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Merck

SML0248

Zolmitriptan

≥98% (HPLC)

Synonym(s):

(4S)-4-((3-(2-(Dimethylamino)ethyl)-1H-indol-5-yl)methyl)-2-oxazolidinone, (S)-4-((3-(2-(Dimethylamino)ethyl)indol-5-yl)methyl)-2-oxazolidinone, 311C90

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About This Item

Empirical Formula (Hill Notation):
C16H21N3O2
CAS Number:
139264-17-8
Molecular Weight:
287.36
NACRES:
NA.77
PubChem Substance ID:
329825258
UNSPSC Code:
12352200
MDL number:
MFCD00871503
Assay:
≥98% (HPLC)
Form:
powder
Quality level:
100

Key Documents

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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

SMILES string

CN(C)CCc1c[nH]c2ccc(C[C@H]3COC(=O)N3)cc12

InChI key

ULSDMUVEXKOYBU-ZDUSSCGKSA-N

assay

≥98% (HPLC)

form

powder

optical activity

[α]/D -3 to -8°, c = 1 in methanol

color

white to beige

solubility

DMSO: ≥5 mg/mL

storage temp.

2-8°C

Quality Level

100

Gene Information

human ... HTR1B(3351), HTR1D(3352)

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Application

Zolmitriptan has been used as a 5-hydroxytryptamine receptor 1B (5-HT1B/D) activator to treat grafts to study its effects on the morphology of the ectopic eye.
Zolmitriptan has been used to induce hyper-innervation of transplants.

Biochem/physiol Actions

Zolmitriptan is a potent, selective. centrally and peripherally acting 5HT1B/1D receptor agonist.
Zolmitriptan is a selective serotonin receptor agonist of the 5HT1B and 5HT1D subtypes, both centrally and peripherally. It has been used clinically for the acute treatment of migraine attacks with or without aura and cluster headaches.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000480091
0000480091
0000225378
0000225378
0000137099

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David W Dodick et al.
Cephalalgia : an international journal of headache, 31(3), 296-300 (2010-10-13)
Endpoints used to evaluate the efficacy of acute anti-migraine drugs do not measure the tolerability. Sustained pain-free response with no adverse events has been recommended as a composite endpoint which measures the efficacy and tolerability attributes that patients desire. The
Michal Douša et al.
Journal of pharmaceutical and biomedical analysis, 58, 1-6 (2011-10-11)
A new impurity was detected and determined using gradient ion-pair UHPLC method with UV detection in zolmitriptan (ZOL). Using MS, NMR and IR study the impurity was identified as (4S,4'S)-4,4'-(2,2'-(4-(dimethylamino)butane-1,1-diyl)bis(3-(2-(dimethylamino) ethyl)-1H-indole-5,2-diyl))bis(methylene)di(oxazolidin-2-one) (ZOL-dimer). The standard of ZOL-dimer was consequently prepared via
Ziya Bayrak et al.
European journal of pharmaceutics and biopharmaceutics : official journal of Arbeitsgemeinschaft fur Pharmazeutische Verfahrenstechnik e.V, 78(3), 499-505 (2011-03-01)
First-pass metabolism can be overcome by sublingual drug delivery, and quick drug entry into the systemic circulation can be obtained. In certain diseases such as migraine therapy, taking fast pharmacological response is an important criteria. In this study, zolmitriptan sublingual
Robhash Kusam Subedi et al.
International journal of pharmaceutics, 419(1-2), 209-214 (2011-08-17)
The effects of different formulation variables including pressure sensitive adhesive (PSA), thickness of the matrix, solvent system, inclusion of crystallization inhibitor, loading amount of drug and enhancers on the transdermal absorption of zolmitriptan were investigated. Acrylic adhesive with hydroxyl functional
B Lee Peterlin et al.
Expert opinion on drug metabolism & toxicology, 3(6), 899-911 (2007-11-22)
Migraine is a common, often disabling, neurovascular disease that has been shown to be associated with abnormal serotonergic activity. Drugs that modulate serotonin receptors are commonly used in the acute treatment of a migraine attack. Zolmitriptan, a 5-hydroxytryptophan(1B/1D) receptor agonist
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