NOSANTINE

Details

Stereochemistry	RACEMIC
Molecular Formula	C14H22N4O2
Molecular Weight	278.3501
Optical Activity	( + / - )
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@](CCCCCC)([C@@H](C)O)N1C=NC2=C1N=CNC2=O

InChI

InChIKey=RSMDQPNZAPMDJC-MNOVXSKESA-N

InChI=1S/C14H22N4O2/c1-3-4-5-6-7-11(10(2)19)18-9-17-12-13(18)15-8-16-14(12)20/h8-11,19H,3-7H2,1-2H3,(H,15,16,20)/t10-,11+/m1/s1

HIDE SMILES / InChI

Molecular Formula	C14H22N4O2
Molecular Weight	278.3501
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/6093811 | https://www.ncbi.nlm.nih.gov/pubmed/6650281 | https://www.ncbi.nlm.nih.gov/pubmed/6179891

Nosantine (NPT 15392) is a novel heterocyclic immunomodulatory compound related to inosine in structure and isoprinosine in action. Nosantine enhances a variety of lymphoid functional activities including proliferative responses to various antigenic and mitogenic stimuli. Such activities imply potential therapeutic use in immunodeficiency related to defects of the thymus and thymus-derived lymphocytes. In head and neck cancer patients the drug induced transitory, immune stimulation during or after treatment without any side effects. NPT 15392 seemed to selectively exert an action on T lymphocytes. Nosantine was found to be a potent and relatively selective inhibitor of mouse lymphocyte cyclic GMP phosphodiesterase, with IC50 values 15-180 times greater for cyclic AMP than cyclic GMP phosphodiesterases. Immunopharmacologic activities of NPT 15392 may include specific cyclic GMP phosphodiesterase inhibition as one of several possible mechanisms.

Approval Year

PubMed

Title	Date	PubMed
Effects of NPT 15392 in vitro on human leukocyte functions.	1982	6179891
Selective inhibition by NPT 15392 of lymphocyte cyclic GMP phosphodiesterase.	1984 Nov 1	6093811
Kinetic analysis of the immunopotentiating effect of the hypoxanthine analogue, NPT-15392, on the interleukin-2 production potential of human lymphocytes.	1986	3491799

Patents

Sample Use Guides

In Vivo Use Guide

Nosantine was administered in a single intraperitoneal injection to Balb/c mice at a dose of 0.1 mg/kg.

Route of Administration: Intraperitoneal

In Vitro Use Guide

Nosantine (NPT 15392) is a potent and relatively selective inhibitor of mouse lymphocyte cyclic GMP phosphodiesterase, with IC50 values 15-180 times greater for cyclic AMP than cyclic GMP phosphodiesterases. The greatest inhibition by NPT 15392 was found using 10 uM substrate, and inhibition was greater in membrane than soluble forms of phosphodiesterase. A major form of cyclic GMP phosphodiesterase was inhibited effectively by NPT 15392 in a competitive manner (Ki = 50 uM). Cyclic AMP phosphodiesterase activity in the same fraction, but representing only a fifth of the total activity, was also inhibited (Ki = 70 uM). Membrane bound enzymes were solubilized and separated into three peaks. One with high affinity for cyclic GMP was strongly inhibited (Ki = 10 uM) by NPT 15392.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:22:01 GMT 2023` Edited by `admin` on `Fri Dec 15 16:22:01 GMT 2023`
Record UNII	NYM432G79C
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NOSANTINE

Official Name

English

NPT 15392

Code

English

NPT-15392

Code

English

nosantine [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C308