Naloxegol Oxalate

CAS No.
1354744-91-4
Chemical Name:
Naloxegol Oxalate
Synonyms
NKTR-118;NKTR 118 oxalate;Naloxegol Oxalate;AZ 13337019 oxalate;Naloxegol oxalate salt;NKTR-118;NKTR118;NKTR 118;Naloxegol Oxalate NKTR-118;(5alpha,6alpha)-4,5-Epoxy-6-(3,6,9,12,15,18,21-heptaoxadocos-1-yloxy)-17-(2-propen-1-yl)-morphinan-3,14-diol ethanedioate;Morphinan-3,14-diol,4,5-epoxy-6-(3,6,9,12,15,18,21-heptaoxadocos-1-yloxy)-17-(2-propen-1-yl)-,(5α,6α)-,ethanedioate(1:1)(salt);Naloxegol OxalateQ: What is Naloxegol Oxalate Q: What is the CAS Number of Naloxegol Oxalate Q: What is the storage condition of Naloxegol Oxalate
CBNumber:
CB13049698
Molecular Formula:
C36H55NO15
Molecular Weight:
741.83
MDL Number:
MFCD29472292
MOL File:
1354744-91-4.mol
MSDS File:
SDS
Last updated:2023-09-27 13:31:52

Naloxegol Oxalate Properties

Melting point 92-95°C
storage temp. -20°C Freezer, Under inert atmosphere
solubility Chloroform (Slightly), Methanol (Slightly)
form Solid
color White to Off-White
FDA UNII 65I14TNM33

SAFETY

Risk and Safety Statements

NFPA 704
0
3 0

Naloxegol Oxalate price More Price(16)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Cayman Chemical 23731 Naloxegol (oxalate) ≥98% 1354744-91-4 5mg $178 2024-03-01 Buy
Cayman Chemical 23731 Naloxegol (oxalate) ≥98% 1354744-91-4 10mg $319 2024-03-01 Buy
Cayman Chemical 23731 Naloxegol (oxalate) ≥98% 1354744-91-4 25mg $573 2024-03-01 Buy
Cayman Chemical 23731 Naloxegol (oxalate) ≥98% 1354744-91-4 50mg $935 2024-03-01 Buy
TRC N284475 NaloxegolOxalate 1354744-91-4 25mg $475 2021-12-16 Buy
Product number Packaging Price Buy
23731 5mg $178 Buy
23731 10mg $319 Buy
23731 25mg $573 Buy
23731 50mg $935 Buy
N284475 25mg $475 Buy

Naloxegol Oxalate Chemical Properties,Uses,Production

Description

Naloxegol oxalate (XXI) is a peripherally acting μ-opioid receptor antagonist that was approved in the USA and EU for the treatment of opioid-induced constipation in adults with chronic non-cancer pain. The drug, a pegylated version of naloxone, has significantly reduced central nervous system (CNS) penetration and works by inhibiting the binding of opioids in the gastrointestinal tract. Naloxegol oxalate was developed by Nektar and licensed to AstraZeneca. Although we were unable to find a single report in the primary or patent literature that describes the exact experimental procedures to prepare naloxegol oxalate, there have been reports on the preparation of closely related analogs with specific reports on improving the selectivity of the reduction step156 and the salt formation of the final drug substance.

Uses

Naloxegol Oxalate is an oxalate form of Naloxegol (N284470) which is a peripherally-selective opioid antagonist.

Synthesis

Naloxone (180) was treated with methoxyethyl chloride in the presence of Hunig?ˉs base to give the protected ketone 181. Reduction of the ketone with potassium trisec- butylborohydride exclusively provided the a-alcohol 182 in 85% yield. Alternatively, sodium trialkylborohydrides could also be used to provide similar a-selective reduction in high yield. Deprotonation of the alcohol with sodium hydride followed by alkylation with CH3(OCH2CH2)7Br (183) provided the pegylated intermediate 184 in 88% yield. Acidic removal of the methoxyethyl ether protecting group followed by treatment with oxalic acid and crystallization provided naloxegol oxalate (XXI) in good yield.

Synthesis_1354744-91-4

Naloxegol Oxalate Preparation Products And Raw materials

Raw materials

Preparation Products