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Dolasetron Mesylate

Synopsis, Chemistry

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TABLET;ORAL - 100MG, TABLET;ORAL - 50MG, INJECTABLE;INJECTION - 100MG/5ML (20MG/ML), INJECTABLE;INJECTION - 12.5MG/0.625ML (20MG/ML)

TABLET;ORAL - 100MG
TABLET;ORAL - 50MG
INJECTABLE;INJECTION - 100MG/5ML (20MG/ML)
INJECTABLE;INJECTION - 12.5MG/0.625ML (20MG/ML)

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Also known as: Dolasetron mesylate, Anzemet, Mdl 73,147ef, 115956-13-3, Mdl 73147ef, 71yf100s3h

Molecular Formula

C₂₀H₂₄N₂O₆S

Molecular Weight

420.5 g/mol

InChI Key

PSGRLCOSIXJUAL-UMBGRREESA-N

Dolasetron Mesylate is an indole derivative with antiemetic activity. As a selective serotonin receptor antagonist, dolasetron mesylate competitively blocks the action of serotonin at 5HT3 receptors, resulting in suppression of chemotherapy- and radiotherapy-induced nausea and vomiting. (NCI04)

1 2D Structure

Dolasetron Mesylate

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

methanesulfonic acid;[(7S)-10-oxo-8-azatricyclo[5.3.1.03,8]undecan-5-yl] 1H-indole-3-carboxylate

2.1.2 InChI

InChI=1S/C19H20N2O3.CH4O3S/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;1-5(2,3)4/h1-4,9,11-14,20H,5-8,10H2;1H3,(H,2,3,4)/t11?,12-,13?,14?;/m0./s1

2.1.3 InChI Key

PSGRLCOSIXJUAL-UMBGRREESA-N

2.1.4 Canonical SMILES

CS(=O)(=O)O.C1C2CC3CC(CC1N3CC2=O)OC(=O)C4=CNC5=CC=CC=C54

2.1.5 Isomeric SMILES

CS(=O)(=O)O.C1[C@H]2CC(CC3N2CC(=O)C1C3)OC(=O)C4=CNC5=CC=CC=C54

2.2 Synonyms

2.2.1 MeSH Synonyms

1. 1h-indole-3-carboxylic Acid, (6r,9as)-octahydro-3-oxo-2,6-methano-2h-quinolizin-8-yl Ester, Rel-, Methanesulfonate, Hydrate (1:1:1)

2. 1h-indole-3-carboxylic Acid, Octahydro-3-oxo-2,6-methano-2h-quinolizin-8-yl Ester, (2-alpha,6-alpha,8-alpha,9a-beta)-

3. 1h-indole-3-carboxylic Acid-trans-octahydro-3-oxo-2,6-methano-2h-quinolizin-8-yl Ester Methanesulfonate

4. Anzemet

5. Dolasetron

6. Dolasetron Mesilate Monohydrate

7. Dolasetron Mesylate

8. Dolasetron Mesylate Monohydrate

9. Indole-3-carboxylic Acid, Ester With (8r)-hexahydro-8-hydroxy-2,6-methano-2h-quinolizin-3(4h)-one

10. Mdl 73,147ef

11. Mdl 73147ef

12. Mdl-73147ef

13. Octahydro-3-oxo-2,6-methano-2h-quinolizin-8-yl 1h-indole-3-carboxylate

2.2.2 Depositor-Supplied Synonyms

1. Dolasetron Mesylate

2. Anzemet

3. Mdl 73,147ef

4. 115956-13-3

5. Mdl 73147ef

6. 71yf100s3h

7. Unii-71yf100s3h

8. Dolasetron Mesylate [usan:usp]

9. Indole-3-carboxylic Acid, Ester With (8r)-hexahydro-8-hydroxy-2,6-methano-2h-quinolizin-3(4h)-one, Monomethanesulfonate

10. Hms3886o16

11. S5679

12. Akos025402394

13. Ac-8828

14. E83754

15. Q27265996

2.3 Create Date

2008-07-11

3 Chemical and Physical Properties

Molecular Formula	C₂₀H₂₄N₂O₆S
Molecular Weight	420.5 g/mol
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	7
Rotatable Bond Count	3
Exact Mass	420.13550766 g/mol
Monoisotopic Mass	420.13550766 g/mol
Topological Polar Surface Area	125 Å²
Heavy Atom Count	29
Formal Charge	0
Complexity	627
Isotope Atom Count	0
Defined Atom Stereocenter Count	1
Undefined Atom Stereocenter Count	1
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	2

4 Pharmacology and Biochemistry

4.1 MeSH Pharmacological Classification

Antiemetics

Drugs used to prevent NAUSEA or VOMITING. (See all compounds classified as Antiemetics.)

Serotonin 5-HT3 Receptor Antagonists

Drugs that bind to but do not activate SEROTONIN 5-HT3 RECEPTORS, thereby blocking the actions of SEROTONIN or SEROTONIN 5-HT3 RECEPTOR AGONISTS. (See all compounds classified as Serotonin 5-HT3 Receptor Antagonists.)

4.2 FDA Pharmacological Classification

4.2.1 Pharmacological Classes

Serotonin-3 Receptor Antagonist [EPC]; Serotonin 3 Receptor Antagonists [MoA]