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    Chemistry

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    Also known as: 139264-17-8, Zomig, Zomigoro, 311c90, Zomigon, Flezol
    Molecular Formula
    C16H21N3O2
    Molecular Weight
    287.36  g/mol
    InChI Key
    ULSDMUVEXKOYBU-ZDUSSCGKSA-N
    FDA UNII
    2FS66TH3YW
    Zolmitriptan
    Zolmitriptan is a member of the triptan class of agents with anti-migraine properties. Zolmitriptan selectively binds to and activates serotonin (5-HT) 1B receptors expressed in intracranial arteries and 5-HT 1D receptors located on peripheral trigeminal sensory nerve terminals in the meninges and central terminals in brainstem sensory nuclei. Receptor binding results in constriction of cranial vessels, reduction of vessel pulsation and inhibition of nociceptive transmission, thereby providing relief of migraine headaches. Zolmitriptan may also relieve migraine headaches by inhibition of pro-inflammatory neuropeptide release.
    Zolmitriptan is a Serotonin-1b and Serotonin-1d Receptor Agonist. The mechanism of action of zolmitriptan is as a Serotonin 1b Receptor Agonist, and Serotonin 1d Receptor Agonist.
    1 2D Structure

    Zolmitriptan

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (4S)-4-[[3-[2-(dimethylamino)ethyl]-1H-indol-5-yl]methyl]-1,3-oxazolidin-2-one
    2.1.2 InChI
    InChI=1S/C16H21N3O2/c1-19(2)6-5-12-9-17-15-4-3-11(8-14(12)15)7-13-10-21-16(20)18-13/h3-4,8-9,13,17H,5-7,10H2,1-2H3,(H,18,20)/t13-/m0/s1
    2.1.3 InChI Key
    ULSDMUVEXKOYBU-ZDUSSCGKSA-N
    2.1.4 Canonical SMILES
    CN(C)CCC1=CNC2=C1C=C(C=C2)CC3COC(=O)N3
    2.1.5 Isomeric SMILES
    CN(C)CCC1=CNC2=C1C=C(C=C2)C[C@H]3COC(=O)N3
    2.2 Other Identifiers
    2.2.1 UNII
    2FS66TH3YW
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 311c90

    2. 4-((3-(2-(dimethylamino)ethyl)-1h-indol-5-yl)methyl)-2-oxazolidinone

    3. Ascotop

    4. Flezol

    5. Zomig

    6. Zomigoro

    2.3.2 Depositor-Supplied Synonyms

    1. 139264-17-8

    2. Zomig

    3. Zomigoro

    4. 311c90

    5. Zomigon

    6. Flezol

    7. Zomig-zmt

    8. C16h21n3o2

    9. Bw-311c90

    10. (s)-4-((3-(2-(dimethylamino)ethyl)-1h-indol-5-yl)methyl)oxazolidin-2-one

    11. Zolmitriptan (zomig)

    12. (s)-4-[3-(2-dimethylamino-ethyl)-1h-indol-5-ylmethyl]-oxazolidin-2-one

    13. Nsc-760383

    14. Cvt-427

    15. 2fs66th3yw

    16. Chembl1185

    17. (s)-4-((3-(2-(dimethylamino)ethyl)indol-5-yl)methyl)-2-oxazolidinone

    18. Chebi:10124

    19. (s)-4-((3-(2-(dimethylamino)ethyl)-1h-indol-5-yl)methyl)-2-oxazolidinone

    20. (4s)-4-[[3-[2-(dimethylamino)ethyl]-1h-indol-5-yl]methyl]-1,3-oxazolidin-2-one

    21. Zomig Nasal Spray

    22. Zomig Zmt

    23. Ascotopand

    24. Ascotop

    25. Zolmitriptan [usan]

    26. 4-[[3-(2-dimethylaminoethyl)-1h-indol-5-yl]methyl]oxazolidin-2-one

    27. (4s)-4-[[3-[2-(dimethylamino)ethyl]-1h-indol-5-yl]methyl]-2-oxazolidinone

    28. (s)-4-[[3-[2-(dimethylamino)ethyl]-1h-indol-5-yl]methyl]-2-oxazolidinone

    29. (4s)-4-({3-[2-(dimethylamino)ethyl]-1h-indol-5-yl}methyl)-1,3-oxazolidin-2-one

