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
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 ethanol on ethylmorphine metabolism in isolated rat hepatocytes: characterization by means of a multicompartmental model.
1997 Apr
[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
[Experimental study on using diclofenac sodium or dionine topically to treat fibrinous membrane after intraocular lens implantation].
2001 Jun 28
Effects of fumonisin B1 present in Fusarium moniliforme culture material on drug metabolising enzyme activities in ducks.
2001 May 19
Evidence for the presence of active cytochrome P450 systems in Schistosoma mansoni and Schistosoma haematobium adult worms.
2002 May 22
Enzyme immunoassay validation for the detection of buprenorphine in urine.
2003 Mar
Interpretation of the presence of 6-monoacetylmorphine in the absence of morphine-3-glucuronide in urine samples: evidence of heroin abuse.
2003 Oct
Genomic characterization and regulation of CYP3a13: role of xenobiotics and nuclear receptors.
2003 Sep
Evaluation of the One-Step ELISA kit for the detection of buprenorphine in urine, blood, and hair specimens.
2004 Jul 16
Biochemical background of toxic interaction between tiamulin and monensin.
2004 Mar 15
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
[Current problems in the quality control of pharmaceutical preparations manufactured in pharmacies II. Paracetamol contraining preparations].
2006
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
[Study of cytotoxic and antiviral effects of some eye drops].
2008
Inhibitory effects of opioids on compound action potentials in frog sciatic nerves and their chemical structures.
2008 Aug 1
Purification of CYP2B-like protein from feral leaping mullet (Liza saliens) liver microsomes and its biocatalytic, molecular, and immunological characterization.
2008 Jul-Aug
Determining plasma morphine levels using GC-MS after solid phase extraction to monitor drug levels in the postoperative period.
2008 Jun
Error in the article: "driving under the influence of opiates: concentration relationships between morphine, codeine, 6-acetyl morphine, and ethyl morphine in blood".
2008 Jun
Driving under the influence of opiates: concentration relationships between morphine, codeine, 6-acetyl morphine, and ethyl morphine in blood.
2008 May
Simultaneous screening and quantification of 25 opioid drugs in post-mortem blood and urine by liquid chromatography-tandem mass spectrometry.
2009 Apr 15
Determination of opiates and cocaine in urine by high pH mobile phase reversed phase UPLC-MS/MS.
2009 Feb 1
Importance of using highly pure internal standards for successful liquid chromatography/tandem mass spectrometric bioanalytical assays.
2009 May
[Pharmacological treatment of acute cough].
2009 May 14
[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
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
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SMS_ID
100000092080
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ChEMBL
CHEMBL1712170
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DRUG BANK
DBSALT002363
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NCI_THESAURUS
C76842
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RXCUI
235782
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PRIMARY RxNorm
MERCK INDEX
m5154
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ECHA (EC/EINECS)
204-734-4
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EPA CompTox
DTXSID70924986
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FDA UNII
MFM5450P3T
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EVMPD
SUB13767MIG
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