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Zolmitriptan

CAS No.
139264-17-8
Chemical Name:
Zolmitriptan
Synonyms
Zomig;Zomi;311c90;bw311c90;Zolmitrptan;zolmitripan;Zolmitriptan;ZOLMITRIPTANE;ZOLIMITRIPTAN;ZolMitriptan API
CBNumber:
CB3313219
Molecular Formula:
C16H21N3O2
Molecular Weight:
287.36
MDL Number:
MFCD00871503
MOL File:
139264-17-8.mol
MSDS File:
SDS

Zolmitriptan Properties

Melting point 136-141°C
alpha D22 -5.79° (c = 0.5 in methanol)
Boiling point 563.3±38.0 °C(Predicted)
Density 1.217±0.06 g/cm3(Predicted)
storage temp. 15-25°C
solubility Soluble in DMSO at 5mg/ml
pka 9.64(at 25℃)
form powder
color white to beige
optical activity [α]/D -3 to -8°, c = 1 in methanol
λmax 225nm(lit.)
Merck 14,10189
Stability Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 3 months.
InChIKey ULSDMUVEXKOYBU-ZDUSSCGKSA-N
CAS DataBase Reference 139264-17-8(CAS DataBase Reference)
FDA UNII 2FS66TH3YW
NCI Drug Dictionary zolmitriptan
ATC code N02CC03

Pharmacokinetic data

Protein binding 25%
Excreted unchanged in urine 60 (as metabolites)
Volume of distribution 2.4(L/kg)
Biological half-life 2.5-3 / 3-3.5

SAFETY

Risk and Safety Statements

Symbol(GHS) 
GHS07
Signal word  Warning
Hazard statements  H302
Precautionary statements  P264-P270-P301+P312+P330-P501
Hazard Codes  Xi,Xn
Risk Statements  36/37/38-22
Safety Statements  26-36
WGK Germany  3
RTECS  RQ2707000
HS Code  29349990

Zolmitriptan price More Price(46)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich SML0248 Zolmitriptan ≥98% (HPLC) 139264-17-8 10mg $97.3 2022-05-15 Buy
Sigma-Aldrich 1727009 Zolmitriptan United States Pharmacopeia (USP) Reference Standard 139264-17-8 200mg $400 2022-05-15 Buy
TCI Chemical Z0024 Zolmitriptan >98.0%(HPLC)(T) 139264-17-8 1g $290 2022-04-27 Buy
TCI Chemical Z0024 Zolmitriptan >98.0%(HPLC)(T) 139264-17-8 200mg $83 2022-04-27 Buy
Alfa Aesar J60616 Zolmitriptan 139264-17-8 100mg $104 2021-12-16 Buy
Product number Packaging Price Buy
SML0248 10mg $97.3 Buy
1727009 200mg $400 Buy
Z0024 1g $290 Buy
Z0024 200mg $83 Buy
J60616 100mg $104 Buy

Zolmitriptan Chemical Properties,Uses,Production

Description

Zolmitriptan is a selective serotonin receptor agonist of the 1B and 1D subtypes. It is mainly used in the acute treatment of migraine attacks with or without aura and cluster headaches. Zolmitriptan takes effect through binding to human 5-HT1Band 5-HT1Dreceptors, leading to cranial blood vessel constriction and the release of sensory neuropeptides through nerve endings in the trigeminal system. 

Chemical Properties

White Crystalline Powder

Originator

Zeneca (UK)

Uses

adrenergic agonist, nasal decongestant

Uses

A Serotonin 5HTID-receptor agonist

Uses

Zolmitriptan is a serotonin 5HTID-receptor agonist and used to treat migraine (1,2,3).

