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MedKoo Cat#: 318258 | Name: Metoclopramide
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Description:

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

Metoclopramide is a medication used mostly for stomach and esophageal problems. It is commonly used to treat nausea and vomiting, to help with emptying of the stomach in people with delayed stomach emptying due to either diabetes or following surgery, and to help with gastroesophageal reflux disease. It is also used to treat migraine headaches.

Chemical Structure

Metoclopramide
Metoclopramide
CAS#364-62-5 (free base)

Theoretical Analysis

MedKoo Cat#: 318258

Name: Metoclopramide

CAS#: 364-62-5 (free base)

Chemical Formula: C14H22ClN3O2

Exact Mass: 299.1401

Molecular Weight: 299.80

Elemental Analysis: C, 56.09; H, 7.40; Cl, 11.83; N, 14.02; O, 10.67

Price and Availability

Size Price Availability Quantity
5g USD 350.00 2 weeks
25g USD 750.00 2 weeks
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Related CAS #
7232-21-5 (HCl) 54143-57-6 364-62-5 (free base)
Synonym
Metoclopramide, Afipran, Maxolon, Reglan, Maxeran, Cerucal
IUPAC/Chemical Name
4-amino-5-chloro-N-[2-(diethylamino)ethyl]-2-methoxybenzamide
InChi Key
TTWJBBZEZQICBI-UHFFFAOYSA-N
InChi Code
InChI=1S/C14H22ClN3O2/c1-4-18(5-2)7-6-17-14(19)10-8-11(15)12(16)9-13(10)20-3/h8-9H,4-7,16H2,1-3H3,(H,17,19)
SMILES Code
O=C(NCCN(CC)CC)C1=CC(Cl)=C(N)C=C1OC
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
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Metoclopramide is a dopamine antagonist.
In vitro activity:
This study aimed at elucidating the effect of metoclopramide on triple-negative breast cancer, MDA-MB-231 cells were treated with various concentrations of metoclopramide, the cell proliferation was detected by MTT method, the apoptosis rate was detected by Annexin V/PI double staining method, the expression change of death-related protein was detected by Western Blot. This study found that metoclopramide inhibits cell proliferation and induces cell apoptosis of MDA-MB-231 in a concentration-dependent manner, and the Bcl family was involved in this process. Reference: Pharmazie. 2021 Apr 1;76(4):172-174. https://pubmed.ncbi.nlm.nih.gov/33849703/
In vivo activity:
The present study evaluated behavioral and neurochemical effects of long-term exposure to MET (methionine) in zebrafish. The results showed that metoclopramide was not only beneficial in improving MET-induced cognitive impairment but it also prevented social withdrawal in zebrafish exposed to MET. In addition, metoclopramide reversed anxiety-like behavior, as indicated by significant changes in locomotion activity. Reference: Zebrafish. 2023 Feb;20(1):19-27. https://pubmed.ncbi.nlm.nih.gov/36577055/
Solvent mg/mL mM comments
Solubility
DMSO 60.0 200.14
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 299.80 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:
