Naloxegol Oxalate | NKTR-118 | AZ-13337019 | CAS#1354744-91-4 | 854601-70-0 | opioid antagonist

MedKoo Cat#: 319933 | Name: Naloxegol Oxalate

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Naloxegol, also known as and NKTR-118 and AZ-13337019, is a peripherally-selective opioid antagonist for the treatment of opioid-induced constipation. It was approved in 2014 in adult patients with chronic, non-cancer pain. Chemically, naloxegol is a pegylated (polyethylene glycol-modified) derivative of α-naloxol. Specifically, the 5-α-hydroxyl group of α-naloxol is connected via an ether linkage to the free hydroxyl group of a monomethoxy-terminated n=7 oligomer of PEG.

Chemical Structure

Naloxegol Oxalate

CAS#1354744-91-4 (oxalate)

Theoretical Analysis

MedKoo Cat#: 319933

Name: Naloxegol Oxalate

CAS#: 1354744-91-4 (oxalate)

Chemical Formula: C36H55NO15

Exact Mass: 0.0000

Molecular Weight: 741.83

Elemental Analysis: C, 58.29; H, 7.47; N, 1.89; O, 32.35

Price and Availability

Size	Price	Availability
10mg	USD 150.00	Ready to ship
25mg	USD 250.00	Ready to ship
50mg	USD 450.00	Ready to ship
100mg	USD 750.00	Ready to ship
200mg	USD 1,350.00	Ready to ship

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Related CAS #

1354744-91-4 (oxalate) 854601-70-0 (free base)

Synonym

NKTR-118; NKTR 118; NKTR118; AZ-13337019; AZ13337019; AZ 13337019; EGylated naloxol; Naloxegol Oxalate; trade names Movantik and Moventig.

IUPAC/Chemical Name

(4R,4aS,7S,7aR,12bS)-7-((2,5,8,11,14,17,20-heptaoxadocosan-22-yl)oxy)-3-allyl-1,2,3,4,5,6,7,7a-octahydro-4aH-4,12-methanobenzofuro[3,2-e]isoquinoline-4a,9-diol oxalate

InChi Key

MNYIRXLCPODKLG-VUTNLTPYSA-N

InChi Code

InChI=1S/C34H53NO11.C2H2O4/c1-3-9-35-10-8-33-30-26-4-5-27(36)31(30)46-32(33)28(6-7-34(33,37)29(35)25-26)45-24-23-44-22-21-43-20-19-42-18-17-41-16-15-40-14-13-39-12-11-38-2;3-1(4)2(5)6/h3-5,28-29,32,36-37H,1,6-25H2,2H3;(H,3,4)(H,5,6)/t28-,29+,32-,33-,34+;/m0./s1

SMILES Code

O[C@@]12CC[C@H](OCCOCCOCCOCCOCCOCCOCCOC)[C@@]3([H])[C@@]14CCN(CC=C)[C@]2([H])CC5=C4C(O3)=C(O)C=C5.O=C(O)C(O)=O

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO, not in water

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO, DMF, PBS, or EtOH

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Certificate of Analysis

View CoA: current batch, Lot#CRB70209

QC Data

View QC data: current batch, Lot#CRB70209

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

	Solvent	mg/mL	mM
Solubility
	Soluble in DMSO	20.0	27.00

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 741.83 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

