Methylnaltrexone | CAS#73232-52-7

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

MedKoo CAT#: 318250

CAS#: 73232-52-7

Description: Methylnaltrexone, used in form of methylnaltrexone bromide (INN, USAN, BAN), is one of the newer agents of peripherally-acting μ-opioid antagonists that act to reverse some of the side effects of opioid drugs such as constipation without affecting analgesia or precipitating withdrawals. Because Methylnaltrexone is a quaternary ammonium cation, it cannot cross the blood–brain barrier, and so has antagonist effects throughout the body, counteracting effects such as itching and constipation, but without affecting opioid effects in the brain such as analgesia.

Chemical Structure

Methylnaltrexone bromide

CAS# 73232-52-7

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 318250
Name: Methylnaltrexone bromide
CAS#: 73232-52-7
Chemical Formula: C21H26BrNO4
Exact Mass: 0.00
Molecular Weight: 436.346
Elemental Analysis: C, 57.81; H, 6.01; Br, 18.31; N, 3.21; O, 14.67

Price and Availability

Size	Price	Availability	Quantity
5mg	USD 350	2 weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Synonym: MOA-728; MOA 728; MOA728; Methylnaltrexone, Relistor, MRZ-2663, Naltrexone MB, MNTX; Methylnaltrexone bromide.

IUPAC/Chemical Name: (4R,4aS,7aR,12bS)-3-(cyclopropylmethyl)-4a,9-dihydroxy-3-methyl-7-oxo-2,3,4,4a,5,6,7,7a-octahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-3-ium bromide

InChi Key: IFGIYSGOEZJNBE-KNLJMPJLSA-N

InChi Code: InChI=1S/C21H25NO4.BrH/c1-22(11-12-2-3-12)9-8-20-17-13-4-5-14(23)18(17)26-19(20)15(24)6-7-21(20,25)16(22)10-13;/h4-5,12,16,19,25H,2-3,6-11H2,1H3;1H/t16-,19+,20+,21-,22?;/m1./s1

SMILES Code: O=C1[C@@](OC2=C(O)C=CC3=C24)([H])[C@@]54CC[N+](C)(CC6CC6)[C@@](C3)([H])[C@]5(O)CC1.[Br-]

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:

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Biological target:	Methylnaltrexone, used in form of methylnaltrexone bromide (INN, USAN, BAN), is one of the newer agents of peripherally-acting μ-opioid antagonists that act to reverse some of the side effects of opioid drugs such as constipation without affecting analgesia or precipitating withdrawals.
In vitro activity:	This study evaluated the impact of modulating the expression MOR (Mu-opioid receptor) and the effect of MNTX (methylnaltrexone) on the proliferation, clonogenic activity, invasion, and migration of two HNSCC (FaDu and MDA686Tu) cell lines expressing MOR and one cell line (UMSCC47) not expressing the receptor. In vitro studies showed that MNTX strongly inhibited the proliferation, clonogenic activity, invasion, and migration of FaDu and MDA686Tu cells but has no effect on UMSCC47 cells. Reference: J Cell Physiol. 2021 Nov;236(11):7698-7710. https://pubmed.ncbi.nlm.nih.gov/34038587/
In vivo activity:	The goal of this study was to determine whether MNTX (methylnaltrexone) alters centrally-mediated behaviors elicited by the opioid analgesics, morphine and oxycodone, and to quantify concentrations of MNTX and NTX (naltrexone) in blood and brain following their administration in mice. MNTX dose-dependently attenuated acute and chronic morphine antinociception. MNTX and NTX dose-dependently antagonized the discriminative stimulus effects of oxycodone. Reference: Neuropharmacology. 2021 Mar 1;185:108437. doi https://pubmed.ncbi.nlm.nih.gov/33316279/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMSO	58.2	133.40
	PBS (pH 7.2)	10.0	22.92
	Water	71.8	164.58

Preparing Stock Solutions

The following data is based on the product molecular weight 436.35 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.

