(24) ring motifs that form sheets in the bc plane. This structural analysis provides an insight into the molecular structure-activity relationships within this class of compound, which is of use for drug development.

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α-{3-[2-(Dimethylammonio)ethyl]-1H-indol-5-yl}-N-methylmethanesulfonamide succinate (sumatriptan succinate)

Abstract: Key indicatorsSingle-crystal X-ray study T = 293 K Mean '(C±C) = 0.004 A Ê R factor = 0.064 wR factor = 0.158 Data-to-parameter ratio = 16.6For details of how these key indicators were automatically derived from the article, see

Cited by 7 publications

References 6 publications

Sumatriptan, an antimigraine drug

Sumatriptan, an antimigraine drug

Frovatriptan salts of aliphatic carboxylic acids

Halide salts of antimigraine agents eletriptan and naratriptan

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