    30. 2-oxazolidinone, 4-((3-(2-(dimethylamino)ethyl)-1h-indol-5-yl)methyl)-, (s)-

    31. Dsstox_cid_25933

    32. Dsstox_rid_81232

    33. Dsstox_gsid_45933

    34. 311-c-90

    35. Zipton

    36. Zolmitriptane

    37. Zolmitriptanum

    38. Zominat

    39. Rapimelt

    40. (4s)-4-((3-(2-(dimethylamino)ethyl)-1h-indol-5-yl)methyl)-2-oxazolidinone

    41. Smr000449310

    42. Cas-139264-17-8

    43. Zomig (tn)

    44. Zolmitriptan Rapidfilm

    45. Unii-2fs66th3yw

    46. 4-((3-(2-(dimethylamino)ethyl)-1h-indol-5-yl)methyl)-2-oxazolidinone

    47. Zolmitriptan [usan:inn:ban]

    48. Ncgc00095155-01

    49. Mfcd00871503

    50. Ks-5072

    51. Spectrum2_000728

    52. Zolmitriptan [mi]

    53. Zolmitriptan [inn]

    54. Zolmitriptan [jan]

    55. Gtpl60

    56. (4s)-4-[[3-(2-dimethylaminoethyl)-1h-indol-5-yl]methyl]-1,3-oxazolidin-2-one

    57. Zolmitriptan [vandf]

    58. Schembl33336

    59. Zolmitriptan [mart.]

    60. Mls000758208

    61. Mls001424172

    62. Bidd:gt0040

    63. Spectrum1505281

    64. Zolmitriptan [usp-rs]

    65. Zolmitriptan [who-dd]

    66. Spbio_000656

    67. Zolmitriptan (jan/usp/inn)

    68. Dtxsid8045933

    69. Zinc15515

    70. Zolmitriptan, >=98% (hplc)

    71. Hms1922b04

    72. Hms2052k17

    73. Hms2093o14

    74. Hms2235i22

    75. Hms3714h11

    76. Hms3884a06

    77. Pharmakon1600-01505281

    78. Zolmitriptan [orange Book]

    79. Zolmitriptan [ep Monograph]

    80. Act04392

    81. Bcp10513

    82. Hy-b0229

    83. Tox21_111455

    84. Zolmitriptan [usp Monograph]

    85. Bdbm50033383

    86. Ccg-38993

    87. Nsc760383

    88. S1649

    89. Akos015850706

    90. Tox21_111455_1

    91. Db00315

    92. Nc00382

    93. Nsc 760383

    94. (s)-n,n-dimethyl-2-[5-(2-oxo-1,3-oxazolidin-4-ylmethyl)-1h-indol-3-yl]ethylamine

    95. Ncgc00263884-02

    96. Ncgc00263884-03

    97. Ncgc00263884-08

    98. Bz164590

    99. Bw-311c90;311c90

    100. Sbi-0206762.p001

    101. B2261

    102. Sw197762-2

    103. Z0024

    104. 64z178

    105. C07218

    106. D00415

    107. Ab00698244-05

    108. Ab00698244_06

    109. Q218820

    110. Sr-05000001693

    111. J-007257

    112. Sr-05000001693-1

    113. Zolmitriptan, United States Pharmacopeia (usp) Reference Standard

    114. (4s)-4-[[3-[2-(dimethylamino)ethyl]-1h-indol-5-yl]methyl-2-oxazolidinone

    115. (s)-4-{3-[2-(dimethylamino)ethyl]-1h-indol-5-ylmethyl}oxazolidin-2-one

    116. (4s)-4-((3-(2-(dimethylamino)ethyl) -1h-indol-5-yl)methyl)-2-oxazolidinone

    117. (s) -n,n-dimethyl-2- [5- (2-oxo-1,3-oxazolidin-4-ylmethyl) -1h -indol-3-yl]ethylamine

