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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.


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D6 & D8, SY.NO. 234\/2,234\/3, ,235\/2 & 542\/2, IKP KNOWLEDGE PARK,","city":"TURKAPALLY-V SHAMIRPET HYDERABAD,TE","supplier":"USP","supplierCountry":"INDIA","foreign_port":"NA","customer":"UNITED STATES PHARMACOPEIA - INDIA PRIVATE LIMITED","customerCountry":"INDIA","quantity":"0.00","actualQuantity":"0.00006","unit":"KGS","unitRateFc":"45150000","totalValueFC":"2972","currency":"USD","unitRateINR":"4059474667","date":"12-Apr-2023","totalValueINR":"243568.48","totalValueInUsd":"2972","indian_port":"HYDERABAD AIR","hs_no":"29349990","bill_no":"5476780","productDescription":"Re-Import","marketType":"REGULATED MARKET","country":"INDIA","selfForZScoreResived":"Pharma Grade","supplierPort":"NA","supplierAddress":"","customerAddress":"P.NO. D6 & D8, SY.NO. 234\/2,234\/3, ,235\/2 & 542\/2, IKP KNOWLEDGE PARK,"}]
06-Jan-2021
24-Jul-2024
KGS
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Average Price (USD/KGS)

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Total Quantity (KGS)

Total Value (USD)

Quantity (KGS) & Unit rate (USD/KGS) over time

API Imports and Exports

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DOSAGE - TABLET;ORAL - 2.5MG

USFDA APPLICATION NUMBER - 20768

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USFDA APPLICATION NUMBER - 21231

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DOSAGE - TABLET, ORALLY DISINTEGRATING;ORAL -...DOSAGE - TABLET, ORALLY DISINTEGRATING;ORAL - 5MG

USFDA APPLICATION NUMBER - 21231

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