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Details

Stereochemistry EPIMERIC
Molecular Formula C20H23N7O6
Molecular Weight 457.4399
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of FOLITIXORIN

SMILES

NC1=NC2=C(N3CN(CC3CN2)C4=CC=C(C=C4)C(=O)N[C@@H](CCC(O)=O)C(O)=O)C(=O)N1

InChI

InChIKey=QYNUQALWYRSVHF-ABLWVSNPSA-N
InChI=1S/C20H23N7O6/c21-20-24-16-15(18(31)25-20)27-9-26(8-12(27)7-22-16)11-3-1-10(2-4-11)17(30)23-13(19(32)33)5-6-14(28)29/h1-4,12-13H,5-9H2,(H,23,30)(H,28,29)(H,32,33)(H4,21,22,24,25,31)/t12?,13-/m0/s1

HIDE SMILES / InChI
Molecular Formula C20H23N7O6
Molecular Weight 457.4399
Charge 0
Count
Stereochemistry EPIMERIC
Additional Stereochemistry No
Defined Stereocenters 1 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Folitixorin, a thymidylate synthase inhibitor is a substrate used by the enzyme methylenetetrahydrofolate reductase (MTHFR) to generate 5-methyltetrahydrofolate. Folitixorin was studied in clinical trials for the treatment of breast cancer, metastatic colorectal cancer and for the treatment of advanced pancreatic cancer. Folitixorin had been granted orphan drug status for the treatment of pancreatic cancer in both the U.S. and EU. However, further development of this drug was discontinued.

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
PubMed

PubMed

TitleDatePubMed
A candidate genetic risk factor for vascular disease: a common mutation in methylenetetrahydrofolate reductase.
1995 May
Renal failure after high-dose methotrexate in a child homozygous for MTHFR C677T polymorphism.
2008 Jan
Patents

Patents

20040219262
3
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:05:14 UTC 2023
Edited
by admin
on Fri Dec 15 16:05:14 UTC 2023
Record UNII
0SXY5ET48B
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
FOLITIXORIN
INN   WHO-DD  
INN  
Official Name English
N5,N10-METHYLENETETRAHYDROFOLIC ACID
Common Name English
5,10-METHYLENETETRAHYDROFOLIC ACID [DSC]
Common Name English
5,10-METHYLENE-5,6,7,8-TETRAHYDROFOLIC ACID
Common Name English
L-GLUTAMIC ACID, N-(4-(3-AMINO-1,2,5,6,6A,7-HEXAHYDRO-1-OXOIMIDAZO(1,5-F)PTERIDIN-8(9H)-YL)BENZOYL)-
Common Name English
5,10-METHYLENE-(6RS)-TETRAHYDROFOLIC ACID
Common Name English
folitixorin [INN]
Common Name English
Folitixorin [WHO-DD]
Common Name English
FOLIC ACID, TETRAHYDRO-N5,N10-METHYLENE-
Common Name English
N5,N10-METHYLENETETRAHYDROPTEROYLGLUTAMIC ACID
Common Name English
N5,N10-METHYLENE-5,6,7,8-TETRAHYDROFOLIC ACID
Common Name English
5,10-METHYLENETETRAFOLATE
Common Name English
5,10-METHYLENETETRAHYDROFOLIC ACID
DSC  
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C2078
Created by admin on Fri Dec 15 16:05:14 UTC 2023 , Edited by admin on Fri Dec 15 16:05:14 UTC 2023
Code System Code Type Description
WIKIPEDIA
5,10-Methylenetetrahydrofolate
Created by admin on Fri Dec 15 16:05:14 UTC 2023 , Edited by admin on Fri Dec 15 16:05:14 UTC 2023
PRIMARY
FDA UNII
0SXY5ET48B
Created by admin on Fri Dec 15 16:05:14 UTC 2023 , Edited by admin on Fri Dec 15 16:05:14 UTC 2023
PRIMARY
NCI_THESAURUS
C61304
Created by admin on Fri Dec 15 16:05:14 UTC 2023 , Edited by admin on Fri Dec 15 16:05:14 UTC 2023
PRIMARY
ChEMBL
CHEMBL117348
Created by admin on Fri Dec 15 16:05:14 UTC 2023 , Edited by admin on Fri Dec 15 16:05:14 UTC 2023
PRIMARY
SMS_ID
100000181840
Created by admin on Fri Dec 15 16:05:14 UTC 2023 , Edited by admin on Fri Dec 15 16:05:14 UTC 2023
PRIMARY
INN
8881
Created by admin on Fri Dec 15 16:05:14 UTC 2023 , Edited by admin on Fri Dec 15 16:05:14 UTC 2023
PRIMARY
EPA CompTox
DTXSID90955873
Created by admin on Fri Dec 15 16:05:14 UTC 2023 , Edited by admin on Fri Dec 15 16:05:14 UTC 2023
PRIMARY
CAS
3432-99-3
Created by admin on Fri Dec 15 16:05:14 UTC 2023 , Edited by admin on Fri Dec 15 16:05:14 UTC 2023
PRIMARY
MESH
C013123
Created by admin on Fri Dec 15 16:05:14 UTC 2023 , Edited by admin on Fri Dec 15 16:05:14 UTC 2023
PRIMARY
CHEBI
1989
Created by admin on Fri Dec 15 16:05:14 UTC 2023 , Edited by admin on Fri Dec 15 16:05:14 UTC 2023
PRIMARY
PUBCHEM
135400185
Created by admin on Fri Dec 15 16:05:14 UTC 2023 , Edited by admin on Fri Dec 15 16:05:14 UTC 2023
PRIMARY
EU-Orphan Drug
EU/3/03/143(WITHDRAWN)
Created by admin on Fri Dec 15 16:05:14 UTC 2023 , Edited by admin on Fri Dec 15 16:05:14 UTC 2023
PRIMARY Treatment pancreatic cancer in combination with 5-fluorouracil 11/6/2003 Withdrawn
Related Record Type Details
Structure of FOLITIXORIN CALCIUM
SALT/SOLVATE -> PARENT
THYMIDYLATE SYNTHASE
TARGET -> INHIBITOR
Related Record Type Details
Structure of LEVOMEFOLATE CALCIUM
PARENT -> IMPURITY
NIH
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