Ondansetron

Modify Date: 2024-01-02 10:21:44

Ondansetron Structure
Ondansetron structure
 Common Name Ondansetron
CAS Number 99614-02-5 Molecular Weight 293.363
Density 1.3±0.1 g/cm3 Boiling Point 546.0±30.0 °C at 760 mmHg
Molecular Formula C18H19N3O Melting Point 231 - 232ºC
MSDS N/A Flash Point 284.0±24.6 °C

 Use of Ondansetron


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].

 Names

Name 9-Methyl-3-((2-methyl-1H-imidazol-1-yl)methyl)-2,3-dihydro-1H-carbazol-4(9H)-one
Synonym More Synonyms

 Ondansetron 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
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.

 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

Material Safety Data Sheet
Section1. Identification of the substance
Product Name: Ondansetron
Synonyms:
Section2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
Section3. Composition/information on ingredients.
Ingredient name:Ondansetron
CAS number:99614-02-5
Section4. First aid measures
Skin contact:Immediately wash skin with copious amounts of water for at least 15 minutes while removing
contaminated clothing and shoes. If irritation persists, seek medical attention.
Eye contact:Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
flushing of the eyes by separating the eyelids with fingers. If irritation persists, seek medical
attention.
Inhalation:Remove to fresh air. In severe cases or if symptoms persist, seek medical attention.
Ingestion:Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.
Section5. Fire fighting measures
In the event of a fire involving this material, alone or in combination with other materials, use dry
powder or carbon dioxide extinguishers. Protective clothing and self-contained breathing apparatus
should be worn.
Section6. Accidental release measures
Personal precautions: Wear suitable personal protective equipment which performs satisfactorily and meets local/state/national
standards.
Respiratory precaution:Wear approved mask/respirator
Hand precaution:Wear suitable gloves/gauntlets
Skin protection:Wear suitable protective clothing
Eye protection:Wear suitable eye protection
Methods for cleaning up: Mix with sand or similar inert absorbent material, sweep up and keep in a tightly closed container
for disposal. See section 12.
Environmental precautions: Do not allow material to enter drains or water courses.
Section7. Handling and storage
Handling:This product should be handled only by, or under the close supervision of, those properly qualified
in the handling and use of potentially hazardous chemicals, who should take into account the fire,
health and chemical hazard data given on this sheet.
Store in closed vessels.
Storage:
Section8. Exposure Controls / Personal protection
Engineering Controls: Use only in a chemical fume hood.
Personal protective equipment: Wear laboratory clothing, chemical-resistant gloves and safety goggles.
General hydiene measures: Wash thoroughly after handling. Wash contaminated clothing before reuse.
Section9. Physical and chemical properties
Appearance:Not specified
Boiling point:No data
No data
Melting point:
Flash point:No data
Density:No data
Molecular formula:C18H19N3O
Molecular weight:293.4
Section10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide, nitrogen oxides.
Section11. Toxicological information
No data.
Section12. Ecological information
No data.
Section13. Disposal consideration
Arrange disposal as special waste, by licensed disposal company, in consultation with local waste
disposal authority, in accordance with national and regional regulations.
Section14. Transportation information
Non-harzardous for air and ground transportation.
Section15. Regulatory information
No chemicals in this material are subject to the reporting requirements of SARA Title III, Section
302, or have known CAS numbers that exceed the threshold reporting levels established by SARA
Title III, Section 313.

SECTION 16 - ADDITIONAL INFORMATION
N/A

 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

 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%

 Synonyms

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
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