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115956-12-2 molecular structure
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(3R)-10-oxo-8-azatricyclo[5.3.1.0^{3,8}]undecan-5-yl 1H-indole-3-carboxylate

ChemBase ID: 637
Molecular Formular: C19H20N2O3
Molecular Mass: 324.3737
Monoisotopic Mass: 324.14739251
SMILES and InChIs

SMILES:
O(C1CC2N3[C@H](CC(C2)C(=O)C3)C1)C(=O)c1c2c([nH]c1)cccc2
Canonical SMILES:
O=C1CN2C3CC1C[C@@H]2CC(C3)OC(=O)c1c[nH]c2c1cccc2
InChI:
InChI=1S/C19H20N2O3/c22-18-10-21-12-5-11(18)6-13(21)8-14(7-12)24-19(23)16-9-20-17-4-2-1-3-15(16)17/h1-4,9,11-14,20H,5-8,10H2/t11?,12-,13?,14?/m1/s1
InChIKey:
UKTAZPQNNNJVKR-DBBXXEFVSA-N

Cite this record

CBID:637 http://www.chembase.cn/molecule-637.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(3R)-10-oxo-8-azatricyclo[5.3.1.0^{3,8}]undecan-5-yl 1H-indole-3-carboxylate
IUPAC Traditional name
dolasetron
Brand Name
Anzemet
Dolasetronum [INN-Latin]
Dolasteron
Synonyms
Dolasetron
CAS Number
115956-12-2
PubChem SID
46505209
160964100
PubChem CID
60654

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID
DrugBank DB00757 external link
PubChem 60654 external link
Data Source Data ID Price

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 12.182263  H Acceptors
H Donor LogD (pH = 5.5) 1.923664 
LogD (pH = 7.4) 2.3176217  Log P 2.3258903 
Molar Refractivity 89.3352 cm3 Polarizability 35.947193 Å3
Polar Surface Area 62.4 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 2.41  LOG S -3.09 
Solubility (Water) 2.61e-01 g/l 

PROPERTIES

PROPERTIES

Physical Property Bioassay(PubChem)
Solubility
Freely soluble in water expand Show data source
Hydrophobicity(logP)
2.1 expand Show data source

DETAILS

DETAILS

DrugBank DrugBank
DrugBank - DB00757 external link
Item Information
Drug Groups approved
Description Dolasetron is an antinauseant and antiemetic agent indicated for the prevention of nausea and vomiting associated with moderately-emetogenic cancer chemotherapy and for the prevention of postoperative nausea and vomiting. Dolasetron is a highly specific and selective serotonin 5-HT3 receptor antagonist. This drug has not shown to have activity at other known serotonin receptors, and has low affinity for dopamine receptors.
Indication For the prevention of nausea and vomiting associated with emetogenic cancer chemotherapy, including initial and repeat courses of chemotherapy. Also used for the prevention of postoperative nausea and vomiting. This drug can be used intravenously for the treatment of postoperative nausea and vomiting.
Pharmacology Dolasetron 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. It is structurally and pharmacologically related to other 5-HT3 receptor agonists. 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. It is suggested 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.
Affected Organisms
Humans and other mammals
Biotransformation Hepatic
Absorption Orally-administered dolasetron is well absorbed
Half Life 8.1 hours
Protein Binding 69-77%
Elimination Hydrodolasetron is eliminated by multiple routes, including renal excretion and, after metabolism, mainly glucuronidation, and hydroxylation.
Distribution * 5.8 L/kg [adults]
Clearance * Apparent cl=9.4 mL/min/kg [Healthy volunteers with IV treatment dose up to 5 mg/kg]
References
Balfour JA, Goa KL: Dolasetron. A review of its pharmacology and therapeutic potential in the management of nausea and vomiting induced by chemotherapy, radiotherapy or surgery. Drugs. 1997 Aug;54(2):273-98. [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
Drugs.com

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Balfour JA, Goa KL: Dolasetron. A review of its pharmacology and therapeutic potential in the management of nausea and vomiting induced by chemotherapy, radiotherapy or surgery. Drugs. 1997 Aug;54(2):273-98. 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
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PATENTS

PATENTS

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