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Alvimopan

Names

[ CAS No. ]:
170098-38-1

[ Name ]:
Alvimopan

[Synonym ]:
Alvimopan dihydrate
Alvimopan
N-{(2S)-2-Benzyl-3-[(3R,4R)-4-(3-hydroxyphenyl)-3,4-dimethyl-1-piperidinyl]propanoyl}glycine dihydrate
Glycine, N-[(2S)-3-[(3R,4R)-4-(3-hydroxyphenyl)-3,4-dimethyl-1-piperidinyl]-1-oxo-2-(phenylmethyl)propyl]-, hydrate (1:2)
Alvimopan (USAN)
Adl 8-2698
Alvimopan anhydrous
UNII-677C126AET
Alvimopan hydrate
Entereg
Alvimopan (dihydrate)

Biological Activity

[Description]:

Alvimopan dihydrate(LY 246736; ADL 8-2698) is a peripherally acting mu-opioid receptor (PAM-OR, IC50= 1.7 nM) antagonist for accelerating gastrointestinal recovery after surgery. IC50 Value: 1.7 nM (Mu-type opioid receptor) [1]Target: mu-opioid receptorin vitro: The dissociation rate of alvimopan from the micro opioid receptor (t(1/2)=30--44 min) was comparable to that of the long acting partial agonist buprenorphine (t(1/2)=44 min), but was slower than those of the antagonists naloxone (t(1/2)=0.82 min) and N-methylnaltrexone (t(1/2)=0.46 min) [2].in vivo: Alvimopan did not significantly accelerate GI-3 compared with placebo [6 mg: hazard ratio (HR) = 1.20, p = 0.080; 12 mg: HR = 1.24, p = 0.038). However, after adjustment for significant covariates (sex/surgical duration), benefits were significant for both doses (6 mg: HR = 1.24, p = 0.037; 12 mg: HR = 1.26, p = 0.028). Alvimopan also significantly accelerated time to GI-2 (6 mg: HR = 1.37, p = 0.008; 12 mg: HR = 1.33, p = 0.018) and DCO (6 mg: HR = 1.31, p = 0.008; 12 mg: HR = 1.28, p = 0.015) [3]. Alvimopan (1 and 3 mg/kg) significantly reversed this delayed GI transit when administered 45 min prior to surgery. However, the effects of alvimopan were less pronounced when administered following surgery [4].Toxicity:The most common treatment-emergent adverse events across all treatment groups were nausea, vomiting, and hypotension; the incidence of nausea and vomiting was reduced by 53 percent in thealvimopan 12-mg group [5].Clinical trial: Intercostal Nerve Block With Liposome Bupivacaine in Subjects Undergoing Posterolateral Thoracotomy. Phase 3

[Related Catalog]:

Signaling Pathways >> GPCR/G Protein >> Opioid Receptor
Signaling Pathways >> Neuronal Signaling >> Opioid Receptor
Research Areas >> Neurological Disease

[References]

[1]. NCBI BioAssay: 325959

[2]. Cassel JA, et al. [(3)H]Alvimopan binding to the micro opioid receptor: comparative binding kinetics of opioid antagonists. Eur J Pharmacol. 2005 Sep 27;520(1-3):29-36.

[3]. Viscusi ER, et al. Alvimopan, a peripherally acting mu-opioid receptor antagonist, compared with placebo in postoperative ileus after major abdominal surgery: results of a randomized, double-blind, controlled study. Surg Endosc. 2006 Jan;20(1):64-70.

[4]. Fukuda H, et al. The selective mu opioid receptor antagonist, alvimopan, improves delayed GI transit of postoperative ileus in rats. Brain Res. 2006 Aug 2;1102(1):63-70.

[5]. Delaney CP, et al. Phase III trial of alvimopan, a novel, peripherally acting, mu opioid antagonist, for postoperative ileus after major abdominal surgery. Dis Colon Rectum. 2005 Jun;48(6):1114-25; discussion 1125-6; author reply 1127-9.


[Related Small Molecules]

PZM-21 | Loperamide hydrochloride | Oliceridine hydrochloride | ADL5859 HCl | JDTic (dihydrochloride) | Naltrindole hydrochloride | LY-2456302 | JTC-801 | Matrine | Met-Enkephalin acetate salt | Cebranopadol | Leu-Enkephalin | DAMGO | Sinomenine HCl | SR17018

Chemical & Physical Properties

[ Density]:
1.166g/cm3

[ Boiling Point ]:
684.1ºC at 760mmHg

[ Melting Point ]:
210-213ºC

[ Molecular Formula ]:
C25H36N2O6

[ Molecular Weight ]:
460.563

[ Flash Point ]:
367.5ºC

[ Exact Mass ]:
460.257324

[ PSA ]:
108.33000

[ LogP ]:
3.25160

[ Vapour Pressure ]:
1.18E-19mmHg at 25°C

[ Index of Refraction ]:
1.572

[ Storage condition ]:
-20℃

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
MC0595275
CHEMICAL NAME :
Glycine, N-(2-((4-(3-hydroxyphenyl)-3,4-dimethyl-1-piperidinyl )methyl)-1-oxo-3-phen ylpropyl)-,dihydrate, (3R-(1(S*),3-alpha,4-alpha))-
CAS REGISTRY NUMBER :
170098-38-1
LAST UPDATED :
199606
DATA ITEMS CITED :
3
MOLECULAR FORMULA :
C25-H32-N2-O4.2H2-O
MOLECULAR WEIGHT :
460.63

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD - Lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
>500 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
DRFUD4 Drugs of the Future. (J.R. Prous, S.A., Apartado de Correos 540, 08080 Barcelona, Spain) V.1- 1975/76- Volume(issue)/page/year: 19,1078,1994
TYPE OF TEST :
LD - Lethal dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
>20 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
DRFUD4 Drugs of the Future. (J.R. Prous, S.A., Apartado de Correos 540, 08080 Barcelona, Spain) V.1- 1975/76- Volume(issue)/page/year: 19,1078,1994
TYPE OF TEST :
LD - Lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
>500 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
DRFUD4 Drugs of the Future. (J.R. Prous, S.A., Apartado de Correos 540, 08080 Barcelona, Spain) V.1- 1975/76- Volume(issue)/page/year: 19,1078,1994

Related Compounds

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