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

Details

Stereochemistry ABSOLUTE
Molecular Formula C19H23NO3.ClH.2H2O
Molecular Weight 385.882
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ETHYLMORPHINE HYDROCHLORIDE DIHYDRATE

SMILES

O.O.Cl.[H][C@@]12OC3=C4C(C[C@@]5([H])N(C)CC[C@@]14[C@@]5([H])C=C[C@@H]2O)=CC=C3OCC

InChI

InChIKey=FKEDUFRSQFFLHR-VSYPDCRNSA-N
InChI=1S/C19H23NO3.ClH.2H2O/c1-3-22-15-7-4-11-10-13-12-5-6-14(21)18-19(12,8-9-20(13)2)16(11)17(15)23-18;;;/h4-7,12-14,18,21H,3,8-10H2,1-2H3;1H;2*1H2/t12-,13+,14-,18-,19-;;;/m0.../s1

HIDE SMILES / InChI
Ethylmorphine is a derivative of morphine with analgesic and antitussive effect. It acts by activating the opioid receptors and thus has a direct influence on the CNS system. Ethylmorphine was approved in Europe for the treatment of dry cough (Codethyline, Dionine).

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
345.0 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
CODETHYLINE

Approved Use

A cough medicine.
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
1.09 μM
1.5 mg/kg bw single, oral
dose: 1.5 mg/kg bw
route of administration: Oral
experiment type: SINGLE
co-administered:
ETHYLMORPHINE serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
222 μM × min
1.5 mg/kg bw single, oral
dose: 1.5 mg/kg bw
route of administration: Oral
experiment type: SINGLE
co-administered:
ETHYLMORPHINE serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
1.97 h
1.5 mg/kg bw single, oral
dose: 1.5 mg/kg bw
route of administration: Oral
experiment type: SINGLE
co-administered:
ETHYLMORPHINE serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
Doses

Doses

DosePopulationAdverse events​
8.5 mg single, oral
Dose: 8.5 mg
Route: oral
Route: single
Dose: 8.5 mg
Sources:
healthy, 10 months
n = 1
Health Status: healthy
Age Group: 10 months
Sex: M
Population Size: 1
Sources:
Other AEs: Sedation...
Other AEs:
Sedation (grade 5)
Sources:
1.5 mg/kg single, oral
Dose: 1.5 mg/kg
Route: oral
Route: single
Dose: 1.5 mg/kg
Sources:
healthy, 24 years
n = 10
Health Status: healthy
Age Group: 24 years
Sex: M
Population Size: 10
Sources:
Other AEs: Dizziness, Drowsiness...
Other AEs:
Dizziness (7 patients)
Drowsiness (slight, 2 patients)
Loose stools (1 patient)
Sources:
AEs

AEs

AESignificanceDosePopulation
Sedation grade 5
8.5 mg single, oral
Dose: 8.5 mg
Route: oral
Route: single
Dose: 8.5 mg
Sources:
healthy, 10 months
n = 1
Health Status: healthy
Age Group: 10 months
Sex: M
Population Size: 1
Sources:
Loose stools 1 patient
1.5 mg/kg single, oral
Dose: 1.5 mg/kg
Route: oral
Route: single
Dose: 1.5 mg/kg
Sources:
healthy, 24 years
n = 10
Health Status: healthy
Age Group: 24 years
Sex: M
Population Size: 10
Sources:
Dizziness 7 patients
1.5 mg/kg single, oral
Dose: 1.5 mg/kg
Route: oral
Route: single
Dose: 1.5 mg/kg
Sources:
healthy, 24 years
n = 10
Health Status: healthy
Age Group: 24 years
Sex: M
Population Size: 10
Sources:
Drowsiness slight, 2 patients
1.5 mg/kg single, oral
Dose: 1.5 mg/kg
Route: oral
Route: single
Dose: 1.5 mg/kg
Sources:
healthy, 24 years
n = 10
Health Status: healthy
Age Group: 24 years
Sex: M
Population Size: 10
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG


OverviewOther

Other InhibitorOther SubstrateOther Inducer
Drug as victim
PubMed

PubMed

TitleDatePubMed
Effects of ethanol on ethylmorphine metabolism in isolated rat hepatocytes: characterization by means of a multicompartmental model.
1997 Apr
Interpretation of the presence of 6-monoacetylmorphine in the absence of morphine-3-glucuronide in urine samples: evidence of heroin abuse.
2003 Oct
Evaluation of the One-Step ELISA kit for the detection of buprenorphine in urine, blood, and hair specimens.
2004 Jul 16
Validation of direct injection electrospray LC-MS/MS for confirmation of opiates in urine drug testing.
2007 Jul
A hybrid FIA/HPLC system incorporating monolithic column chromatography.
2007 Sep 26
Determining plasma morphine levels using GC-MS after solid phase extraction to monitor drug levels in the postoperative period.
2008 Jun
Importance of using highly pure internal standards for successful liquid chromatography/tandem mass spectrometric bioanalytical assays.
2009 May
Characterization of xenobiotic metabolizing enzymes in bovine small intestinal mucosa.
2010 Jun 1
Death of a 10-month-old boy after exposure to ethylmorphine.
2010 Mar 1
Patents

Sample Use Guides

The recommended dose in adults is 50 mg of codethyline per day, i.e. 10 tablets (1 tablet contains 5 mg of ethylmorphine hydrochloride) per day over several intakes, at a minimum of 4 hours apart. In children the normal dose is 1 tablet per intake, to be renewed after 6 hours if necessary, without exceeding 4 tablets per day.
Route of Administration: Oral
In Vitro Use Guide
Unknown
Name Type Language
ETHYLMORPHINE HYDROCHLORIDE DIHYDRATE
MI   WHO-DD  
Common Name English
ETHYLMORPHINE HYDROCHLORIDE DIHYDRATE [MI]
Common Name English
ETHYLMORPHINE HYDROCHLORIDE HYDRATE
JAN  
Common Name English
(5.ALPHA.,6.ALPHA.)-7,8-DIDEHYDRO-4,5-EPOXY-3-ETHOXY-17-METHYLMORPHINAN-6-OL HYDROCHLORIDE DIHYDRATE
Systematic Name English
CODETHYLINE HYDROCHLORIDE DIHYDRATE
Common Name English
ETHYLMORPHINE HYDROCHLORIDE HYDRATE [JAN]
Common Name English
Ethylmorphine hydrochloride dihydrate [WHO-DD]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C67413
Created by admin on Fri Dec 15 17:26:53 GMT 2023 , Edited by admin on Fri Dec 15 17:26:53 GMT 2023
Code System Code Type Description
MERCK INDEX
m5154
Created by admin on Fri Dec 15 17:26:53 GMT 2023 , Edited by admin on Fri Dec 15 17:26:53 GMT 2023
PRIMARY Merck Index
NCI_THESAURUS
C87358
Created by admin on Fri Dec 15 17:26:53 GMT 2023 , Edited by admin on Fri Dec 15 17:26:53 GMT 2023
PRIMARY
EPA CompTox
DTXSID90986728
Created by admin on Fri Dec 15 17:26:53 GMT 2023 , Edited by admin on Fri Dec 15 17:26:53 GMT 2023
PRIMARY
SMS_ID
300000037439
Created by admin on Fri Dec 15 17:26:53 GMT 2023 , Edited by admin on Fri Dec 15 17:26:53 GMT 2023
PRIMARY
FDA UNII
407X3NQV4N
Created by admin on Fri Dec 15 17:26:53 GMT 2023 , Edited by admin on Fri Dec 15 17:26:53 GMT 2023
PRIMARY
PUBCHEM
5360215
Created by admin on Fri Dec 15 17:26:53 GMT 2023 , Edited by admin on Fri Dec 15 17:26:53 GMT 2023
PRIMARY
CAS
6746-59-4
Created by admin on Fri Dec 15 17:26:53 GMT 2023 , Edited by admin on Fri Dec 15 17:26:53 GMT 2023
PRIMARY