Alizapride

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MedKoo CAT#: 317167

CAS#: 59338-93-1(free base)

Description: Alizapride (Litican, Plitican, Superan, Vergentan) is a dopamine antagonist with prokinetic and antiemetic effects used in the treatment of nausea and vomiting, including postoperative nausea and vomiting. It is structurally related to metoclopramide and other benzamides.

Chemical Structure

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Alizapride
CAS# 59338-93-1(free base)
Instruction

Theoretical Analysis

MedKoo Cat#: 317167
Name: Alizapride
CAS#: 59338-93-1(free base)
Chemical Formula: C16H21N5O2
Exact Mass: 315.17
Molecular Weight: 315.380
Elemental Analysis: C, 60.94; H, 6.71; N, 22.21; O, 10.15

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

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Related CAS #: 59338-87-3 (HCl)   59338-93-1(free base)  

Synonym: Alizapride; 59338-93-1; Limican; Plitican; Vergentan; Superan; Alizaprida; Litican; MS 5080; MS5080; MS-5080

IUPAC/Chemical Name: N-((1-allylpyrrolidin-2-yl)methyl)-6-methoxy-1H-benzo[d][1,2,3]triazole-5-carboxamide

InChi Key: KSEYRUGYKHXGFW-UHFFFAOYSA-N

InChi Code: InChI=1S/C16H21N5O2/c1-3-6-21-7-4-5-11(21)10-17-16(22)12-8-13-14(19-20-18-13)9-15(12)23-2/h3,8-9,11H,1,4-7,10H2,2H3,(H,17,22)(H,18,19,20)

SMILES Code: O=C(C1=C(OC)C=C(NN=N2)C2=C1)NCC3N(CC=C)CCC3

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

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 315.38 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
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Dewinter G, Teunkens A, Vermeulen K, Devroe S, Van Hemelrijck J, Meuleman C, Vergote I, Fieuws S, Van de Velde M, Rex S. Alizapride and ondansetron for the prevention of postoperative nausea and vomiting in patients undergoing laparoscopic gynaecological surgery: A double-blind, randomised, placebo- controlled noninferiority study. Eur J Anaesthesiol. 2016 Feb;33(2):96-103. doi: 10.1097/EJA.0000000000000288. PMID: 26086285.


2: Joss RA, Galeazzi RL, Bischoff AK, Brunner KW. Alizapride, a new substituted benzamide, as an antiemetic during cancer chemotherapy. Eur J Clin Pharmacol. 1985;27(6):721-5. doi: 10.1007/BF00547056. PMID: 3987777.


3: Bleiberg H, Gerard B, Dalesio O, Crespeigne N, Rozencweig M. Activity of a new antiemetic agent: alizapride. A randomized double-blind crossover controlled trial. Cancer Chemother Pharmacol. 1988;22(4):316-20. doi: 10.1007/BF00254238. PMID: 3048762.


4: Closset M, Goderniaux N, Colsoul ML, Soumoy L, Bihin B, Jamart J, Odou P, Hecq JD, Galanti L. Long term stability of an admixture of alizapride and ondansetron in 0.9% sodium chloride solution polyolefin bags stored at 5±3°C. J Oncol Pharm Pract. 2021 Sep;27(6):1328-1332. doi: 10.1177/1078155220950442. Epub 2020 Sep 9. PMID: 32903143.


5: Joss RA, Galeazzi RL, Bischoff AK, Pirovino M, Ryssel HJ, Brunner KW. The antiemetic activity of high-dose alizapride and high-dose metoclopramide in patients receiving cancer chemotherapy: a prospective, randomized, double-blind trial. Clin Pharmacol Ther. 1986 Jun;39(6):619-24. doi: 10.1038/clpt.1986.109. PMID: 3519041.


6: Booij LH, Rachmat S, Bulder ER. Alizapride in prevention of postoperative nausea and vomiting. Neth J Surg. 1988 Feb;40(1):6-9. PMID: 3281060.


7: Huys J, Troch M, Bourguignon RP, Smets P. High-dose alizapride versus high- dose domperidone: a double-blind comparative study in the management of cis- platinum-induced emesis. Curr Med Res Opin. 1985;9(6):400-6. doi: 10.1185/03007998509109611. PMID: 3886305.


8: Roché H, Hyman G, Nahas G, Stoopler M, Ellison R, Desjardins R. Comparative effects of intravenously administered alizapride and prochlorperazine in cisplatin-induced emesis. Cancer Invest. 1987;5(2):89-93. doi: 10.3109/07357908709018461. PMID: 3607576.