Manufacturing Process

(S)-4-(4-[N'-(2-Oxotetrahydropyran-3-iliden)hidrazino]benzyl}-1,3-oxazolidin- 2-one
A solution of 2.8 g (40.6 mmoles) of sodium nitrite in 12 ml of water was added slowly to a solution of 9.1 g (39.8 mmoles) of (S)-4-(4-aminobenzyl)- 1,3-oxazolidyne-2-one hydrochloride in 17 ml of water and 29 ml of concentrated HCl, keeping the reaction temperature below 0°C. The mixture was stirred at this temperature for 15 minutes. Once that time had elapsed the diazonium salt solution was added rapidly to a suspension of 30 g (239 mmoles) of sodium sulphite in 106 ml of water precooled to 0°C under nitrogen atmosphere. The red solution was stirred at 0°C for 10 minutes and then left to reach 65°C in 1 hour. It was stirred at 65°C for 30 minutes, and 18.2 ml of concentrated HCl then added. The mixture was stirred at the same temperature under nitrogen atmosphere for 3 hours and then left to cool to room temperature. To this solution was added a solution of 35 mmoles of α- keto-γ-valerolactone (prepared by decarboxylation of 11.8 g (63.7 mmoles) of a ethoxyalyl-γ-butyrolactone in 15.2 ml of 2 N H 2 SO 4 at reflux) and left under stirring at room temperature for 12 hours. When that time had elapsed the mixture was cooled to 0°C and stirred for one hour. The precipitate formed was filtered, washed with cold water and dried in an hotair oven at 40°C, giving a white solid which was crystallised from ethanol/water to give 10.5 g (87%) of the title hydrazone as a white solid. Melting point 223.3°-224.7°C.
(S)-6-(2-Oxo-1,3-oxazolidin-4-ylmethyl)-4,9-dihydro-3H-pyrano-[3,4-b]indol- 1-one
3.8 g (12.5 mmoles) of (S)-4-{4-[N'-(2-oxotetrahydropyran-3-iliden) hydrazino]benzyl}-1,3-oxazolidin-2-one were suspended in 32 ml of a saturated solution of hydrogen chloride in acetic acid. The mixture was stirred at room temperature for 16 h, 10 ml of water/ice was added to the reaction mixture and stirred at 0°C for 20 min. The precipitate was filtered, washed with cold water and dried in hot-air oven at 40°C. The residue was crystallised with methanol to yield 3.3 g (92%) of the title indole as a yellow crystalline solid. Melting point 215°-217°C.
(S)-3-(2-Hydroxyethyl)-5-(2-oxo-1,3-oxazolidin-4-ylmethyl)-1-H-indol-2- carboxylicacid methyl ester
To a suspension of 500 mg (1.74 mmoles) of the (S)-6-(2-oxo-1,3-oxazolidin- 4-ylmethyl)-4,9-dihydro-3-pyrano-[3,4-b]indol-1-one in 10 ml of methanol were added 0.12 ml (1.9 mmoles) of methanesulfonic acid. The mixture was left under stirring at the reflux temperature for 3 hours. The solvent was evaporated to dryness under reduced pressure, the residue dissolved with 10 ml of a saturated bicarbonate solution and extracted three times with dichloromethane. The combined organic phases were dried and evaporated to dryness and the evaporated solid recrystallised from ethanol to give 517 mg (93%) of the title ester as a yellow crystalline solid. Melting point 178°- 180°C.
(S)-3-(2-Hydroxyethyl)-5-(2-oxo-1,3-oxazolidin-4-ylmethyl)-1H-indol-2- carboxylicacid ethyl ester
9.5 g (31.3 mmoles) of (S)-4-{4-[N'-(2-oxotetrahydropyran-3-ilyden) hydrazine]benzyl}-1,3-oxazolidin-2-one were suspended in 76 ml of a 2 N solution of hydrogen chloride in absolute ethanol. The mixture was left under stirring at 75°C for 30 min. The solvent was evaporated to dryness under reduced pressure, 50 ml of a saturated solution of potassium carbonate added, and then extracted three times with 50 ml of dichloromethane. The combined organic phases were dried on anhydrous sodium sulphate and recrystallised from methanol to give a yellow crystalline solid. Melting point 154°-156°C. evaporated to dryness. The residue was recrystallised from isopropyl alcohol/heptane to give 9.25 g (89%) of the title indole. The product was

brand name

Zomig (AstraZeneca); Zomig (IPR).

