U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C10H14N2O
Molecular Weight 178.231
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NIKETHAMIDE

SMILES

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

InChI

InChIKey=NCYVXEGFNDZQCU-UHFFFAOYSA-N
InChI=1S/C10H14N2O/c1-3-12(4-2)10(13)9-6-5-7-11-8-9/h5-8H,3-4H2,1-2H3

HIDE SMILES / InChI
Nikethamide is a respiratory and circulatory stimulant with some central nervous system activity. Widely known by its former trade name of Coramine, it was used in the mid-twentieth century as a medical countermeasure against tranquilizer overdoses, before the advent of endotracheal intubation and positive-pressure lung expansion. Nikethamide is available as a short-acting over-the-counter drug in several South American and European countries, combined with glucose in form of lozenges. Nikethamide is especially useful for mountain climbers to increase endurance at high altitudes. Contraindications include hypertension, cardiovascular pathologies, and epilepsy. In some sports, nikethamide is listed by the World Anti-Doping Agency as a banned substance. Croatian tennis player Marin Čilić was suspended from competition for nine months after he tested positive for nikethamide in April 2013

Originator

Sources: Zeitschrift fuer die Gesamte Experimentelle Medizin 52, 197-213. From: Chem. Zentr. 1926, II, 2456.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Coramine

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Replacement of cyanogen bromide solution PH. EUR. with 1,3-dibromo-5,5-dimethylhydantoin (DBH). Analytical methods of pharmacopoeias with DBH in respect to environmental and economical concern, Part 13.
2002 Apr
Spectrophotometric determination of nikethamide by charge--transfer complexation with chloranilic acid.
2002 Jul-Aug
Effects of ethylene glycol-based graft, star-shaped, and dendritic polymers on solubilization and controlled release of paclitaxel.
2003 Dec 5
Confirmation of amphetamine, methamphetamine, MDA and MDMA in urine samples using disk solid-phase extraction and gas chromatography-mass spectrometry after immunoassay screening.
2003 Jul 25
Aqueous N,N-diethylnicotinamide (DENA) solution as a medium for accelerated release study of paclitaxel.
2004
Origin of the disjunct tetraploid Cardamine amporitana (Brassicaceae) assessed with nuclear and chloroplast DNA sequence data.
2004 Aug
Comparative ITS and AFLP analysis of diploid Cardamine (Brassicaceae) taxa from closely related polyploid complexes.
2004 May
Evolution of the trnF(GAA) gene in Arabidopsis relatives and the brassicaceae family: monophyletic origin and subsequent diversification of a plastidic pseudogene.
2005 Apr
Hydrotropic polymer micelle system for delivery of paclitaxel.
2005 Jan 3
Importance of sequence and structural elements within a viral replication repressor.
2005 Mar 15
The difference between simple and complex leaves.
2006 Aug
The genetic basis for differences in leaf form between Arabidopsis thaliana and its wild relative Cardamine hirsuta.
2006 Aug
Antioxidant activity of wild plants collected in Valsesia, an alpine region of Northern Italy.
2006 Jul
Paclitaxel-loaded microparticles and implants for the treatment of brain cancer: preparation and physicochemical characterization.
2006 May 18
Hydrotropic polymeric micelles for enhanced paclitaxel solubility: in vitro and in vivo characterization.
2007 Jan
Hybridization between two polyploid Cardamine (Brassicaceae) species in North-western Spain: discordance between morphological and genetic variation patterns.
2007 Jun
Impact of foliar herbivory on the development of a root-feeding insect and its parasitoid.
2007 May
Diaqua-bis(4-chloro-benzoato-κO)bis-(N,N-diethyl-nicotinamide-κN)manganese(II).
2008 Feb 29
Consistent geographic structure among multiple nuclear sequences and cpDNA polymorphisms of Cardamine nipponica Franch. et Savat. (Brassicaceae).
2008 Jul
[GABA A receptor participates in respiratory enhancement induced by nikethamide in neonatal rats].
2008 Mar
A developmental framework for dissected leaf formation in the Arabidopsis relative Cardamine hirsuta.
2008 Sep
Diaqua-bis(2-chloro-benzoato-κO)bis-(N,N-diethyl-nicotinamide-κN)manganese(II).
2009 Apr 10
Diaqua-bis(2-bromo-benzoato-κO)bis-(N,N-diethyl-nicotinamide-κN)manganese(II).
2009 Apr 18
Diaqua-bis(2-bromo-benzoato-κO)bis-(N,N-diethyl-nicotinamide-κN)zinc(II).
2009 Apr 2
Diaqua-bis(2-chloro-benzoato-κO)bis-(N,N-diethyl-nicotinamide-κN)nickel(II).
2009 Apr 22
Diaqua-bis(N,N-diethyl-nicotinamide-κN)bis-(4-formyl-benzoato-κO)nickel(II).
2009 Feb 25
Diaqua-bis(N,N-diethyl-nicotinamide-κN)bis-(4-formyl-benzoato-κO)manganese(II).
2009 Feb 25
Tetra-kis[μ-4-(diethyl-amino)benzoato-κO:O']bis-[(N,N-diethyl-nicotinamide-κN)zinc(II)].
2009 Jul 18
Diaqua-bis(N,N-diethyl-nicotinamide-κN)bis-[4-(dimethyl-amino)benzoato-κO]nickel(II).
2009 Jul 31
Evidence for the association of the DAOA (G72) gene with schizophrenia and bipolar disorder but not for the association of the DAO gene with schizophrenia.
2009 Jul 8
Molecular evolution of phytochromes in Cardamine nipponica (Brassicaceae) suggests the involvement of PHYE in local adaptation.
2009 Jun
Comment on 'Laparoscopic heminephroureterectomy for duplex kidney anomalies in the pediatric population' by J. Seibold, D. Schilling, U. Nagele, A.G. Anastasiadis, K.D. Sievert, A. Stenzl, S. Corvin. J Pediatr Urol 2008;4:345-7.
2009 Jun
Diaqua-bis(2-bromo-benzoato-κO)bis-(N,N-diethyl-nicotinamide-κN)nickel(II).
2009 Jun 13
Diaqua-bis(N,N-diethyl-nicotinamide-κN)bis-(4-formyl-benzoato-κO)cobalt(II).
2009 Mar 11
Tetra-kis[μ-4-(dimethyl-amino)benzoato-κO:O']bis-[(N,N-diethyl-nicotinamide-κN)zinc(II)].
2009 Nov 14
Diaqua-bis(N,N-diethyl-nicotinamide-κN)bis-(4-methyl-benzoato-κO)cobalt(II).
2010 Apr 21
Diaqua-bis-(2-bromo-benzoato-κO)bis-(N,N-diethyl-nicotinamide-κN)cobalt(II).
2010 Aug 18
Leaf and floral parts feeding by orange tip butterfly larvae depends on larval position but not on glucosinolate profile or nitrogen level.
2010 Dec
Endophytic fungi diversity of aquatic/riparian plants and their antifungal activity in vitro.
2010 Feb
Weeds of change: Cardamine hirsuta as a new model system for studying dissected leaf development.
2010 Jan
Differentiating Arabidopsis shoots from leaves by combined YABBY activities.
2010 Jul
Tetra-kis(μ-4-methyl-benzoato-κO:O')bis-[(N,N-diethyl-nicotinamide-κN)zinc(II)].
2010 Mar 31
Patents

Patents

Sample Use Guides

In Vivo Use Guide
administered to adults in a dose of 1-2 ml 1-3 times a day, children under the skin - 0.1-0.75 ml
Route of Administration: Other
In Vitro Use Guide
Unknown
Name Type Language
NIKETHAMIDE
INN   EP  
Official Name English
CARDITONIC
Brand Name English
Nikethamide [WHO-DD]
Common Name English
NIKETHAMIDE [MI]
Common Name English
NSC-130820
Code English
NIKETHYL
Brand Name English
NIKETHAMIDE [EP MONOGRAPH]
Common Name English
nikethamide [INN]
Common Name English
CORAMINE
Brand Name English
N,N-DIETHYLNICOTINAMIDE
Systematic Name English
NIKETHAMIDE [MART.]
Common Name English
Classification Tree Code System Code
WHO-ATC R07AB02
Created by admin on Fri Dec 15 15:06:36 GMT 2023 , Edited by admin on Fri Dec 15 15:06:36 GMT 2023
WHO-VATC QR07AB02
Created by admin on Fri Dec 15 15:06:36 GMT 2023 , Edited by admin on Fri Dec 15 15:06:36 GMT 2023
NCI_THESAURUS C47795
Created by admin on Fri Dec 15 15:06:36 GMT 2023 , Edited by admin on Fri Dec 15 15:06:36 GMT 2023
WHO-ATC R07AB52
Created by admin on Fri Dec 15 15:06:36 GMT 2023 , Edited by admin on Fri Dec 15 15:06:36 GMT 2023
Code System Code Type Description
NSC
130820
Created by admin on Fri Dec 15 15:06:36 GMT 2023 , Edited by admin on Fri Dec 15 15:06:36 GMT 2023
PRIMARY
EPA CompTox
DTXSID9046524
Created by admin on Fri Dec 15 15:06:36 GMT 2023 , Edited by admin on Fri Dec 15 15:06:36 GMT 2023
PRIMARY
MESH
D009552
Created by admin on Fri Dec 15 15:06:36 GMT 2023 , Edited by admin on Fri Dec 15 15:06:36 GMT 2023
PRIMARY
DRUG BANK
DB13655
Created by admin on Fri Dec 15 15:06:36 GMT 2023 , Edited by admin on Fri Dec 15 15:06:36 GMT 2023
PRIMARY
CAS
59-26-7
Created by admin on Fri Dec 15 15:06:36 GMT 2023 , Edited by admin on Fri Dec 15 15:06:36 GMT 2023
PRIMARY
SMS_ID
100000091927
Created by admin on Fri Dec 15 15:06:36 GMT 2023 , Edited by admin on Fri Dec 15 15:06:36 GMT 2023
PRIMARY
NCI_THESAURUS
C76625
Created by admin on Fri Dec 15 15:06:36 GMT 2023 , Edited by admin on Fri Dec 15 15:06:36 GMT 2023
PRIMARY
WIKIPEDIA
NIKETHAMIDE
Created by admin on Fri Dec 15 15:06:36 GMT 2023 , Edited by admin on Fri Dec 15 15:06:36 GMT 2023
PRIMARY
PUBCHEM
5497
Created by admin on Fri Dec 15 15:06:36 GMT 2023 , Edited by admin on Fri Dec 15 15:06:36 GMT 2023
PRIMARY
ECHA (EC/EINECS)
200-418-5
Created by admin on Fri Dec 15 15:06:36 GMT 2023 , Edited by admin on Fri Dec 15 15:06:36 GMT 2023
PRIMARY
MERCK INDEX
m7897
Created by admin on Fri Dec 15 15:06:36 GMT 2023 , Edited by admin on Fri Dec 15 15:06:36 GMT 2023
PRIMARY Merck Index
RXCUI
7424
Created by admin on Fri Dec 15 15:06:36 GMT 2023 , Edited by admin on Fri Dec 15 15:06:36 GMT 2023
PRIMARY RxNorm
EVMPD
SUB09286MIG
Created by admin on Fri Dec 15 15:06:36 GMT 2023 , Edited by admin on Fri Dec 15 15:06:36 GMT 2023
PRIMARY
INN
403
Created by admin on Fri Dec 15 15:06:36 GMT 2023 , Edited by admin on Fri Dec 15 15:06:36 GMT 2023
PRIMARY
ChEMBL
CHEMBL2104607
Created by admin on Fri Dec 15 15:06:36 GMT 2023 , Edited by admin on Fri Dec 15 15:06:36 GMT 2023
PRIMARY
DRUG CENTRAL
3383
Created by admin on Fri Dec 15 15:06:36 GMT 2023 , Edited by admin on Fri Dec 15 15:06:36 GMT 2023
PRIMARY
FDA UNII
368IVD6M32
Created by admin on Fri Dec 15 15:06:36 GMT 2023 , Edited by admin on Fri Dec 15 15:06:36 GMT 2023
PRIMARY