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Details

Stereochemistry ACHIRAL
Molecular Formula C18H27NO5
Molecular Weight 337.4107
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PROPANIDID

SMILES

CCCOC(=O)CC1=CC(OC)=C(OCC(=O)N(CC)CC)C=C1

InChI

InChIKey=KEJXLQUPYHWCNM-UHFFFAOYSA-N
InChI=1S/C18H27NO5/c1-5-10-23-18(21)12-14-8-9-15(16(11-14)22-4)24-13-17(20)19(6-2)7-3/h8-9,11H,5-7,10,12-13H2,1-4H3

HIDE SMILES / InChI

Molecular Formula C18H27NO5
Molecular Weight 337.4107
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/1524155 https://www.google.ch/patents/WO2004037750A2?cl=en

Propanidid (Epontol) is an analgetically potent and shortterm anesthetic, widely used in the 1960s. It was originally introduced by Bayer in 1963. Epontol, an injectable emulsion formulation of propanidid, provided by Bayer, was withdrawn from the market in Great Britain in 1983 because of concern over anaphylactoid reactions. Thus, in spite of the fact that propanidid provides shorter and more predictable recovery times than propofol, it has not been accepted widely as an injectable anesthetic. Even though Cremophor EL has been shown to cause anaphylactic reactions in humans in several cases (both when given intravenously and orally), it is still debated whether or not propanidid itself may have contributed to the reactions. It has been argued that the toxic effects or reactions to propanidid (and Althesin) were due to the drugs themselves. Several cases of negative reactions have been recorded for different drugs using Cremophor EL as solubilizer. This suggest that the negative reactions were mainly caused by Cremophor and not by the drug substances themselves. Propanidid is presumed to work as a GABA receptor agonist.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
26.0 µM [EC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
Epontol

Approved Use

Propanidid is used as an IV anaesthesia for rapid induction and maintainence of general anaesthesia of short duration.
PubMed