    118. (s)-4-({3-[2-(dimethylamino)ethyl]-1h-indol-5-yl}methyl)-1,3-oxazolidin-2-one

    119. (s)-n,n-dimethyl-2-[5-(2-oxo-1,3-oxazolidin-4-ylmethyl)-1h -indol-3-yl]ethylamine

    120. 2-oxazolidinone, 4-[[3-[2-(dimethylamino)ethyl]-1h-indol-5-yl]methyl]-, (4s)-

    121. 139264-25-8

    122. Zmt

    2.4 Create Date
    2005-08-08
    3 Chemical and Physical Properties
    Molecular Weight 287.36 g/mol
    Molecular Formula C16H21N3O2
    XLogP32.2
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count3
    Rotatable Bond Count5
    Exact Mass287.16337692 g/mol
    Monoisotopic Mass287.16337692 g/mol
    Topological Polar Surface Area57.4 Ų
    Heavy Atom Count21
    Formal Charge0
    Complexity375
    Isotope Atom Count0
    Defined Atom Stereocenter Count1
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 6  
    Drug NameZolmitriptan
    PubMed HealthZolmitriptan
    Drug ClassesAntimigraine
    Drug LabelZOMIG (zolmitriptan) Tablets and ZOMIG-ZMT (zolmitriptan) Orally Disintegrating Tablets contain zolmitriptan, which is a selective 5-hydroxytryptamine 1B/1D (5-HT1B/1D) receptor agonist. Zolmitriptan is chemically designated as (S)-4-[[3-[2-(dime...
    Active IngredientZolmitriptan
    Dosage FormTablet; Tablet, orally disintegrating
    RouteOral
    Strength2.5mg; 5mg
    Market StatusPrescription
    CompanyMylan Pharms; Apotex; Teva Pharms Usa; Invagen Pharms; Sun Pharma Global; Glenmark Generics; Zydus Pharms Usa

    2 of 6  
    Drug NameZomig
    PubMed HealthZolmitriptan (Into the nose)
    Drug ClassesAntimigraine
    Drug LabelZOMIG (zolmitriptan) Tablets and ZOMIG-ZMT (zolmitriptan) Orally Disintegrating Tablets contain zolmitriptan, which is a selective 5-hydroxytryptamine 1B/1D (5-HT1B/1D) receptor agonist. Zolmitriptan is chemically designated as (S)-4-[[3-[2-(dime...
    Active IngredientZolmitriptan
    Dosage FormTablet; Spray
    RouteOral; Nasal
    Strength2.5mg; 2.5mg/spray; 5mg; 5mg/spray
    Market StatusPrescription
    CompanyIpr; Astrazeneca

    3 of 6  
    Drug NameZomig-zmt
    PubMed HealthZolmitriptan (By mouth)
    Drug ClassesAntimigraine
    Drug LabelZOMIG (zolmitriptan) Tablets and ZOMIG-ZMT (zolmitriptan) Orally Disintegrating Tablets contain zolmitriptan, which is a selective 5-hydroxytryptamine 1B/1D (5-HT1B/1D) receptor agonist. Zolmitriptan is chemically designated as (S)-4-[[3-[2-(dime...
    Active IngredientZolmitriptan
    Dosage FormTablet, orally disintegrating
    RouteOral
    Strength2.5mg; 5mg
    Market StatusPrescription
    CompanyAstrazeneca

    4 of 6  
    Drug NameZolmitriptan
    PubMed HealthZolmitriptan
    Drug ClassesAntimigraine
    Drug LabelZOMIG (zolmitriptan) Tablets and ZOMIG-ZMT (zolmitriptan) Orally Disintegrating Tablets contain zolmitriptan, which is a selective 5-hydroxytryptamine 1B/1D (5-HT1B/1D) receptor agonist. Zolmitriptan is chemically designated as (S)-4-[[3-[2-(dime...
    Active IngredientZolmitriptan
    Dosage FormTablet; Tablet, orally disintegrating
    RouteOral
    Strength2.5mg; 5mg
    Market StatusPrescription
    CompanyMylan Pharms; Apotex; Teva Pharms Usa; Invagen Pharms; Sun Pharma Global; Glenmark Generics; Zydus Pharms Usa

