Ondansetron Hydrochloride
Basic information
- CAS
99614-01-4- Standard SMILES
Cc1nccn1CC1CCc2c(c3ccccc3n2C)C1=O.Cl- InChIKey
MKBLHFILKIKSQM-UHFFFAOYSA-N- Molecular formula
- C18H20ClN3O
- Average molar mass
- 329.8 g/mol
- Monoisotopic mass
- 329.12949
Overview
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.
Names & identifiers
- Preferred name
- Ondansetron Hydrochloride
- IUPAC
- 9-methyl-3-[(2-methylimidazol-1-yl)methyl]-2,3-dihydro-1H-carbazol-4-one;hydrochloride
- English name
- Ondansetron hydrochloride
- Molecular formula
- C18H19N3O.ClH
- Molecular weight
- 329.82
Names & synonyms
ONDANSETRON HYDROCHLORIDE99614-01-4ONDANSETRON HClZophrenOndansetron HCl dihydrateNSC-665799ZOFRAN PRESERVATIVE FREE2999F27MADSN 307NSC665799Zofran and dextrose in plastic containerOndansetron hydrochloride preservative free
Show more names
sn307ZudanEMesetZofranOsetronGR 38032FNSC 665799GR 38032 HCl
DTXSID701027913Setofilm4H-Carbazol-4-one, 1,2,3,9-tetrahydro-9-methyl-3-((2-methyl-1H-imidazol-1-yl)methyl)-, monohydrochlorideOndansetron hydrochloride and dextrose in plastic containerONDANSETRON HYDROCHLORIDE ANHYDROUSOndemetOndansetron MonohydrochlorideGR-C507/75
Database identifiers
- CAS
99614-01-4- PubChem CID
- 68647
- DTXSID
DTXSID701027913- ChEMBL
CHEMBL1201111、CHEMBL3186492
Properties
Computed structural properties
- Topological polar surface area
- 39.8 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 2
- Heavy atoms
- 23
- Formal charge
- 0
- Complexity
- 440
Experimental & physicochemical properties
Solubility47.7 [ug/mL] (The mean of the results at pH 7.4)
Human Drugs
Breast Feeding; Lactation; Milk, Human; Antiemetics; Gastrointestinal Agents; Serotonin Antagonists; Serotonin 5-HT3 Receptor Antagonists
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Physicochemical properties
- Melting point
- 178.5 · 178.5-179.5°C
- storage temp.
- -20 °C · Inert atmosphere,Store in freezer, under -20°C
- solubility
- 2 O: · H2O: >5 mg/mL
- form
- solid
- pka
- 7.4 · 7.4(at 25℃)
- color
- white
- BCS Class
- 1 · 1 (CLogP), 3 (LogP)
- InChI
- 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
- InChIKey
- MKBLHFILKIKSQM-UHFFFAOYSA-N
- SMILES
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Danger
H301 (98.8%): Toxic if swallowed [Danger Acute toxicity, oral]
P264, P264+P265, P270, P273, P280, P301+P316, P305+P354+P338, P317, P321, P330, P391, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 82 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesAcute Tox. 3 (98.8%)
Toxicology
TreatmentThere is no specific antidote for ondansetron overdose. Patients should be managed with appropriate supportive therapy. (L1712)
Exposure RoutesOndansetron is well absorbed after oral administration and undergoes limited first-pass metabolism.
Toxicity Summary
Ondansetron is a selective serotonin 5-HT<sub>3</sub> receptor antagonist. The antiemetic activity of the drug is brought about through the inhibition of 5-HT<sub>3</sub> receptors present both centrally (medullary chemoreceptor zone) and peripherally (GI tract). This inhibition of 5-HT<sub>3</sub> receptors in turn inhibits the visceral afferent stimulation of the vomiting center, likely indirectly at the level of the area postrema, as well as through direct inhibition of serotonin activity within the area postrema and the chemoreceptor trigger zone.
Signs and SymptomsLow blood pressure and fainting, sudden blindness, severe constipation
Chemistry & industry
Pharmacology
Metabolism/MetabolitesHepatic
Half Life: 5.7 hours
FDA Pharmacological Classification
ONDANSETRON HCL
Serotonin-3 Receptor Antagonist [EPC]; Serotonin 3 Receptor Antagonists [MoA]
ONDANSETRON HYDROCHLORIDE
Serotonin 3 Receptor Antagonists [MoA]; Serotonin-3 Receptor Antagonist [EPC]
ONDANSETRON TABLETS
Serotonin 3 Receptor Antagonists [MoA]; Serotonin-3 Receptor Antagonist [EPC]
MeSH Pharmacological Classification
Drugs used to prevent NAUSEA or VOMITING.
Agents, usually topical, that relieve itching (pruritus).
Drugs that bind to but do not activate SEROTONIN 5-HT3 RECEPTORS, thereby blocking the actions of SEROTONIN or SEROTONIN 5-HT3 RECEPTOR AGONISTS.
Uses & manufacturing
UsesFor the prevention of nausea and vomiting associated with emetogenic cancer chemotherapy, postoperation, and radiation. Also used for the treatment of postoperative nausea and vomiting.
Applications
UsesA specific serotonin (5-HT3) receptor antagonist. Antiemetic.
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Compound notes
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