(3R)-10-oxo-8-azatricyclo[5.3.1.03,8]undec-5-yl 1H-indole-3-carboxylate
Basic information
- CAS
115956-12-2- Standard SMILES
O=C(OC1CC2CC3C[C@H](C1)N2CC3=O)c1c[nH]c2ccccc12- InChIKey
UKTAZPQNNNJVKR-DBBXXEFVSA-N- Molecular formula
- C19H20N2O3
- Average molar mass
- 324.4 g/mol
- Monoisotopic mass
- 324.1473925
Overview
See also: Dolasetron (annotation moved to); Dolasetron Mesylate (annotation moved to).
Names & identifiers
- Preferred name
- (3R)-10-oxo-8-azatricyclo[5.3.1.03,8]undec-5-yl 1H-indole-3-carboxylate
- IUPAC
- [(7R)-10-oxo-8-azatricyclo[5.3.1.03,8]undecan-5-yl] 1H-indole-3-carboxylate
- English name
- dolasetron
- Molecular formula
- C19H20N2O3
- Molecular weight
- 324.37
Names & synonyms
HSDB 7565115956-12-2DOLASETRON MESYLATEExo Granisetron IsomerSCHEMBL1819898SCHEMBL4450258SCHEMBL29390207(3R)-10-oxo-8-azatricyclo[5.3.1.03,8]undec-5-yl 1H-indole-3-carboxylateUKTAZPQNNNJVKR-PIGZVRMJSA-N(2R,5S,6R,8S)-3-oxooctahydro-1H-2,6-methanoquinolizin-8-yl 1H-indole-3-carboxylate(2S,6R,8R)-3-oxooctahydro-2H-2,6-methanoquinolizin-8-yl 1H-indole-3-carboxylateDOLASETRON
Show more names
DolasteronDorasetronDolasetronumUnii-82wi2L7Q6edolasetron USP/EP/BPDolasetronum [inn-latin]Dolasetron, 10 mM in DMSOOctahydro-3-oxo-2,6-Methano-2H-quinolizin-8-yl Ester
Database identifiers
- CAS
115956-12-2- PubChem CID
- 60654
Properties
Computed structural properties
- XLogP
- 3.4
- Topological polar surface area
- 62.4 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 3
- Heavy atoms
- 24
- Formal charge
- 0
- Complexity
- 535
Experimental & physicochemical properties
LogP2.1
Solubility2.61e-01 g/L
Melting Point278 °C
Physical DescriptionSolid
Physicochemical properties
- Melting point
- 278 · 278 ºC
- Boiling point
- 535.1 · 535.1±50.0 °C(Predicted)
- Density
- 1.37 · 1.37±0.1 g/cm3(Predicted)
- storage temp.
- 2 · Sealed in dry,2-8°C
- solubility
- Chloroform (Slightly), DMSO (Slightly), Methanol (Sparingly)
- pka
- 15.36 · 15.36±0.30(Predicted)
- form
- Solid
- color
- White
- Water Solubility
- Soluble
- CAS DataBase Reference
- 115956 · 115956-12-2
- FDA UNII
- 82 WI2L7Q6E · 82WI2L7Q6E
- ATC code
- 4 AA04 · A04AA04
- Symbol(GHS)
- 5 · GHS05,GHS07
- Signal word
- Danger
- Hazard statements
- 302 · H302-H318
- Precautionary statements
- 264 · P264-P270-P280-P301+P312-P330-P305+P351+P338-P310-P501
- Hazardous Substances Data
- 115956 · 115956-12-2(Hazardous Substances Data)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- Signal word
- Danger
- Symbol(GHS)
- GHS05,GHS07
- Hazard statements
- H302-H318
- Precautionary statements
- P264-P270-P280-P301+P312-P330-P305+P351+P338-P310-P501
- Hazardous Substances Data
- 115956-12-2(Hazardous Substances Data)
Chemistry & industry
Pharmacology
Cellular LocationsMembrane
Applications
DescriptionDolasetron is an antagonist of the serotonin (5-HT) receptor subtype 5-HT3 (Ki = 20 nM). It is selective for 5-HT3 receptors over 5-HT1A, 5-HT1B, 5-HT2, dopamine D2, α1-, α2-, β-adrenergic, M1-5 muscarinic acetylcholine, and neurokinin-1 (NK1) receptors (IC50s = >10 μM for all). Dolasetron inhibits 5-HT-induced membrane currents in NG 108-15 cells (IC50 = 3.8 nM). It increases the latency to emesis and reduces the number of vomiting and retching episodes induced by cisplatin in ferrets when administered at doses of 0.5 or 2 mg/kg. Formulations containing dolasetron have been used in the prevention of postoperative or chemotherapy-induced nausea.
Usesprevention and treatment of postoperative nausea and vomiting
UsesDolasetron is a bridged pseudopelletierine derivative; specific serotonin (5HT3) receptor antagonist.It is used as antiemetic.
UsesBridged pseudopelletierine derivative; specific serotonin (5HT3) receptor antagonist. Antiemetic.
Upstream & downstream products
Downstream products
Additional notes
DefinitionChEBI: LSM-5418 is an indolyl carboxylic acid.
Related reactions
0 records
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Compound notes
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