U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C32H34N4O6
Molecular Weight 570.6356
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NALDEMEDINE

SMILES

CC(C)(NC(=O)C1=C(O)[C@@H]2OC3=C(O)C=CC4=C3[C@@]25CCN(CC6CC6)[C@H](C4)[C@]5(O)C1)C7=NC(=NO7)C8=CC=CC=C8

InChI

InChIKey=AXQACEQYCPKDMV-RZAWKFBISA-N
InChI=1S/C32H34N4O6/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/h3-7,10-11,17,22,26,37-38,40H,8-9,12-16H2,1-2H3,(H,34,39)/t22-,26+,31+,32-/m1/s1

HIDE SMILES / InChI

Molecular Formula C32H34N4O6
Molecular Weight 570.6356
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

Naldemedine (Symproic) is an opioid antagonist indicated for the treatment of opioid-induced constipation (OIC) in adult patients with chronic non-cancer pain. Naldemedine is an opioid antagonist with binding affinities for mu-, delta-, and kappa-opioid receptors. Naldemedine functions as a peripherally-acting mu-opioid receptor antagonist in tissues such as the gastrointestinal tract, thereby decreasing the constipating effects of opioids. Naldemedine is a derivative of naltrexone to which a side chain has been added that increases the molecular weight and the polar surface area, thereby reducing its ability to cross the blood-brain barrier (BBB). Naldemedine is also a substrate of the P-glycoprotein (P-gp) efflux transporter. Based on these properties, the CNS penetration of naldemedine is expected to be negligible at the recommended dose levels, limiting the potential for interference with centrally-mediated opioid analgesia. Naldemedine was approved in 2017 in both the US and Japan for the treatment of Opioid-induced Constipation.

CNS Activity

Curator's Comment: Naldemedine is a derivative of naltrexone to which a side chain has been added that increases the molecular weight and the polar surface area, thereby reducing its ability to cross the blood-brain barrier (BBB). Naldemedine is also a substrate of the P-glycoprotein (P-gp) efflux transporter. Based on these properties, the CNS penetration of naldemedine is expected to be negligible at the recommended dose levels, limiting the potential for interference with centrally-mediated opioid analgesia.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
161.08 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Secondary
Symproic

Approved Use

SYMPROIC is indicated for the treatment of opioid-induced constipation (OIC) in adult patients with chronic non-cancer pain.

Launch Date

2017
Secondary
SYMPROIC

Approved Use

SYMPROIC is an opioid antagonist indicated for the treatment of opioid-induced constipation (OIC) in adult patients with chronic non-cancer pain

Launch Date

2017
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
1.98 ng/mL
0.1 mg single, oral
dose: 0.1 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
NALDEMEDINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
11.6 ng × h/mL
0.1 mg single, oral
dose: 0.1 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
NALDEMEDINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
8.3 h
0.1 mg single, oral
dose: 0.1 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
NALDEMEDINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
Doses

Doses

DosePopulationAdverse events​
100 mg single, oral
Highest studied dose
Dose: 100 mg
Route: oral
Route: single
Dose: 100 mg
Sources:
healthy, 21.8 years
n = 6
Health Status: healthy
Age Group: 21.8 years
Sex: M
Population Size: 6
Sources:
Other AEs: Abdominal pain, Diarrhea...
Other AEs:
Abdominal pain (16.7%)
Diarrhea (16.7%)
Sources:
30 mg 1 times / day multiple, oral
Highest studied dose
Dose: 30 mg, 1 times / day
Route: oral
Route: multiple
Dose: 30 mg, 1 times / day
Sources:
healthy, 28.3 years
n = 9
Health Status: healthy
Age Group: 28.3 years
Sex: M
Population Size: 9
Sources:
Other AEs: Abdominal discomfort, Diarrhea...
Other AEs:
Abdominal discomfort (11.1%)
Diarrhea (11.1%)
Sources:
0.2 mg 1 times / day steady, oral
Recommended
Dose: 0.2 mg, 1 times / day
Route: oral
Route: steady
Dose: 0.2 mg, 1 times / day
Sources: Page: p. 189
unhealthy, adult
n = 1163
Health Status: unhealthy
Age Group: adult
Sex: M+F
Population Size: 1163
Sources: Page: p. 189
Disc. AE: Abdominal pain, Diarrhea...
AEs leading to
discontinuation/dose reduction:
Abdominal pain (3.2%)
Diarrhea (3.2%)
Vomiting (3.2%)
Nausea (3.2%)
Colitis (0.1%)
Diverticulitis (0.1%)
Hematochezia (0.1%)
Transaminases abnormal (0.5%)
Edema peripheral (0.1%)
Hyperglycemia (0.1%)
Insomnia (0.1%)
Generalized spasm (0.1%)
Paralysis (0.1%)
Photosensitivity (0.1%)
Rash (0.1%)
Thrombosis (0.1%)
Supraventricular tachycardia (0.1%)
Sources: Page: p. 189
AEs

