CAS 99614-02-5|Zophren|PMS-ondansetron|9-methyl-3-[(2-methyl-1H-imidazol-1-yl)methyl]-2,3,4,9-tetrahydro-1H-carbazol-4-one|Sandoz ondansetron|ondansetron|PHL-ondansetron|Zofran ODT|Ondansetron|Apo-o...

General Information

Structure

Molecular Formula

C₁₈H₁₉N₃O

Molecular Mass

293.36296

Exact Mass

293.15281224

Charge

InChI

InChI=1S/C18H19N3O/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

InChIKey

FELGMEQIXOGIFQ-UHFFFAOYSA-N

Canonic Smiles

O=C1C(CCc2c1c1ccccc1n2C)Cn1ccnc1C

Isomeric Smiles

O=C1C(CCc2n(c3c(c12)cccc3)C)Cn1c(ncc1)C

Calculated Properties

Provided by Enamine

CLogP

2.72

H Donor

Polar Surface Area

39.82

Rotatable Bonds

JChem

Polar Surface Area

39.82

H Donor

H Acceptors

Rotatable Bonds

Lipinski's Rule of Five

true

Log P

2.35

LogD (pH = 5.5)

1.34

LogD (pH = 7.4)

2.11

Acid pKa

16.13

Molar Refractivity

86.78

Polarizability

34.02

LOG S

-2.15

Data Source

Academic Data

Commercial Catalog

Data Source

Names and Identifiers

Brand Name

ZudanZofran ODTZofranPMS-ondansetronRatio-ondansetronApo-ondansetronZophrenSandoz ondansetronPHL-ondansetronNovo-ondansetron

Synonyms

OndansetronZofran9-Methyl-3-((2-methyl-1H-imidazol-1-yl)methyl)-2,3-dihydro-1H-carbazol-4(9H)-one1,2,3,4-tetrahydro-9-methyl-3-(2-methyl-1h-imidazol-1-ylmethyl)carbazol-4-one

IUPAC name

9-methyl-3-[(2-methyl-1H-imidazol-1-yl)methyl]-2,3,4,9-tetrahydro-1H-carbazol-4-one

IUPAC Traditional name

ondansetron

API Name

Ondansetron

Names and Identifiers

Registration numbers

CAS Number

PubChem SID

PubChem CID

DrugBank ID

Registration numbers

Properties

Physical Property

Hydrophobicity(logP)

2.4

Product Information

Salt Data

Free Base

Purity

95+%

97%

Safety Information

Storage Condition

-20°C

Pharmacology Properties

Target

Serotonin receptor

Properties

Related Proteins

No Data Available

Click here to submit data

Molecular Spectra

No Data Available

Click here to submit data

Molecule Details

DrugBank

DB00904

Drug Groups

approved

Description

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. [PubChem]

Indication

For the prevention of nausea and vomiting associated with emetogenic cancer chemotherapy, postoperation, and radiation. Also used for the treatment of postoperative nausea and vomiting.

Pharmacology

Ondansetron is a highly specific and selective serotonin 5-HT₃ receptor antagonist, not shown to have activity at other known serotonin receptors and with low affinity for dopamine receptors. The serontonin 5-HT₃ receptors are located on the nerve terminals of the vagus in the periphery, and centrally in the chemoreceptor trigger zone of the area postrema. The temporal relationship between the emetogenic action of emetogenic drugs and the release of serotonin, as well as the efficacy of antiemetic agents suggest that chemotherapeutic agents release serotonin from the enterochromaffin cells of the small intestine by causing degenerative changes in the GI tract. The serotonin then stimulates the vagal and splanchnic nerve receptors that project to the medullary vomiting center, as well as the 5-HT₃ receptors in the area postrema, thus initiating the vomiting reflex, causing nausea and vomiting.

Toxicity

Low blood pressure and fainting, sudden blindness, severe constipation

Affected Organisms

Humans and other mammals

Biotransformation

Hepatic

Absorption

Ondansetron is well absorbed after oral administration and undergoes limited first-pass metabolism.

Half Life

5.7 hours

Protein Binding

70%-76% (Plasma protein binding)

Clearance

* 0.38 L/h/kg [Normal Adult Volunteers (19-40 yrs)]
* 0.32 L/h/kg [Normal Adult Volunteers (61-74 yrs)]
* 0.26 L/h/kg [Normal Adult Volunteers (>=75 yrs)]

References

• Ramsook C, Sahagun-Carreon I, Kozinetz CA, Moro-Sutherland D: A randomized clinical trial comparing oral ondansetron with placebo in children with vomiting from acute gastroenteritis. Ann Emerg Med. 2002 Apr;39(4):397-403. [Pubmed]

• Yilmaz HL, Yildizdas RD, Sertdemir Y: Clinical trial: oral ondansetron for reducing vomiting secondary to acute gastroenteritis in children--a double-blind randomized study. Aliment Pharmacol Ther. 2010 Jan;31(1):82-91. Epub . [Pubmed]

• Gregory RE, Ettinger DS: 5-HT3 receptor antagonists for the prevention of chemotherapy-induced nausea and vomiting. A comparison of their pharmacology and clinical efficacy. Drugs. 1998 Feb;55(2):173-89. [Pubmed]

