ANDOLAST

Details

Stereochemistry	ACHIRAL
Molecular Formula	C15H11N9O
Molecular Weight	333.3075
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

O=C(NC1=CC=C(C=C1)C2=NN=NN2)C3=CC=C(C=C3)C4=NN=NN4

InChI

InChIKey=VXEBMQZDPONDFB-UHFFFAOYSA-N

InChI=1S/C15H11N9O/c25-15(11-3-1-9(2-4-11)13-17-21-22-18-13)16-12-7-5-10(6-8-12)14-19-23-24-20-14/h1-8H,(H,16,25)(H,17,18,21,22)(H,19,20,23,24)

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24625824
Curator's Comment: the description was created based on several sources, including https://www.pharmacodia.com/web/drug/1_548.html | https://www.google.com/patents/US7482371 | https://www.ncbi.nlm.nih.gov/pubmed/25845448

Andolast is a small molecule activator of Calcium-activated potassium channels and an inhibitor of IgE-mediated anaphylaxis. Andolast is under investigation as an anti-asthmatic and for the treatment of COPD.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Calcium-activated potassium channel alpha/beta 1 5 Target ID: CHEMBL3038495 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18473808	Activator 1430
immunoglobulin production 1 Target ID: GO:0002377 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1282105	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Chronic obstructive pulmonary disease 174 Sources: https://www.google.com/patents/US7482371 http://en.pharmacodia.com/web/drug/1_548.html	Primary		Phase III 656	Unknown Approved Use Unknown
Mild to moderate asthma 1 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25845448 https://www1.magellanrx.com/media/620999/mrx-pipeline_april-2017_web_0417_links.pdf	Primary		Phase III 656	Unknown Approved Use Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
30.5 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11745909	8 mg single, respiratory dose: 8 mg route of administration: Respiratory experiment type: SINGLE co-administered:		ANDOLAST plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

AUC

Value	Dose	Co-administered	Analyte	Population
9626 ng × min/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11745909	8 mg single, respiratory dose: 8 mg route of administration: Respiratory experiment type: SINGLE co-administered:		ANDOLAST plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
4.6 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11745909	8 mg single, respiratory dose: 8 mg route of administration: Respiratory experiment type: SINGLE co-administered:		ANDOLAST plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

Doses

Dose	Population	Adverse events
8 mg single, respiratory Highest studied dose Dose: 8 mg Route: respiratory Route: single Dose: 8 mg Sources: https://pubmed.ncbi.nlm.nih.gov/11745909 Page: p.78	unhealthy, ADULT n = 12 Health Status: unhealthy Condition: asthma Age Group: ADULT Sex: M+F Food Status: FASTED Population Size: 12 Sources: https://pubmed.ncbi.nlm.nih.gov/11745909 Page: p.78	Sources: https://pubmed.ncbi.nlm.nih.gov/11745909 Page: p.78

Sourcing

Vendor/Aggregator	ID	URL
Alfa Chemistry	ACM132640223	http://www.alfa-chemistry.com/search.aspx?q=ACM132640223
BOC Sciences	132640-22-3	http://www.bocsci.com/description.asp?cas=132640-22-3
Enamine	Z994168344	https://www.enaminestore.com/blog/real/?codes=Z994168344
MuseChem	M115295	https://www.musechem.com/product/M115295.html
eMolecules	110069222	https://orderbb.emolecules.com/search/#?query=110069222

PubMed

Title	Date	PubMed
Antiallergic and cytoprotective activity of new N-phenylbenzamido acid derivatives.	1992 Oct 2	1433173
BK channel modulators: a comprehensive overview.	2008	18473808
The COPD pipeline.	2014 Apr	24625824
Efficacy of Andolast in Mild to Moderate Asthma: A Randomized, Controlled, Double-Blind Multicenter Study (The Andast Trial).	2015	25845448

Patents

Sample Use Guides

In Vivo Use Guide

In clinical trials andolast is administered in three different doses (2, 4, or 8 mg) three times a day for 12 weeks.

Route of Administration: Respiratory

In Vitro Use Guide

Peripheral blood mononuclear cells (PBMCs) from 40 asthmatics, 16 non-asthmatics allergic, and 9 normal donors were stimulated with IL-4 and/or anti-CD40 antibody. T cells from 9 additional allergic donors were activated with anti-CD3/CD28 antibodies to express IL-4 mRNA. After incubation in the absence or presence of Andolast (0.1 mkM, 1 mkM, 10 mkM), immunoglobulin concentrations were measured by enzyme immunoassay, and mRNA levels were analyzed by RT-PCR. Andolast significantly inhibited IgE synthesis by stimulated PBMCs from both asthma patients and combined allergic/Calcium-activated donors.

Name

Type

Language

ANDOLAST

Official Name

English

4,4'-DI-1H-TETRAZOL-5-YLBENZANILIDE

Systematic Name

English

andolast [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C319