    5 of 6  
    Drug NameZomig
    PubMed HealthZolmitriptan (Into the nose)
    Drug ClassesAntimigraine
    Drug LabelZOMIG (zolmitriptan) Tablets and ZOMIG-ZMT (zolmitriptan) Orally Disintegrating Tablets contain zolmitriptan, which is a selective 5-hydroxytryptamine 1B/1D (5-HT1B/1D) receptor agonist. Zolmitriptan is chemically designated as (S)-4-[[3-[2-(dime...
    Active IngredientZolmitriptan
    Dosage FormTablet; Spray
    RouteOral; Nasal
    Strength2.5mg; 2.5mg/spray; 5mg; 5mg/spray
    Market StatusPrescription
    CompanyIpr; Astrazeneca

    6 of 6  
    Drug NameZomig-zmt
    PubMed HealthZolmitriptan (By mouth)
    Drug ClassesAntimigraine
    Drug LabelZOMIG (zolmitriptan) Tablets and ZOMIG-ZMT (zolmitriptan) Orally Disintegrating Tablets contain zolmitriptan, which is a selective 5-hydroxytryptamine 1B/1D (5-HT1B/1D) receptor agonist. Zolmitriptan is chemically designated as (S)-4-[[3-[2-(dime...
    Active IngredientZolmitriptan
    Dosage FormTablet, orally disintegrating
    RouteOral
    Strength2.5mg; 5mg
    Market StatusPrescription
    CompanyAstrazeneca

    4.2 Drug Indication

    Zolmitriptan is indicated for the acute treatment of migraine with or without auras in patients aged 18 and over.

    FDA Label

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Zolmitriptan, like other triptans, is a serotonin (5-hydroxytryptamine; 5-HT) receptor agonist, with enhanced specificity for the 5-HT1B and 5-HT1D receptor subtypes. It is through the downstream effects of 5-HT1B/1D activation that triptans are proposed to provide acute relief of migraines. Zolmitriptan is also a vasoconstrictor, leading to possible adverse cardiovascular effects such as myocardial ischemia/infarction, arrhythmias, cerebral and subarachnoid hemorrhage, stroke, gastrointestinal ischemia, and peripheral vasospastic reactions. In addition, chest/throat/neck/jaw pain, tightness, and/or pressure has been reported, along with the possibility of medication overuse headaches and serotonin syndrome. Patients with phenylketonuria should be advised that ZOMIG-ZMT contains phenylalanine.

    5.2 MeSH Pharmacological Classification

    Serotonin 5-HT1 Receptor Agonists

    Endogenous compounds and drugs that specifically stimulate SEROTONIN 5-HT1 RECEPTORS. Included under this heading are agonists for one or more of the specific 5-HT1 receptor subtypes. (See all compounds classified as Serotonin 5-HT1 Receptor Agonists.)

    5.3 FDA Pharmacological Classification
    5.3.1 Active Moiety
    ZOLMITRIPTAN
    5.3.2 FDA UNII
    2FS66TH3YW
    5.3.3 Pharmacological Classes
    Serotonin 1d Receptor Agonists [MoA]; Serotonin-1b and Serotonin-1d Receptor Agonist [EPC]; Serotonin 1b Receptor Agonists [MoA]
    5.4 ATC Code

