Ondansetron hydrochloride
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MedKoo CAT#: 100676

CAS#: 99614-02-5

Description: This medication is used alone or with other medications to prevent nausea and vomiting caused by cancer drug treatment (chemotherapy) and radiation therapy. It is also used to prevent and treat nausea and vomiting after surgery. It works by blocking one of the body's natural substances (serotonin) that causes vomiting.


Chemical Structure

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Ondansetron hydrochloride
CAS# 99614-02-5

Theoretical Analysis

MedKoo Cat#: 100676
Name: Ondansetron hydrochloride
CAS#: 99614-02-5
Chemical Formula: C18H19N3O
Exact Mass: 293.15281
Molecular Weight: 293.36
Elemental Analysis: C, 73.69; H, 6.53; N, 14.32; O, 5.45

Price and Availability

Size Price Availability Quantity
5.0mg USD 200.0 2 Weeks
10.0mg USD 250.0 2 Weeks
25.0mg USD 300.0 2 Weeks
50.0mg USD 350.0 2 Weeks
100.0mg USD 400.0 2 Weeks
200.0mg USD 450.0 2 Weeks
500.0mg USD 500.0 2 Weeks
1.0g USD 550.0 2 Weeks
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Related CAS #: 103639-04-9  

Synonym: US brand name: Zofran. Code names: GR 38032F; GRC50775; SN307. Chemical name: (RS)9methyl3(2methyl1Himidazol1yl)methyl23dihydro1Hcarbazol4(9H)one.

IUPAC/Chemical Name: 1, 2, 3, 9-tetrahydro-9-methyl-3-[(2-methyl-1H-imidazol-1- yl)methyl]-4H-carbazol-4-one, monohydrochloride, dihydrate

InChi Key: VRSLTNZJOUZKLX-UHFFFAOYSA-N

InChi Code: InChI=1S/C18H19N3O.ClH.2H2O/c1-12-19-9-10-21(12)11-13-7-8-16-17(18(13)22)14-5-3-4-6-15(14)20(16)2;;;/h3-6,9-10,13H,7-8,11H2,1-2H3;1H;2*1H2

SMILES Code: O=C1C(CN2C=CN=C2C)CCC(N3C)=C1C4=C3C=CC=C4.[H]Cl.[H]O[H].[H]O[H]

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Preparing Stock Solutions

The following data is based on the product molecular weight 293.36 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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 1: Billio A, Morello E, Clarke MJ. Serotonin receptor antagonists for highly emetogenic chemotherapy in adults. Cochrane Database Syst Rev. 2010 Jan 20;(1):CD006272. Review. PubMed PMID: 20091591.

2: Frost F, Dailler F, Duflo F. [Ondansetron: a meta-analysis on its efficacy to prevent postoperative nausea and vomiting after craniotomy in adults and children]. Ann Fr Anesth Reanim. 2010 Jan;29(1):19-24. Epub 2010 Jan 15. French. PubMed PMID: 20080017.

3: Pikó B, Bassam A. [Treatment of tumor therapy-induced nausea and vomiting]. Magy Onkol. 2009 Mar;53(1):39-45. Review. Hungarian. PubMed PMID: 19318325.

4: Saito M, Aogi K, Sekine I, Yoshizawa H, Yanagita Y, Sakai H, Inoue K, Kitagawa C, Ogura T, Mitsuhashi S. Palonosetron plus dexamethasone versus granisetron plus dexamethasone for prevention of nausea and vomiting during chemotherapy: a double-blind, double-dummy, randomised, comparative phase III trial. Lancet Oncol. 2009 Feb;10(2):115-24. Epub 2009 Jan 8. Erratum in: Lancet Oncol. 2010 Mar;11(3)226. PubMed PMID: 19135415.

5: Reddy GK, Gralla RJ, Hesketh PJ. Novel neurokinin-1 antagonists as antiemetics for the treatment of chemotherapy-induced emesis. Support Cancer Ther. 2006 Apr 1;3(3):140-2. PubMed PMID: 18632487.

6: Annemans L, Strens D, Lox E, Petit C, Malonne H. Cost-effectiveness analysis of aprepitant in the prevention of chemotherapy-induced nausea and vomiting in Belgium. Support Care Cancer. 2008 Aug;16(8):905-15. Epub 2007 Oct 27. PubMed PMID: 17965891.