Therapeutic Function

Serotoninergic

General Description

Zolmitriptan, the second triptan marketed (approved in1997), has a much better bioavailability (40%–48%) thansumatriptan. It is rapidly absorbed after oral or nasal sprayadministration. It also has an orally disintegrating tablet formulation(Zomig ZMT), which can be taken without water.Zolmitriptan undergoes rapid N-demethylation via CYP1A2to a more potent, active metabolite, N-desmethylzolmitriptan,which is 2 to 6 times more potent than the parentdrug. This active metabolite was detected 5 minutesafter dosing and accounts for about two thirds of the plasmaconcentration of the administered dose of the parent drug.284Thus, it is reasonable to assume that the therapeutic effectsand especially the CNS side effects of zolmitriptan must bein part attributed to the plasma levels of this active metabolite,at least until it is further degraded by hepatic MAO-Ato its inactive indole acetic acid derivatives.

Biochem/physiol Actions

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.

Clinical Use

Zomig was launched in Germany, Denmark, Sweden and the UK for use as an antimigraine agent (with and without aura). It can be prepared by three related routes of 5 to 7 steps starting from L-4-nitrophenylalanine. Zomig is a 5-HT1D/1B receptor agonist (10 fold ratio) with modest (< 100x) affinity for 5-HT1A and 5-HT1F receptors. It has no affinity for other serotonin receptors or receptors of other neurotransmitters. It has a novel dual action mechanism: centrally it acts on the trigeminal nucleus caudalis and peripherally is acts on the trigeminovascular system. Zomig was effective in treating headaches and nonheadache (photophobia, phonophobia and nausea) symptoms. It was 2-3 times more potent than sumatriptan and is metabolized to three compounds, one of which is 2-8 times more active than the parent. It caused a 40-50% decrease in headache after 1 h and a 73-77% after 4 h. There was a 30% reoccurance of headache but 90% effective treatment with a second dose. It blocks neurogenic inflammation by inhibiting release of peptides, causes vasoconstriction, and inhibits neuronal depolarization at peripheral sites in the cranium. It is 40% bioavailable and a 10 time theraputic dose showed no safety concerns.

Drug interactions

Potentially hazardous interactions with other drugs
Antibacterials: quinolones possibly inhibit metabolism - reduce dose of zolmitriptan.
Antidepressants: increased risk of CNS toxicity with citalopram - avoid; risk of CNS toxicity with MAOIs and moclobemide - reduce dose of zolmitriptan to max 7.5 mg; SSRIs inhibit metabolism of zolmitriptan, reduce dose with fluvoxamine; possibly increased serotonergic effects with duloxetine and venlafaxine; increased serotonergic effects with St John’s wort - avoid concomitant use.
Cimetidine: inhibits metabolism of zolmitriptan; maximum dose is 5 mg.
Dapoxetine: possible increased risk of serotonergic effects - avoid for 2 weeks after stopping 5HT1 agonists.
Ergot alkaloids: increased risk of vasospasm.
Linezolid: risk of CNS toxicity - reduce dose of zolmitriptan.

Metabolism

Zolmitriptan is eliminated largely by hepatic biotransformation followed by urinary excretion of the metabolites. There are three major metabolites: the indole acetic acid, (the major metabolite in plasma and urine), the N-oxide and N-desmethyl analogues. Only the N-desmethylated metabolite is active. The primary metabolism of zolmitriptan is mediated mainly by the cytochrome P450 isoenzyme CYP1A2 while monoamine oxidase type A is responsible for further metabolism of the N-desmethyl metabolite. Over 60
% of a dose is excreted in the urine, mainly as the indole acetic acid, and about 30
% appears in the faeces, mainly as unchanged drug.

References

https://www.drugbank.ca/drugs/DB00315
Rothner, A. D., et al. "Zolmitriptan oral tablet in migraine treatment: high placebo responses in adolescents." Headache the Journal of Head & Face Pain 46.1(2006):101.
Hedlund, C, et al. "Zolmitriptan nasal spray in the acute treatment of cluster headache: a meta-analysis of two studies. " Neurology49.9(2009):1315–1323.