9: Vanacker B, Van Aken H. Alizapride in the prevention of postoperative vomiting. A double-blind comparison. Acta Anaesthesiol Belg. 1988;39(4):247-50. PMID: 3232497.


10: Pollera CF, Nardi M, Marolla P, Calabresi F. Alizapride alone or alizapride- dexamethasone compared with metoclopramide-dexamethasone in patients at high risk of acute emesis after cisplatin. A randomized cross-over study. Acta Oncol. 1991;30(6):725-9. doi: 10.3109/02841869109092447. PMID: 1958393.


11: Horta ML, Morejon LC, da Cruz AW, Dos Santos GR, Welling LC, Terhorst L, Costa RC, Alam RU. Study of the prophylactic effect of droperidol, alizapride, propofol and promethazine on spinal morphine-induced pruritus. Br J Anaesth. 2006 Jun;96(6):796-800. doi: 10.1093/bja/ael072. Epub 2006 Apr 5. PMID: 16597655.


12: Kauste A, Tuominen M, Heikkinen H, Gordin A, Korttila K. Droperidol, alizapride and metoclopramide in the prevention and treatment of post-operative emetic sequelae. Eur J Anaesthesiol. 1986 Jan;3(1):1-9. PMID: 3780685.


13: Warzee PL, Dive CC. Manometric study of the activity of alizapride on the motor function of the human sphincter of Oddi. J Clin Pharm Ther. 1988 Aug;13(4):281-4. doi: 10.1111/j.1365-2710.1988.tb00194.x. PMID: 3235478.


14: Aprile S, Del Grosso E, Grosa G. In vitro metabolic fate of alizapride: evidence for the formation of reactive metabolites based on liquid chromatography-tandem mass spectrometry. J Mass Spectrom. 2012 Jun;47(6):737-50. doi: 10.1002/jms.3011. PMID: 22707166.


15: Athanasopoulos A, Hecq JD, Vanbeckbergen D, Jamart J, Galanti L. Long-term stability of the hydrochlorides of tramadol and alizapride in dextrose 5% polyolefin bag at 5+/-3 degrees C. Ann Pharm Fr. 2010 May;68(3):157-62. doi: 10.1016/j.pharma.2010.03.004. Epub 2010 May 15. PMID: 20569772.


16: Colsoul ML, Hecq JD, Soumoy L, Charles O, Goderniaux N, Bihin B, Jamart J, Galanti L. Long-term stability of an infusion containing paracetamol, alizapride, ketorolac and tramadol in glass bottles at 5±3°C. Eur J Hosp Pharm. 2020 Mar;27(e1):e74-e78. doi: 10.1136/ejhpharm-2019-001966. Epub 2019 Jun 11. PMID: 32296510; PMCID: PMC7147551.


17: Niederle N, Schütte J, Schmidt CG. Crossover comparison of the antiemetic efficacy of nabilone and alizapride in patients with nonseminomatous testicular cancer receiving cisplatin therapy. Klin Wochenschr. 1986 Apr 15;64(8):362-5. doi: 10.1007/BF01728184. PMID: 3009962.


18: Debray H, Guihard J, Peyramond D, Tron P. Traitement des vomissements du nourrisson et de l'enfant liés à une pathologie infectieuse aiguë. Etude comparative alizapride versus métopimazine [Treatment of vomiting in infants and children induced by acute infectious pathology. A comparative study of alizapride versus metopimazine]. Ann Pediatr (Paris). 1990 Dec;37(10):683-7. French. PMID: 2291597.


19: Rey E, Stettler E, D'athis P, Pons G. Pharmacokinetics of alizapride in children receiving chemotherapy for solid tumour. Fundam Clin Pharmacol. 2001 Jun;15(3):217-20. doi: 10.1046/j.1472-8206.2001.00022.x. PMID: 11468033.


20: Simar J, Godet M, Hecq JD, Closset M, Gillet P, Langhendries C, Bihin B, Jamart J, Galanti L. Long-term stability of dexamethasone and alizapride or ondansetron in sodium chloride 0.9% polyolefin bag at 5±3°C. Ann Pharm Fr. 2017 Jan;75(1):30-39. doi: 10.1016/j.pharma.2016.08.001. Epub 2016 Sep 12. PMID: 27634586.