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Added issue. Added the cs1 style template to denote Vancouver ("vanc") citation style, because references contain "vauthors" attribute to specify the list of authors.
 
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{{Short description|Chemical compound}}
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{{Drugbox|
{{cs1 config|name-list-style=vanc}}
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|IUPAC_name = N,N-diethyl-4-hydroxy-3-methoxybenzamide
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{{Drugbox
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| image=Ethamivan.svg
| Verifiedfields = changed
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| width= 200
| Watchedfields = changed
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| CAS_number= 304-84-7
| verifiedrevid = 447989190
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| ATC_prefix=R07
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| IUPAC_name = ''N'',''N''-Diethyl-4-hydroxy-3-methoxybenzamide
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| ATC_suffix=AB04
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| image = Ethamivan.svg
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| PubChem= 9363
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| width = 200
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| DrugBank=
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| C=12 | H=17 | N=1 | O=3
| molecular_weight = 223.268
| bioavailability=
| metabolism =
| elimination_half-life=
| excretion =
| pregnancy_category =
| legal_status =
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| routes_of_administration=
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}}


<!--Clinical data-->
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'''Ethamivan''' ('''Etamivan''', '''Analepticon''') is a respiratory [[stimulant]] drug<ref>Hirsh K, Wang SC. Respiratory stimulant effects of ethamivan and picrotoxin. ''Journal of Pharmacology and Experimental Therapeutics''. 1975 May;193(2):657-63.</ref> related to [[nikethamide]]. It was mainly used in the treatment of [[barbiturate]] [[overdose]]<ref>Wheeldon PJ, Perry AW. The use of ethamivan in the treatment of barbiturate poisoning. ''Canadian Medical Association Journal''. 1963 Jul 6;89:20-2.</ref> and [[chronic obstructive pulmonary disease]],<ref>Sproule BJ, Jans RL, Breitkreutz H, Mahon W. Effects of ethamivan in patients with chronic respiratory disease. ''Canadian Medical Association Journal''. 1964 Dec 5;91:1203-8.</ref> but has now largely fallen into disuse. Some research suggests that it may have [[drug abuse|abuse]] potential.<ref>Ma C, Duan H, Zhang H, Xu Y, Zhou T. Studies on analytical method for 10 drugs of abuse in urine using HPLC. (Chinese) ''Yao Xue Xue Bao''. 1998 Oct;33(10):764-7.</ref>
| tradename = Analepticon
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| routes_of_administration =


<!--Identifiers-->
| CAS_number_Ref = {{cascite|correct|??}}
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| CAS_number = 304-84-7
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| ATC_prefix = R07
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| ATC_suffix = AB04
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| PubChem = 9363
| DrugBank_Ref = {{drugbankcite|changed|drugbank}}
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| DrugBank = DB08989
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 8996
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = M44O63YPV9
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D04080


<!--Chemical data-->
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| C=12 | H=17 | N=1 | O=3
| smiles = CCN(CC)C(=O)c1ccc(O)c(OC)c1
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI=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
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = BQJODPIMMWWMFC-UHFFFAOYSA-N
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}}


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'''Etamivan''' ([[International Nonproprietary Name|INN]], or '''ethamivan''' ([[United States Adopted Name|USAN]]); trade names '''Analepticon''', '''Emivan''', and '''Vandid''') is a [[respiratory stimulant]] drug<ref name="pmid1173598">{{cite journal | vauthors = Hirsh K, Wang SC | title = Respiratory stimulant effects of ethamivan and picrotoxin | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 193 | issue = 2 | pages = 657–63 | date = May 1975 | pmid = 1173598 }}</ref> related to [[nikethamide]]. It was mainly used in the treatment of [[barbiturate]] [[overdose]]<ref name="pmid14000228">{{cite journal | vauthors = Wheeldon PJ, Perry AW | title = The use of ethamivan in the treatment of barbiturate poisoning | journal = Canadian Medical Association Journal | volume = 89 | pages = 20–2 | date = July 1963 | issue = 1 | pmid = 14000228 | pmc = 1921664 }}</ref> and [[chronic obstructive pulmonary disease]],<ref name="pmid14226094">{{cite journal | vauthors = Sproule BJ, Jans RL, Breitkreutz H, Mahon W | title = Effects of ethamivan in patients with chronic respiratory disease | journal = Canadian Medical Association Journal | volume = 91 | pages = 1203–8 | date = December 1964 | issue = 23 | pmid = 14226094 | pmc = 1928498 }}</ref> but has now largely fallen into disuse.


