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Details

Stereochemistry RACEMIC
Molecular Formula C13H14O3
Molecular Weight 218.2485
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PROPRANOLOL GLYCOL

SMILES

OCC(O)COC1=C2C=CC=CC2=CC=C1

InChI

InChIKey=BYNNMWGWFIGTIC-UHFFFAOYSA-N
InChI=1S/C13H14O3/c14-8-11(15)9-16-13-7-3-5-10-4-1-2-6-12(10)13/h1-7,11,14-15H,8-9H2

HIDE SMILES / InChI

Molecular Formula C13H14O3
Molecular Weight 218.2485
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description
Curator's Comment: The description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/11489433 | https://www.ncbi.nlm.nih.gov/pubmed/432438 | https://www.ncbi.nlm.nih.gov/pubmed/7895597 | https://www.ncbi.nlm.nih.gov/pubmed/1875045

Propranolol glycol is a major metabolite of propranolol in man with potent anticonvulsant activity. Propranolol glycol appears to be more potent for this effect than propranolol. The onset of action of propranolol glycol is instantaneous but delayed for propranolol. Maximal anticonvulsant activity for propranolol glycol is obtained immediately and for propranolol 10 minutes after administration. The delayed onset of this action of propranolol and the immediate anticonvulsant activity of propranolol glycol strongly suggest that the anticonvulsant properties of propranolol may be related to its conversion to propranolol glycol. Propranolol and propramioiol glycol have a similar spectrum of gross behavioral effects ranging from quietness at low doses to paralysis at high doses. These observations suggest the possibility that propranolol glycol may be contributing to some of the therapeutically significant effects of propranolol in the central nervous system.

Originator

Sources: Monatshefte fuer Chemie (1909), 29, 951-8.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Central nervous system effects and metabolic disposition of a glycol metabolite of propranolol.
1974 Jan
Patents

Patents

Sample Use Guides

The anticonvulsant activity of propranolol glycol was determined by injecting mice with propranolol glycol (2.5-40 mg/kg)
Route of Administration: Intravenous
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Thu Jul 06 16:24:47 UTC 2023
Edited
by admin
on Thu Jul 06 16:24:47 UTC 2023
Record UNII
FU45BO16RF
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PROPRANOLOL GLYCOL
Common Name English
3-(.ALPHA.-NAPHTHOXY)-1,2-PROPANEDIOL
Systematic Name English
3-(1-NAPHTHALENYLOXY)-1,2-PROPANEDIOL
Systematic Name English
PROPRANOLOL RELATED COMPOUND A [USP-RS]
Common Name English
1-(.ALPHA.-NAPHTHOXY)-2,3-PROPYLENE GLYCOL
Systematic Name English
PROPRANOLOL HYDROCHLORIDE IMPURITY A [EP IMPURITY]
Common Name English
1,2-PROPANEDIOL, 3-(1-NAPHTHALENYLOXY)-
Systematic Name English
PROPRANOLOL GLYCOL, (±)-
Common Name English
(2RS)-3-(NAPHTHALEN-1-YLOXY)PROPANE-1,2-DIOL
Systematic Name English
3-(.ALPHA.-NAPHTHOXY)-1,2-PROPYLENE GLYCOL
Systematic Name English
Code System Code Type Description
RXCUI
2105554
Created by admin on Thu Jul 06 16:24:47 UTC 2023 , Edited by admin on Thu Jul 06 16:24:47 UTC 2023
PRIMARY
PUBCHEM
37369
Created by admin on Thu Jul 06 16:24:47 UTC 2023 , Edited by admin on Thu Jul 06 16:24:47 UTC 2023
PRIMARY
FDA UNII
FU45BO16RF
Created by admin on Thu Jul 06 16:24:47 UTC 2023 , Edited by admin on Thu Jul 06 16:24:47 UTC 2023
PRIMARY
CAS
36112-95-5
Created by admin on Thu Jul 06 16:24:47 UTC 2023 , Edited by admin on Thu Jul 06 16:24:47 UTC 2023
PRIMARY
RS_ITEM_NUM
1576016
Created by admin on Thu Jul 06 16:24:47 UTC 2023 , Edited by admin on Thu Jul 06 16:24:47 UTC 2023
PRIMARY
Related Record Type Details
ENANTIOMER -> RACEMATE
ENANTIOMER -> RACEMATE
Related Record Type Details
PARENT -> METABOLITE
Related Record Type Details
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP