CAS 103639-04-9 Zofran (HCID 59774)

Overview

Ondansetron hydrochloride is a member of carbazoles.

Names & identifiers

Preferred name: Zofran
IUPAC: 9-methyl-3-[(2-methylimidazol-1-yl)methyl]-2,3-dihydro-1H-carbazol-4-one;dihydrate;hydrochloride
English name: Ondansetron hydrochloride
Molecular formula: C18H22ClN3O2
Molecular weight: 347.84

Names & synonyms

ZofranRefChem:934563Ondansetron hydrochloride dihydrate103639-04-9Ondansetron hydrochloride hydrateSetrodonDTXSID90488579-methyl-3-[(2-methylimidazol-1-yl)methyl]-2,3-dihydro-1H-carbazol-4-one;dihydrate;hydrochlorideGR-38032FMFCD00374371CHEBI:7774DTXCID6028783

Show more names

AKOS NCG1-0013ondansetron hydOndansetronHclUsp28Ondansetron hydrochlODANSETRON HYDROCHLORIDEOndansetron hydrochloridOndansetronHClmonohydrateOndansetron hydrochlorideGR 38032SN 307NSC 665799Ondansetron impurity A CRS

Ondansetron (hydrochloride dihydrate)9-Methyl-3-((2-methyl-1H-imidazol-1-yl)methyl)-1,2,3,9-tetrahydro-4H-carbazol-4-one hydrochloride dihydrateKS-1091ONDANSETRON HYDROCHLORIDE [MART.]CAS-103639-04-94H-Carbazol-4-one,1,2,3,9-tetrahydro-9-methyl-3-[(2-methyl-1H-imidazol-1-yl)methyl]-,monohydrochloride, dihydrateUNII-NMH84OZK2BZensana

Database identifiers

CAS: 103639-04-9
PubChem CID: 59774
DTXSID: DTXSID9048857
ChEBI: CHEBI:7774
UNII: NMH84OZK2B
EC Number: 600-465-5

Properties

Computed structural properties

Topological polar surface area: 41.8 Å²
Hydrogen bond donors: 3
Hydrogen bond acceptors: 4
Rotatable bonds: 2
Heavy atoms: 25
Formal charge: 0
Complexity: 440

Experimental & physicochemical properties

Human DrugsBreast Feeding; Lactation; Milk, Human; Antiemetics; Gastrointestinal Agents; Serotonin Antagonists; Serotonin 5-HT3 Receptor Antagonists

Physicochemical properties

Melting point: 231 · 231-232 C
storage temp.: -20 °C · -20°C
solubility: 2 O: · H2O: >5mg/mL
form: powder
color: white
Water Solubility: 2 O: · H2O: >5mg/mL
InChI: InChI=1S/C18H19N3O.ClH.H2O/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;1H2
InChIKey: FELGMEQIXOGIFQ-ZDUSSCGKSA-N
SMILES: O=C1C(CCC2N(C)C3=CC=CC=C3C1=2)CN1C=CN=C1C.Cl.O
CAS DataBase Reference: 103639 · 103639-04-9(CAS DataBase Reference)
NCI Dictionary of Cancer Terms: ondansetron hydrochloride
FDA UNII: 84 OZK2B · NMH84OZK2B
NCI Drug Dictionary: ondansetron hydrochloride
UNSPSC Code: 41116107 · 41116107
NACRES: 32 · NA.32
Symbol(GHS): 5 · GHS05,GHS06,GHS09
Signal word: Danger
Hazard statements: 301 · H301-H318-H410
Precautionary statements: 273 · P273-P280-P301+P310+P330-P305+P351+P338+P310
PPE: 2 · Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
Hazard Codes: T,Xi
Risk Statements: 25 · 25-36/37/38-50/53-41
Safety Statements: 45 · 45-37/39-26-61-39
RIDADR: 2811 · UN 2811
WGK Germany: 3 · 3
RTECS: 6375500 · FE6375500
HazardClass: 6.1 · 6.1
PackingGroup: III
HS Code: 2933290000 · 2933290000
Storage Class: 6.1 C · 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
Hazard Classifications: 3 OralAquatic · Acute Tox. 3 OralAquatic Acute 1Aquatic Chronic 2Eye Dam. 1
Limited Quantities: 5 kg · 5.0 kg (11 lbs) (solid)
Excepted Quantities: Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)

Safety & regulation

GHS classification

GHS Classification · 4 items

Danger

H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]

P264, P264+P265, P270, P273, P280, P301+P316, P305+P351+P338, P305+P354+P338, P317, P321, P330, P337+P317, P391, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 117 reports by companies from 16 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Hazard Classes and CategoriesAcute Tox. 3 (100%)

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 · 1 item

Ondansetron is a selective serotonin 5-HT3 receptor antagonist. The antiemetic activity of the drug is brought about through the inhibition of 5-HT3 receptors present both centrally (medullary chemoreceptor zone) and peripherally (GI tract). This inhibition of 5-HT3 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

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation

Safety data

PPE: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
wgk: 3
rtecs: FE6375500
ridadr: UN 2811
hs_code: 2933290000
risk_code: 25-36/37/38-50/53-41
Signal word: Danger
Symbol(GHS): GHS05,GHS06,GHS09
hazard_code: T,Xi
safety_code: 45-37/39-26-61-39
hazard_class: 6.1
Storage Class: 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
packing_group: III
Hazard statements: H301-H318-H410
Limited Quantities: 5.0 kg (11 lbs) (solid)
Excepted Quantities: Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)
Hazard Classifications: Acute Tox. 3 OralAquatic Acute 1Aquatic Chronic 2Eye Dam. 1
Precautionary statements: P273-P280-P301+P310+P330-P305+P351+P338+P310

Chemistry & industry

Pharmacology

Metabolism/MetabolitesHepatic Half Life: 5.7 hours

MeSH Pharmacological Classification · 3 items

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 · 6 items

DescriptionOndansetron hydrochloride is a selective 5HT3-antagonist approved for the management of nausea and vomiting induced by cancer chemotherapy and radiotherapy. It is reported to have a superior side-effect profile compared with metoclopramide, representing an important advance in the treatment of nausea and vomiting associated with chemotherapy. Ondansetron hydrochloride is the first specific 5HT3-antagonist to reach the market. It is also under investigation for a number of other indications, including anxiety and schizophrenia.

UsesAntiemetic;Serotonergic receptor antagonist

UsesA serotonin type 3 receptor antagonist.

UsesThese Secondary Standards are qualified as Certified Reference Materials. These are suitable for use in several analytical applications including but not limited to pharma release testing, pharma method development for qualitative and quantitative analyses, food and beverage quality control testing, and other calibration requirements.

UsesOndansetron hydrochloride dihydrate has been used as a 5-HT3 antagonist to attenuate rostro ventromedial medulla (RVM)/cholecystokinin (CCK)-induced mechanical hypersensitivity and to block the effects of trichostatin A (TSA) on 5-HT3 protein.

General DescriptionOndansetron Hydrochloride acts as a 5HT3 (serotonin) antagonist and is a powerful antiemetic drug. It is widely used for the prevention and treatment of nausea and vomiting related to post-operative states, cancer chemotherapy and radiotherapy, and chronic medical illness. It has been found to exhibit inconsistent bioavailability resulting from its poor aqueous solubility and high first-pass hepatic metabolism.Pharmaceutical secondary standards for application in quality control, provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards.