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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
Simultaneous determination of codeine and ethyl morphine HCL in tablet formulations using LC.
2001 Aug
Biochemical background of toxic interaction between tiamulin and monensin.
2004 Mar 15
Determining plasma morphine levels using GC-MS after solid phase extraction to monitor drug levels in the postoperative period.
2008 Jun
[The effect of warfarin was potentiated by an antitussive. Cocillana-Etyfin increased the PK(INR) value].
2009 Nov 4-12
Death of a 10-month-old boy after exposure to ethylmorphine.
2010 Mar 1
Bovine liver slices combined with an androgen transcriptional activation assay: an in-vitro model to study the metabolism and bioactivity of steroids.
2010 May
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