1. Chen Y, Zhang M, Ji X, Zhao J, Qin S, Ji Y, Fan R, Liu Y, Lu P. The anti-cancer effect of metoclopramide on triple-negative breast cancer cells. Pharmazie. 2021 Apr 1;76(4):172-174. doi: 10.1691/ph.2021.0977. PMID: 33849703. 2. Riether C, Radpour R, Kallen NM, Bürgin DT, Bachmann C, Schürch CM, Lüthi U, Arambasic M, Hoppe S, Albers CE, Baerlocher GM, Ochsenbein AF. Metoclopramide treatment blocks CD93-signaling-mediated self-renewal of chronic myeloid leukemia stem cells. Cell Rep. 2021 Jan 26;34(4):108663. doi: 10.1016/j.celrep.2020.108663. PMID: 33503440. 3. Ved H, Doshi G, Bhatia N, Kale P. Metoclopramide as a Potential Antipsychotic Against Long-Term Methionine Exposure in Zebrafish. Zebrafish. 2023 Feb;20(1):19-27. doi: 10.1089/zeb.2022.0033. Epub 2022 Dec 27. PMID: 36577055. 4. Shen TJ, Hanh VT, Nguyen TQ, Jhan MK, Ho MR, Lin CF. Repurposing the Antiemetic Metoclopramide as an Antiviral Against Dengue Virus Infection in Neuronal Cells. Front Cell Infect Microbiol. 2021 Feb 2;10:606743. doi: 10.3389/fcimb.2020.606743. PMID: 33634036; PMCID: PMC7902071.
In vitro protocol:
1. Chen Y, Zhang M, Ji X, Zhao J, Qin S, Ji Y, Fan R, Liu Y, Lu P. The anti-cancer effect of metoclopramide on triple-negative breast cancer cells. Pharmazie. 2021 Apr 1;76(4):172-174. doi: 10.1691/ph.2021.0977. PMID: 33849703. 2. Riether C, Radpour R, Kallen NM, Bürgin DT, Bachmann C, Schürch CM, Lüthi U, Arambasic M, Hoppe S, Albers CE, Baerlocher GM, Ochsenbein AF. Metoclopramide treatment blocks CD93-signaling-mediated self-renewal of chronic myeloid leukemia stem cells. Cell Rep. 2021 Jan 26;34(4):108663. doi: 10.1016/j.celrep.2020.108663. PMID: 33503440.
In vivo protocol:
1. Ved H, Doshi G, Bhatia N, Kale P. Metoclopramide as a Potential Antipsychotic Against Long-Term Methionine Exposure in Zebrafish. Zebrafish. 2023 Feb;20(1):19-27. doi: 10.1089/zeb.2022.0033. Epub 2022 Dec 27. PMID: 36577055. 2. Shen TJ, Hanh VT, Nguyen TQ, Jhan MK, Ho MR, Lin CF. Repurposing the Antiemetic Metoclopramide as an Antiviral Against Dengue Virus Infection in Neuronal Cells. Front Cell Infect Microbiol. 2021 Feb 2;10:606743. doi: 10.3389/fcimb.2020.606743. PMID: 33634036; PMCID: PMC7902071.
1: Eken C. Critical reappraisal of intravenous metoclopramide in migraine attack: a systematic review and meta-analysis. Am J Emerg Med. 2015 Mar;33(3):331-7. doi: 10.1016/j.ajem.2014.11.013. Epub 2014 Nov 15. Review. PubMed PMID: 25579820. 2: Lin SY. Molecular perspectives on solid-state phase transformation and chemical reactivity of drugs: metoclopramide as an example. Drug Discov Today. 2015 Feb;20(2):209-22. doi: 10.1016/j.drudis.2014.10.001. Epub 2014 Oct 19. Review. PubMed PMID: 25450770. 3: Silva CC, Bennett C, Saconato H, Atallah ÁN. Metoclopramide for post-pyloric placement of naso-enteral feeding tubes. Cochrane Database Syst Rev. 2015 Jan 7;1:CD003353. doi: 10.1002/14651858.CD003353.pub2. Review. PubMed PMID: 25564770. 4: van der Meer YG, Venhuizen WA, Heyland DK, van Zanten AR. Should we stop prescribing metoclopramide as a prokinetic drug in critically ill patients? Crit Care. 2014 Sep 23;18(5):502. doi: 10.1186/s13054-014-0502-4. Review. PubMed PMID: 25672546; PubMed Central PMCID: PMC4331179. 5: BET 1: Metoclopramide or prochlorperazine for headache in acute migraine? Emerg Med J. 2013 Jul;30(7):595-6. doi: 10.1136/emermed-2013-202853.1. Review. PubMed PMID: 23765765. 6: Wu SJ, Xiong XZ, Cheng TY, Lin YX, Cheng NS. Efficacy of ondansetron vs. metoclopramide in prophylaxis of postoperative nausea and vomiting after laparoscopic cholecystectomy: a systematic review and meta-analysis. Hepatogastroenterology. 2012 Oct;59(119):2064-74. Review. PubMed PMID: 22282127. 7: Reichmann JP, Kirkbride MS. Reviewing the evidence for using continuous subcutaneous metoclopramide and ondansetron to treat nausea & vomiting during pregnancy. Manag Care. 2012 May;21(5):44-7. Review. PubMed PMID: 22670486. 