TALOTREXIN AMMONIUM

Investigational

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C27H27N9O6.H3N
Molecular Weight	590.5905
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

N.NC1=NC2=C(N=C(CNC3=CC=C(C=C3)C(=O)N[C@@H](CCCNC(=O)C4=CC=CC=C4C(O)=O)C(O)=O)C=N2)C(N)=N1

InChI

InChIKey=CURXCENNYPPKOS-FYZYNONXSA-N

InChI=1S/C27H27N9O6.H3N/c28-21-20-22(36-27(29)35-21)32-13-16(33-20)12-31-15-9-7-14(8-10-15)23(37)34-19(26(41)42)6-3-11-30-24(38)17-4-1-2-5-18(17)25(39)40;/h1-2,4-5,7-10,13,19,31H,3,6,11-12H2,(H,30,38)(H,34,37)(H,39,40)(H,41,42)(H4,28,29,32,35,36);1H3/t19-;/m0./s1

HIDE SMILES / InChI

Molecular Formula	H3N
Molecular Weight	17.0305
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	C27H27N9O6
Molecular Weight	573.56
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.biospace.com/article/releases/hana-biosciences-inc-receives-orphan-drug-designation-for-talotrexin-pt-523-for-the-treatment-of-acute-lymphoblastic-leukemia-/ | https://clinicaltrials.gov/ct2/show/NCT00458744 | https://clinicaltrials.gov/ct2/show/NCT00112060

Talotrexin (also known as PT-523) was developed as a nonpolyglutamatable antifolate drug for the treatment of various types of tumors. It is known that antifolates are a class of cytotoxic or antineoplastic agents, which inhibit or prevent the maturation and proliferation of malignant cells. Talotrexin was studied in clinical trials for the treatment of brain and central nervous system tumors, leukemia, lymphoma, unspecified childhood solid tumor. However, this study was withdrawn because of toxicity. In addition, was studied in phase I/II multicenter clinical trial in patients with non-small-cell Lung carcinoma, this study was also withdrawn. The withdrawal was related to incidences of dose-limiting mucositis and myelosuppression. However, on May 22, 2006, was announced that the U.S. Food and Drug Administration has granted orphan drug designation for talotrexin in patients with acute lymphoblastic leukemia (ALL).

Originator

Approval Year

PubMed

Title	Date	PubMed
Cancer chemotherapy: targeting folic acid synthesis.	2010-11-19	21301589
Clinical potency of methotrexate, aminopterin, talotrexin and pemetrexed in childhood leukemias.	2010-05	19784838
Emerging therapeutic options for Philadelphia-positive acute lymphocytic leukemia.	2007-03	17355221
Treatment of acute lymphoblastic leukaemia : a new era.	2007	17927282
The inverse relationship between reduced folate carrier function and pemetrexed activity in a human colon cancer cell line.	2006-02	16505119

Sample Use Guides

In Vivo Use Guide

10 mg/m2 dose of PT523 administered day 1 of a 28-day cycle as a 5 minute IV infusion (IV bolus)

Route of Administration: Intravenous

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:15:54 GMT 2025` Edited by `admin` on `Mon Mar 31 18:15:54 GMT 2025`
Record UNII	686WJT9102
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NSC-712783

Preferred Name

English

TALOTREXIN AMMONIUM

Official Name

English

PT-523

Code

English

Talotrexin ammonium [WHO-DD]

Common Name

English

2-[[(4S)-4-Carboxy-4-[[4-[[(2,4-diaminopteridin-6-yl)methyl]amino]benzoyl]amino]butyl]carbamoyl]benzoic acid monoammonium salt

Common Name

English

BENZOIC ACID, 2-((((4S)-4-CARBOXY-4-((4-(((2,4-DIAMINO-6-PTERIDINYL)METHYL)AMINO)BENZOYL)AMINO)BUTYL)AMINO)CARBONYL), MONOAMMONIUM SALT

Common Name

English

PT523

Code

English

TALOTREXIN AMMONIUM [USAN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C2153