3D Mol Similar

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+

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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; View all

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; View all

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. ?

View all

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

View all

6. Synthesis Route

139264-17-8Total: 9 Synthesis Route

659738-69-9

139264-17-8 300 Suppliers

Literatures:
LABORATORIOS VITA, S. A. Patent: WO2004/14901 A1, 2004 ; Location in patent: Page 18-19 ;
Yield: ~87%

868622-23-5

139264-17-8 300 Suppliers

Literatures:
Aminul, Islam; Chandan, Bhar; Sahadev, Katam Patent: US2005/245585 A1, 2005 ; Location in patent: Page/Page column 8 ;
Yield: ~74%

191864-24-1 4 Suppliers

139264-17-8 300 Suppliers

Literatures:
Aminul, Islam; Chandan, Bhar; Sahadev, Katam Patent: US2005/245585 A1, 2005 ; Location in patent: Page/Page column 8-9 ;
Yield: ~46%

View all

7. Precursor and Product

precursor:

868622-23-5

1116-77-4

139264-19-0

187975-62-8

50-00-0

19718-92-4

152305-23-2

659738-69-9

139264-15-6

191864-24-1

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; View all

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-HT_1D/1B receptor agonist (10 fold ratio) with modest (< 100x) affinity for 5-HT_1A and 5-HT_1F 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.; View all

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==

10. Question & Answer

Can Zolmitriptan effectively treat migraines? Jul 27 2022
After experiencing symptoms of migraines, it is important to take them seriously. When it comes to treating migraines caused by different factors, the choice of treatment methods or medications may va..
What is Zolmitriptan and how does it treat migraines? Oct 20 2021
Zolmitriptan is a medication used for the acute treatment of moderate to severe migraines with or without aura. Developed by Glaxo-Wellcome in Germany, Zolmitriptan is a highly selective 5-HT1B/1D rec..
What is the importance of clinical treatment for migraine without aura? Jan 11 2021
Migraine without aura is a common chronic neurovascular disease in clinical neurology, characterized by intermittent headache attacks and neurological dysfunction. It poses great harm to patients and ..

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