Sumatriptan, an antimigraine drug

Ravikumar, K.; Sridhar, B.; Krishnan, H.

doi:10.1107/s1600536806005101

Cited by 7 publications

(7 citation statements)

References 7 publications

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“…From an overall perspective, the molecular geometry of (I) ( Table 1) is in good agreement with that of sumatriptan, (II) (Ravikumar et al, 2006). Both side chains are folded in the same direction, giving the molecule a cup-like appearance, with the planar indole ring system occupying the base.…”

Section: Commentsupporting

confidence: 52%

Zolmitriptan, an antimigraine drug

Ravikumar

Sridhar

Krishnan³

2007

Acta Cryst E

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Zolmitriptan, C16H21N3O2, a selective serotonin (5‐HT) receptor agonist, is chemically designated as (S)‐4‐{3‐[2‐(dimethylamino)ethyl]‐1H‐indol‐5‐ylmethyl}oxazolidin‐2‐one. The molecular geometry is similar to that of sumatriptan, but the two differ in their side‐chain orientations. Intermolecular N—H⋯O and N—H⋯N hydrogen bonds form a screw‐symmetric helical chain along the b axis.

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Section: Commentsupporting

confidence: 52%

Zolmitriptan, an antimigraine drug

Ravikumar

Sridhar

Krishnan³

2007

Acta Cryst E

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“…By decreasing the width of blood vessels in the brain, rizatriptan relieves the pain of migraine headaches (Teall et al, 1998). The present study is a continuation of our ongoing programme on the structural elucidation of drug molecules [sumatriptan succinate (Ravikumar et al, 2004), sumatriptan (Ravikumar et al, 2006) and zolmitriptan (Ravikumar et al, 2007)].…”

Section: Commentmentioning

confidence: 83%

Rizatriptan benzoate, a drug for the treatment of migraine headache

Ravikumar

Sridhar

Krishnan³

2007

Acta Cryst E

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Rizatriptan benzoate [systematic name: N,N‐dimethyl‐3‐[5‐(1H‐1,2,4‐triazol‐1‐ylmethyl)‐1H‐indol‐3‐yl]ethanaminium benzoate], C15H20N5+·C7H5O2−, is a selective serotonin receptor agonist. Bond lengths and angles are similar to those of sumatriptan and zolmitriptan, but the three compounds differ in their side‐chain orientations. The benzoate anion acts as an acceptor for hydrogen bonds from rizatriptan cations, forming hydrogen‐bonded chains running along the b axis.

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“…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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Sumatriptan, an antimigraine drug

Cited by 7 publications

References 7 publications

Zolmitriptan, an antimigraine drug

Zolmitriptan, an antimigraine drug

Rizatriptan benzoate, a drug for the treatment of migraine headache

Frovatriptan salts of aliphatic carboxylic acids

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