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Alvimopan

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Name

Alvimopan

EINECS 1312995-182-4
CAS No. 156053-89-3 Density 1.166 g/cm3
PSA 89.87000 LogP 3.38020
Solubility N/A Melting Point 210-213oC
Formula C25H32N2O4 Boiling Point 684.1 °C at 760 mmHg
Molecular Weight 424.54 Flash Point 367.5 °C
Transport Information N/A Appearance N/A
Safety Risk Codes N/A
Molecular Structure Molecular Structure of 156053-89-3 (Alvimopan) Hazard Symbols N/A
Synonyms

Glycine,N-[2-[[4-(3-hydroxyphenyl)-3,4-dimethyl-1-piperidinyl]methyl]-1-oxo-3-phenylpropyl]-,[3R-[1(S*),3a,4a]]-;ADL 8-2698;Entereg;LY 246736;glycine, N-[(2S)-3-[(3R,4R)-4-(3-hydroxyphenyl)-3,4-dimethyl-1-piperidinyl]-1-oxo-2-(phenylmethyl)propyl]-;N-{(2S)-2-benzyl-3-[(3R,4R)-4-(3-hydroxyphenyl)-3,4-dimethylpiperidin-1-yl]propanoyl}glycine;Glycine,N-[(2S)-2-[[(3R,4R)-4-(3-hydroxyphenyl)-3,4-dimethyl-1-piperidinyl]methyl]-1-oxo-3-phenylpropyl]-;

Article Data 13

Alvimopan Specification

1. Introduction of Alvimopan
Alvimopan is one kind of white powder. The IUPAC name of Alvimopan is N-{(2S)-2-benzyl-3-[(3R,4R)-4-(3-hydroxyphenyl)-3,4-dimethylpiperidin-1-yl]propanoyl}glycine. Its water water solubility <0.1 mg/mL.Its Product Categories is Aromatics;Chiral Reagents;Intermediates & Fine Chemicals;Pharmaceuticals.

2. Properties of Alvimopan
Physical properties about Alvimopan are:
(1)ACD/LogP: 3.38; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.87; (4)ACD/LogD (pH 7.4): 0.85; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 5.14; (8)ACD/KOC (pH 7.4): 4.91; (9)#H bond acceptors: 6; (10)#H bond donors: 3; (11)#Freely Rotating Bonds: 9; (12)Polar Surface Area: 59.08 Å2; (13)Index of Refraction: 1.572; (14)Molar Refractivity: 119.76 cm3; (15)Molar Volume: 363.7 cm3; (16)Polarizability: 47.47 ×10-24cm3; (17)Surface Tension: 48.1 dyne/cm; (18)Density: 1.166 g/cm3; (19)Flash Point: 367.5 °C; (20)Enthalpy of Vaporization: 105.39 kJ/mol; (21)Boiling Point: 684.1 °C at 760 mmHg; (22)Vapour Pressure: 1.18E-19 mmHg at 25°C.

3. Structure Descriptors of Alvimopan
(1)SMILES: O=C(O)CNC(=O)[C@@H](Cc1ccccc1)CN3CC[C@@](c2cccc(O)c2)([C@H](C3)C)C
(2)InChI: InChI=1/C25H32N2O4/c1-18-16-27(12-11-25(18,2)21-9-6-10-22(28)14-21)17-20(24(31)26-15-23(29)30)13-19-7-4-3-5-8-19/h3-10,14,18,20,28H,11-13,15-17H2,1-2H3,(H,26,31)(H,29,30)/t18-,20-,25+/m0/s1
(3)InChIKey: UPNUIXSCZBYVBB-JVFUWBCBBV

4. Uses of Alvimopan
Alvimopan is a drug which behaves as a peripherally acting μ-opioid antagonist and can treat constipation patients. It is substrate for p-glycoprotein, but not substrate for the cytochrome P450 enzyme system. The Alvimopan is indicated in patients to avoid postoperative ileus following partial large or small bowel resection with primary anastomosis. The mechanism of Alvimopan is that it binds to peripheral mu-receptors with a Ki of 0.2 ng/mL and dissociates slower than most other ligands. Beside, Alvimopan is a peripherally selective opioid antagonist being investigated for the treatment of various gastrointestinal diseases and disorders. In addition, Alvimopan can be used for surgery and gastrointestinal disorders which are caused by the use of opioids, idiopathic constipation and irritable bowel syndrome.

Alvimopan is not substrate for the cytochrome P450 enzyme system. Therefore, no interactions are expected with hepatically metabolized drugs. Alvimopan is substrate for p-glycoprotein. Expect interactions with known p-glycoprotein inhibitors such as amiodarone, depridil, diltiazem, cyclosporine, itraconazole, quinine, quinidine, spironolactone, and verapamil.

 

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