AEs

AESignificanceDosePopulation
Abdominal pain 16.7%
100 mg single, oral
Highest studied dose
Dose: 100 mg
Route: oral
Route: single
Dose: 100 mg
Sources:
healthy, 21.8 years
n = 6
Health Status: healthy
Age Group: 21.8 years
Sex: M
Population Size: 6
Sources:
Diarrhea 16.7%
100 mg single, oral
Highest studied dose
Dose: 100 mg
Route: oral
Route: single
Dose: 100 mg
Sources:
healthy, 21.8 years
n = 6
Health Status: healthy
Age Group: 21.8 years
Sex: M
Population Size: 6
Sources:
Abdominal discomfort 11.1%
30 mg 1 times / day multiple, oral
Highest studied dose
Dose: 30 mg, 1 times / day
Route: oral
Route: multiple
Dose: 30 mg, 1 times / day
Sources:
healthy, 28.3 years
n = 9
Health Status: healthy
Age Group: 28.3 years
Sex: M
Population Size: 9
Sources:
Diarrhea 11.1%
30 mg 1 times / day multiple, oral
Highest studied dose
Dose: 30 mg, 1 times / day
Route: oral
Route: multiple
Dose: 30 mg, 1 times / day
Sources:
healthy, 28.3 years
n = 9
Health Status: healthy
Age Group: 28.3 years
Sex: M
Population Size: 9
Sources:
Colitis 0.1%
Disc. AE
0.2 mg 1 times / day steady, oral
Recommended
Dose: 0.2 mg, 1 times / day
Route: oral
Route: steady
Dose: 0.2 mg, 1 times / day
Sources: Page: p. 189
unhealthy, adult
n = 1163
Health Status: unhealthy
Age Group: adult
Sex: M+F
Population Size: 1163
Sources: Page: p. 189
Diverticulitis 0.1%
Disc. AE
0.2 mg 1 times / day steady, oral
Recommended
Dose: 0.2 mg, 1 times / day
Route: oral
Route: steady
Dose: 0.2 mg, 1 times / day
Sources: Page: p. 189
unhealthy, adult
n = 1163
Health Status: unhealthy
Age Group: adult
Sex: M+F
Population Size: 1163
Sources: Page: p. 189
Edema peripheral 0.1%
Disc. AE
0.2 mg 1 times / day steady, oral
Recommended
Dose: 0.2 mg, 1 times / day
Route: oral
Route: steady
Dose: 0.2 mg, 1 times / day
Sources: Page: p. 189
unhealthy, adult
n = 1163
Health Status: unhealthy
Age Group: adult
Sex: M+F
Population Size: 1163
Sources: Page: p. 189
Generalized spasm 0.1%
Disc. AE
0.2 mg 1 times / day steady, oral
Recommended
Dose: 0.2 mg, 1 times / day
Route: oral
Route: steady
Dose: 0.2 mg, 1 times / day
Sources: Page: p. 189
unhealthy, adult
n = 1163
Health Status: unhealthy
Age Group: adult
Sex: M+F
Population Size: 1163
Sources: Page: p. 189
Hematochezia 0.1%
Disc. AE
0.2 mg 1 times / day steady, oral
Recommended
Dose: 0.2 mg, 1 times / day
Route: oral
Route: steady
Dose: 0.2 mg, 1 times / day
Sources: Page: p. 189
unhealthy, adult
n = 1163
Health Status: unhealthy
Age Group: adult
Sex: M+F
Population Size: 1163
Sources: Page: p. 189
Hyperglycemia 0.1%
Disc. AE
0.2 mg 1 times / day steady, oral
Recommended
Dose: 0.2 mg, 1 times / day
Route: oral
Route: steady
Dose: 0.2 mg, 1 times / day
Sources: Page: p. 189
unhealthy, adult
n = 1163
Health Status: unhealthy
Age Group: adult
Sex: M+F
Population Size: 1163
Sources: Page: p. 189
Insomnia 0.1%
Disc. AE
0.2 mg 1 times / day steady, oral
Recommended
Dose: 0.2 mg, 1 times / day
Route: oral
Route: steady
Dose: 0.2 mg, 1 times / day
Sources: Page: p. 189
unhealthy, adult
n = 1163
Health Status: unhealthy
Age Group: adult
Sex: M+F
Population Size: 1163
Sources: Page: p. 189
Paralysis 0.1%
Disc. AE
0.2 mg 1 times / day steady, oral
Recommended
Dose: 0.2 mg, 1 times / day
Route: oral
Route: steady
Dose: 0.2 mg, 1 times / day
Sources: Page: p. 189
unhealthy, adult
n = 1163
Health Status: unhealthy
Age Group: adult
Sex: M+F
Population Size: 1163
Sources: Page: p. 189
Photosensitivity 0.1%
Disc. AE
0.2 mg 1 times / day steady, oral
Recommended
Dose: 0.2 mg, 1 times / day
Route: oral
Route: steady
Dose: 0.2 mg, 1 times / day
Sources: Page: p. 189
unhealthy, adult
n = 1163
Health Status: unhealthy
Age Group: adult
Sex: M+F
Population Size: 1163
Sources: Page: p. 189
Rash 0.1%
Disc. AE
0.2 mg 1 times / day steady, oral
Recommended
Dose: 0.2 mg, 1 times / day
Route: oral
Route: steady
Dose: 0.2 mg, 1 times / day
Sources: Page: p. 189
unhealthy, adult
n = 1163
Health Status: unhealthy
Age Group: adult
Sex: M+F
Population Size: 1163
Sources: Page: p. 189
Supraventricular tachycardia 0.1%
Disc. AE
0.2 mg 1 times / day steady, oral
Recommended
Dose: 0.2 mg, 1 times / day
Route: oral
Route: steady
Dose: 0.2 mg, 1 times / day
Sources: Page: p. 189
unhealthy, adult
n = 1163
Health Status: unhealthy
Age Group: adult
Sex: M+F
Population Size: 1163
Sources: Page: p. 189
Thrombosis 0.1%
Disc. AE
0.2 mg 1 times / day steady, oral
Recommended
Dose: 0.2 mg, 1 times / day
Route: oral
Route: steady
Dose: 0.2 mg, 1 times / day
Sources: Page: p. 189
unhealthy, adult
n = 1163
Health Status: unhealthy
Age Group: adult
Sex: M+F
Population Size: 1163
Sources: Page: p. 189
Transaminases abnormal 0.5%
Disc. AE
0.2 mg 1 times / day steady, oral
Recommended
Dose: 0.2 mg, 1 times / day
Route: oral
Route: steady
Dose: 0.2 mg, 1 times / day
Sources: Page: p. 189
unhealthy, adult
n = 1163
Health Status: unhealthy
Age Group: adult
Sex: M+F
Population Size: 1163
Sources: Page: p. 189
Abdominal pain 3.2%
Disc. AE
0.2 mg 1 times / day steady, oral
Recommended
Dose: 0.2 mg, 1 times / day
Route: oral
Route: steady
Dose: 0.2 mg, 1 times / day
Sources: Page: p. 189
unhealthy, adult
n = 1163
Health Status: unhealthy
Age Group: adult
Sex: M+F
Population Size: 1163
Sources: Page: p. 189
Diarrhea 3.2%
Disc. AE
0.2 mg 1 times / day steady, oral
Recommended
Dose: 0.2 mg, 1 times / day
Route: oral
Route: steady
Dose: 0.2 mg, 1 times / day
Sources: Page: p. 189
unhealthy, adult
n = 1163
Health Status: unhealthy
Age Group: adult
Sex: M+F
Population Size: 1163
Sources: Page: p. 189
Nausea 3.2%
Disc. AE
0.2 mg 1 times / day steady, oral
Recommended
Dose: 0.2 mg, 1 times / day
Route: oral
Route: steady
Dose: 0.2 mg, 1 times / day
Sources: Page: p. 189
unhealthy, adult
n = 1163
Health Status: unhealthy
Age Group: adult
Sex: M+F
Population Size: 1163
Sources: Page: p. 189
Vomiting 3.2%
Disc. AE
0.2 mg 1 times / day steady, oral
Recommended
Dose: 0.2 mg, 1 times / day
Route: oral
Route: steady
Dose: 0.2 mg, 1 times / day
Sources: Page: p. 189
unhealthy, adult
n = 1163
Health Status: unhealthy
Age Group: adult
Sex: M+F
Population Size: 1163
Sources: Page: p. 189
OverviewDrug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
low or no [IC50 >20 uM]
low or no [IC50 >20 uM]
low or no [IC50 >20 uM]
low or no [IC50 >20 uM]
low or no [IC50 >20 uM]
low or no [Inhibition 20 uM]
low or no [Inhibition 20 uM]
low or no [Inhibition 20 uM]
low or no [Inhibition 20 uM]
low or no
modest
no
no
no
no
no
no
no
no
no
no
not significant
weak
weak
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
no
no
no
no
no
no
no
no
no
no
no
no
no
no
no
no
no
no
no
no
no
no
yes
yes
yes
yes (co-administration study)
Comment: administered with fluconazole and itraconazole (CYP3A4 inhibitors): itraconazole increased Cmax, AUC0-last, and AUC0-inf of naldemedine by 1.12-fold, 2.65-fold, and 2.91-fold, respectively; fluconazole increased Cmax, AUC0-last, and AUC0-inf of naldemedine by 1.38 fold, 1.88 fold, and 1.90 fold, respectively; adminstered with rifampin (CYP3A4 inducer):reduced naldemedine Cmax by ~39 % and AUCinf by ~83 %;
Page: 84.0
yes
yes (co-administration study)
Comment: administered with cyclosporine (P-gp inhibitor): cyclosporine increased Cmax, AUClast and AUCinf of nalmedine by 1.45 fold, 1.79 fold and 1.78 fold, respectively;
Page: 15.0
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
PubMed

