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SML0277

Sigma-Aldrich

Methylnaltrexone bromide

≥97% (HPLC)

Synonyme(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

Formule empirique (notation de Hill):
C21H26NO4 · Br
Numéro CAS:
73232-52-7
Poids moléculaire :
436.34
Numéro MDL:
MFCD06407831
Code UNSPSC :
12352200
ID de substance PubChem :
329825285
Nomenclature NACRES :
NA.77
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Niveau de qualité

100

Essai

≥97% (HPLC)

Forme

powder

Conditions de stockage

desiccated

Couleur

white to beige

Solubilité

H2O: ≥5 mg/mL

Conditions d'expédition

wet ice

Température de stockage

−20°C

Chaîne SMILES 

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

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

Clé InChI

IFGIYSGOEZJNBE-KNLJMPJLSA-N

Informations sur le gène

human ... OPRM1(4988)

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Description générale

Methylnaltrexone does not cross blood brain barrier and does not affect the opioid effects in the brain, such as analgesia.[1] It is used to treat opioid-induced constipation (OIC).[2]

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.[3] It is also used as a mu-opioid receptor (MOR) antagonist to abrogate morphine tolerance and opioid-induced hyperalgesia (OIH).[4]

Actions biochimiques/physiologiques

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.

Caractéristiques et avantages

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.

Pictogrammes

Health hazard
GHS08

Mention d'avertissement

Warning

Mentions de danger

H371

Classification des risques

STOT SE 2 Oral

Organes cibles

Gastrointestinal tract

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

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Certificats d'analyse (COA)

Lot/Batch Number
0000368079
0000368079
0000189929
0000189930
0000187274

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Consulter la Bibliothèque de documents

Neal E Slatkin et al.
Journal of pain and symptom management, 42(5), 754-760 (2011-11-03)
Methylnaltrexone is a selective peripherally acting mu-opioid receptor antagonist that decreases the constipating effects of opioids without affecting centrally mediated analgesia. In two double-blind, placebo-controlled, Phase III studies of methylnaltrexone for opioid-induced constipation in patients with advanced illness, abdominal pain
A Brokjaer et al.
Neurogastroenterology and motility : the official journal of the European Gastrointestinal Motility Society, 27(5), 693-704 (2015-03-27)
Opioid antagonists are increasingly used to abolish the gastrointestinal side effects of opioids. However, they can potentially interfere with local analgesia exerted via opioid receptors in the gut. Thus, in the current study we aimed to explore the effect of
Lucas Anissian et al.
Journal of hospital medicine, 7(2), 67-72 (2011-10-15)
Methylnaltrexone has been shown to be effective for treating opioid-induced constipation (OIC) in chronic settings, but its effects on acute OIC have not been studied. To assess safety and efficacy of subcutaneous methylnaltrexone in patients with acute OIC after orthopedic
Peter Holzer
Current pharmaceutical design, 18(37), 6010-6020 (2012-07-04)
The therapeutic action of opioid analgesics is compromised by peripheral adverse effects among which opioid-induced constipation (OIC) is the most disabling, with a prevalence reported to vary between 15 and 90 %. Although OIC is usually treated with laxatives, there
Methylnaltrexone for reversal of constipation due to chronic methadone use: a randomized controlled trial
Yuan CS, et al.
JAMA : The Journal of the American Medical Association, 283(3), 367-372 (2000)
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