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. Gorur A, Patiño M, Shi T, Corrales G, Takahashi H, Rangel R, Gleber-Netto FO, Pickering C, Myers JN, Cata JP. Low doses of methylnaltrexone inhibits head and neck squamous cell carcinoma growth in vitro and in vivo by acting on the mu-opioid receptor. J Cell Physiol. 2021 Nov;236(11):7698-7710. doi: 10.1002/jcp.30421. Epub 2021 May 26. PMID: 34038587. 2. Liu X, Yang J, Yang C, Huang X, Han M, Kang F, Li J. Morphine promotes the malignant biological behavior of non-small cell lung cancer cells through the MOR/Src/mTOR pathway. Cancer Cell Int. 2021 Nov 25;21(1):622. doi: 10.1186/s12935-021-02334-8. PMID: 34823532; PMCID: PMC8613927. 3. Walentiny DM, Komla E, Moisa LT, Mustafa MA, Poklis JL, Akbarali HI, Beardsley PM. Methylnaltrexone crosses the blood-brain barrier and attenuates centrally-mediated behavioral effects of morphine and oxycodone in mice. Neuropharmacology. 2021 Mar 1;185:108437. doi: 10.1016/j.neuropharm.2020.108437. Epub 2020 Dec 11. PMID: 33316279; PMCID: PMC7887091. 4. Singleton PA, Mambetsariev N, Lennon FE, Mathew B, Siegler JH, Moreno-Vinasco L, Salgia R, Moss J, Garcia JG. Methylnaltrexone potentiates the anti-angiogenic effects of mTOR inhibitors. J Angiogenes Res. 2010 Feb 19;2(1):5. doi: 10.1186/2040-2384-2-5. PMID: 20298531; PMCID: PMC2831839.
In vitro protocol:	1. Gorur A, Patiño M, Shi T, Corrales G, Takahashi H, Rangel R, Gleber-Netto FO, Pickering C, Myers JN, Cata JP. Low doses of methylnaltrexone inhibits head and neck squamous cell carcinoma growth in vitro and in vivo by acting on the mu-opioid receptor. J Cell Physiol. 2021 Nov;236(11):7698-7710. doi: 10.1002/jcp.30421. Epub 2021 May 26. PMID: 34038587. 2. Liu X, Yang J, Yang C, Huang X, Han M, Kang F, Li J. Morphine promotes the malignant biological behavior of non-small cell lung cancer cells through the MOR/Src/mTOR pathway. Cancer Cell Int. 2021 Nov 25;21(1):622. doi: 10.1186/s12935-021-02334-8. PMID: 34823532; PMCID: PMC8613927.
In vivo protocol:	1. Walentiny DM, Komla E, Moisa LT, Mustafa MA, Poklis JL, Akbarali HI, Beardsley PM. Methylnaltrexone crosses the blood-brain barrier and attenuates centrally-mediated behavioral effects of morphine and oxycodone in mice. Neuropharmacology. 2021 Mar 1;185:108437. doi: 10.1016/j.neuropharm.2020.108437. Epub 2020 Dec 11. PMID: 33316279; PMCID: PMC7887091. 2. Singleton PA, Mambetsariev N, Lennon FE, Mathew B, Siegler JH, Moreno-Vinasco L, Salgia R, Moss J, Garcia JG. Methylnaltrexone potentiates the anti-angiogenic effects of mTOR inhibitors. J Angiogenes Res. 2010 Feb 19;2(1):5. doi: 10.1186/2040-2384-2-5. PMID: 20298531; PMCID: PMC2831839.

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1: Rauck RL. Treatment of opioid-induced constipation: focus on the peripheral μ-opioid receptor antagonist methylnaltrexone. Drugs. 2013 Aug;73(12):1297-306. doi: 10.1007/s40265-013-0084-5. Review. PubMed PMID: 23881667.

2: Grover M, Camilleri M. Treatment with Methylnaltrexone and IVIG for Paraneoplastic Gastrointestinal Dysmotility. Gastroenterol Hepatol (N Y). 2013 Jan;9(1):51-3. Review. PubMed PMID: 24707236; PubMed Central PMCID: PMC3975980.

3: Bader S, Dürk T, Becker G. Methylnaltrexone for the treatment of opioid-induced constipation. Expert Rev Gastroenterol Hepatol. 2013 Jan;7(1):13-26. doi: 10.1586/egh.12.63. Review. PubMed PMID: 23265145.

4: Brick N. Laxatives or methylnaltrexone for the management of constipation in palliative care patients. Clin J Oncol Nurs. 2013 Feb;17(1):91-2. doi: 10.1188/13.CJON.91-92. Review. PubMed PMID: 23372103.