• Gan TJ: Selective serotonin 5-HT3 receptor antagonists for postoperative nausea and vomiting: are they all the same? CNS Drugs. 2005;19(3):225-38. [Pubmed]

External Links

• [Wikipedia]

• [RxList]

• [PDRhealth]

• [Drugs.com]

Selleck Chemicals

S1996

Biological Activity:
Ondansetron (Zofran) is a serotonin 5-HT3 receptor antagonist used mainly as an antiemetic. Its effects are thought to be on both peripheral and central nerves. Ondansetron (Zofran) decreases the activity of the vagus nerve, which deactivates the vomiting center in the medulla oblongata, and also inhibits serotonin receptors in the chemoreceptor trigger zone. Ondansetron (Zofran) has little effect on vomiting caused by motion sickness, and does not have any effect on dopamine receptors or muscarinic receptors. The 5-HT3 receptor antagonists are the primary drugs used to treat and prevent chemotherapy-induced nausea and vomiting (CINV). Ondansetron (Zofran) is also effective in controlling post-operative nausea and vomiting (PONV) and post-radiation nausea and vomiting, and is a possible therapy for nausea and vomiting due to acute or chronic medical illness or acute gastroenteritis. Although ondansetron is highly effective, the high cost of the brand-name version had limited its use to controlling PONV and CINV.Ondansetron (Zofran) is also used off-label to treat hyperemesis gravidarum in pregnant women, but there is no conclusive data available on its safety in pregnancy, especially during the first trimester. Ondansetron (Zofran) is also used to treat cyclic vomiting syndrome. [1]References on Ondansetron (Zofran)[1] http://en.wikipedia.org/wiki/Ondansetron, ,

Molecule Details

References

PubChem Literature

From Data Sources

• Gan TJ: Selective serotonin 5-HT3 receptor antagonists for postoperative nausea and vomiting: are they all the same? CNS Drugs. 2005;19(3):225-38. Pubmed

• http://en.wikipedia.org/wiki/Ondansetron

References

Bioactivity

PubChem BioAssay

Bioactivity

Navigation

General Information

Calculated Properties

• RDKit

• Provided by Enamine

• JChem

Data Source

• Academic Data

• Commercial Catalog

Names and Identifiers

• Brand Name

• Synonyms

• IUPAC name

• IUPAC Traditional name

• API Name

Names and Identifiers

Registration numbers

• CAS Number

• PubChem SID

• PubChem CID

• DrugBank ID

Properties

• Physical Property

• Product Information

• Safety Information

• Pharmacology Properties

Related Proteins

Molecular Spectra

Molecule Details

• DrugBank

• Selleck Chemicals

References

• PubChem Literature

• From Data Sources

Bioactivity

• PubChem BioAssay

Brand Name

ZudanZofran ODTZofranPMS-ondansetronRatio-ondansetronApo-ondansetronZophrenSandoz ondansetronPHL-ondansetronNovo-ondansetron

Synonyms

OndansetronZofran9-Methyl-3-((2-methyl-1H-imidazol-1-yl)methyl)-2,3-dihydro-1H-carbazol-4(9H)-one1,2,3,4-tetrahydro-9-methyl-3-(2-methyl-1h-imidazol-1-ylmethyl)carbazol-4-one

IUPAC name

9-methyl-3-[(2-methyl-1H-imidazol-1-yl)methyl]-2,3,4,9-tetrahydro-1H-carbazol-4-one

IUPAC Traditional name

ondansetron

API Name

Ondansetron

CAS Number

99614-02-5

PubChem SID

16096424346504819

Physical Property

Hydrophobicity(logP)

2.4

Product Information

Salt Data

Free Base

Purity

95+%

97%

Safety Information

Storage Condition

-20°C

Pharmacology Properties

Target

Serotonin receptor

DrugBank

DB00904

Drug Groups

approved

Description

Indication

For the prevention of nausea and vomiting associated with emetogenic cancer chemotherapy, postoperation, and radiation. Also used for the treatment of postoperative nausea and vomiting.

Pharmacology

Toxicity

Low blood pressure and fainting, sudden blindness, severe constipation

Affected Organisms

Humans and other mammals

Biotransformation

Hepatic

Absorption

Ondansetron is well absorbed after oral administration and undergoes limited first-pass metabolism.

Half Life

5.7 hours

Protein Binding

70%-76% (Plasma protein binding)

Clearance

* 0.38 L/h/kg [Normal Adult Volunteers (19-40 yrs)]
* 0.32 L/h/kg [Normal Adult Volunteers (61-74 yrs)]
* 0.26 L/h/kg [Normal Adult Volunteers (>=75 yrs)]

References

• Gan TJ: Selective serotonin 5-HT3 receptor antagonists for postoperative nausea and vomiting: are they all the same? CNS Drugs. 2005;19(3):225-38. [Pubmed]

External Links

• [Wikipedia]

• [RxList]

• [PDRhealth]

• [Drugs.com]

Selleck Chemicals

S1996

From Data Sources

• Gan TJ: Selective serotonin 5-HT3 receptor antagonists for postoperative nausea and vomiting: are they all the same? CNS Drugs. 2005;19(3):225-38. Pubmed

• http://en.wikipedia.org/wiki/Ondansetron

Molecule

ID:780