PubMed

TitleDatePubMed
Clinical studies on induction agents. 28. A further comparison of venous complications following thiopentone, methohexitone and propanidid.
1969 Aug
Methohexitone and propanidid. A comparative investigation of the side effects.
1969 Feb
Cyclizine anaphylaxis, when administered with propanidid.
1969 Jan
A comparison of propaniid and thiopentone as induction agents for electro-convulsive therapy.
1969 Jun
[Resuscitation in acute allergic reactions to drugs].
1980 Nov
Intravenous Induction Agents--propanidid.
2002 Jun
Is Peri-Operative Isolated Systolic Hypertension (ISH) a Cardiac Risk Factor?
2008 Feb
The future of anaesthetic pharmacology.
2009 Oct
Research on electroconvulsive therapy in India: An overview.
2010 Jan
Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment: https://www.ncbi.nlm.nih.gov/pubmed/6608951
The dose required to inhibit the reflex in 95% of patients was 7.22 mg kg-1 and prevented adrenergic responses to nociceptive stimulation. The dose of propanidid required to induce loss of nystagmus was greater than that necessary to abolish response to verbal command. The reflex inhibition rate increased proportionally to the dose up to 8 mg kg-1; larger doses exerted a facilitatory effect and reduced the reflex inhibition rate.
Route of Administration: Intravenous
Propanidid potentiated the GABA (5 uM; EC20 concentration)-mediated current (EC50 values of 26 uM). Propanidid (50 uM) produced >50% inhibition of specific binding at GABAA chloride channels (65%).
Substance Class Chemical
Created
by admin
on Sat Dec 16 16:53:42 UTC 2023
Edited
by admin
on Sat Dec 16 16:53:42 UTC 2023
Record UNII
AO82L471NS
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PROPANIDID
INN   MART.   MI   USAN   WHO-DD  
USAN   INN  
Official Name English
PROPANIDID [MART.]
Common Name English
BAYER-1420
Code English
FBA 1420
Code English
Propanidid [WHO-DD]
Common Name English
BAYER 1420
Code English
FBA-1420
Code English
BENZENEACETIC ACID, 4-(2-(DIETHYLAMINO)-2-OXOETHOXY)-3-METHOXY-, PROPYL ESTER
Common Name English
Propyl {4-[(diethylcarbamoyl)methoxy]-3-methoxyphenyl}acetate
Systematic Name English
PROPANIDID [MI]
Common Name English
propanidid [INN]
Common Name English
PROPANIDID [USAN]
Common Name English
EPONTOL
Brand Name English
WH-5668
Code English
WH 5668
Code English
TH-2180
Code English
Classification Tree Code System Code
WHO-VATC QN01AX04
Created by admin on Sat Dec 16 16:53:43 UTC 2023 , Edited by admin on Sat Dec 16 16:53:43 UTC 2023
NCI_THESAURUS C245
Created by admin on Sat Dec 16 16:53:43 UTC 2023 , Edited by admin on Sat Dec 16 16:53:43 UTC 2023
WHO-ATC N01AX04
Created by admin on Sat Dec 16 16:53:43 UTC 2023 , Edited by admin on Sat Dec 16 16:53:43 UTC 2023
Code System Code Type Description
FDA UNII
AO82L471NS
Created by admin on Sat Dec 16 16:53:43 UTC 2023 , Edited by admin on Sat Dec 16 16:53:43 UTC 2023
PRIMARY
MERCK INDEX
m9187
Created by admin on Sat Dec 16 16:53:43 UTC 2023 , Edited by admin on Sat Dec 16 16:53:43 UTC 2023
PRIMARY Merck Index
DRUG CENTRAL
3494
Created by admin on Sat Dec 16 16:53:43 UTC 2023 , Edited by admin on Sat Dec 16 16:53:43 UTC 2023
PRIMARY
ECHA (EC/EINECS)
215-822-7
Created by admin on Sat Dec 16 16:53:43 UTC 2023 , Edited by admin on Sat Dec 16 16:53:43 UTC 2023
PRIMARY
ChEMBL
CHEMBL2105345
Created by admin on Sat Dec 16 16:53:43 UTC 2023 , Edited by admin on Sat Dec 16 16:53:43 UTC 2023
PRIMARY
MESH
D011410
Created by admin on Sat Dec 16 16:53:43 UTC 2023 , Edited by admin on Sat Dec 16 16:53:43 UTC 2023
PRIMARY
DRUG BANK
DB13234
Created by admin on Sat Dec 16 16:53:43 UTC 2023 , Edited by admin on Sat Dec 16 16:53:43 UTC 2023
PRIMARY
NCI_THESAURUS
C84110
Created by admin on Sat Dec 16 16:53:43 UTC 2023 , Edited by admin on Sat Dec 16 16:53:43 UTC 2023
PRIMARY
EPA CompTox
DTXSID7048825
Created by admin on Sat Dec 16 16:53:43 UTC 2023 , Edited by admin on Sat Dec 16 16:53:43 UTC 2023
PRIMARY
RXCUI
8758
Created by admin on Sat Dec 16 16:53:43 UTC 2023 , Edited by admin on Sat Dec 16 16:53:43 UTC 2023
PRIMARY RxNorm
INN
1639
Created by admin on Sat Dec 16 16:53:43 UTC 2023 , Edited by admin on Sat Dec 16 16:53:43 UTC 2023
PRIMARY
CAS
1421-14-3
Created by admin on Sat Dec 16 16:53:42 UTC 2023 , Edited by admin on Sat Dec 16 16:53:42 UTC 2023
PRIMARY
WIKIPEDIA
PROPANIDID
Created by admin on Sat Dec 16 16:53:43 UTC 2023 , Edited by admin on Sat Dec 16 16:53:43 UTC 2023
PRIMARY
SMS_ID
100000081150
Created by admin on Sat Dec 16 16:53:43 UTC 2023 , Edited by admin on Sat Dec 16 16:53:43 UTC 2023
PRIMARY
EVMPD
SUB10096MIG
Created by admin on Sat Dec 16 16:53:43 UTC 2023 , Edited by admin on Sat Dec 16 16:53:43 UTC 2023
PRIMARY
PUBCHEM
15004
Created by admin on Sat Dec 16 16:53:43 UTC 2023 , Edited by admin on Sat Dec 16 16:53:43 UTC 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY