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Details

Stereochemistry ACHIRAL
Molecular Formula C17H12N2O2
Molecular Weight 276.2894
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of MEISOINDIGO

SMILES

CN1C(=O)\C(C2=C1C=CC=C2)=C3\C(=O)NC4=C3C=CC=C4

InChI

InChIKey=QNOCRUSVMMAKSC-CCEZHUSRSA-N
InChI=1S/C17H12N2O2/c1-19-13-9-5-3-7-11(13)15(17(19)21)14-10-6-2-4-8-12(10)18-16(14)20/h2-9H,1H3,(H,18,20)/b15-14+

HIDE SMILES / InChI

Description
Curator's Comment: The description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/25151579 | https://www.ncbi.nlm.nih.gov/pubmed/20233051 | https://www.ncbi.nlm.nih.gov/pubmed/12685829

Meisoindigo ((E)-1,1'-dimethyl-[3,3'-biindolinylidene]-2,2'-dione) is a derivative of Indigo Naturalis, that has been used in China for chronic myeloid leukemia. In vitro cell line studies have shown that this agent might induce apoptosis and myeloid differentiation of acute myeloid leukemia (AML). Meisoindigo has been a routine therapeutic agent in the clinical treatment of chronic myelogenous leukemia (CML) in China since the 1980s. In phase III clinical trial of Meisoindigo involving 402 patients, it was shown that Meisoindigo was equally efficient for both newly diagnosed and previously treated CML patients after oral administration. The hematological complete response (CR) and partial response (PR) rates, respectively, were 45.0 and 39.3% for newly diagnosed patients and 35.9 and 41.4% for previously treated patients. Meisoindigo was generally well tolerated. The most frequent side‑effects were bone, joint and/or muscle pain of varying degrees when the dosage was more than the suitable one.

Originator

Sources: Compt. rend. (1913), 156, 898-901.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
1.9 ng/mL
10 mg/kg single, oral
dose: 10 mg/kg
route of administration: Oral
experiment type: SINGLE
co-administered:
MEISOINDIGO plasma
Rattus norvegicus
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
19.6 ng × h/mL
10 mg/kg single, oral
dose: 10 mg/kg
route of administration: Oral
experiment type: SINGLE
co-administered:
MEISOINDIGO plasma
Rattus norvegicus
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
yes
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Anti-HIV-1 activity and cellular pharmacology of various analogs of gossypol.
1993 Jul 20
[Expression and function of Ahi-1 gene in Jurkat cells].
2009 Apr
Patents

Sample Use Guides

50–200 mg/d
Route of Administration: Oral
NB4 (APL cells, M3 subtype according to FAB), NB4.007/6 (retinoic acid resistant cells developed through continuously culturing NB4 in the medium containing retinoic acid), HL60 (AML cells, M2 subtype according to FAB), and U937 (myelomonocytic leukemia cells, M5 subtype according to FAB) were used for activity evaluation. The inhibitory effects of meisoindigo on the four human leukemic cells were tested by treating the cells with meisoindigo at various concentrations (0, 1, 2, 4, 8, 12, 16, 20 μM). The cells were cultured in 24‑well plates. The number of the cells was counted by trypan blue exclusion method. The initial cell numbers (NB4, NB4.007/6, HL60 and U937) were 3x10^6 cell/ml. After incubation for 24, 48 and 72 h, the plates were taken out and the number of viable cells was counted.
Name Type Language
MEISOINDIGO
Common Name English
NATURA-.ALPHA.
Brand Name English
2H-INDOL-2-ONE, 3-(1,2-DIHYDRO-2-OXO-3H-INDOL-3-YLIDENE)-1,3-DIHYDRO-1-METHYL-
Systematic Name English
(3E)-1-METHYL-3-(2-OXOINDOLIN-3-YLIDENE)INDOLIN-2-ONE
Systematic Name English
TAK-114
Code English
Meisoindigo [WHO-DD]
Common Name English
Code System Code Type Description
FDA UNII
92UIP6405R
Created by admin on Fri Dec 15 17:28:13 GMT 2023 , Edited by admin on Fri Dec 15 17:28:13 GMT 2023
PRIMARY
CAS
97207-47-1
Created by admin on Fri Dec 15 17:28:13 GMT 2023 , Edited by admin on Fri Dec 15 17:28:13 GMT 2023
PRIMARY
PUBCHEM
5479433
Created by admin on Fri Dec 15 17:28:13 GMT 2023 , Edited by admin on Fri Dec 15 17:28:13 GMT 2023
PRIMARY
CLINICAL_TRIALS.GOV
MEISOINDIGO
Created by admin on Fri Dec 15 17:28:13 GMT 2023 , Edited by admin on Fri Dec 15 17:28:13 GMT 2023
PRIMARY Official Title: A Single-center, Single- and Multiple-Dose Phase 1 Study to Evaluate the Safety and Pharmacokinetics of TAK-114 in Healthy Adult Japanese and Caucasian Male SubjectsPurpose: The purpose of this study is to evaluate the safety and tolerability of TAK-114 following single and multiple ascending oral doses in healthy Japanese subjects.
EPA CompTox
DTXSID901025868
Created by admin on Fri Dec 15 17:28:13 GMT 2023 , Edited by admin on Fri Dec 15 17:28:13 GMT 2023
PRIMARY