Ondansetron

Names

[ Name ]:
Ondansetron

[Synonym ]:
ONDANSETRON HYDROCHLORIDE DIHYDRATE
9-Methyl-3-[(2-methyl-1H-imidazol-1-yl)methyl]-1,2,3,9-tetrahydro-4H-carbazol-4-one
GR 38032F
4H-Carbazol-4-one, 1,2,3,9-tetrahydro-9-methyl-3-((2-methyl-1H-imidazol-1-yl)methyl)-
9-METHYL-3-[(2-METHYL-1H-IMIDAZOLYL)METHYL]-1,2,3,9-TETRAHYDRO-4H-CARBAZOLE-4-ONE
1,2,3,9-Tetrahydro-9-methyl-3-[(2-methyl-1H-imidazol-1-yl)methyl]-4H-carbazol-4-one
ONDANSETRON-D5
ONDANSETRON HCL D6
9-METHYL-3-(2-METHYL-1H-IMIDAZOLYL)-METHYL-1,2,3,9-TETRAHYDRO-4H-CARBAZOLE-4-ONE
Zofran
ONDANSETRONBASE
R(+)-Ondansetron
Ondansetro
ONDANSETRON HYDROCHLORIDE
9-METHYL-3-[(2-METHYL-1H-IMIDAZOLYL)-METHYL]-1,2,3,9-TETRAHYDRO-4H-CARBAZOLE-4-ONE
GR 38032X
ONDANESTRON
GR-38032F
MFCD00764297
4H-Carbazol-4-one, 1,2,3,9-tetrahydro-9-methyl-3-[(2-methyl-1H-imidazol-1-yl)methyl]-
ONDANSETRON FOR LC SYSTEM SUITABILITY, EP STANDARD
Ondansetron
ONDANSETRON HCL
EINECS 619-449-4

Biological Activity

[Description]:

Ondansetron(GR38032) is a serotonin 5-HT3 receptor antagonist used mainly as anantiemetic (to treat nausea and vomiting), often following chemotherapy.IC50 Value: Target: 5- HT3 Receptorin vitro: 5-HT evoked transient inward currents (EC50 = 3.4 microM; Hill coefficient = 1.8) that were blocked by the 5-HT3 receptor antagonist ondansetron (IC50 = 103 pM) [1]. The 5-HT3A receptor antagonist ondansetron (0.3 nM) reversibly inhibited the 5-HT (30 microM) signal by 70% and at 3 nM it abolished the response [2].in vivo: Acute ondansetron administration at the lowest dose (0.1 mg/kg, IP) tested had no effect, while other doses (0.33 and 1 mg/kg, IP) produced improvements in auditory gating [3]. Different doses of ondansetron were injected intraperitoneally (i.p.) at fixed times during the day to determine both the sublethal (TD50) and lethal (LD50) doses, which were, respectively, 3.7 +/- 0.6 mg/kg and 4.6 +/- 0.5 mg/kg [4]. ondansetron (0.25-1.0 mg/kg, subcutaneously) given before the challenge dose of ethanol (2.4 g/kg, intraperitoneally) injection, significantly and dose dependently attenuated the expression of sensitization. In addition, ondansetron (1.0 mg/kg, subcutaneously) given before ethanol injection on days 1, 4, 7, and 10 significantly blocked the development (days 1, 4, 7, and 10), and expression (day 15) of sensitization to the locomotor stimulant effect of ethanol injection [5]. Toxicity: Ondansetron may be safe in lower doses used to prevent nausea and vomiting in radiation treatment or postoperatively. However, as there is a report that a lower dose of ondansetron prolonged the QT interval in healthy volunteers, this needs to be clarified by the FDA [6].

[Related Catalog]:

Signaling Pathways >> GPCR/G Protein >> 5-HT Receptor

Signaling Pathways >> Neuronal Signaling >> 5-HT Receptor

Research Areas >> Neurological Disease

[References]

[1]. Brown AM, et al. Ion permeation and conduction in a human recombinant 5-HT3 receptor subunit (h5-HT3A). J Physiol. 1998 Mar 15;507 ( Pt 3):653-65.

[2]. Barann M, et al. Recombinant human 5-HT3A receptors in outside-out patches of HEK 293 cells: basic properties and barbiturate effects. Naunyn Schmiedebergs Arch Pharmacol. 2000 Sep;362(3):255-65.

[3]. Wildeboer KM, et al. Ondansetron results in improved auditory gating in DBA/2 mice through a cholinergic mechanism. Brain Res. 2009 Dec 1;1300:41-50.

[4]. Khedhaier A, et al. Circadian rhythms in toxic effects of the serotonin antagonist ondansetron in mice. Chronobiol Int. 2003 Nov;20(6):1103-16.

[5]. Umathe SN, et al. The 5-HT3 receptor antagonist, ondansetron, blocks the development and expression of ethanol-induced locomotor sensitization in mice. Behav Pharmacol. 2009 Feb;20(1):78-83.

[6]. Doggrell SA, et al. Cardiac safety concerns for ondansetron, an antiemetic commonly used for nausea linked to cancer treatment and following anaesthesia. Expert Opin Drug Saf. 2013 May;12(3):421-31.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
546.0±30.0 °C at 760 mmHg

[ Melting Point ]:
231 - 232ºC

[ Molecular Formula ]:
C₁₈H₁₉N₃O

[ Molecular Weight ]:
293.363

[ Flash Point ]:
284.0±24.6 °C

[ Exact Mass ]:
293.152802

[ PSA ]:
39.82000

[ LogP ]:
2.07

[ Vapour Pressure ]:
0.0±1.5 mmHg at 25°C

[ Index of Refraction ]:
1.678

[ Storage condition ]:
−20°C

[ Water Solubility ]:
H2O: >5 mg/mL

MSDS

Click to get detail MSDS

Safety Information

[ Hazard Codes ]:
T: Toxic;Xi: Irritant;

[ Risk Phrases ]:
R25

[ Safety Phrases ]:
S45

[ RIDADR ]:
UN 2811 6.1/PG 3

[ WGK Germany ]:
3

[ RTECS ]:
FE6375500

[ HS Code ]:
2933990090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2933990090

[ Summary ]:
2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Related Compounds

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