7: Olver I, Shelukar S, Thompson KC. Nanomedicines in the treatment of emesis during chemotherapy: focus on aprepitant. Int J Nanomedicine. 2007;2(1):13-8. Review. PubMed PMID: 17722507; PubMed Central PMCID: PMC2673828.

8: Girish C, Manikandan S. Aprepitant: a substance P antagonist for chemotherapy induced nausea and vomiting. Indian J Cancer. 2007 Jan-Mar;44(1):25-30. Review. PubMed PMID: 17401221.

9: McNulty R. Are all 5-HT3 receptor antagonists the same? J Natl Compr Canc Netw. 2007 Jan;5(1):35-43. PubMed PMID: 17239324.

10: Lordick F, Ehlken B, Ihbe-Heffinger A, Berger K, Krobot KJ, Pellissier J, Davies G, Deuson R. Health outcomes and cost-effectiveness of aprepitant in outpatients receiving antiemetic prophylaxis for highly emetogenic chemotherapy in Germany. Eur J Cancer. 2007 Jan;43(2):299-307. Epub 2006 Nov 28. PubMed PMID: 17134890.



Additional Information

ondansetron hydrochloride is the hydrochloride salt of the racemic form of ondansetron, a carbazole derivative and a selective, competitive serotonin 5-hydroxytrptamine type 3 (5-HT3) receptor antagonist with antiemetic activity. Although its mechanism of action has not been fully characterized, ondansetron appears to competitively block the action of serotonin at 5HT3 receptors peripherally in the gastrointestinal tract as well as centrally in the area postrema of the CNS, where the chemoreceptor trigger zone (CTZ) for vomiting is located, resulting in the suppression of chemotherapy- and radiotherapy-induced nausea and vomiting. Check for active clinical trials or closed clinical trials using this agent. (NCI Thesaurus)
 
The active ingredient in ZOFRAN Injection and ZOFRAN Injection Premixed is ondansetron hydrochloride (HCl), the racemic form of ondansetron and a selective blocking agent of the serotonin 5-HT3 receptor type. Chemically it is (±) 1, 2, 3, 9-tetrahydro-9-methyl-3-[(2-methyl-1H-imidazol-1- yl)methyl]-4H-carbazol-4-one, monohydrochloride, dihydrate.
 
The empirical formula is C18H19N3O•HCl•2H2O, representing a molecular weight of 365.9. Ondansetron HCl is a white to off-white powder that is soluble in water and normal saline. Sterile Injection for Intravenous (I.V.) or Intramuscular (I.M.) Administration: Each 1 mL of aqueous solution in the 2-mL single-dose vial contains 2 mg of ondansetron as the hydrochloride dihydrate; 9.0 mg of sodium chloride, USP; and 0.5 mg of citric acid monohydrate, USP and 0.25 mg of sodium citrate dihydrate, USP as buffers in Water for Injection, USP. Each 1 mL of aqueous solution in the 20-mL multidose vial contains 2 mg of ondansetron as the hydrochloride dihydrate; 8.3 mg of sodium chloride, USP; 0.5 mg of citric acid monohydrate, USP and 0.25 mg of sodium citrate dihydrate, USP as buffers; and 1.2 mg of methylparaben, NF and 0.15 mg of propylparaben, NF as preservatives in Water for Injection, USP. ZOFRAN Injection is a clear, colorless, nonpyrogenic, sterile solution. The pH of the injection solution is 3.3 to 4.0. Sterile, Premixed Solution for Intravenous Administration in Single-Dose, Flexible Plastic Containers: Each 50 mL contains ondansetron 32 mg (as the hydrochloride dihydrate); dextrose 2,500 mg; and citric acid 26 mg and sodium citrate 11.5 mg as buffers in Water for Injection, USP. It contains no preservatives. The osmolarity of this solution is 270 mOsm/L (approx.), and the pH is 3.0 to 4.0. The flexible plastic container is fabricated from a specially formulated, nonplasticized, thermoplastic co-polyester (CR3). Water can permeate from inside the container into the overwrap but not in amounts sufficient to affect the solution significantly. Solutions inside the plastic container also can leach out certain of the chemical components in very small amounts before the expiration period is attained. However, the safety of the plastic has been confirmed by tests in animals according to USP biological standards for plastic containers.