OXOLAMINE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C14H19N3O
Molecular Weight	245.3202
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCN(CC)CCC1=NC(=NO1)C2=CC=CC=C2

InChI

InChIKey=IDCHQQSVJAAUQQ-UHFFFAOYSA-N

InChI=1S/C14H19N3O/c1-3-17(4-2)11-10-13-15-14(16-18-13)12-8-6-5-7-9-12/h5-9H,3-4,10-11H2,1-2H3

HIDE SMILES / InChI

Description
Sources: https://www.ilacprospektusu.com/ilac/619/perebron-10-mg-120-ml-surup | https://www.ncbi.nlm.nih.gov/pubmed/13720535 | https://www.ncbi.nlm.nih.gov/pubmed/7140166

Oxolamine under brand names Symphocal, Perebron is used in some countries as a cough suppressant for the treatment of pharyngitis, tracheitis, bronchitis, bronchiectasis, pertussis. Oxolamine possesses anti-inflammatory activity, which causes a reduction in the irritation of the nervous receptors of the respiratory tract.

Approval Year

Conditions

Condition	Modality	Highest Phase	Product
Cough 106 Sources: https://www.ilacprospektusu.com/ilac/619/perebron-10-mg-120-ml-surup	Palliative	Approved 8583	Perebron Approved Use Unknown
Tracheitis 3 Sources: https://www.ilacprospektusu.com/ilac/619/perebron-10-mg-120-ml-surup	Palliative	Approved 8583	Perebron Approved Use Unknown
Bronchitis 51 Sources: https://www.ilacprospektusu.com/ilac/619/perebron-10-mg-120-ml-surup	Palliative	Approved 8583	Perebron Approved Use Unknown
Pertussis 3 Sources: https://www.ilacprospektusu.com/ilac/619/perebron-10-mg-120-ml-surup	Palliative	Approved 8583	Perebron Approved Use Unknown

Doses

Dose	Population	Adverse events
15 mL single, oral Overdose Dose: 15 mL Route: oral Route: single Dose: 15 mL Sources: https://pubmed.ncbi.nlm.nih.gov/2716683/	unhealthy, CHILD Health Status: unhealthy Age Group: CHILD Sex: M Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/2716683/	Disc. AE: Visual hallucinations... AEs leading to discontinuation/dose reduction: Visual hallucinations Sources: https://pubmed.ncbi.nlm.nih.gov/2716683/

AEs

AE	Significance	Dose	Population
Visual hallucinations	Disc. AE	15 mL single, oral Overdose Dose: 15 mL Route: oral Route: single Dose: 15 mL Sources: https://pubmed.ncbi.nlm.nih.gov/2716683/	unhealthy, CHILD Health Status: unhealthy Age Group: CHILD Sex: M Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/2716683/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2252	inhibitor 2438	inhibitor 2507

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP2C19 2057 CYP1A2 2153

Drug as perpetrator

Target	Modality	Activity
CYP2D6 2546	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwyODkiLCJ1c2VfY3VzdG9tX3F1ZXJ5Ijp0cnVlLCJzZWFyY2hfdGVybSI6IiIsInRleHRfZmlsdGVyIjoiQ0hFTUJMMTQ0ODA0NCJ9fQ==	inconclusive [IC50 6.3096 uM]
CYP2C19 2141	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzNjIyIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDE0NDgwNDQifX0=	no [IC50 >10 uM]
CYP2C9 2497	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzMzk3IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDE0NDgwNDQifX0=	no [IC50 >10 uM]
CYP3A4 2633	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzNDAiLCJ1c2VfY3VzdG9tX3F1ZXJ5Ijp0cnVlLCJzZWFyY2hfdGVybSI6IiIsInRleHRfZmlsdGVyIjoiQ0hFTUJMMTQ0ODA0NCJ9fQ==	no [IC50 >10 uM]
CYP1A2 2333	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzMzU2IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IiBDSEVNQkwxNDQ4MDQ0In19	yes [IC50 5.0119 uM]

PubMed

Title	Date	PubMed
Gender difference in the pharmacokinetic interaction between oral warfarin and oxolamine in rats: inhibition of CYP2B1 by oxolamine in male rats.	2007-04	17295362
Effect of oxolamine on anticoagulant effect of warfarin.	2006-01-15	16390929
Effect of oxolamine on cough sensitivity in COPD patients.	2002-01	11863211

Patents

Sample Use Guides

In Vivo Use Guide

In general, 15-25 mg per kilogram per day should be given by dividing four equal doses. In children over 2 years: 1-2 ml of 5 ml Adults: 2 ml of 5 ml 4 times daily 4 hours a day, after an equal amount of water.

Route of Administration: Oral

In Vitro Use Guide

Unknown

Name

Type

Language

OKSALAMIN

Preferred Name

English

OXOLAMINE

Official Name

English

5-(2-(DIETHYLAMINO)ETHYL)-3-PHENYL-1,2,4-OXADIAZOLE

Systematic Name

English

OXOLAMINE [MI]

Common Name

English

SKF-9976 FREE BASE

Code

English

Oxolamine [WHO-DD]

Common Name

English

OXOLAMINE [MART.]

Common Name

English

oxolamine [INN]

Common Name

English

AF-438 FREE BASE

Code

English

SKF 9976 FREE BASE

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C257