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Ondansetron HCl (formerly GR 38032F, GR-C507/75; SN307; GR-C507/75; GRC-50775; GR-38032; SN-307; GR38032; Zofran) is an anti-emetic drug that acts as a potent serotonin 5-HT3 receptor antagonist. Its main purpose is to avoid nausea and vomiting that can result from radiation therapy and chemotherapy for cancer. At 0.3 nM, the 5-HT3A receptor antagonist ondansetron reversibly inhibited the 5-HT (30 microM) signal by 70%, and at 3 nM, it completely eliminated the response. Acute ondansetron administration improved auditory gating at 0.33 and 1 mg/kg, IP, but had no effect at the lowest tested dose of 0.1 mg/kg IP.
Physicochemical Properties
| Molecular Formula | C18H19N3O |
| Molecular Weight | 329.82 |
| Exact Mass | 329.129 |
| Elemental Analysis | C, 65.55; H, 6.11; Cl, 10.75; N, 12.74; O, 4.85 |
| CAS # | 99614-01-4 |
| Related CAS # | Ondansetron hydrochloride dihydrate; 103639-04-9; Ondansetron; 99614-02-5; Ondansetron-d3 hydrochloride; 1346605-02-4; Ondansetron-d6 hydrochloride; 1225442-22-7 |
| PubChem CID | 68647 |
| Appearance | Solid powder |
| Density | 1.27g/cm3 |
| Boiling Point | 546ºC at 760mmHg |
| Melting Point | 178.5-179.5ºC |
| Flash Point | 284ºC |
| LogP | 3.93 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 2 |
| Rotatable Bond Count | 2 |
| Heavy Atom Count | 23 |
| Complexity | 440 |
| Defined Atom Stereocenter Count | 0 |
| SMILES | O=C1C(CN2C=CN=C2C)CCC(N3C)=C1C4=C3C=CC=C4.[H]Cl |
| InChi Key | MKBLHFILKIKSQM-UHFFFAOYSA-N |
| InChi Code | InChI=1S/C18H19N3O.ClH/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 |
| Chemical Name | 9-methyl-3-[(2-methylimidazol-1-yl)methyl]-2,3-dihydro-1H-carbazol-4-one;hydrochloride |
| Synonyms | GR 38032F; GRC 50775; SN 307; GR-38032F; GRC-50775; SN-307; GR38032F; GRC50775; SN307; GR 38032F; trade name: Zofran |
| HS Tariff Code | 2934.99.9001 |
| Storage |
Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition | Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs) |
Biological Activity
| Targets | 5-HT3 Receptor | ||
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| Cell Assay | Ondansetron, an antagonist of the 5-HT3 receptor, inhibited the transient inward currents that 5-HT evoked (EC50 = 3.4 microM; Hill coefficient = 1.8) (IC50 = 103 pM). Ondansetron, a 5-HT3A receptor antagonist, reversibly inhibited the 5-HT (30 microM) signal by 70% at 0.3 nM and completely eliminated the response at 3 nM. | ||
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| Toxicity/Toxicokinetics |
Effects During Pregnancy and Lactation ◉ Summary of Use during Lactation Ondansetron is frequently used for nausea during and after cesarean section, usually in doses of 4 to 8 mg intravenously. Use during and after cesarean section appears to not affect the onset of breastfeeding. No adverse infant effects have been reported in this setting or among women who received ondansetron postpartum in a pharmacokinetic study. Use of ondansetron in nursing mothers beyond the immediate postpartum setting has not been studied well, but the drug is labeled for use in infants as young as 1 month of age. A computer model demonstrated that the amounts in milk are much less than this dose. No special precautions are required. ◉ Effects in Breastfed Infants In a pharmacokinetic study of 78 women who received ondansetron intravenously postpartum, no adverse effects were reported in their breastfed infants. ◉ Effects on Lactation and Breastmilk A randomized, double-blind study compared placebo to intravenous ondansetron 4 mg given after cesarean section as prophylaxis for postoperative nausea and vomiting. There was no difference in the time of the first breastfeeding between the two groups. In a retrospective study of women undergoing cesarean section deliveries, 3 regimens were compared: dexmedetomidine before anesthesia and during delivery (n = 115), normal saline before anesthesia and during delivery and dexmedetomidine after delivery (n = 109), and normal saline before anesthesia and during delivery (n = 168). All women received ondansetron 4 mg as needed and before removal of sutures. The average total amount of ondansetron consumed in the women ranged from 6 mg to 9 mg in the various groups. The time to first production of milk was similar in all groups (25 to 28 minutes). |
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| References |
[1]. Ondansetron, dexamethasone and an NK1 antagonist block radiation sickness in mice. Pharmacol Biochem Behav. 2005 Sep;82(1):24-9. [2]. Ondansetron. A review of its pharmacology and preliminary clinical findings in novel applications. Drugs. 1996 Nov;52(5):773-94. |
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| Additional Infomation |
Ondansetron Hydrochloride is the hydrochloride salt of the racemic form of ondansetron, a carbazole derivative and a selective, competitive serotonin 5-hydroxytryptamine 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. A competitive serotonin type 3 receptor antagonist. It is effective in the treatment of nausea and vomiting caused by cytotoxic chemotherapy drugs, including cisplatin, and has reported anxiolytic and neuroleptic properties. See also: Ondansetron (has active moiety). Drug Indication Treatment of alcohol use disorder |
Solubility Data
| Solubility (In Vitro) |
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| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples. Injection Formulations (e.g. IP/IV/IM/SC) Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] *Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin → 500 μL Saline) Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO → 100 μLPEG300 → 200 μL castor oil → 650 μL Saline) Injection Formulation 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (i.e. 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline) Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH → 900 μL Corn oil) Injection Formulation 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Oral Formulations Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). Oral Formulation 3: Dissolved in PEG400 Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose Oral Formulation 6: Mixing with food powders Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.0320 mL | 15.1598 mL | 30.3196 mL | |
| 5 mM | 0.6064 mL | 3.0320 mL | 6.0639 mL | |
| 10 mM | 0.3032 mL | 1.5160 mL | 3.0320 mL |