    N02CC03

    S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355

    N - Nervous system

    N02 - Analgesics

    N02C - Antimigraine preparations

    N02CC - Selective serotonin (5ht1) agonists

    N02CC03 - Zolmitriptan

    5.5 Absorption, Distribution and Excretion

    Absorption

    Zolmitriptan tablets have a mean absolute oral bioavailability of approximately 40%, with food having no effect on the rate or extent of absorption. The dosing kinetics are linear over a range of 2.5 to 50 mg with 75% of the eventual Cmax being attained within 1 hour of dosing. The median Tmax for the tablet form is 1.5 hours, while for the orally disintegrating tablet form, it is 3 hours. The AUC across studies was in the range of 84.4-173.8 ng/mL*h while the Cmax was between 16 and 25.2 ng/mL. Zolmitriptan administered as a nasal spray is detected in the plasma within 2-5 minutes, compared to 10-15 minutes for the tablet form; the faster kinetics likely reflect fast absorption across the nasal mucosa. The bioavailability compared to the tablet is 102%, and plasma zolmitriptan concentration is maintained for 4-6 hours after intranasal delivery. The active N-desmethyl metabolite of zolmitriptan has a mean plasma concentration that is roughly two-thirds of zolmitriptan, regardless of dosage route or concentration.

    Route of Elimination

    Zolmitriptan is primarily excreted in urine (approximately 65%) and feces (approximately 30%). Within urine, the most common form is the indole acetic acid metabolite (31%), followed by the N-oxide (7%), and N-desmethyl (4%) metabolites; the majority of zolmitriptan recovered in feces remains unchanged.

    Volume of Distribution

    Zolmitriptan has a volume of distribution between 7 and 8.4 L/kg.

    Clearance

    Zolmitriptan has a clearance of 31.5 mL/min/kg for oral tablets and 25.9 mL/min/kg for nasal administration; one-sixth of the clearance is renal.

    5.6 Metabolism/Metabolites

    Zolmitriptan is metabolized in the liver, and studies using cytochrome P450 inhibitors like [cimetidine] suggest that it is likely metabolized by CYP1A2, as well as by monoamine oxidase (MAO). Zolmitriptan metabolism results in three major metabolites: an active N-desmethyl metabolite (183C91) as well as inactive N-oxide (1652W92) and indole acetic acid (2161W92) metabolites.

    Zolmitriptan has known human metabolites that include N-Desmethylzolmitriptan and Zolmitriptan N-oxide.

    S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560

    5.7 Biological Half-Life

    Zolmitriptan has a mean elimination half-life of approximately three hours, while its active N-desmethyl metabolite has a slightly longer (approximately 3.5 hours) half-life.

    5.8 Mechanism of Action

    Migraines are complex physiological events characterized by unilateral throbbing headaches combined with photophobia and other aversions to sensory input. Migraine attacks are generally divided into phases: the premonitory phase, which typically involves irritability, fatigue, yawning, and stiff neck; the headache phase, which lasts for between four and 72 hours; and the postdrome phase, which lasts for up to a day following resolution of pain and whose symptoms are similar to those of the premonitory phase. In addition, neurological deficits, collectively termed migraine aura, may precede the headache phase. The underlying pathophysiology of migraines is a matter of active research but involves both neurological and vascular components. The head pain associated with migraine is thought to be a consequence of activation of the nociceptive nerves comprising the trigeminocervical complex (TCC). Terminals of nociceptive nerves that innervate the dura matter release vasoactive peptides, such as calcitonin gene-related peptide (CGRP), resulting in cranial vasodilation. Finally, when present, migraine aura appears to correlate with a transient wave(s) of cortical depolarization, termed cortical spreading depression (CSD). Triptans, including zolmitriptan, are proposed to act in three ways. The main mechanism is through modulation of nociceptive nerve signalling in the central nervous system through 5-HT1B/1D receptors throughout the TCC and associated areas of the brain. In addition, triptans can enhance vasoconstriction, both through direct 5-HT1B-mediated dilation of cranial blood vessels, as well as through 5-HT1D-mediated suppression of CGRP release. Although triptans are classically described solely in terms of their effects on 5-HT1B/1D receptors, they also act as 5-HT1F agonists as well. This 5-HT subtype is also found throughout the TCC, but is not present appreciably in cerebral vasculature; the significance of triptan-mediated 5-HT1F activation is currently not well described. Additionally, CSD that initiates in the ipsilateral parietal region may exert its effects in a manner that relies on 5-HT1B/1D receptor activation, suggesting that triptans may have some effect on CSD-mediated symptoms.

    API Reference Price

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    06-Jan-2021
    24-Jul-2024
    KGS
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