ETHAMIVAN

US Previously Marketed

First approved in 1961

Details

Stereochemistry	ACHIRAL
Molecular Formula	C12H17NO3
Molecular Weight	223.2683
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCN(CC)C(=O)C1=CC(OC)=C(O)C=C1

InChI

InChIKey=BQJODPIMMWWMFC-UHFFFAOYSA-N

InChI=1S/C12H17NO3/c1-4-13(5-2)12(15)9-6-7-10(14)11(8-9)16-3/h6-8,14H,4-5H2,1-3H3

HIDE SMILES / InChI

Molecular Formula	C12H17NO3
Molecular Weight	223.2683
Charge	0
Count

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/4387399

Ethamivan or etamivan, a respiratory stimulant was used in pulmonary emphysema.

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
Pulmonary emphysema 6 Sources: https://www.ncbi.nlm.nih.gov/pubmed/4387399	Primary		Not Provided 504	Unknown Approved Use Unknown
Respiratory depression 7 Sources: https://www.ncbi.nlm.nih.gov/pubmed/14079719 http://www.drugfuture.com/chemdata/ethamivan.html https://www.ncbi.nlm.nih.gov/pubmed/4390496	Primary		Approved 8429	Emivan Approved Use Pharmaceutical Preparation Used as a Respiratory and Central Nervous System Stimulant Launch Date 1960

Doses

Dose	Population	Adverse events
10000 mg multiple, intravenous Highest studied dose Dose: 10000 mg Route: intravenous Route: multiple Dose: 10000 mg Sources: https://pubmed.ncbi.nlm.nih.gov/14000228	unhealthy, 21 years n = 1 Health Status: unhealthy Condition: barbiturate poisoning Age Group: 21 years Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/14000228	Sources: https://pubmed.ncbi.nlm.nih.gov/14000228
500 mg single, oral Highest studied dose Dose: 500 mg Route: oral Route: single Dose: 500 mg Sources: https://pubmed.ncbi.nlm.nih.gov/14226094	unhealthy n = 5 Health Status: unhealthy Condition: CHRONIC RESPIRATORY DISEASE Population Size: 5 Sources: https://pubmed.ncbi.nlm.nih.gov/14226094	Sources: https://pubmed.ncbi.nlm.nih.gov/14226094
2.5 mg/kg single, intravenous Highest studied dose Dose: 2.5 mg/kg Route: intravenous Route: single Dose: 2.5 mg/kg Sources: https://pubmed.ncbi.nlm.nih.gov/14226094	unhealthy n = 5 Health Status: unhealthy Condition: CHRONIC RESPIRATORY DISEASE Population Size: 5 Sources: https://pubmed.ncbi.nlm.nih.gov/14226094	Other AEs: Nausea, Vomiting... Other AEs: Nausea (4 patients) Vomiting (1 patient) Muscle twitching (4 patients) Dysphoria (4 patients) Fatigue (4 patients) Dizziness (2 patients) Dyspnea (2 patients) Ear buzzing (1 patient) Vertigo (2 patients) Visual hallucinations (1 patient) Pruritus (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/14226094

