ETHYLMORPHINE

US Previously Marketed

First marketed in 1921

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C19H23NO3
Molecular Weight	313.3915
Optical Activity	UNSPECIFIED
Defined Stereocenters	5 / 5
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCOc1ccc2C[C@]3([H])[C@]4([H])C=C[C@@]([H])([C@@]5([H])[C@]4(CCN3C)c2c1O5)O

InChI

InChIKey=OGDVEMNWJVYAJL-LEPYJNQMSA-N

InChI=1S/C19H23NO3/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/t12-,13+,14-,18-,19-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C19H23NO3
Molecular Weight	313.3915
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	5 / 5
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: http://www.bepharbel.com/uploads/produits_rcp/4yo9nqr3lf_be-spc-en-codethyline-clean.pdf

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).

CNS Activity

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Opioid receptors; mu/kappa/delta 32 Target ID: CHEMBL2095181 Sources: http://www.bepharbel.com/uploads/produits_rcp/4yo9nqr3lf_be-spc-en-codethyline-clean.pdf	Agonist 2470		345.0 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Cough 103 Sources: http://www.bepharbel.com/uploads/pdf/qltj3rob2v_DH_V04_INSERT-CODETHYLINE-MEDISPEHERE-FR.pdf	Primary		Approved 8043	CODETHYLINE Approved Use A cough medicine.

C_max

Value	Dose	Co-administered	Analyte	Population
1.09 μM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7654478	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

Value	Dose	Co-administered	Analyte	Population
222 μM × min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7654478	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

T_1/2

Value	Dose	Co-administered	Analyte	Population
1.97 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7654478	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

Dose	Population	Adverse events
8.5 mg single, oral Dose: 8.5 mg Route: oral Route: single Dose: 8.5 mg Sources: https://pubmed.ncbi.nlm.nih.gov/20158595	healthy, 10 months n = 1 Health Status: healthy Age Group: 10 months Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/20158595	Other AEs: Sedation... Other AEs: Sedation (grade 5) Sources: https://pubmed.ncbi.nlm.nih.gov/20158595
1.5 mg/kg single, oral Dose: 1.5 mg/kg Route: oral Route: single Dose: 1.5 mg/kg Sources: https://pubmed.ncbi.nlm.nih.gov/7654478	healthy, 24 years n = 10 Health Status: healthy Age Group: 24 years Sex: M Population Size: 10 Sources: https://pubmed.ncbi.nlm.nih.gov/7654478	Other AEs: Dizziness, Drowsiness... Other AEs: Dizziness (7 patients) Drowsiness (slight, 2 patients) Loose stools (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/7654478

AEs

AE	Significance	Dose	Population
Sedation	grade 5	8.5 mg single, oral Dose: 8.5 mg Route: oral Route: single Dose: 8.5 mg Sources: https://pubmed.ncbi.nlm.nih.gov/20158595	healthy, 10 months n = 1 Health Status: healthy Age Group: 10 months Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/20158595
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: https://pubmed.ncbi.nlm.nih.gov/7654478	healthy, 24 years n = 10 Health Status: healthy Age Group: 24 years Sex: M Population Size: 10 Sources: https://pubmed.ncbi.nlm.nih.gov/7654478
Dizziness	7 patients	1.5 mg/kg single, oral Dose: 1.5 mg/kg Route: oral Route: single Dose: 1.5 mg/kg Sources: https://pubmed.ncbi.nlm.nih.gov/7654478	healthy, 24 years n = 10 Health Status: healthy Age Group: 24 years Sex: M Population Size: 10 Sources: https://pubmed.ncbi.nlm.nih.gov/7654478
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: https://pubmed.ncbi.nlm.nih.gov/7654478	healthy, 24 years n = 10 Health Status: healthy Age Group: 24 years Sex: M Population Size: 10 Sources: https://pubmed.ncbi.nlm.nih.gov/7654478

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1601		substrate 1118

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
CYP2D6 1118	substrate 3113 Sources: https://pubmed.ncbi.nlm.nih.gov/7756104/ \| https://pubmed.ncbi.nlm.nih.gov/7654478/	yes
CYP3A4 1601	substrate 3113 Sources: https://pubmed.ncbi.nlm.nih.gov/7756104/	yes

Sourcing

Vendor/Aggregator	ID	URL
ABI Chem	AC1Q37UW
Ambinter	Amb22801513	http://www.ambinter.com/reference/22801513
Angene	AGN-PC-0OHUE6
Aurora Fine Chemicals LLC	A17.879.672	http://online.aurorafinechemicals.com/info?ID=A17.879.672
ChemMol	99147254	http://www.chemmol.com/chemmol/99147254.html
Chemieliva Pharmaceutical Co., Ltd	PBCM1411510
Compound Cloud	23724836
Compound Cloud	5359271
Debye Scientific	DB-056088
Glentham Life Sciences	GP3600	http://www.glentham.com/products/product/GP3600/
LGC Standards	LGCAMP0799.07-01	https://www.lgcstandards.com/US/en/p/LGCAMP0799.07-01
LGC Standards	LGCFOR0799.07	https://www.lgcstandards.com/US/en/p/LGCFOR0799.07
LGC Standards	MM0799.07	https://www.lgcstandards.com/US/en/p/MM0799.07
NovoSeek	5359271
Sigma Aldrich	E-052
Sigma Aldrich	E8512
Sigma Aldrich	E8512\|SIGMA
Sigma-Aldrich	E-052_CERILLIAN	https://www.sigmaaldrich.com/catalog/product/cerillian/e052?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	E8512_SIGMA	https://www.sigmaaldrich.com/catalog/product/sigma/e8512?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Smolecule	S620625	https://www.smolecule.com/products/s620625
Tetrahedron	TS61083
ZINC	ZINC000003629718	http://zinc15.docking.org/substances/ZINC000003629718
eMolecules	193735204