5: Gatti A, Sabato AF. Management of opioid-induced constipation in cancer patients: focus on methylnaltrexone. Clin Drug Investig. 2012 May 1;32(5):293-301. doi: 10.2165/11598000-000000000-00000. Review. PubMed PMID: 22413747.

6: Rotshteyn Y, Boyd TA, Yuan CS. Methylnaltrexone bromide: research update of pharmacokinetics following parenteral administration. Expert Opin Drug Metab Toxicol. 2011 Feb;7(2):227-35. doi: 10.1517/17425255.2011.549824. Epub 2011 Jan 11. Review. PubMed PMID: 21222554.

7: Licup N, Baumrucker SJ. Methylnaltrexone: treatment for opioid-induced constipation. Am J Hosp Palliat Care. 2011 Feb;28(1):59-61. doi: 10.1177/1049909110373507. Epub 2010 Aug 27. Review. PubMed PMID: 20801917.

8: Candy B, Jones L, Goodman ML, Drake R, Tookman A. Laxatives or methylnaltrexone for the management of constipation in palliative care patients. Cochrane Database Syst Rev. 2011 Jan 19;(1):CD003448. doi: 10.1002/14651858.CD003448.pub3. Review. Update in: Cochrane Database Syst Rev. 2015;5:CD003448. PubMed PMID: 21249653.

9: Garnock-Jones KP, McKeage K. Methylnaltrexone. Drugs. 2010 May 7;70(7):919-28. doi: 10.2165/11204520-000000000-00000. Review. PubMed PMID: 20426500.

10: Chappell D, Conzen P. [Methylnaltrexone. A new approach for therapy of opioid-induced obstipation]. Schmerz. 2009 Oct;23(5):471-8. doi: 10.1007/s00482-009-0824-3. Review. German. PubMed PMID: 19690895.

11: Diego L, Atayee R, Helmons P, von Gunten CF. Methylnaltrexone: a novel approach for the management of opioid-induced constipation in patients with advanced illness. Expert Rev Gastroenterol Hepatol. 2009 Oct;3(5):473-85. doi: 10.1586/egh.09.42. Review. PubMed PMID: 19817669.

12: Kast RE. Use of FDA approved methamphetamine to allow adjunctive use of methylnaltrexone to mediate core anti-growth factor signaling effects in glioblastoma. J Neurooncol. 2009 Sep;94(2):163-7. doi: 10.1007/s11060-009-9863-y. Epub 2009 Mar 26. Review. PubMed PMID: 19322519.

13: Baker DE. Methylnaltrexone bromide: new drug for the treatment of opioid-induced bowel dysfunction. Rev Gastroenterol Disord. 2009 Summer;9(3):E84-93. Review. PubMed PMID: 19898269.

14: Hendrikx JJ, Beijnen JH, Schellens JH. Methylnaltrexone. Oncologist. 2009 Jul;14(7):679-82. doi: 10.1634/theoncologist.2009-0049. Epub 2009 Jul 15. Review. PubMed PMID: 19605844.

15: Cannom RR, Mason RJ. Methylnaltrexone: the answer to opioid-induced constipation? Expert Opin Pharmacother. 2009 Apr;10(6):1039-45. doi: 10.1517/14656560902833914 . Review. PubMed PMID: 19364251.

16: Reichle FM, Conzen PF. Methylnaltrexone, a new peripheral mu-receptor antagonist for the prevention and treatment of opioid-induced extracerebral side effects. Curr Opin Investig Drugs. 2008 Jan;9(1):90-100. Review. PubMed PMID: 18183536.

17: Shaiova L, Rim F, Friedman D, Jahdi M. A review of methylnaltrexone, a peripheral opioid receptor antagonist, and its role in opioid-induced constipation. Palliat Support Care. 2007 Jun;5(2):161-6. Review. PubMed PMID: 17578067.

18: Yuan CS. Methylnaltrexone mechanisms of action and effects on opioid bowel dysfunction and other opioid adverse effects. Ann Pharmacother. 2007 Jun;41(6):984-93. Epub 2007 May 15. Review. PubMed PMID: 17504835.

19: Methylnaltrexone: MNTX. Drugs R D. 2006;7(6):374-8. Review. PubMed PMID: 17073520.

20: Yuan CS. Clinical status of methylnaltrexone, a new agent to prevent and manage opioid-induced side effects. J Support Oncol. 2004 Mar-Apr;2(2):111-7; discussion 119-22. Review. PubMed PMID: 15328815.

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