AEs

AE	Significance	Dose	Population
Ear buzzing	1 patient	2.5 mg/kg single, intravenous Highest studied dose Dose: 2.5 mg/kg Route: intravenous Route: single Dose: 2.5 mg/kg Sources: https://pubmed.ncbi.nlm.nih.gov/14226094	unhealthy n = 5 Health Status: unhealthy Condition: CHRONIC RESPIRATORY DISEASE Population Size: 5 Sources: https://pubmed.ncbi.nlm.nih.gov/14226094
Pruritus	1 patient	2.5 mg/kg single, intravenous Highest studied dose Dose: 2.5 mg/kg Route: intravenous Route: single Dose: 2.5 mg/kg Sources: https://pubmed.ncbi.nlm.nih.gov/14226094	unhealthy n = 5 Health Status: unhealthy Condition: CHRONIC RESPIRATORY DISEASE Population Size: 5 Sources: https://pubmed.ncbi.nlm.nih.gov/14226094
Visual hallucinations	1 patient	2.5 mg/kg single, intravenous Highest studied dose Dose: 2.5 mg/kg Route: intravenous Route: single Dose: 2.5 mg/kg Sources: https://pubmed.ncbi.nlm.nih.gov/14226094	unhealthy n = 5 Health Status: unhealthy Condition: CHRONIC RESPIRATORY DISEASE Population Size: 5 Sources: https://pubmed.ncbi.nlm.nih.gov/14226094
Vomiting	1 patient	2.5 mg/kg single, intravenous Highest studied dose Dose: 2.5 mg/kg Route: intravenous Route: single Dose: 2.5 mg/kg Sources: https://pubmed.ncbi.nlm.nih.gov/14226094	unhealthy n = 5 Health Status: unhealthy Condition: CHRONIC RESPIRATORY DISEASE Population Size: 5 Sources: https://pubmed.ncbi.nlm.nih.gov/14226094
Dizziness	2 patients	2.5 mg/kg single, intravenous Highest studied dose Dose: 2.5 mg/kg Route: intravenous Route: single Dose: 2.5 mg/kg Sources: https://pubmed.ncbi.nlm.nih.gov/14226094	unhealthy n = 5 Health Status: unhealthy Condition: CHRONIC RESPIRATORY DISEASE Population Size: 5 Sources: https://pubmed.ncbi.nlm.nih.gov/14226094
Dyspnea	2 patients	2.5 mg/kg single, intravenous Highest studied dose Dose: 2.5 mg/kg Route: intravenous Route: single Dose: 2.5 mg/kg Sources: https://pubmed.ncbi.nlm.nih.gov/14226094	unhealthy n = 5 Health Status: unhealthy Condition: CHRONIC RESPIRATORY DISEASE Population Size: 5 Sources: https://pubmed.ncbi.nlm.nih.gov/14226094
Vertigo	2 patients	2.5 mg/kg single, intravenous Highest studied dose Dose: 2.5 mg/kg Route: intravenous Route: single Dose: 2.5 mg/kg Sources: https://pubmed.ncbi.nlm.nih.gov/14226094	unhealthy n = 5 Health Status: unhealthy Condition: CHRONIC RESPIRATORY DISEASE Population Size: 5 Sources: https://pubmed.ncbi.nlm.nih.gov/14226094
Dysphoria	4 patients	2.5 mg/kg single, intravenous Highest studied dose Dose: 2.5 mg/kg Route: intravenous Route: single Dose: 2.5 mg/kg Sources: https://pubmed.ncbi.nlm.nih.gov/14226094	unhealthy n = 5 Health Status: unhealthy Condition: CHRONIC RESPIRATORY DISEASE Population Size: 5 Sources: https://pubmed.ncbi.nlm.nih.gov/14226094
Fatigue	4 patients	2.5 mg/kg single, intravenous Highest studied dose Dose: 2.5 mg/kg Route: intravenous Route: single Dose: 2.5 mg/kg Sources: https://pubmed.ncbi.nlm.nih.gov/14226094	unhealthy n = 5 Health Status: unhealthy Condition: CHRONIC RESPIRATORY DISEASE Population Size: 5 Sources: https://pubmed.ncbi.nlm.nih.gov/14226094
Muscle twitching	4 patients	2.5 mg/kg single, intravenous Highest studied dose Dose: 2.5 mg/kg Route: intravenous Route: single Dose: 2.5 mg/kg Sources: https://pubmed.ncbi.nlm.nih.gov/14226094	unhealthy n = 5 Health Status: unhealthy Condition: CHRONIC RESPIRATORY DISEASE Population Size: 5 Sources: https://pubmed.ncbi.nlm.nih.gov/14226094
Nausea	4 patients	2.5 mg/kg single, intravenous Highest studied dose Dose: 2.5 mg/kg Route: intravenous Route: single Dose: 2.5 mg/kg Sources: https://pubmed.ncbi.nlm.nih.gov/14226094	unhealthy n = 5 Health Status: unhealthy Condition: CHRONIC RESPIRATORY DISEASE Population Size: 5 Sources: https://pubmed.ncbi.nlm.nih.gov/14226094

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY547425	https://www.001chemical.com/chem/304-84-7
3B Scientific (Wuhan) Corp	3B3-021459	http://www.3bsc.com/index/pro_info.php?id=43535
AA Blocks	AA002ZX3	https://www.aablocks.com/goods/Goods/detail?id=AA002ZX3
AHH Chemical co.,ltd	MT-60342	http://www.ahhchemical.com/product/MT-60342.html
AK Scientific, Inc. (AKSCI)	2787AH	http://www.aksci.com/item_detail.php?cat=2787AH
AbMole Bioscience	M2688	http://www.abmole.com/products/ethamivan.html
Ambinter	Amb2099632	http://www.ambinter.com/reference/2099632
Angel Pharmatech	AG-19751	http://www.angelpharmatech.com/304-84-7.html
BioSynth	J-017977	https://www.biosynth.com/en/products/all-products/products/J-017977.html
BroadPharm	BP-12587	http://www.broadpharm.com/bykeyword.php?s=BP-12587
Chem Scene	CS-4684	http://www.chemscene.com/304-84-7.html
ChemMol	83602365	http://www.chemmol.com/chemmol/83602365.html
ChemMol	99068659	http://www.chemmol.com/chemmol/99068659.html
Chemspace	CSSB00000038098	https://chem-space.com/CSSB00000038098
Clearsynth	CS-T-87508	https://www.clearsynth.com/en/CST87508.html
DC Chemicals	DC37326	http://www.dcchemicals.com//product_show-Analepticon.html
Debye Scientific	DB-047788	http://www.debyesci.com/cas_304-84-7.html
LGC Standards	LGCFOR1682.00	https://www.lgcstandards.com/US/en/p/LGCFOR1682.00
LGC Standards	MM1682.00	https://www.lgcstandards.com/US/en/p/MM1682.00
Lab Network	LN00189195	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00189195
MedChem Express	HY-B1096	https://www.medchemexpress.com/Etamivan.html
MolPort	MolPort-001-791-638	https://www.molport.com/shop/molecule-link/MolPort-001-791-638
Molcore	MC547425	https://www.molcore.com/product/304-84-7
MuseChem	I003067	https://www.musechem.com/product/I003067.html
Sigma-Aldrich	S360554_ALDRICH	https://www.sigmaaldrich.com/catalog/product/aldrich/s360554
Sigma-Aldrich	E0137_SIGMA	https://www.sigmaaldrich.com/catalog/product/sigma/e0137?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sinfoo Biotech	S018513	http://www.sinfoobiotech.com/product/1021911
Smolecule	S527498	http://www.smolecule.com/products/s527498
THE BioTek	bt-267805	https://www.thebiotek.com/product/inhibitors/bt-267805
mcule	MCULE-4849532738	https://mcule.com/MCULE-4849532738/

PubMed

Title	Date	PubMed
Effect of ethamivan on alveolar ventilation in patients with chronic lung disease.	1962 Dec 20	13974643
Effect of oral ethamivan on daily fluctuations of carbon dioxide tension in pulmonary emphysema with carbon dioxide retention.	1969 Jan	4387399
Respiratory depression in the coma of myxedema: treatment with ethamivan intravenously.	1969 Oct	4390496
Pentylenetetrazol and ethamivan effects on brain serotonin metabolism.	1970 Jul 15	4394604

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Oral

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Fri Dec 15 14:58:24 GMT 2023` Edited by `admin` on `Fri Dec 15 14:58:24 GMT 2023`
Record UNII	M44O63YPV9
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ETHAMIVAN

Official Name

English

N,N-Diethylvanillamide

Systematic Name

English

ETAMIVAN [MART.]

Common Name

English

VANDID

Brand Name

English

etamivan [INN]

Common Name

English

ETHAMIVAN [MI]

Common Name

English

BENZAMIDE, N,N-DIETHYL-4-HYDROXY-3-METHOXY-

Systematic Name

English

Etamivan [WHO-DD]

Common Name

English

ETHAMIVAN [USAN]

Common Name

English

EMIVAN

Common Name

English

ETAMIVAN

Official Name

English

NSC-406087

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C47795