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Details

Stereochemistry ACHIRAL
Molecular Formula C20H15NO3
Molecular Weight 317.338
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of KARTOGENIN

SMILES

OC(=O)C1=CC=CC=C1C(=O)NC2=CC=C(C=C2)C3=CC=CC=C3

InChI

InChIKey=SLUINPGXGFUMLL-UHFFFAOYSA-N
InChI=1S/C20H15NO3/c22-19(17-8-4-5-9-18(17)20(23)24)21-16-12-10-15(11-13-16)14-6-2-1-3-7-14/h1-13H,(H,21,22)(H,23,24)

HIDE SMILES / InChI

Molecular Formula C20H15NO3
Molecular Weight 317.338
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/24928394

Kartogenin is an activator of the smad4/smad5 pathway, and promotes the selective differentiation of multipotent mesenchymal stem cells into chondrocytes. It is promising agent for treatment of osteoarthritis.

Originator

Curator's Comment: # Novartis

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: Q13951
Gene ID: 865.0
Gene Symbol: CBFB
Target Organism: Homo sapiens (Human)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
A heterocyclic molecule kartogenin induces collagen synthesis of human dermal fibroblasts by activating the smad4/smad5 pathway.
2014 Jul 18
Creating an Animal Model of Tendinopathy by Inducing Chondrogenic Differentiation with Kartogenin.
2016
Kartogenin treatment prevented joint degeneration in a rodent model of osteoarthritis: A pilot study.
2016 Oct
Patents

Sample Use Guides

Sprague Dawley rats at 4 months of age were randomized into three groups: osteoarthritis (OA), kartogenin treatment (KGN), and control. On day 0, all the rats from OA and KGN group were anaesthetized with 2% isoflurane, a medial arthrotomy was performed and the anterior cruciate ligament was transected (ACLT) on the right knee. Postoperatively, 0.03mg/kg buprenorphine hydrochloride was administered by subcutaneous injection and as needed subsequently for pain control. Rats from KGN treatment group received weekly intra-articular injections of 125mM KGN in 50 ml of saline in the ACL transected knee joint.
Route of Administration: Other
Human dermal fibroblasts in vitro were treated with various concentrations of kartogenin, with dimethyl sulfoxide (DMSO) serving as the negative control. Real-time reverse-transcription PCT, Western blot, and immunofluorescence analyses were performed to examine the expression of collagen and transforming growth factor beta (TGF-β) signaling pathway.
Substance Class Chemical
Created
by admin
on Sat Dec 16 09:29:34 GMT 2023
Edited
by admin
on Sat Dec 16 09:29:34 GMT 2023
Record UNII
Q93BBN11CP
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
KARTOGENIN
Common Name English
N-P-BIPHENYLYLPHTHALIMIDE
Common Name English
2-((4-PHENYLPHENYL)CARBAMOYL)BENZOIC ACID
Systematic Name English
J3.342.662C
Code English
PHTHALIMIDE, N-4-BIPHENYLYL-
Systematic Name English
N-BIPHENYL-4-YL-PHTHALAMIC ACID
Systematic Name English
2-(((1,1'-BIPHENYL)-4-YLAMINO)CARBONYL)BENZOIC ACID
Systematic Name English
2-(N-(4-PHENYLPHENYL)CARBAMOYL)BENZOIC ACID
Systematic Name English
2-((BIPHENYL-4-YL)CARBAMOYL)BENZOIC ACID
Systematic Name English
BENZOIC ACID, 2-(((1,1'-BIPHENYL)-4-YLAMINO)CARBONYL)-
Systematic Name English
2-(4-BIPHENYLYLCARBAMOYL)BENZOIC ACID
Systematic Name English
2-((4-BIPHENYLYLAMINO)CARBONYL)BENZOIC ACID
Systematic Name English
2-((1,1'-BIPHENYL)-4-YLCARBAMOYL)BENZOIC ACID
Systematic Name English
PHTHALANILIC ACID, 4'-PHENYL-
Common Name English
Code System Code Type Description
EPA CompTox
DTXSID30385074
Created by admin on Sat Dec 16 09:29:34 GMT 2023 , Edited by admin on Sat Dec 16 09:29:34 GMT 2023
PRIMARY
CAS
4727-31-5
Created by admin on Sat Dec 16 09:29:34 GMT 2023 , Edited by admin on Sat Dec 16 09:29:34 GMT 2023
PRIMARY
PUBCHEM
2826191
Created by admin on Sat Dec 16 09:29:34 GMT 2023 , Edited by admin on Sat Dec 16 09:29:34 GMT 2023
PRIMARY
FDA UNII
Q93BBN11CP
Created by admin on Sat Dec 16 09:29:34 GMT 2023 , Edited by admin on Sat Dec 16 09:29:34 GMT 2023
PRIMARY