Palonosetron HCl
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MedKoo CAT#: 100695

CAS#: 135729-62-3 (HCl); 135729-61-2 (free base).

Description: Palonosetron (INN, trade name Aloxi) is a 5-HT3 antagonist used in the prevention and treatment of chemotherapy-induced nausea and vomiting (CINV). It is used for the control of delayed CINV—nausea and vomiting and there are tentative data to suggest that it may be better than granisetron. Palonosetron is administered intravenously, as a single dose, 30 minutes before chemotherapy, or as a single oral capsule one hour before chemotherapy. The oral formulation was approved on August 22, 2008 for prevention of acute CINV alone, as a large clinical trial did not show oral administration to be as effective as intravenous use against delayed CINV. (Source: http://en.wikipedia.org/wiki/Palonosetron).


Chemical Structure

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Palonosetron HCl
CAS# 135729-62-3 (HCl); 135729-61-2 (free base).

Theoretical Analysis

MedKoo Cat#: 100695
Name: Palonosetron HCl
CAS#: 135729-62-3 (HCl); 135729-61-2 (free base).
Chemical Formula: C19H25ClN2O
Exact Mass:
Molecular Weight: 332.87
Elemental Analysis: C, 68.56; H, 7.57; Cl, 10.65; N, 8.42; O, 4.81

Price and Availability

Size Price Availability Quantity
500.0mg USD 350.0 2 Weeks
1.0g USD 650.0 2 Weeks
2.0g USD 1050.0 2 Weeks
5.0g USD 1950.0 2 Weeks
10.0g USD 2950.0 2 Weeks
20.0g USD 4250.0 2 Weeks
50.0g USD 6450.0 2 Weeks
100.0g USD 9950.0 2 Weeks
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Synonym: RS 25233-197; RS25233-197; RS-25233-197; RS25233-198; RS-25233-198; RS 25233-198; RS-25259-197; Palonosetron hydrochloride; US brand name: Aloxi.

IUPAC/Chemical Name: (R)-2-((S)-quinuclidin-3-yl)-2,3,3a,4,5,6-hexahydro-1H-benzo[de]isoquinolin-1-one hydrochloride

InChi Key: OLDRWYVIKMSFFB-KPVRICSOSA-N

InChi Code: InChI=1S/C19H24N2O.ClH/c22-19-16-6-2-4-14-3-1-5-15(18(14)16)11-21(19)17-12-20-9-7-13(17)8-10-20;/h2,4,6,13,15,17H,1,3,5,7-12H2;1H/t15-,17+;/m0./s1

SMILES Code: O=C1N([C@@H]2CN3CCC2CC3)C[C@@]4([H])C5=C1C=CC=C5CCC4.[H]Cl

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Preparing Stock Solutions

The following data is based on the product molecular weight 332.87 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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 1: Celio L, Frustaci S, Denaro A, Buonadonna A, Ardizzoia A, Piazza E, Fabi A, Capobianco AM, Isa L, Cavanna L, Bertolini A, Bichisao E, Bajetta E; for the Italian Trials in Medical Oncology Group. Palonosetron in combination with 1-day versus 3-day dexamethasone for prevention of nausea and vomiting following moderately emetogenic chemotherapy: a randomized, multicenter, phase III trial. Support Care Cancer. 2010 Jun 25. [Epub ahead of print] PubMed PMID: 20574663.

2: Longo F, Mansueto G, Lapadula V, De Sanctis R, Quadrini S, Grande R, Gori B, Altavilla A, D'Antoni I, Del Signore E, Stumbo L, De Luca C, Cimadon B, Cortesi E, Gamucci T, Di Seri M. Palonosetron plus 3-day aprepitant and dexamethasone to prevent nausea and vomiting in patients receiving highly emetogenic chemotherapy. Support Care Cancer. 2010 Jun 16. [Epub ahead of print] PubMed PMID: 20552375.

3: Botrel TE, Clark OA, Clark L, Paladini L, Faleiros E, Pegoretti B. Efficacy of palonosetron (PAL) compared to other serotonin inhibitors (5-HT(3)R) in preventing chemotherapy-induced nausea and vomiting (CINV) in patients receiving moderately or highly emetogenic (MoHE) treatment: systematic review and meta-analysis. Support Care Cancer. 2010 May 22. [Epub ahead of print] PubMed PMID: 20495832.

