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Merck
CN

SML0277

Methylnaltrexone bromide

≥97% (HPLC), narcotic antagonist, powder

Synonym(s):

17-(Cyclopropylmethyl)-4,5α-epoxy-3,14-dihydroxy-17-methyl-6-oxomorphinanium bromide, MNTX, Methylnaltrexonium, Mrz-2663, N-Methylnaltrexone, Naltrexone MB, Quaternary ammonium naltrexone

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About This Item

Empirical Formula (Hill Notation):
C21H26NO4 · Br
CAS Number:
73232-52-7
Molecular Weight:
436.34
UNSPSC Code:
12352200
PubChem Substance ID:
329825285
NACRES:
NA.77
MDL number:
MFCD06407831

Key Documents

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Product Name

Methylnaltrexone bromide, ≥97% (HPLC)

SMILES string

[Br-].C[N@+]1(CC[C@]23[C@H]4Oc5c(O)ccc(C[C@@H]1[C@]2(O)CCC4=O)c35)CC6CC6

InChI key

IFGIYSGOEZJNBE-KNLJMPJLSA-N

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

assay

≥97% (HPLC)

form

powder

storage condition

desiccated

color

white to beige

solubility

H2O: ≥5 mg/mL

shipped in

wet ice

storage temp.

−20°C

Quality Level

100

Gene Information

human ... OPRM1(4988)

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Features and Benefits

This compound is featured on the Opioid Receptors page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Application

Methylnaltrexone bromide has been used as a drug to measure plasma protein binding (PPB), permeability (Pm) and the membrane coefficient (KIAM) for the prediction of blood brain barrier (BBB) penetration. It is also used as a mu-opioid receptor (MOR) antagonist to abrogate morphine tolerance and opioid-induced hyperalgesia (OIH).

Biochem/physiol Actions

Methylnaltrexone bromide is a narcotic antagonist.
Methylnaltrexone bromide is a narcotic antagonist. It is a peripheral mu-opiod receptor antagonist that cannot cross the blood-brain barrier. It reverses many opioid side-effects without interfering with pain relief.

General description

Methylnaltrexone does not cross blood brain barrier and does not affect the opioid effects in the brain, such as analgesia. It is used to treat opioid-induced constipation (OIC).

pictograms

Health hazard
GHS08

signalword

Warning

hcodes

H371

Hazard Classifications

STOT SE 2 Oral

target_organs

Gastrointestinal tract

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
0000368079
0000368079
0000189929
0000189930
0000187274

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Danial E Baker
Reviews in gastroenterological disorders, 9(3), E84-E93 (2009-11-10)
Constipation is a common problem associated with opiates and opioid compounds used for the treatment of pain and other medical conditions, and can influence patient quality of life. Methylnaltrexone appears effective in the therapy of opioid-induced constipation and will be
Methylnaltrexone for treatment of opioid-induced constipation in advanced illness patients.
Slatkin N, et al.
The Journal of Supportive Oncology, 7(1), 39-46 (2009)
L Garten et al.
Archives of disease in childhood. Fetal and neonatal edition, 97(2), F151-F153 (2011-10-29)
Methylnaltrexone, a peripherally acting µ-opioid receptor antagonist, has been studied in adults for the treatment of opioid-induced constipation in advanced illness. Here, the authors document the first neonate to receive methylnaltrexone in an attempt to resolve morphine-induced urinary retention. An
Edward Michna et al.
Pain medicine (Malden, Mass.), 12(8), 1223-1230 (2011-08-04)
Methylnaltrexone, a selective peripherally acting mu-opioid receptor antagonist, effectively treats opioid-induced constipation (OIC) in patients with advanced illness and shows efficacy in patients with chronic nonmalignant pain. The objective was to identify patients who achieved maximal treatment effect based on
Florian Pfab et al.
Current opinion in clinical nutrition and metabolic care, 15(2), 166-173 (2012-01-12)
Gastrointestinal motility disorders (GMDs) are common in the ICU. When encountering these problems, one typically thinks of prokinetics. This review summarizes current evidence of treatments. Prokinetics are not the first-line therapy for GMDs. In fact, the clinical implications of using
View All Related Papers

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