Adverse effects which are common to the respiratory stimulant class include sneezing, coughing, and [[laryngospasm]] when infused too rapidly. More serious adverse events include muscle twitching, tremors, and convulsions. The dose to treat barbiturate intoxication or [[carbon dioxide narcosis]] in adults ranges from 0.5 mg/kg to 5.0 mg/kg, infused intravenously over several minutes. Epilepsy and the use of [[monoamine oxidase inhibitor]]s or other [[adrenergic]] drugs are contraindications.<ref>{{cite book |page=N-61 |title=AMA Drug Evaluations |edition=3rd |date=1977 |publisher=Pub. Sciences Group |location=Littleton, Mass. |author=American Medical Association Dept of Drugs |isbn=978-0-88416-175-2 |oclc=1024170745}}</ref>
{{Pharma-stub}}


==References==
==References==
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{{stimulants}}
{{stimulants}}
{{Other respiratory system products}}
{{Other respiratory system products}}

[[Category:Stimulants]]
[[Category:Stimulants]]
[[Category:Respiratory agents]]
[[Category:Phenols]]
[[Category:Benzamides]]
[[Category:Phenol ethers]]


{{respiratory-system-drug-stub}}

Latest revision as of 08:02, 8 January 2024

Etamivan
Clinical data
Trade namesAnalepticon
ATC code
Identifiers
  • N,N-Diethyl-4-hydroxy-3-methoxybenzamide
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
CompTox Dashboard (EPA)
ECHA InfoCard100.005.599 Edit this at Wikidata
Chemical and physical data
FormulaC12H17NO3
Molar mass223.272 g·mol−1
3D model (JSmol)
  • CCN(CC)C(=O)c1ccc(O)c(OC)c1
  • 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 ☒N
  • Key:BQJODPIMMWWMFC-UHFFFAOYSA-N ☒N
 ☒NcheckY (what is this?)  (verify)

Etamivan (INN, or ethamivan (USAN); trade names Analepticon, Emivan, and Vandid) is a respiratory stimulant drug[1] related to nikethamide. It was mainly used in the treatment of barbiturate overdose[2] and chronic obstructive pulmonary disease,[3] but has now largely fallen into disuse.

Adverse effects which are common to the respiratory stimulant class include sneezing, coughing, and laryngospasm when infused too rapidly. More serious adverse events include muscle twitching, tremors, and convulsions. The dose to treat barbiturate intoxication or carbon dioxide narcosis in adults ranges from 0.5 mg/kg to 5.0 mg/kg, infused intravenously over several minutes. Epilepsy and the use of monoamine oxidase inhibitors or other adrenergic drugs are contraindications.[4]

References

[edit]
  1. ^ Hirsh K, Wang SC (May 1975). "Respiratory stimulant effects of ethamivan and picrotoxin". The Journal of Pharmacology and Experimental Therapeutics. 193 (2): 657–63. PMID 1173598.
  2. ^ Wheeldon PJ, Perry AW (July 1963). "The use of ethamivan in the treatment of barbiturate poisoning". Canadian Medical Association Journal. 89 (1): 20–2. PMC 1921664. PMID 14000228.
  3. ^ Sproule BJ, Jans RL, Breitkreutz H, Mahon W (December 1964). "Effects of ethamivan in patients with chronic respiratory disease". Canadian Medical Association Journal. 91 (23): 1203–8. PMC 1928498. PMID 14226094.
  4. ^ American Medical Association Dept of Drugs (1977). AMA Drug Evaluations (3rd ed.). Littleton, Mass.: Pub. Sciences Group. p. N-61. ISBN 978-0-88416-175-2. OCLC 1024170745.


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