4: Aapro MS, Walko CM. Aprepitant: drug-drug interactions in perspective. Ann Oncol. 2010 May 20. [Epub ahead of print] PubMed PMID: 20488873.

5: Rozzi A, Nardoni C, Corona M, Restuccia MR, Fabi A, Bria E, Minniti G, Lanzetta G. Palonosetron for the prevention of chemotherapy-induced nausea and vomiting in glioblastoma patients treated with temozolomide: a phase II study. Support Care Cancer. 2010 May 14. [Epub ahead of print] PubMed PMID: 20467757.

6: Yeh YC, McDonnell A, Klinger EV, Fowler B, Matta L, Voit D, Reddy P. Comparison of healthcare resource use between patients receiving ondansetron or palonosetron as prophylaxis for chemotherapy-induced nausea and vomiting. J Oncol Pharm Pract. 2010 May 7. [Epub ahead of print] PubMed PMID: 20452991.

7: Tomillero A, Moral MA. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2010 Jan-Feb;32(1):47-86. PubMed PMID: 20383346.

8: Saito M, Tsukuda M. Review of palonosetron: emerging data distinguishing it as a novel 5-HT(3) receptor antagonist for chemotherapy-induced nausea and vomiting. Expert Opin Pharmacother. 2010 Apr;11(6):1003-14. Review. Erratum in: Expert Opin Pharmacother. 2010 May;11(7):1231. PubMed PMID: 20307224.

9: Ripaldi M, Parasole R, De Simone G, D'Amico MR, Migliorati R, Zanotta G, Loffredo G, Petruzziello F, Poggi V. Palonosetron to prevent nausea and vomiting in children undergoing BMT. Efficacy and safety. Bone Marrow Transplant. 2010 Feb 22. [Epub ahead of print] PubMed PMID: 20173793.

10: Ruhlmann C, Herrstedt J. Palonosetron hydrochloride for the prevention of chemotherapy-induced nausea and vomiting. Expert Rev Anticancer Ther. 2010 Feb;10(2):137-48. Review. PubMed PMID: 20131990. on of safety and pharmacokinetics of consecutive multiple-day dosing of palonosetron in healthy subjects. J Clin Pharmacol. 2005 May;45(5):589-96. PubMed PMID: 15831783.



Additional Information

P alonosetron hydrochloride is the hydrochloride salt of palonosetron, a carbazole derivative and a selective serotonin receptor antagonist with antiemetic activity. Palonosetron competitively blocks the action of serotonin at 5-hydroxytryptamine type 3 (5-HT3) receptors located on vagal afferents in the chemoreceptor trigger zone (CTZ), resulting in suppression of chemotherapy-induced nausea and vomiting. The CTZ is located in the area postrema on the dorsal surface of the medulla oblongata at the caudal end of the fourth ventricle and outside the blood-brain barrier (BBB). Check for active clinical trials or closed clinical trials using this agent. (NCI Thesaurus)
 
Palonosetron is administered intravenously, as a single dose, 30 minutes before chemotherapy, or as a single oral capsule one hour before chemotherapy. The oral formulation was approved on August 22, 2008 for prevention of acute CINV alone, as a large clinical trial did not show oral administration to be as effective as intravenous use against delayed CINV.
 
ALOXI is an antiemetic and antinauseant agent. It is a serotonin subtype 3 (5-HT3) receptor antagonist with a strong binding affinity for this receptor. The empirical formula is C19H24N2O.HCl, with a molecular weight of 332.87. Palonosetron hydrochloride is a white to off-white crystalline powder. It is freely soluble in water, soluble in propylene glycol, and slightly soluble in ethanol and 2-propanol. ALOXI Injection is a sterile, clear, colorless, non-pyrogenic, isotonic, buffered solution for intravenous administration. Each 5 mL vial of ALOXI Injection contains 0.25 mg palonosetron base as hydrochloride, 207.5 mg mannitol, disodium edetate and citrate buffer in water for intravenous administration. The pH of the solution is 4.5 to 5.5.
 
Mechanism of Action
Palonosetron is a 5-HT3 receptor antagonist with a strong binding affinity for this receptor and little or no affinity for other receptors. Cancer chemotherapy may be associated with a high incidence of nausea and vomiting, particularly when certain agents, such as cisplatin, are used. 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 thought that chemotherapeutic agents produce nausea and vomiting by releasing serotonin from the enterochromaffin cells of the small intestine and that the released serotonin then activates 5-HT3 receptors located on vagal afferents to initiate the vomiting reflex.