PubMed

Title	Date	PubMed
Acute renal failure due to concomitant action of methotrexate and indomethacin.	1986 Jun 14	2872506
Biotransformation and pharmacokinetics of ethylmorphine after a single oral dose.	1995 Jun	7654478
Effects of ethanol on ethylmorphine metabolism in isolated rat hepatocytes: characterization by means of a multicompartmental model.	1997 Apr	9140136
[Experimental study on using diclofenac sodium or dionine topically to treat fibrinous membrane after intraocular lens implantation].	2001 Jun 28	12536684
Effects of fumonisin B1 present in Fusarium moniliforme culture material on drug metabolising enzyme activities in ducks.	2001 May 19	11369472
Evidence for the presence of active cytochrome P450 systems in Schistosoma mansoni and Schistosoma haematobium adult worms.	2002 May 22	12023046
Enzyme immunoassay validation for the detection of buprenorphine in urine.	2003 Mar	12670004
Interpretation of the presence of 6-monoacetylmorphine in the absence of morphine-3-glucuronide in urine samples: evidence of heroin abuse.	2003 Oct	14508389
Genomic characterization and regulation of CYP3a13: role of xenobiotics and nuclear receptors.	2003 Sep	12958193
Biochemical background of toxic interaction between tiamulin and monensin.	2004 Mar 15	15013817
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	15572279
Automated multiple development thin-layer chromatography for separation of opiate alkaloids and derivatives.	2005 Jul 8	16008057
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	15806585
[Current problems in the quality control of pharmaceutical preparations manufactured in pharmacies II. Paracetamol contraining preparations].	2006	17575797
Validation of direct injection electrospray LC-MS/MS for confirmation of opiates in urine drug testing.	2007 Jul	17535017
Electrospray LC-MS method with solid-phase extraction for accurate determination of morphine-, codeine-, and ethylmorphine-glucuronides and 6-acetylmorphine in urine.	2007 Mar	17536742
A hybrid FIA/HPLC system incorporating monolithic column chromatography.	2007 Sep 26	17903475
[Study of cytotoxic and antiviral effects of some eye drops].	2008	19354165
Inhibitory effects of opioids on compound action potentials in frog sciatic nerves and their chemical structures.	2008 Aug 1	18593589
Purification of CYP2B-like protein from feral leaping mullet (Liza saliens) liver microsomes and its biocatalytic, molecular, and immunological characterization.	2008 Jul-Aug	18752317
Determining plasma morphine levels using GC-MS after solid phase extraction to monitor drug levels in the postoperative period.	2008 Jun	18568238
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	18544226
Driving under the influence of opiates: concentration relationships between morphine, codeine, 6-acetyl morphine, and ethyl morphine in blood.	2008 May	18430293
Simultaneous screening and quantification of 25 opioid drugs in post-mortem blood and urine by liquid chromatography-tandem mass spectrometry.	2009 Apr 15	19232849
Determination of opiates and cocaine in urine by high pH mobile phase reversed phase UPLC-MS/MS.	2009 Feb 1	19144579
Importance of using highly pure internal standards for successful liquid chromatography/tandem mass spectrometric bioanalytical assays.	2009 May	19308966
[Pharmacological treatment of acute cough].	2009 May 14	19448753
[The effect of warfarin was potentiated by an antitussive. Cocillana-Etyfin increased the PK(INR) value].	2009 Nov 4-12	19998819
Characterization of xenobiotic metabolizing enzymes in bovine small intestinal mucosa.	2010 Jun 1	20557447
Effect of cytisine on some brain and hepatic biochemical parameters in spontaneously hypertensive rats.	2010 Mar	21217867
Death of a 10-month-old boy after exposure to ethylmorphine.	2010 Mar 1	20158595
Bovine liver slices combined with an androgen transcriptional activation assay: an in-vitro model to study the metabolism and bioactivity of steroids.	2010 May	20237917

Patents

Sample Use Guides

In Vivo Use Guide

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 `Sat Jun 26 06:45:46 UTC 2021` Edited by `admin` on `Sat Jun 26 06:45:46 UTC 2021`
Record UNII	RWO67D87EU
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ETHYLMORPHINE

Common Name

English

IDS-NE-005(SECT.2)

Code

English

R05DA01

Code

English

CODETHYLINE

Common Name

English

ETHYLMORPHINE [WHO-DD]

Common Name

English

3-ETHOXYMORPHINE

Common Name

English

ETHYLMORPHINE [MI]

Common Name

English

(5.ALPHA.,6.ALPHA.)-7,8-DIDEHYDRO-4,5-EPOXY-3-ETHOXY-17-METHYLMORPHINAN-6-OL

Systematic Name

English

Classification Tree Code System Code

WHO-VATC

QS01XA06