Zolmitriptan Preparation Products And Raw materials

Global( 444)Suppliers
Supplier Tel Email Country ProdList Advantage
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View Lastest Price from Zolmitriptan manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
2022-07-07 Zolmitriptan
139264-17-8
US $265.00-245.00 / KG 1KG 99% 9000kg/per week Hebei Lingding Biological Technology Co., Ltd
2022-02-25 Zolmitriptan
139264-17-8
US $0.00 / KG 100g 98%+ 100kg WUHAN CIRCLE POWDER TECHNOLOGY CO.,LTD
2022-02-24 Zolmitriptan
139264-17-8
US $30.00 / KG 1KG 99.9% 1000kg/month Shanxi Lianxu New Material Co., LTD
  • Zolmitriptan
    139264-17-8
  • US $265.00-245.00 / KG
  • 99%
  • Hebei Lingding Biological Technology Co., Ltd
  • Zolmitriptan
    139264-17-8
  • US $0.00 / KG
  • 98%+
  • WUHAN CIRCLE POWDER TECHNOLOGY CO.,LTD
  • Zolmitriptan
    139264-17-8
  • US $30.00 / KG
  • 99.9%
  • Shanxi Lianxu New Material Co., LTD
ZOLMITRIPTANE (4r)-4-[[3-(2-dimethylaminoethyl)-1h-indol-5-yl]methyl]oxazolidin-2-one Zolmitriptan Assists Mi Qu Pu Tanzania Zolmitriptan (150 mg) (4R)-4-({3-[2-(diMethylaMino)ethyl]-1H-indol-5-yl}Methyl)-1,3-oxazolidin-2-one ZolMitriptan(ZoMig) ZolMitriptan API ZOLIMITRIPTAN (R)-4-((3-(2-(diMethylaMino)ethyl)-1H-indol-5-yl)Methyl)oxazolidin-2-one Zolmitriptan (4R)-4-[[3-(2-Dimethylaminoethyl)-1H-indol-5-yl]methyl]oxazolidin-2-one (S)-4-((3-(2-(Dimethylamino)ethyl)indol-5-yl)methyl)-2-oxazolidinone (s)-2-oxazolidinon (s)-4-((3-(2-(dimethylamino)ethyl)-1h-indol-5-yl)methyl)-2-oxazolidinone 311c90 bw311c90 Zolmitrptan (4S)-4-[[3-[2-(Dimethylamino)ethyl]-1H-indol-5-yl]methyl-2-oxazolidinone Zomi (S)-4-[3-(2-DIMETHYLAMINO-ETHYL)-1H-INDOL-5-YLMETHYL]-OXAZOLIDIN-2-ONE (S)-4-(4-hydrazinobenzyl)-2-oxazolidinone(S)-4-(4-aminobenzyl)-2-oxazolidinone4-(2-Dimethylamino) butyaldehyde diethyl acetal zolmitripan (S)-4-[3-(2-Dimethylamino-ethyl)-1H-indol-5- Zolmitriptan, 98%, a selective 5-HT1B/1D/1F receptor agonist Zolmitriptan CRS 2-Oxazolidinone, 4-[[3-[2-(dimethylamino)ethyl]-1H-indol-5-yl]methyl]-, (4S)- Zolmitriptan for system suitability Zolmitriptan fandachem Zolmitriptan USP/EP/BP ZolmitriptanQ: What is Zolmitriptan Q: What is the CAS Number of Zolmitriptan Q: What is the storage condition of Zolmitriptan Q: What are the applications of Zolmitriptan Zolmitriptan APIs Zolmitriptan (1727009) Zomig 1,4-Benzenediamine,2,11-dibromo- 139264-17-8 13924-17-8 C16H15NO2D6 C16H21N3O2 ALBALON Other APIs All Inhibitors Antimigraine ZOLMITRIPTAN Inhibitors Intermediates & Fine Chemicals Pharmaceuticals API