1: Al-Huniti N. Reply to: Letter to the Editor "Effect of Quinidine, a Strong P-Glycoprotein Inhibitor, on the Pharmacokinetics and Central Nervous System Distribution of Naloxegol". J Clin Pharmacol. 2016 Apr;56(4):508. doi: 10.1002/jcph.674. PubMed PMID: 26954553. 2: Ruan X. The Effect of Quinidine, a Strong P-Glycoprotein Inhibitor, on the Pharmacokinetics and Central Nervous System Distribution of Naloxegol. J Clin Pharmacol. 2016 Apr;56(4):506-7. doi: 10.1002/jcph.651. PubMed PMID: 26954552. 3: Naloxegol (Movantik) for Opioid-Induced Constipation. JAMA. 2016 Jan 12;315(2):194-5. doi: 10.1001/jama.2015.17459. PubMed PMID: 26757469. 4: Bui K, Zhou D, Sostek M, She F, Al-Huniti N. Effects of CYP3A Modulators on the Pharmacokinetics of Naloxegol. J Clin Pharmacol. 2015 Dec 17. doi: 10.1002/jcph.693. [Epub ahead of print] PubMed PMID: 26678015. 5: ▼Naloxegol for opioid-induced constipation. Drug Ther Bull. 2015 Dec;53(12):138-40. doi: 10.1136/dtb.2015.12.0369. PubMed PMID: 26660436. 6: Tack J, Lappalainen J, Diva U, Tummala R, Sostek M. Efficacy and safety of naloxegol in patients with opioid-induced constipation and laxative-inadequate response. United European Gastroenterol J. 2015 Oct;3(5):471-80. doi: 10.1177/2050640615604543. PubMed PMID: 26535126; PubMed Central PMCID: PMC4625753. 7: Naloxegol (Movantik) for opioid-induced constipation. Med Lett Drugs Ther. 2015 Sep 28;57(1478):135-7. Review. PubMed PMID: 26393826. 8: Corsetti M, Tack J. Naloxegol: the first orally administered, peripherally acting, mu opioid receptor antagonist, approved for the treatment of opioid-induced constipation. Drugs Today (Barc). 2015 Aug;51(8):479-89. doi: 10.1358/dot.2015.51.8.2364896. Review. PubMed PMID: 26380386. 9: Bui K, She F, Hutchison M, Brunnström Å, Sostek M. Absorption, distribution, metabolism, and excretion of [14C]-labeled naloxegol in healthy subjects. Int J Clin Pharmacol Ther. 2015 Oct;53(10):838-46. doi: 10.5414/CP202276. PubMed PMID: 26329350; PubMed Central PMCID: PMC4564822. 10: Al-Huniti N, Chapel S, Xu H, Bui KH, Sostek M. Population pharmacokinetics of naloxegol in a population of 1247 healthy subjects and patients. Br J Clin Pharmacol. 2016 Jan;81(1):89-100. doi: 10.1111/bcp.12756. Epub 2015 Oct 27. PubMed PMID: 26317320; PubMed Central PMCID: PMC4693583. 11: Anantharamu T, Sharma S, Gupta AK, Dahiya N, Singh Brashier DB, Sharma AK. Naloxegol: First oral peripherally acting mu opioid receptor antagonists for opioid-induced constipation. J Pharmacol Pharmacother. 2015 Jul-Sep;6(3):188-92. doi: 10.4103/0976-500X.162015. PubMed PMID: 26312011; PubMed Central PMCID: PMC4544149. 12: Bui K, She F, Zhou D, Butler K, Al-Huniti N, Sostek M. The effect of quinidine, a strong P-glycoprotein inhibitor, on the pharmacokinetics and central nervous system distribution of naloxegol. J Clin Pharmacol. 2016 Apr;56(4):497-505. doi: 10.1002/jcph.613. Epub 2015 Nov 9. PubMed PMID: 26248047. 13: Hussar DA, Jeon MM. Naloxegol oxalate, pirfenidone, and nintedanib. J Am Pharm Assoc (2003). 2015 Jul-Aug;55(4):461-3. doi: 10.1331/JAPhA.2015.15523. PubMed PMID: 26161491. 14: Jones R, Prommer E, Backstedt D. Naloxegol: A Novel Therapy in the Management of Opioid-Induced Constipation. Am J Hosp Palliat Care. 2015 Jul 6. pii: 1049909115593937. [Epub ahead of print] PubMed PMID: 26150678. 15: Bruner HC, Atayee RS, Edmonds KP, Buckholz GT. Clinical utility of naloxegol in the treatment of opioid-induced constipation. J Pain Res. 2015 Jun 12;8:289-94. doi: 10.2147/JPR.S61326. eCollection 2015. Review. PubMed PMID: 26109876; PubMed Central PMCID: PMC4472065. 16: Drug Enforcement Administration, Department of Justice. Schedules of controlled substances: removal of naloxegol from control. Final rule. Fed Regist. 2015 Jan 23;80(15):3468-70. PubMed PMID: 25730920. 17: Garnock-Jones KP. Naloxegol: a review of its use in patients with opioid-induced constipation. Drugs. 2015 Mar;75(4):419-25. doi: 10.1007/s40265-015-0357-2. Review. PubMed PMID: 25666542. 18: Corsetti M, Tack J. Naloxegol , a new drug for the treatment of opioid-induced constipation. Expert Opin Pharmacother. 2015 Feb;16(3):399-406. doi: 10.1517/14656566.2015.991306. Epub 2014 Dec 13. Review. PubMed PMID: 25496063. 19: Leonard J, Baker DE. Naloxegol: treatment for opioid-induced constipation in chronic non-cancer pain. Ann Pharmacother. 2015 Mar;49(3):360-5. doi: 10.1177/1060028014560191. Epub 2014 Dec 3. Review. PubMed PMID: 25471070. 20: Poulsen JL, Brock C, Olesen AE, Nilsson M, Drewes AM. Clinical potential of naloxegol in the management of opioid-induced bowel dysfunction. Clin Exp Gastroenterol. 2014 Sep 19;7:345-58. doi: 10.2147/CEG.S52097. eCollection 2014. Review. PubMed PMID: 25278772; PubMed Central PMCID: PMC4179399.