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Details

Stereochemistry RACEMIC
Molecular Formula C11H16N2O3
Molecular Weight 224.2563
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NIFENALOL

SMILES

CC(C)NCC(O)C1=CC=C(C=C1)[N+]([O-])=O

InChI

InChIKey=UAORFCGRZIGNCI-UHFFFAOYSA-N
InChI=1S/C11H16N2O3/c1-8(2)12-7-11(14)9-3-5-10(6-4-9)13(15)16/h3-6,8,11-12,14H,7H2,1-2H3

HIDE SMILES / InChI

Molecular Formula C11H16N2O3
Molecular Weight 224.2563
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Nifenalol is the beta-receptor antagonist. It has optical isomers. The racemic mixture and the levo-isomer are active in antagonizing beta-receptors, but the dextro-isomer is inactive. The levo-isomer seems to be about twice as active in blocking beta-receptors as the racemate. Nifenalol is virtually devoid of local anesthetic properties in contrast to procaine, propranolol, and butidrine. Nifenalol exacerbated the fighting behavior in male mice by foot-shock. Nifenalol has been studied in patients with coronary artery disease. It afforded the coronary patient good protection against angina and ischemic changes in the EKG. It was further noted that nifenalol had no antiarrhythmic action and that it was devoid of evident side effects. Nifenalol possessed weak action against tremorine and oxotremorine induced tremor.

Approval Year

PubMed

PubMed

TitleDatePubMed
[Blood glucose concentration and insulin activity in serum after administration of the beta receptor blockader nifenalol-HC1 (INPEA). Studies in metabolically healthy people and diabetics].
1977 Jun
Effect of (+) INPEA, (+) sotalol and deoxysotalol on the in vitro production of prostaglandins E and F by the rat uterus.
1980 Apr
Arrhythmogenic effect of beta-adrenoceptor-blocking drugs in Purkinje fibres of guinea-pig hearts.
1996 Jan-Feb
Patents

Sample Use Guides

Dog: 5 or 15 mg/kg
Route of Administration: Intravenous
In Vitro Use Guide
The effects of nifenalol (NIF) on contractile forces and on action potentials (APs) were investigated in isolated guinea pig atrial and papillary muscles, respectively. Log 1/ED40 values for the negative inotropic effects of this drug was 0.74 mmol/l in this order. NIF (0.2 mmol/l) produced about 20% reduction of Vmax at 1 Hz.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:41:58 GMT 2023
Edited
by admin
on Fri Dec 15 15:41:58 GMT 2023
Record UNII
D1DE63830P
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
NIFENALOL
INN   MART.   MI   WHO-DD  
INN  
Official Name English
nifenalol [INN]
Common Name English
1-(4-NITROPHENYL)-2-(ISOPROPYLAMINO)ETHANOL
Systematic Name English
N-ISOPROPYL-1-(P-NITROPHENYL)ETHANOLAMINE
Common Name English
BENZENEMETHANOL, .ALPHA.-(((1-METHYLETHYL)AMINO)METHYL)-4-NITRO-, (±)-
Systematic Name English
DL-.ALPHA.-((ISOPROPYLAMINO)METHYL)-P-NITROBENZYL ALCOHOL
Common Name English
2-(P-NITROPHENYL)-1-ISOPROPYLAMINO-2-ETHANOL
Common Name English
(±)-.ALPHA.-((ISOPROPYLAMINO)METHYL)-P-NITROBENZYL ALCOHOL
Common Name English
Nifenalol [WHO-DD]
Common Name English
BENZENEMETHANOL, .ALPHA.-(((1-METHYLETHYL)AMINO)METHYL)-4-NITRO-
Systematic Name English
DL-INPEA
Code English
(±)-INPEA
Common Name English
(±)-NIFENALOL
Common Name English
(±)-1-(P-NITROPHENYL)-2-ISOPROPYLAMINOETHANOL
Common Name English
DL-N-ISOPROPYL-P-NITROPHENYLETHANOLAMINE
Common Name English
1-(P-NITROPHENYL)-1-HYDROXY-2-(ISOPROPYLAMINO)ETHANE
Common Name English
NIFENALOL [MART.]
Common Name English
(±)-2-ISOPROPYLAMINO-1-(4-NITROPHENYL)ETHANOL
Systematic Name English
NIFENALOL [MI]
Common Name English
BENZYL ALCOHOL, .ALPHA.-((ISOPROPYLAMINO)METHYL)-P-NITRO-
Common Name English
BENZYL ALCOHOL, .ALPHA.-((ISOPROPYLAMINO)METHYL)-P-NITRO-, (±)-
Common Name English
RACEMIC NIFENALOL
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29576
Created by admin on Fri Dec 15 15:41:58 GMT 2023 , Edited by admin on Fri Dec 15 15:41:58 GMT 2023
Code System Code Type Description
FDA UNII
D1DE63830P
Created by admin on Fri Dec 15 15:41:58 GMT 2023 , Edited by admin on Fri Dec 15 15:41:58 GMT 2023
PRIMARY
MERCK INDEX
m1218
Created by admin on Fri Dec 15 15:41:58 GMT 2023 , Edited by admin on Fri Dec 15 15:41:58 GMT 2023
PRIMARY Merck Index
EVMPD
SUB09255MIG
Created by admin on Fri Dec 15 15:41:58 GMT 2023 , Edited by admin on Fri Dec 15 15:41:58 GMT 2023
PRIMARY
CAS
7413-36-7
Created by admin on Fri Dec 15 15:41:58 GMT 2023 , Edited by admin on Fri Dec 15 15:41:58 GMT 2023
PRIMARY
SMS_ID
100000084402
Created by admin on Fri Dec 15 15:41:58 GMT 2023 , Edited by admin on Fri Dec 15 15:41:58 GMT 2023
PRIMARY
PUBCHEM
6317
Created by admin on Fri Dec 15 15:41:58 GMT 2023 , Edited by admin on Fri Dec 15 15:41:58 GMT 2023
PRIMARY
MESH
C100250
Created by admin on Fri Dec 15 15:41:58 GMT 2023 , Edited by admin on Fri Dec 15 15:41:58 GMT 2023
PRIMARY
NCI_THESAURUS
C76554
Created by admin on Fri Dec 15 15:41:58 GMT 2023 , Edited by admin on Fri Dec 15 15:41:58 GMT 2023
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DRUG CENTRAL
3380
Created by admin on Fri Dec 15 15:41:58 GMT 2023 , Edited by admin on Fri Dec 15 15:41:58 GMT 2023
PRIMARY
ECHA (EC/EINECS)
231-023-6
Created by admin on Fri Dec 15 15:41:58 GMT 2023 , Edited by admin on Fri Dec 15 15:41:58 GMT 2023
PRIMARY
EPA CompTox
DTXSID9048693
Created by admin on Fri Dec 15 15:41:58 GMT 2023 , Edited by admin on Fri Dec 15 15:41:58 GMT 2023
PRIMARY
WIKIPEDIA
Nifenalol
Created by admin on Fri Dec 15 15:41:58 GMT 2023 , Edited by admin on Fri Dec 15 15:41:58 GMT 2023
PRIMARY
ChEMBL
CHEMBL127349
Created by admin on Fri Dec 15 15:41:58 GMT 2023 , Edited by admin on Fri Dec 15 15:41:58 GMT 2023
PRIMARY
INN
2734
Created by admin on Fri Dec 15 15:41:58 GMT 2023 , Edited by admin on Fri Dec 15 15:41:58 GMT 2023
PRIMARY
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SALT/SOLVATE -> PARENT
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ACTIVE MOIETY