MedKoo Cat#: 562013 | Name: Metopimazine

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Metopimazine is a selective and peripherally restricted antagonist of dopamine D3 and D2 receptors.

Chemical Structure

Metopimazine
Metopimazine
CAS#14008-44-7

Theoretical Analysis

MedKoo Cat#: 562013

Name: Metopimazine

CAS#: 14008-44-7

Chemical Formula: C22H27N3O3S2

Exact Mass: 445.1494

Molecular Weight: 445.59

Elemental Analysis: C, 59.30; H, 6.11; N, 9.43; O, 10.77; S, 14.39

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
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Synonym
Metopimazine; NG-101; NG101; NG 101; Vogalene; Nortrip; EXP 999; EXP-999; EXP999;
IUPAC/Chemical Name
1-[3-(2-Methylsulfonylphenothiazin-10-yl)propyl]piperidine-4-carboxamide
InChi Key
BQDBKDMTIJBJLA-UHFFFAOYSA-N
InChi Code
InChI=1S/C22H27N3O3S2/c1-30(27,28)17-7-8-21-19(15-17)25(18-5-2-3-6-20(18)29-21)12-4-11-24-13-9-16(10-14-24)22(23)26/h2-3,5-8,15-16H,4,9-14H2,1H3,(H2,23,26)
SMILES Code
O=C(C1CCN(CCCN2C3=C(C=CC=C3)SC4=CC=C(S(=O)(C)=O)C=C24)CC1)N
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
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

Preparing Stock Solutions

The following data is based on the product molecular weight 445.59 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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Epub 2013 Aug 12. PubMed PMID: 23935001. 4: Hubert-Roux M, Bounoure F, Skiba M, Bozec P, Churlaud F, Lange CM. Fragmentation pathways of metopimazine and its metabolite using ESI-MS(n), HR-MS and H/D exchange. J Mass Spectrom. 2010 Oct;45(10):1121-9. doi: 10.1002/jms.1790. PubMed PMID: 20690157. 5: Naguib IA, Abdelkawy M. Development and validation of stability indicating HPLC and HPTLC methods for determination of sulpiride and mebeverine hydrochloride in combination. Eur J Med Chem. 2010 Sep;45(9):3719-25. doi: 10.1016/j.ejmech.2010.05.021. Epub 2010 May 15. PubMed PMID: 20538381. 6: Kilgore KH, Hill JE, Powell JF, Watson CA, Yanong RP. Investigational use of metomidate hydrochloride as a shipping additive for two ornamental fishes. J Aquat Anim Health. 2009 Sep;21(3):133-9. doi: 10.1577/H08-030.1. PubMed PMID: 20043397. 7: Dupuis LL, Nathan PC. Optimizing emetic control in children receiving antineoplastic therapy: beyond the guidelines. Paediatr Drugs. 2010;12(1):51-61. doi: 10.2165/11316190-000000000-00000. Review. PubMed PMID: 20034341. 8: Ellebaek E, Herrstedt J. Optimizing antiemetic therapy in multiple-day and multiple cycles of chemotherapy. Curr Opin Support Palliat Care. 2008 Mar;2(1):28-34. doi: 10.1097/SPC.0b013e3282f44a75. Review. PubMed PMID: 18685391. 9: Bounoure F, Lahiani Skiba M, Besnard M, Arnaud P, Mallet E, Skiba M. Effect of iontophoresis and penetration enhancers on transdermal absorption of metopimazine. J Dermatol Sci. 2008 Dec;52(3):170-7. doi: 10.1016/j.jdermsci.2008.06.009. Epub 2008 Aug 3. PubMed PMID: 18678472. 10: Frédéric B, Malika LS, Marie H, Eric M, Philippe A, Mohamed S. Percutaneous absorption of metopimazine and effect of cyclodextrins. Drug Dev Ind Pharm. 2008 May;34(5):478-84. doi: 10.1080/03639040701743873 . PubMed PMID: 18473229. 11: Valeyre P, Favier R, Adam M, Quinet B, Grimprel E, Parez N. [Tolerance and efficacy of mefloquine as the first line treatment of uncomplicated P. falciparum malaria in children]. Pathol Biol (Paris). 2008 Feb;56(1):21-8. doi: 10.1016/j.patbio.2007.09.003. Epub 2008 Jan 4. French. PubMed PMID: 18178023. 12: Jolliet P, Nion S, Allain-Veyrac G, Tilloy-Fenart L, Vanuxeem D, Berezowski V, Cecchelli R. Evidence of lowest brain penetration of an antiemetic drug, metopimazine, compared to domperidone, metoclopramide and chlorpromazine, using an in vitro model of the blood-brain barrier. Pharmacol Res. 2007 Jul;56(1):11-7. Epub 2006 Dec 19. PubMed PMID: 17572097. 13: Gazy AA, Hassan EM, Abdel-Hay MH, Belal TS. Differential pulse cathodic voltammetric determination of floctafenine and metopimazine. J Pharm Biomed Anal. 2007 Mar 12;43(4):1535-9. Epub 2006 Dec 11. PubMed PMID: 17161576. 14: Herrstedt J, Sigsgaard TC, Nielsen HA, Handberg J, Langer SW, Ottesen S, Dombernowsky P. Randomized, double-blind trial comparing the antiemetic effect of tropisetron plus metopimazine with tropisetron plus placebo in patients receiving multiple cycles of multiple-day cisplatin-based chemotherapy. Support Care Cancer. 2007 Apr;15(4):417-26. Epub 2006 Nov 9. PubMed PMID: 17093916. 15: Khamales S, Bethune-Volters A, Chidiac J, Bensaoula O, Delgado A, Di Palma M. A randomized, double-blind trial assessing the efficacy and safety of sublingual metopimazine and ondansetron in the prophylaxis of chemotherapy-induced delayed emesis. Anticancer Drugs. 2006 Feb;17(2):217-24. Erratum in: Anticancer Drugs. 2006 Jun;17(5):599. Khamales, Slimane [added]. PubMed PMID: 16428941. 16: Bloch J, Rixe O, Meric JB, Delgado A, Khayat D. Comparison of the efficacy and safety of combinations of metopimazine or ondansetron with methylprednisolone in the prevention of delayed emesis in patients receiving chemotherapy. Curr Med Res Opin. 2005 Nov;21(11):1763-71. PubMed PMID: 16307696. 17: Nathan PC, Tomlinson G, Dupuis LL, Greenberg ML, Ota S, Bartels U, Feldman BM. A pilot study of ondansetron plus metopimazine vs. ondansetron monotherapy in children receiving highly emetogenic chemotherapy: a Bayesian randomized serial N-of-1 trials design. Support Care Cancer. 2006 Mar;14(3):268-76. Epub 2005 Jul 29. PubMed PMID: 16052316. 18: Dupuis LL, Nathan PC. Options for the prevention and management of acute chemotherapy-induced nausea and vomiting in children. Paediatr Drugs. 2003;5(9):597-613. Review. PubMed PMID: 12956617. 19: Sigsgaard T, Herrstedt J, Handberg J, Kjaer M, Dombernowsky P. Ondansetron plus metopimazine compared with ondansetron plus metopimazine plus prednisolone as antiemetic prophylaxis in patients receiving multiple cycles of moderately emetogenic chemotherapy. J Clin Oncol. 2001 Apr 1;19(7):2091-7. PubMed PMID: 11283143. 20: Sigsgaard T, Herrstedt J, Christensen P, Andersen O, Dombernowsky P. 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