PubMed

TitleDatePubMed
Naldemedine (Symproic) for opioid-induced constipation.
2017 Dec 4
Formulary Drug Review: Naldemedine.
2017 Jul
Spotlight on naldemedine in the treatment of opioid-induced constipation in adult patients with chronic noncancer pain: design, development, and place in therapy.
2018
Evidence Based Review of Pharmacotherapy for Opioid-Induced Constipation in Noncancer Pain.
2018 Apr
Phase 1, Randomized, Double-Blind, Placebo-Controlled Studies on the Safety, Tolerability, and Pharmacokinetics of Naldemedine in Healthy Volunteers.
2018 Jun
Efficacy of Treatments for Opioid-Induced Constipation: Systematic Review and Meta-analysis.
2018 Oct
Patents

Sample Use Guides

Administration (2.1): • Alteration of analgesic dosing regimen prior to initiating SYMPROIC is not required • Patients receiving opioids for less than 4 weeks may be less responsive to SYMPROIC • Discontinue SYMPROIC if treatment with the opioid pain medication is also discontinued Dosage (2.2): • The recommended dosage of SYMPROIC is 0.2 mg orally once daily with or without food.
Route of Administration: Oral
In binding assays, the IC50 and Ki values of S-297995 (Naldemedine) monotosylate for rat mu opioid receptor were 3.21 and 1.40 nM, respectively. S-297995 exhibited antagonistic activity with IC50 and Kb values for rat mu opioid receptor of 161.08 and 0.56 nM, respectively.
Substance Class Chemical
Created
by admin
on Sat Dec 16 01:29:29 GMT 2023
Edited
by admin
on Sat Dec 16 01:29:29 GMT 2023
Record UNII
03KSI6WLXH
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
NALDEMEDINE
INN   USAN   WHO-DD  
INN   USAN  
Official Name English
NALDEMEDINE [MI]
Common Name English
NALDEMEDINE [USAN]
Common Name English
17-(CYCLOPROPYLMETHYL)-6,7-DIDEHYDRO-4,5A-EPOXY-3,6,14-TRIHYDROXY-N-(2-(3-PHENYL-1,2,4-OXADIAZOL-5-YL)PROPAN-2-YL)MORPHINAN-7-CARBOXAMIDE
Common Name English
Naldemedine [WHO-DD]
Common Name English
naldemedine [INN]
Common Name English
S-297995
Code English
Classification Tree Code System Code
WHO-ATC A06AH05
Created by admin on Sat Dec 16 01:29:29 GMT 2023 , Edited by admin on Sat Dec 16 01:29:29 GMT 2023
NDF-RT N0000175691
Created by admin on Sat Dec 16 01:29:29 GMT 2023 , Edited by admin on Sat Dec 16 01:29:29 GMT 2023
Code System Code Type Description
INN
9484
Created by admin on Sat Dec 16 01:29:29 GMT 2023 , Edited by admin on Sat Dec 16 01:29:29 GMT 2023
PRIMARY
DAILYMED
03KSI6WLXH
Created by admin on Sat Dec 16 01:29:29 GMT 2023 , Edited by admin on Sat Dec 16 01:29:29 GMT 2023
PRIMARY
MERCK INDEX
m12021
Created by admin on Sat Dec 16 01:29:29 GMT 2023 , Edited by admin on Sat Dec 16 01:29:29 GMT 2023
PRIMARY
CAS
916072-89-4
Created by admin on Sat Dec 16 01:29:29 GMT 2023 , Edited by admin on Sat Dec 16 01:29:29 GMT 2023
PRIMARY
RXCUI
1876597
Created by admin on Sat Dec 16 01:29:29 GMT 2023 , Edited by admin on Sat Dec 16 01:29:29 GMT 2023
PRIMARY
EVMPD
SUB177220
Created by admin on Sat Dec 16 01:29:29 GMT 2023 , Edited by admin on Sat Dec 16 01:29:29 GMT 2023
PRIMARY
PUBCHEM
54732242
Created by admin on Sat Dec 16 01:29:29 GMT 2023 , Edited by admin on Sat Dec 16 01:29:29 GMT 2023
PRIMARY
SMS_ID
100000163094
Created by admin on Sat Dec 16 01:29:29 GMT 2023 , Edited by admin on Sat Dec 16 01:29:29 GMT 2023
PRIMARY
WIKIPEDIA
Naldemedine
Created by admin on Sat Dec 16 01:29:29 GMT 2023 , Edited by admin on Sat Dec 16 01:29:29 GMT 2023
PRIMARY
USAN
ZZ-09
Created by admin on Sat Dec 16 01:29:29 GMT 2023 , Edited by admin on Sat Dec 16 01:29:29 GMT 2023
PRIMARY
NCI_THESAURUS
C175156
Created by admin on Sat Dec 16 01:29:29 GMT 2023 , Edited by admin on Sat Dec 16 01:29:29 GMT 2023
PRIMARY
DRUG CENTRAL
5220
Created by admin on Sat Dec 16 01:29:29 GMT 2023 , Edited by admin on Sat Dec 16 01:29:29 GMT 2023
PRIMARY
ChEMBL
CHEMBL2105755
Created by admin on Sat Dec 16 01:29:29 GMT 2023 , Edited by admin on Sat Dec 16 01:29:29 GMT 2023
PRIMARY
DRUG BANK
DB11691
Created by admin on Sat Dec 16 01:29:29 GMT 2023 , Edited by admin on Sat Dec 16 01:29:29 GMT 2023
PRIMARY
FDA UNII
03KSI6WLXH
Created by admin on Sat Dec 16 01:29:29 GMT 2023 , Edited by admin on Sat Dec 16 01:29:29 GMT 2023
PRIMARY
EPA CompTox
DTXSID501030350
Created by admin on Sat Dec 16 01:29:29 GMT 2023 , Edited by admin on Sat Dec 16 01:29:29 GMT 2023
PRIMARY
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