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Details

Stereochemistry ACHIRAL
Molecular Formula C8H5NO2
Molecular Weight 147.1308
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ISATIN

SMILES

O=C1NC2=C(C=CC=C2)C1=O

InChI

InChIKey=JXDYKVIHCLTXOP-UHFFFAOYSA-N
InChI=1S/C8H5NO2/c10-7-5-3-1-2-4-6(5)9-8(7)11/h1-4H,(H,9,10,11)

HIDE SMILES / InChI
Molecular Formula C8H5NO2
Molecular Weight 147.1308
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Isatin (1H-indole-2,3-dione) is a naturally occurring heterocycle that was first synthesised by Erdmann and Laurent in 1840. Isatin possesses a wide range of biological activities. Isatin has anxiogenic, sedative, anticonvulsant activities and acts as a potent antagonist on atrial natriuretic peptide receptors in vitro. Isatin is an endogenous monoamine oxidase (MAO) inhibitor involved in stress and anxiety. Additionally, isatin inhibits alkaline phosphatase (ALP), nitric oxide (NO)-stimulated soluble guanylate cyclase, and other enzymes.

CNS Activity

Originator

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
Inhibitor
8297
 7.94 µM [IC50]
Inhibitor
8297
 31.8 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Preclinical
Unknown

Approved Use

Unknown
Primary
Preclinical
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Glucosylation of isatin-3-oxime followed by 2D in situ NMR in plant cells at highest magnetic field without labelling.
2001
Synthesis and anti-HIV activity of 4-[(1,2-dihydro-2-oxo-3H-indol-3-ylidene) amino]-N(4,6-dimethyl-2-pyrimidinyl)-benzene sulfonamide and its derivatives.
2001 Dec
Antituberculous activity of norfloxacin mannich bases with isatin derivatives.
2001 Jul-Aug
An efficient conversion of 5-nitroisatin into 5-nitroindole derivative.
2001 Mar 26
A novel nonpeptidic caspase-3/7 inhibitor, (S)-(+)-5-[1-(2-methoxymethylpyrrolidinyl)sulfonyl]isatin reduces myocardial ischemic injury.
2002 Dec 5
[Effect of oxidized indoles on monoamine oxidase activity in the rat brain mitochondria].
2002 Mar-Apr
Substrate specificity of mouse aldo-keto reductase AKR7A5.
2003 Feb 1
Isatin, an endogenous MAO inhibitor, improves bradykinesia and dopamine levels in a rat model of Parkinson's disease induced by Japanese encephalitis virus.
2003 Jan 15
Characterization of dark liver pigment observed in rats after subchronic dosing of the beta3-adrenergic receptor agonist LY368842.
2003 Jul
Effect of acute stress and gender on isatin in rat tissues and serum.
2004 Feb
A microtitre format assay for proline in human serum or plasma.
2004 May
Design, synthesis and biological evaluation of novel non-nucleoside HIV-1 reverse transcriptase inhibitors with broad-spectrum chemotherapeutic properties.
2004 Nov 15
An isatin-beta-thiosemicarbazone-resistant vaccinia virus containing a mutation in the second largest subunit of the viral RNA polymerase is defective in transcription elongation.
2004 Oct 22
[The effect of long-term administration of isatin and himantan to mice on sensitivity of brain monoamine oxidase B to inhibition by deprenyl in vivo and in vitro].
2004 Sep-Oct
Combinatorial optimization of isatin-beta-thiosemicarbazones as anti-poxvirus agents.
2005 Apr 21
Isatin, an endogenous monoamine oxidase inhibitor, triggers a dose- and time-dependent switch from apoptosis to necrosis in human neuroblastoma cells.
2005 Aug
In vivo effects of isatin on rat platelet eicosanoids.
2005 Feb
Antimicrobial and mutagenic properties of organotin(IV) complexes with isatin and N-alkylisatin bisthiocarbonohydrazones.
2005 Feb
Protein engineering of toluene ortho-monooxygenase of Burkholderia cepacia G4 for regiospecific hydroxylation of indole to form various indigoid compounds.
2005 Jan
Isatin-Schiff base copper(II) complexes and their influence on cellular viability.
2005 Jul
Enzymatic properties of a member (AKR1C19) of the aldo-keto reductase family.
2005 Jun
Total synthesis of nigellicine and nigeglanine hydrobromide.
2005 Jun 9
Biological activities of isatin and its derivatives.
2005 Mar
Design, synthesis and anti-plasmodial evaluation in vitro of new 4-aminoquinoline isatin derivatives.
2005 May 2
Lanthanum(III) and praseodymium(III) complexes with isatin thiosemicarbazones.
2005 Sep
Patents

Patents

04128644
7
04711890
3
05284951
2
05348968
1
05486512
1
05807883
1
05840873
1
05998463
8
06335448
1
07081470
1
07273857
11
07300928
11
07405235
1
07846962
2
08263596
7
08779162
1
JP2003520851A
1
JP4641942B2
8
JPH02229166A
1
JPH07207188A
1
JPH08119942A
3
JPH08295692A
1
JPH0940672A
1

Sample Use Guides

In Vivo Use Guide
Rats: Isatin (100 mg/kg, i.p.) inhibited APO-induced rotations of Parkinsonian rats to 39.1+/-3.7% of the control (n=12), while it had no apparent effects on electrical stimuli-induced DA release either in normal rats or in model rats. In addition, the content of 5-hydroxytryptamine but not DA was increased in both normal rats and model rats after isatin (100 mg/kg, i.p.) was administered.
Route of Administration: Intraperitoneal
In Vitro Use Guide
In vitro 10 and 100 uM isatin reduced irreversible inhibition of MAO A and MAO B assayed after rat mitochondria wash.
Substance Class Chemical
Created
by admin
on Sat Dec 16 01:54:09 GMT 2023
Edited
by admin
on Sat Dec 16 01:54:09 GMT 2023
Record UNII
82X95S7M06
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ISATIN
INCI   MI  
INCI  
Official Name English
ISATIN [MI]
Common Name English
NSC-9262
Code English
2,3-DIKETOINDOLINE
Systematic Name English
INDOLE-2,3-DIONE
Systematic Name English
2,3-DIHYDRO-1H-INDOLE-2,3-DIONE
Systematic Name English
1H-INDOLE-2,3-DIONE
Systematic Name English
2,3-DIOXO-2,3-DIHYDROINDOLE
Systematic Name English
O-AMINOBENZOYLFORMIC ANHYDRIDE
Common Name English
PSEUDOISATIN
Common Name English
ISATIN [INCI]
Common Name English
Code System Code Type Description
WIKIPEDIA
ISATIN
Created by admin on Sat Dec 16 01:54:10 GMT 2023 , Edited by admin on Sat Dec 16 01:54:10 GMT 2023
PRIMARY
PUBCHEM
7054
Created by admin on Sat Dec 16 01:54:10 GMT 2023 , Edited by admin on Sat Dec 16 01:54:10 GMT 2023
PRIMARY
DRUG BANK
DB02095
Created by admin on Sat Dec 16 01:54:10 GMT 2023 , Edited by admin on Sat Dec 16 01:54:10 GMT 2023
PRIMARY
EPA CompTox
DTXSID3038694
Created by admin on Sat Dec 16 01:54:10 GMT 2023 , Edited by admin on Sat Dec 16 01:54:10 GMT 2023
PRIMARY
CHEBI
27539
Created by admin on Sat Dec 16 01:54:09 GMT 2023 , Edited by admin on Sat Dec 16 01:54:09 GMT 2023
PRIMARY
CAS
91-56-5
Created by admin on Sat Dec 16 01:54:09 GMT 2023 , Edited by admin on Sat Dec 16 01:54:09 GMT 2023
PRIMARY
FDA UNII
82X95S7M06
Created by admin on Sat Dec 16 01:54:10 GMT 2023 , Edited by admin on Sat Dec 16 01:54:10 GMT 2023
PRIMARY
NSC
9262
Created by admin on Sat Dec 16 01:54:10 GMT 2023 , Edited by admin on Sat Dec 16 01:54:10 GMT 2023
PRIMARY
ECHA (EC/EINECS)
202-077-8
Created by admin on Sat Dec 16 01:54:10 GMT 2023 , Edited by admin on Sat Dec 16 01:54:10 GMT 2023
PRIMARY
MESH
D007510
Created by admin on Sat Dec 16 01:54:10 GMT 2023 , Edited by admin on Sat Dec 16 01:54:10 GMT 2023
PRIMARY
MERCK INDEX
m6418
Created by admin on Sat Dec 16 01:54:10 GMT 2023 , Edited by admin on Sat Dec 16 01:54:10 GMT 2023
PRIMARY Merck Index
NIH
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