NALOXEGOL

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C34H53NO11
Molecular Weight	651.7847
Optical Activity	UNSPECIFIED
Defined Stereocenters	5 / 5
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

[H][C@@]12OC3=C(O)C=CC4=C3[C@@]15CCN(CC=C)[C@H](C4)[C@]5(O)CC[C@@H]2OCCOCCOCCOCCOCCOCCOCCOC

InChI

InChIKey=XNKCCCKFOQNXKV-ZRSCBOBOSA-N

InChI=1S/C34H53NO11/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/h3-5,28-29,32,36-37H,1,6-25H2,2H3/t28-,29+,32-,33-,34+/m0/s1

HIDE SMILES / InChI

Molecular Formula	C34H53NO11
Molecular Weight	651.7847
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	5 / 5
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description

MOVANTIK (naloxegol) is a peripherally-acting mu-opioid receptor antagonist indicated for the treatment of opioid-induced constipation (OIC) in adult patients with chronic noncancer pain. It is being investigated for the treatment of constipation as a side effect of prescription opioid pain medicines.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Mu-type opioid receptor 61	Antagonist 2,778		7.4 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Opioid-induced constipation 8	Secondary		Approved 8,429	MOVANTIK

C_max

Value	Dose	Analyte	Population
81.1 ng/mL	25 mg 1 times / day multiple, oral	NALOXEGOL OXALATE plasma	Homo sapiens
8 ng/mL	5 mg 1 times / day multiple, oral	NALOXEGOL OXALATE plasma	Homo sapiens
100 ng/mL	50 mg 1 times / day multiple, oral	NALOXEGOL OXALATE plasma	Homo sapiens

AUC

Value	Dose	Analyte	Population
334.8 ng × h/mL	25 mg 1 times / day multiple, oral	NALOXEGOL OXALATE plasma	Homo sapiens
39 ng × h/mL	5 mg 1 times / day multiple, oral	NALOXEGOL OXALATE plasma	Homo sapiens
403.6 ng × h/mL	50 mg 1 times / day multiple, oral	NALOXEGOL OXALATE plasma	Homo sapiens

T_1/2

Value	Dose	Analyte	Population
14.1 h	25 mg 1 times / day multiple, oral	NALOXEGOL OXALATE plasma	Homo sapiens
17.4 h	5 mg 1 times / day multiple, oral	NALOXEGOL OXALATE plasma	Homo sapiens
20.3 h	50 mg 1 times / day multiple, oral	NALOXEGOL OXALATE plasma	Homo sapiens
6 h	unknown, unknown	NALOXEGOL OXALATE plasma	Homo sapiens

F_unbound

Value	Dose	Co-administered	Analyte	Population
95.8%	unknown, unknown		NALOXEGOL OXALATE plasma	Homo sapiens

Doses

Show entries

Dose	Population	Adverse events
1000 mg single, oral Highest studied dose	healthy, 18 - 45 years n = 6	Other AEs: Gastrointestinal disorder (NOS), Nausea...
250 mg 2 times / day steady, oral Highest studied dose	healthy, 59 years (range: 18 - 65 years) n = 6	Other AEs: Myalgia, Restless leg syndrome...
25 mg 1 times / day steady, oral Recommended	unhealthy, adult n = 446	Disc. AE: Diarrhea, Abdominal pain...
12.5 mg 1 times / day steady, oral	unhealthy, adult n = 441	Disc. AE: Diarrhea, Abdominal pain...

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AEs

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AE	Significance	Dose	Population
Dizziness	16.7%	1000 mg single, oral Highest studied dose	healthy, 18 - 45 years n = 6
Gastrointestinal disorder (NOS)	16.7%	1000 mg single, oral Highest studied dose	healthy, 18 - 45 years n = 6
Nausea	16.7%	1000 mg single, oral Highest studied dose	healthy, 18 - 45 years n = 6
Somnolence	16.7%	1000 mg single, oral Highest studied dose	healthy, 18 - 45 years n = 6
CNS disorder (NOS)	33.3%	1000 mg single, oral Highest studied dose	healthy, 18 - 45 years n = 6

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Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 1,587 inducer 781 substrate 1,737	inhibitor 1,767	inhibitor 1,852

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 1,524 CYP2C19 1,478 P-gp 1,461 BCRP 699 OAT1 599 OAT3 642 OCT2 647 OATP1B1 788 OATP1B3 706	CYP3A 191 P-gp 1,537 OATP1B1 406 BCRP 561	CYP1A2 701 CYP2B6 547

Drug as perpetrator

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Target	Modality	Activity
BCRP 773	inhibitor 3,277	no [IC50 >100 uM]
OAT1 603	inhibitor 3,277	no [IC50 >100 uM]
OAT3 644	inhibitor 3,277	no [IC50 >100 uM]
OATP1B1 803	inhibitor 3,277	no [IC50 >100 uM]
OATP1B3 715	inhibitor 3,277	no [IC50 >100 uM]

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Drug as victim

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Target	Modality	Activity	Clinical evidence
BCRP 561	substrate 3,367	no
OATP1B1 406	substrate 3,367	no
CYP3A 191	substrate 3,367	yes
CYP3A4 1,737	substrate 3,367	yes	yes (co-administration study)
P-gp 1,537	substrate 3,367	yes	yes (co-administration study)

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Sourcing

Sourcing

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Vendor/Aggregator	ID	URL
ChEBI	CHEBI:82975	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:82975
ChemicalBook	CB32614743	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB32614743
ZINC	ZINC000095564694	http://zinc15.docking.org/substances/ZINC000095564694

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PubMed

Title	Date	PubMed
Incidence, prevalence, and management of opioid bowel dysfunction.	2001 Nov	11755892

Patents

Sample Use Guides

In Vivo Use Guide

The recommended MOVANTIK dosage is 25 mg once daily in the morning. If patients are not able to tolerate MOVANTIK, reduce the dosage to 12.5 mg once daily.

Route of Administration: Oral

In Vitro Use Guide

Unknown

Substance Class	Chemical
Record UNII	44T7335BKE
Record Status	`Validated (UNII)`
Record Version

Show entries

Name

Type

Language

NALOXEGOL

Official Name

English

NALOXEGOL [USAN]

Common Name

English

AZ-13337019

Code

English

NALOXEGOL [NFLIS-DRUG]

Common Name

English

NKTR-118

Code

English

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Classification Tree

Code System

Code

Established Pharmacologic Class

NDF-RT

N0000175691

Peripheral opioid receptor antagonists

WHO-VATC

QA06AH03

Peripheral opioid receptor antagonists

WHO-ATC

A06AH03

Agent Affecting Nervous System

NCI_THESAURUS

C681

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Code System

Code

Type

Description

DRUG CENTRAL

4832

PRIMARY

EPA CompTox

DTXSID80234684

PRIMARY

CAS

854601-70-0

PRIMARY

SMS_ID

100000152160

PRIMARY

RXCUI

1551777

PRIMARY

RxNorm

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Related Record

Type

Details


					1PE72K8X46

MU-TYPE OPIOID RECEPTOR

TARGET -> INHIBITOR


					22ES734693

MULTIDRUG RESISTANCE PROTEIN 1

TRANSPORTER -> SUBSTRATE


					8E4LAA4357

CYTOCHROME P450 2D6

METABOLIC ENZYME -> SUBSTRATE

Interaction Type:

MINOR


					PUO0521HZV

CYTOCHROME P450 3A4

METABOLIC ENZYME -> SUBSTRATE

Interaction Type:

MAJOR


					6D53G0FD0Z

PLASMA PROTEIN FRACTION (HUMAN)

BINDER->LIGAND

Interaction Type:

BINDING

Amount:

4.2 % (average)

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Related Record

Type

Details


					SVN3WC4C23

CARBOXYMETHYL-PEG6-NALOXOL

METABOLITE -> PARENT


					UN8DF3ZPX5

HO-PEG5-NALOXOL

METABOLITE -> PARENT

Qualification:

PLASMA; URINE


					V475ZW9MQR

3,6,9,12-TETRAOXATETRADECANOIC ACID, 14-(((5.ALPHA.,6.ALPHA.)-4,5-EPOXY-3,14-DIHYDROXY-17-(2-PROPEN-1-YL)MORPHINAN-6-YL)OXY)-

METABOLITE -> PARENT

Qualification:

FECAL; PLASMA; URINE


					2ZU68V975P

ACETIC ACID, 2-(2-(2-(2-(((5.ALPHA.,6.ALPHA.)-4,5-EPOXY-3,14-DIHYDROXY-17-(2-PROPEN-1-YL)MORPHINAN-6-YL)OXY)ETHOXY)ETHOXY)ETHOXY)-

METABOLITE -> PARENT

Qualification:

FECAL; URINE

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Related Record

Type

Details


					44T7335BKE

NALOXEGOL

ACTIVE MOIETY

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Name	Property Type	Amount	Parameters
Tmax	PHARMACOKINETIC	[1 to 1.5] hours (average)	ORAL ADMINISTRATION

Biological Half-life	PHARMACOKINETIC	[6 to 11] hours (average)

Volume of Distribution	PHARMACOKINETIC	[13.8 to 30.5] Liters/Kilogram (average)

SMILES

InChI

CNS Activity

Originator

Approval Year

Targets

Conditions

Cmax

AUC

T1/2

Funbound

Doses

AEs

Overview

OverviewOther

Drug as perpetrator​

Drug as victim

Sourcing

PubMed

Patents

Sample Use Guides

C_max

T_1/2

F_unbound

Drug as perpetrator