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

Details

Stereochemistry ABSOLUTE
Molecular Formula C19H23NO3.ClH
Molecular Weight 349.852
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ETHYLMORPHINE HYDROCHLORIDE

SMILES

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=ZPPBASOODYCKDP-YZZSNFJZSA-N
InChI=1S/C19H23NO3.ClH/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/t12-,13+,14-,18-,19-;/m0./s1

HIDE SMILES / InChI

Molecular Formula C19H23NO3
Molecular Weight 313.3908
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 5 / 5
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
Acute renal failure due to concomitant action of methotrexate and indomethacin.
1986 Jun 14
Biotransformation and pharmacokinetics of ethylmorphine after a single oral dose.
1995 Jun
[Effects of diclofenac sodium combined with dionine in cases with fibrinous membrane after intraocular lens implantation].
2001 Apr 28
Simultaneous determination of codeine and ethyl morphine HCL in tablet formulations using LC.
2001 Aug
Effects of fumonisin B1 present in Fusarium moniliforme culture material on drug metabolising enzyme activities in ducks.
2001 May 19
Screening for drugs of abuse in hair with ion spray LC-MS-MS.
2004 Oct 29
Expression and characterization of human cytochrome P450 4F11: Putative role in the metabolism of therapeutic drugs and eicosanoids.
2004 Sep 15
Inhibition of rat liver CYP2D in vitro and after 1-day and long-term exposure to neuroleptics in vivo-possible involvement of different mechanisms.
2005 Jan
Automated multiple development thin-layer chromatography for separation of opiate alkaloids and derivatives.
2005 Jul 8
Validated toxicological determination of 30 drugs of abuse as optimized derivatives in oral fluid by long column fast gas chromatography/electron impact mass spectrometry.
2005 Jun
Validation of direct injection electrospray LC-MS/MS for confirmation of opiates in urine drug testing.
2007 Jul
Electrospray LC-MS method with solid-phase extraction for accurate determination of morphine-, codeine-, and ethylmorphine-glucuronides and 6-acetylmorphine in urine.
2007 Mar
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
Driving under the influence of opiates: concentration relationships between morphine, codeine, 6-acetyl morphine, and ethyl morphine in blood.
2008 May
[The effect of warfarin was potentiated by an antitussive. Cocillana-Etyfin increased the PK(INR) value].
2009 Nov 4-12
Characterization of xenobiotic metabolizing enzymes in bovine small intestinal mucosa.
2010 Jun 1
Effect of cytisine on some brain and hepatic biochemical parameters in spontaneously hypertensive rats.
2010 Mar
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
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:52:05 GMT 2023
Edited
by admin
on Fri Dec 15 15:52:05 GMT 2023
Record UNII
MFM5450P3T
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ETHYLMORPHINE HYDROCHLORIDE
EP   MI   WHO-DD  
Common Name English
Ethylmorphine hydrochloride [WHO-DD]
Common Name English
ETHYLMORPHINE HCL
Common Name English
(5.ALPHA.,6.ALPHA.)-7,8-DIDEHYDRO-4,5-EPOXY-3-ETHOXY-17-METHYLMORPHINAN-6-OL HYDROCHLORIDE
Systematic Name English
CODETHYLINE HYDROCHLORIDE
Common Name English
ETHYLMORPHINE HYDROCHLORIDE ANHYDROUS [MI]
Common Name English
ETHYLMORPHINE HYDROCHLORIDE [EP MONOGRAPH]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C67413
Created by admin on Fri Dec 15 15:52:05 GMT 2023 , Edited by admin on Fri Dec 15 15:52:05 GMT 2023
Code System Code Type Description
PUBCHEM
5360692
Created by admin on Fri Dec 15 15:52:05 GMT 2023 , Edited by admin on Fri Dec 15 15:52:05 GMT 2023
PRIMARY
CAS
125-30-4
Created by admin on Fri Dec 15 15:52:05 GMT 2023 , Edited by admin on Fri Dec 15 15:52:05 GMT 2023
PRIMARY
SMS_ID
100000092080
Created by admin on Fri Dec 15 15:52:05 GMT 2023 , Edited by admin on Fri Dec 15 15:52:05 GMT 2023
PRIMARY
ChEMBL
CHEMBL1712170
Created by admin on Fri Dec 15 15:52:05 GMT 2023 , Edited by admin on Fri Dec 15 15:52:05 GMT 2023
PRIMARY
DRUG BANK
DBSALT002363
Created by admin on Fri Dec 15 15:52:05 GMT 2023 , Edited by admin on Fri Dec 15 15:52:05 GMT 2023
PRIMARY
NCI_THESAURUS
C76842
Created by admin on Fri Dec 15 15:52:05 GMT 2023 , Edited by admin on Fri Dec 15 15:52:05 GMT 2023
PRIMARY
RXCUI
235782
Created by admin on Fri Dec 15 15:52:05 GMT 2023 , Edited by admin on Fri Dec 15 15:52:05 GMT 2023
PRIMARY RxNorm
MERCK INDEX
m5154
Created by admin on Fri Dec 15 15:52:05 GMT 2023 , Edited by admin on Fri Dec 15 15:52:05 GMT 2023
PRIMARY
ECHA (EC/EINECS)
204-734-4
Created by admin on Fri Dec 15 15:52:05 GMT 2023 , Edited by admin on Fri Dec 15 15:52:05 GMT 2023
PRIMARY
EPA CompTox
DTXSID70924986
Created by admin on Fri Dec 15 15:52:05 GMT 2023 , Edited by admin on Fri Dec 15 15:52:05 GMT 2023
PRIMARY
FDA UNII
MFM5450P3T
Created by admin on Fri Dec 15 15:52:05 GMT 2023 , Edited by admin on Fri Dec 15 15:52:05 GMT 2023
PRIMARY
EVMPD
SUB13767MIG
Created by admin on Fri Dec 15 15:52:05 GMT 2023 , Edited by admin on Fri Dec 15 15:52:05 GMT 2023
PRIMARY
Related Record Type Details
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SOLVATE->ANHYDROUS
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IMPURITY -> PARENT
IMPURITY -> PARENT
IMPURITY -> PARENT
IMPURITY -> PARENT
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ACTIVE MOIETY