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Home> Encyclopedia >Central Nervous System Agents>Pharmaceutical Intermediates>Pharmaceutical
Zolmitriptan structure
Zolmitriptan structure

Zolmitriptan

Iupac Name:(4S)-4-[[3-[2-(dimethylamino)ethyl]-1H-indol-5-yl]methyl]-1,3-oxazolidin-2-one
CAS No.: 139264-17-8
Molecular Weight:287.363
Modify Date.: 2022-11-10 16:15
Introduction: 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. View more+
1. Names and Identifiers
1.1 Name
Zolmitriptan
1.2 Synonyms

(4R)-4-({3-[2-(diMethylaMino)ethyl]-1H-indol-5-yl}Methyl)-1,3-oxazolidin-2-one (4r)-4-[[3-(2-dimethylaminoethyl)-1h-indol-5-yl]methyl]oxazolidin-2-one (4S)-4-({3-[2-(Dimethylamino)ethyl]-1H-indol-5-yl}methyl)-1,3-oxazolidin-2-one (S)-4-[[3-[2-(Dimethylamino)ethyl]-1H-indol-5-yl]methyl]-2-oxazolidinone (S)-N,N-Dimethyl-2-[5-(2-oxo-1,3-oxazolidin-4-ylmethyl)-1H-indol-3-yl]ethylamine 2-Oxazolidinone, 4-[[3-[2-(dimethylamino)ethyl]-1H-indol-5-yl]methyl]-, (4S)- AscoTop Assists Mi Qu Pu Tanzania BW 311C90 MFCD00871503 Zolmitriptan (150 mg) ZolMitriptan API ZolMitriptan(ZoMig) ZOLMITRIPTANE Zomig Zomigon Zomigoro

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1.3 CAS No.
139264-17-8
1.4 CID
60857
1.5 EINECS(EC#)
1806241-263-5
1.6 Molecular Formula
C16H21N3O2 (isomer)
1.7 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
1.8 InChIkey
ULSDMUVEXKOYBU-ZDUSSCGKSA-N
1.9 Canonical Smiles
CN(C)CCC1=CNC2=C1C=C(C=C2)CC3COC(=O)N3
1.10 Isomers Smiles
CN(C)CCC1=CNC2=C1C=C(C=C2)C[C@H]3COC(=O)N3
2. Properties
2.1 Density
1.217
2.1 Melting point
136-141℃
2.1 Boiling point
563.3 °C at 760 mmHg
2.1 Refractive index
1.619
2.1 Flash Point
294.5 °C
2.1 Precise Quality
287.16300
2.1 PSA
57.36000
2.1 logP
2.25170
2.1 Solubility
Soluble in DMSO at 5mg/ml
2.2 Λmax
225nm(lit.)
2.3 Appearance
White or kind of white powder
2.4 Storage
Refrigerator
2.5 Chemical Properties
White Crystalline Powder
2.6 Color/Form
Powder
2.7 Physical
Solid
2.8 pKa
9.64(at 25℃)
2.9 Water Solubility
Soluble
2.10 StorageTemp
15-25°C
3. Use and Manufacturing
3.1 GHS Classification
Signal: Warning
GHS Hazard Statements
Aggregated GHS information provided by 14 companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

H302 (92.86%): Harmful if swallowed [Warning Acute toxicity, oral]
H315 (21.43%): Causes skin irritation [Warning Skin corrosion/irritation]
H319 (21.43%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
H335 (21.43%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]
H371 (35.71%): May cause damage to organs [Warning Specific target organ toxicity, single exposure]

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

Precautionary Statement Codes
P260, P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P309+P311, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, and P501
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3.2 Usage
A Serotonin 5HTID-receptor agonist
4. Safety and Handling
4.1 Hazard Codes
Xi
4.1 Risk Statements
R36/37/38
4.1 Safety Statements
S26;S36
4.1 RIDADR
NONH for all modes of transport
4.1 WGK Germany
3
4.1 RTECS
RQ2707000
4.1 Safety

Hazard Codes:? Xi
The Risk Statements information of? Zolmitriptan:
36/37/38:? Irritating to eyes, respiratory system and skin?
The Safety Statements information of? Zolmitriptan:
26:? In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
36:? Wear suitable protective clothing

4.2 Specification

? Zolmitriptan , with CAS number of 139264-17-8, can be called (S)-4-((3-(2-(Dimethylamino)ethyl)-1H-indol-5-yl)methyl)-2-oxazolidinone ; (S)-4-((3-(2-(Dimethylamino)ethyl)indol-5-yl)methyl)-2-oxazolidinone ; 2-Oxazolidinone, 4-((3-(2-(dimethylamino)ethyl)-1H-indol-5-yl)methyl)-, (S)- ; 4-((3-(2-(Dimethylamino)ethyl)-1H-indol-5-yl)methyl)-2-oxazolidinone .?The usage of Zolmitriptan is as an serotonin 5HTID-receptor agonist.

4.3 Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
women TDLo oral 6mg/kg/43W-I (6mg/kg) BEHAVIORAL: HEADACHE Lancet. Vol. 353, Pg. 378, 1999.
?

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5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Acute toxicity - Oral, Category 4

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word

Warning

Hazard statement(s)

H302 Harmful if swallowed

Precautionary statement(s)
Prevention

P264 Wash ... thoroughly after handling.

P270 Do not eat, drink or smoke when using this product.

Response

P301+P312 IF SWALLOWED: Call a POISON CENTER/doctor/\u2026if you feel unwell.

P330 Rinse mouth.

Storage

none

Disposal

P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

8. Other Information
8.0 Merck
14,10189
8.1 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. 
8.2 Chemical Properties
White Crystalline Powder
8.3 Uses
A Serotonin 5HTID-receptor agonist
8.4 Uses
adrenergic agonist, nasal decongestant
8.5 Brand name
Zomig (AstraZeneca); Zomig (IPR).
8.6 Originator
Zeneca (UK)
8.7 Uses
Zolmitriptan is a serotonin 5HTID-receptor agonist and used to treat migraine (1,2,3).
8.8 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
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8.9 Therapeutic Function
Serotoninergic
8.10 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.
8.11 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.
8.12 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.
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8.13 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.
8.14 Usage
A serotonin 5HT1D-receptor agonist
9. Computational chemical data
  • Molecular Weight: 287.363g/mol
  • Molecular Formula: C16H21N3O2
  • Compound Is Canonicalized: True
  • XLogP3-AA: 2.2
  • Exact Mass: 287.16337692
  • Monoisotopic Mass: 287.16337692
  • Complexity: 375
  • Rotatable Bond Count: 5
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 3
  • Topological Polar Surface Area: 57.4
  • Heavy Atom Count: 21
  • Defined Atom Stereocenter Count: 1
  • Undefined Atom Stereocenter Count: 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Isotope Atom Count: 0
  • Covalently-Bonded Unit Count: 1
  • CACTVS Substructure Key Fingerprint: AAADceB7MAAAAAAAAAAAAAAAAAAAAWLAAAAwAAAAAAAAAFgB8AAAHgAQAAAADCjhngY+yPPJlACoAzRnXACCgCAxAiAI2aA4ZJkKIOLAkZGNIAhklgDYyAeQwOAOiAACAAACAAAQAAQAAAQAAAAAAAAAAA==
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