8: Malcolm WF, Cotten CM. Metoclopramide, H2 blockers, and proton pump inhibitors: pharmacotherapy for gastroesophageal reflux in neonates. Clin Perinatol. 2012 Mar;39(1):99-109. doi: 10.1016/j.clp.2011.12.015. Epub 2012 Jan 11. Review. PubMed PMID: 22341540. 9: Mishriky BM, Habib AS. Metoclopramide for nausea and vomiting prophylaxis during and after Caesarean delivery: a systematic review and meta-analysis. Br J Anaesth. 2012 Mar;108(3):374-83. doi: 10.1093/bja/aer509. Epub 2012 Feb 3. Review. PubMed PMID: 22307240. 10: Surawski RJ, Quinn DK. Metoclopramide and homicidal ideation: a case report and literature review. Psychosomatics. 2011 Sep-Oct;52(5):403-9. doi: 10.1016/j.psym.2011.02.001. Review. PubMed PMID: 21907057. 11: Simpson PM, Bendall JC, Middleton PM. Review article: Prophylactic metoclopramide for patients receiving intravenous morphine in the emergency setting: a systematic review and meta-analysis of randomized controlled trials. Emerg Med Australas. 2011 Aug;23(4):452-7. doi: 10.1111/j.1742-6723.2011.01433.x. Epub 2011 Jun 12. Review. PubMed PMID: 21824312. 12: Merker M, Kranke P, Morin AM, Rüsch D, Eberhart LH. [Prophylaxis of nausea and vomiting in the postoperative phase: relative effectiveness of droperidol and metoclopramide]. Anaesthesist. 2011 May;60(5):432-40, 442-5. doi: 10.1007/s00101-010-1825-4. Epub 2010 Dec 12. Review. German. PubMed PMID: 21153527. 13: Craig WR, Hanlon-Dearman A, Sinclair C, Taback SP, Moffatt M. WITHDRAWN: Metoclopramide, thickened feedings, and positioning for gastro-oesophageal reflux in children under two years. Cochrane Database Syst Rev. 2010 May 12;(5):CD003502. doi: 10.1002/14651858.CD003502.pub3. Review. PubMed PMID: 20464724. 14: Rao AS, Camilleri M. Review article: metoclopramide and tardive dyskinesia. Aliment Pharmacol Ther. 2010 Jan;31(1):11-9. doi: 10.1111/j.1365-2036.2009.04189.x. Epub . Review. PubMed PMID: 19886950. 15: Dingli K, Morgan R, Leen C. Acute dystonic reaction caused by metoclopramide, versus tetanus. BMJ. 2007 Apr 28;334(7599):899-900. Review. PubMed PMID: 17463462; PubMed Central PMCID: PMC1857743. 16: Naproxen sodium/metoclopramide: metoclopramide/naproxen-sodium, MT 100, naproxen-sodium/metoclopramide. Drugs R D. 2006;7(4):259-61. Review. PubMed PMID: 16784251. 17: Pasricha PJ, Pehlivanov N, Sugumar A, Jankovic J. Drug Insight: from disturbed motility to disordered movement--a review of the clinical benefits and medicolegal risks of metoclopramide. Nat Clin Pract Gastroenterol Hepatol. 2006 Mar;3(3):138-48. Review. PubMed PMID: 16511548. 18: Craig WR, Hanlon-Dearman A, Sinclair C, Taback S, Moffatt M. Metoclopramide, thickened feedings, and positioning for gastro-oesophageal reflux in children under two years. Cochrane Database Syst Rev. 2004 Oct 18;(4):CD003502. Review. Update in: Cochrane Database Syst Rev. 2010;(5):CD003502. PubMed PMID: 15495056. 19: Tfelt-Hansen P. The effectiveness of combined oral lysine acetylsalicylate and metoclopramide (Migpriv) in the treatment of migraine attacks. Comparison with placebo and oral sumatriptan. Funct Neurol. 2000;15 Suppl 3:196-201. Review. PubMed PMID: 11200792. 20: Huerta Blanco R, Hernández Cabrera M, Quiñones Morales I, Cardenes Santana MA. [Complete heart block induced by intravenous metoclopramide]. An Med Interna. 2000 Apr;17(4):222-3. Review. Spanish. PubMed PMID: 10893782.

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