Naldemedine tosylateProduct ingredient for Naldemedine

Name
Naldemedine tosylate
Drug Entry
Naldemedine

Naldemedine is an opioid receptor antagonist Label. It is a modified form of Naltrexone to which a side chain has been added to increase molecular weight and polar surface area resulting in restricted transport across the blood brain barrier. Naldemedine was approved in 2017 in both the US and Japan for the treatment of Opioid-induced Constipation.

Accession Number
DBSALT002556
Structure
Synonyms
Naldemedine tosilate
UNII
V1N8F1RVVO
CAS Number
1345728-04-2
Weight
Average: 742.84
Monoisotopic: 742.267250122
Chemical Formula
C39H42N4O9S
InChI Key
WCYDLROFMZJJLE-RTMHEQJQSA-N
InChI
InChI=1S/C32H34N4O6.C7H8O3S/c1-30(2,29-33-27(35-42-29)18-6-4-3-5-7-18)34-28(39)20-15-32(40)22-14-19-10-11-21(37)25-23(19)31(32,26(41-25)24(20)38)12-13-36(22)16-17-8-9-17;1-6-2-4-7(5-3-6)11(8,9)10/h3-7,10-11,17,22,26,37-38,40H,8-9,12-16H2,1-2H3,(H,34,39);2-5H,1H3,(H,8,9,10)/t22-,26+,31+,32-;/m1./s1
IUPAC Name
(1S,5R,13R,17S)-4-(cyclopropylmethyl)-10,14,17-trihydroxy-N-[2-(3-phenyl-1,2,4-oxadiazol-5-yl)propan-2-yl]-12-oxa-4-azapentacyclo[9.6.1.0^{1,13}.0^{5,17}.0^{7,18}]octadeca-7,9,11(18),14-tetraene-15-carboxamide; 4-methylbenzene-1-sulfonic acid
SMILES
CC1=CC=C(C=C1)S(O)(=O)=O.[H][C@@]12OC3=C4C(C[C@@]5([H])N(CC6CC6)CC[C@@]14[C@@]5(O)CC(C(=O)NC(C)(C)C1=NC(=NO1)C1=CC=CC=C1)=C2O)=CC=C3O
ChemSpider
30790726
ChEMBL
CHEMBL3039508
Wikipedia
Naldemedine
Predicted Properties
PropertyValueSource
Water Solubility0.227 mg/mLALOGPS
logP3.14ALOGPS
logP2.43Chemaxon
logS-3.4ALOGPS
pKa (Strongest Acidic)9.86Chemaxon
pKa (Strongest Basic)9.05Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count8Chemaxon
Hydrogen Donor Count4Chemaxon
Polar Surface Area141.18 Å2Chemaxon
Rotatable Bond Count7Chemaxon
Refractivity165.78 m3·mol-1Chemaxon
Polarizability60.95 Å3Chemaxon
Number of Rings9Chemaxon
Bioavailability1Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon