U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS
This repository is under review for potential modification in compliance with Administration directives.

Details

Stereochemistry ABSOLUTE
Molecular Formula 2C20H23N7O6.H2O4S
Molecular Weight 1012.958
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ARFOLITIXORIN HEMISULFATE

SMILES

OS(O)(=O)=O.NC1=NC(=O)C2=C(NC[C@@H]3CN(CN23)C4=CC=C(C=C4)C(=O)N[C@@H](CCC(O)=O)C(O)=O)N1.NC5=NC(=O)C6=C(NC[C@@H]7CN(CN67)C8=CC=C(C=C8)C(=O)N[C@@H](CCC(O)=O)C(O)=O)N5

InChI

InChIKey=KHQZYLZNYVRXOD-NVGTXZLJSA-N
InChI=1S/2C20H23N7O6.H2O4S/c2*21-20-24-16-15(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;1-5(2,3)4/h2*1-4,12-13H,5-9H2,(H,23,30)(H,28,29)(H,32,33)(H4,21,22,24,25,31);(H2,1,2,3,4)/t2*12-,13+;/m11./s1

HIDE SMILES / InChI

Molecular Formula C20H23N7O6
Molecular Weight 457.4399
Charge 0
Count
MOL RATIO 2 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula H2O4S
Molecular Weight 98.078
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

METHYLENETETRAHYDROFOLIC ACID, L-(+), an endogenous biomodulator that was developed under the brand name modufolin or arfolitixorin by the Isofol Medical. Arfolitixorin is developed to increase the efficacy of standard of care chemotherapy for advanced colorectal cancer. This drug is currently being studied in a global phase 3 clinical trial. Besides, the drug successfully completed phase II as rescue therapy for osteosarcoma. 21 May 2019 Isofol Medical has received clinical patent protection for the arfolitixorinin USA. It relates to a method of increasing blood concentration of deoxyuridine, a blood biomarker for inhibition of tumor growth in human cancer treatment.

Approval Year

Cmax

ValueDoseCo-administeredAnalytePopulation
2860 ng/mL
30 mg/m² single, intravenous
METHYLENETETRAHYDROFOLIC ACID, L-( )- plasma
Homo sapiens
4410 ng/mL
60 mg/m² single, intravenous
METHYLENETETRAHYDROFOLIC ACID, L-( )- plasma
Homo sapiens
21200 ng/mL
240 mg/m² single, intravenous
METHYLENETETRAHYDROFOLIC ACID, L-( )- plasma
Homo sapiens
39.4 pmol/mL
416 μg/m² single, intravenous
METHYLENETETRAHYDROFOLIC ACID, L-( )- plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
1460 ng × h/mL
30 mg/m² single, intravenous
METHYLENETETRAHYDROFOLIC ACID, L-( )- plasma
Homo sapiens
2370 ng × h/mL
60 mg/m² single, intravenous
METHYLENETETRAHYDROFOLIC ACID, L-( )- plasma
Homo sapiens
10600 ng × h/mL
240 mg/m² single, intravenous
METHYLENETETRAHYDROFOLIC ACID, L-( )- plasma
Homo sapiens
210 pmol × h/mL
416 μg/m² single, intravenous
METHYLENETETRAHYDROFOLIC ACID, L-( )- plasma
Homo sapiens

PubMed

Sample Use Guides

In Vivo Use Guide
IV injection every second week for 8 weeks 30 to 240 mg/m2
Route of Administration: Intravenous
Substance Class Chemical
Record UNII
LZ73JVT65C
Record Status Validated (UNII)
Record Version