PTEROIC ACID

Details

Stereochemistry	ACHIRAL
Molecular Formula	C14H12N6O3
Molecular Weight	312.2835
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

NC1=NC2=NC=C(CNC3=CC=C(C=C3)C(O)=O)N=C2C(=O)N1

InChI

InChIKey=JOAQINSXLLMRCV-UHFFFAOYSA-N

InChI=1S/C14H12N6O3/c15-14-19-11-10(12(21)20-14)18-9(6-17-11)5-16-8-3-1-7(2-4-8)13(22)23/h1-4,6,16H,5H2,(H,22,23)(H3,15,17,19,20,21)

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/15341734

Pteroic acid belongs to the class of chemical entities known as pterins. These are polycyclic aromatic compounds containing a pterin moiety, which consists of a pteridine ring bearing a ketone and an amine group to form 2-aminopteridin-4(3H)-one. It is known that pteroic acid inhibits Dihydropterate synthase from Bacillus anthracis, which is a target for the sulfonamide class of antibiotics. However, increasing resistance has encouraged the development of new therapeutic agents against this enzyme.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
B. anthracis Dihydropteroate synthase 1 Target ID: B. anthracis Dihydropteroate synthase Sources: https://www.ncbi.nlm.nih.gov/pubmed/15341734	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2578

PubMed

Title	Date	PubMed
Synthesis and evaluation of pteroic acid-conjugated nitroheterocyclic phosphoramidates as folate receptor-targeted alkylating agents.	2001 Jan 4	11141089
Synthesis of N-acetyl-D-galactosamine and folic acid conjugated ribozymes.	2002 Sep-Oct	12236789
Crystal structure of 7,8-dihydropteroate synthase from Bacillus anthracis: mechanism and novel inhibitor design.	2004 Sep	15341734
Targeting the tumor-associated folate receptor with an 111In-DTPA conjugate of pteroic acid.	2005 May 25	15898791
Preclinical evaluation of novel organometallic 99mTc-folate and 99mTc-pteroate radiotracers for folate receptor-positive tumour targeting.	2006 Sep	16763819
Reactivity of conjugated and unconjugated pterins with singlet oxygen (O2(1Deltag)): physical quenching and chemical reaction.	2007 May-Jun	17076587

Patents

Sample Use Guides

In Vivo Use Guide

oral administration of from 2 to 10 mg of pteroic acid resulted in only a very small amount of urinary pteroic acid. Following the intravenous administration of 2 mg of pteroic acid the microbiological assays of the urine indicated that from 15 to 46% of the compound was excreted as pteroic acid and that only about 1% appeared to be converted to pteroylglutamic acid.

Route of Administration: Other

In Vitro Use Guide

Unknown

Name

Type

Language

PTEROIC ACID

Common Name

English

4-(((2-AMINO-3,4-DIHYDRO-4-OXO-6-PTERIDINYL)METHYL)AMINO)BENZOIC ACID

Systematic Name

English

FOLIC ACID HYDRATE IMPURITY D [EP IMPURITY]

Common Name

English

P-((2-AMINO-4-HYDROXY-6-PTERIDYLMETHYL)AMINO)BENZOIC ACID

Common Name

English

PTEROIC ACID [MI]

Common Name

English

4-[[(2-amino-4-oxo-1,4-dihydropteridin-6-yl)methyl]amino]benzoic acid

Common Name

English

PYROFOLIC ACID

Common Name

English

NSC-14972

Code

English

BENZOIC ACID, 4-(((2-AMINO-3,4-DIHYDRO-4-OXO-6-PTERIDINYL)METHYL)AMINO)-

Systematic Name

English

Code System Code Type Description

CAS

119-24-4