ETOFYLLINE NICOTINATE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C15H15N5O4
Molecular Weight	329.3107
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CN1C2=C(N(CCOC(=O)C3=CN=CC=C3)C=N2)C(=O)N(C)C1=O

InChI

InChIKey=ZWIAODBBEZGVPY-UHFFFAOYSA-N

InChI=1S/C15H15N5O4/c1-18-12-11(13(21)19(2)15(18)23)20(9-17-12)6-7-24-14(22)10-4-3-5-16-8-10/h3-5,8-9H,6-7H2,1-2H3

HIDE SMILES / InChI

Molecular Formula	C15H15N5O4
Molecular Weight	329.3107
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.drugs.com/international/etofylline.html | https://www.lybrate.com/medicine/etofylline | https://www.ncbi.nlm.nih.gov/pubmed/2997628 | https://www.ncbi.nlm.nih.gov/pubmed/1652045

Etofylline [7-(2-hydroxyethyl)theophylline] is a N-7-substituted derivative of theophylline, a smooth muscle relaxant. Etofylline is used to relieve bronchoconstriction. It may act as a phosphodiesterase inhibitor and adenosine receptor antagonist.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
phosphoric diester hydrolase activity 4 Target ID: GO:0008081 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1652045 \| https://www.drugs.com/international/etofylline.html	Inhibitor 8504
Adenosine A1 receptor 54 Target ID: CHEMBL226 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2997628 \| https://www.ncbi.nlm.nih.gov/pubmed/1652045	Antagonist 2849
Adenosine A2 receptor 9 Target ID: CHEMBL2094257 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2997628 \| https://www.ncbi.nlm.nih.gov/pubmed/1652045	Antagonist 2849

Conditions

Condition	Modality	Highest Phase	Product
Asthma 244 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7325766	Primary	Approved 8583	ETOFYLLINE Approved Use 1. Asthma 2. Chronic obstructive pulmonary disease 3. Chronic bronchitis 4. Emphysema 5. It can be used in premature infants who stop breathing
Chronic obstructive pulmonary disease 175 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7325766	Primary	Approved 8583	ETOFYLLINE Approved Use 1. Asthma 2. Chronic obstructive pulmonary disease 3. Chronic bronchitis 4. Emphysema 5. It can be used in premature infants who stop breathing
Melanoma 88 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22293828	Primary	Preclinical	Unknown Approved Use Unknown

T_1/2

Value	Dose	Co-administered	Analyte	Population
4.1 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7263108/	200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered:		ETOFYLLINE plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN
4.1 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7263108/	200 mg single, intravenous dose: 200 mg route of administration: Intravenous experiment type: SINGLE co-administered:		ETOFYLLINE plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2252 activator 150	inhibitor 2438	inhibitor 2507	inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP2C19 2057 CYP1A2 2153 OATP1B3 961 BCRP 910 OATP1B1 1079 CYP19A1 429 P-gp 1741	P-gp 2052

Drug as perpetrator

Target	Modality	Activity
CYP1A2 2333	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzMzU2IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDY5OSJ9fQ==	no [IC50 >10 uM]
CYP2C19 2141	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzNjIyIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDY5OSJ9fQ==	no [IC50 >10 uM]
CYP2D6 2546	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwyODkiLCJ1c2VfY3VzdG9tX3F1ZXJ5Ijp0cnVlLCJzZWFyY2hfdGVybSI6IiIsInRleHRfZmlsdGVyIjoiQ0hFTUJMNjk5In19	no [IC50 >10 uM]
CYP3A4 2633	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzNDAiLCJ1c2VfY3VzdG9tX3F1ZXJ5Ijp0cnVlLCJzZWFyY2hfdGVybSI6IiIsInRleHRfZmlsdGVyIjoiQ0hFTUJMNjk5In19	no [IC50 >10 uM]
BCRP 985	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/1892#section=BioAssay-Results Page: 63.0	no
CYP19A1 430	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/1892#section=BioAssay-Results Page: 312.0	no
CYP2C9 2497	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzMzk3IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDY5OSJ9fQ==	no
CYP3A4 2633	activator 342 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/1892#section=BioAssay-Results Page: 43.0	no
OATP1B1 1095	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwxNjk3NjY4IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDY5OSJ9fQ==	yes [Inhibition 10 uM]
OATP1B3 970	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwxNzQzMTIxIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDY5OSJ9fQ==	yes [Inhibition 10 uM]
P-gp 1932	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/1892#section=BioAssay-Results Page: 14.0	yes

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
P-gp 2052	substrate 4014 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/1892#section=BioAssay-Results Page: 339 \| 340	no

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/1892#section=BioAssay-Results Page: 219.0

PubMed

Title	Date	PubMed
A liquid chromatography method for quantifying caffeine dissolution from pharmaceutical formulations into colloidal, fat-rich media.	2010-07-01	20483672
Surface-imprinted nanostructured layer-by-layer film for molecular recognition of theophylline derivatives.	2008-10-21	18788771
Simultaneous determination of multi drug components Theophylline, Etofylline, Guaiphenesine and Ambroxol Hydrochloride by validated RP-HPLC method in liquid dosage form.	2008-04	18390446
Simultaneous determination of salbutamol sulphate, bromhexine hydrochloride and etofylline in pharmaceutical formulations with the use of four rapid derivative spectrophotometric methods.	2007-07-30	17658320
A simple and rapid HPLC/UV method for the simultaneous quantification of theophylline and etofylline in human plasma.	2007-04-01	17110179
Investigation of the aqueous dissolution of semicrystalline poly(ethylene oxide) using infrared chemical imaging: the effects of molecular weight and crystallinity.	2005-08	16105205
Prediction of genotoxicity of chemical compounds by statistical learning methods.	2005-06	15962942
The effects of intravenously administered methylxanthines on the proportion of goblet cells containing fucosylated glycoconjugates in rabbit tracheal epithelium.	2004-02	15032328
Method development for determining the antibacterial linezolid in human serum by micellar electrokinetic capillary chromatography.	2002-11-07	12408933
Determination of theophylline by HPLC and GC-IDMS, the effect of chemically similar xanthine derivatives on the specificity of the method and the possibility of paracetamol as interfering substance.	2002	12389716
The effects of intravenously administered methylxanthine preparations on the glycoconjugate composition of goblet cells in rabbit tracheal epithelium.	2002	11993845

Sample Use Guides

In Vivo Use Guide

up to 1.5 g/day

Route of Administration: Other

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Mon Mar 31 20:55:30 GMT 2025` Edited by `admin` on `Mon Mar 31 20:55:30 GMT 2025`
Record UNII	SN6D1V68DL
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ETOFYLLINE NICOTINATE [MI]

Preferred Name

English

ETOFYLLINE NICOTINATE

Common Name

English

Etofylline nicotinate [WHO-DD]

Common Name

English

Classification Tree Code System Code

WHO-ATC

C04AD04