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Details

Stereochemistry ACHIRAL
Molecular Formula C28H27N5O5
Molecular Weight 513.5445
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of AVORALSTAT

SMILES

COC1=CC(=C(C=C1C=C)C(=O)NC2=CC=C(C=C2)C(N)=N)C3=C(N=C(C=C3)C(=O)NCC4CC4)C(O)=O

InChI

InChIKey=TUWMKPVJGGWGNL-UHFFFAOYSA-N
InChI=1S/C28H27N5O5/c1-3-16-12-21(26(34)32-18-8-6-17(7-9-18)25(29)30)20(13-23(16)38-2)19-10-11-22(33-24(19)28(36)37)27(35)31-14-15-4-5-15/h3,6-13,15H,1,4-5,14H2,2H3,(H3,29,30)(H,31,35)(H,32,34)(H,36,37)

HIDE SMILES / InChI
Avoralstat, a small molecule inhibitor of plasma kallikrein, participated in clinical trials phase III to prevent hereditary angioedema, but these studied were discontinued due to insufficient efficacy study. Recently published article has described that avoralstat could improve the quality of life in C1‐INH‐HAE patients. Hereditary angioedema (HAE) with C1 inhibitor deficiency (C1‐INH‐HAE) is an autosomal dominant disorder characterized by recurrent episodes of swelling of the skin, pharynx, gastrointestinal tract, genitals, and is due primarily to mutations in the SERPING1 gene that results in insufficient production of the natural plasma kallikrein inhibitor, C1 inhibitor (C1‐INH).

Approval Year

PubMed

PubMed

TitleDatePubMed

Sample Use Guides

avoralstat capsules (100 mg) is taken three times daily by mouth
Route of Administration: Oral
Name Type Language
AVORALSTAT
INN   WHO-DD  
INN  
Official Name English
2-PYRIDINECARBOXYLIC ACID, 3-(2-(((4-(AMINOIMINOMETHYL)PHENYL)AMINO)CARBONYL)-4-ETHENYL-5-METHOXYPHENYL)-6-(((CYCLOPROPYLMETHYL)AMINO)CARBONYL)-
Systematic Name English
BCX-4161
Code English
avoralstat [INN]
Common Name English
3-(2-((4-CARBAMIMIDOYLPHENYL)CARBAMOYL)-4-ETHENYL-5-METHOXYPHENYL)-6-((CYCLOPROPYLMETHYL)CARBAMOYL)PYRIDINE-2-CARBOXYLIC ACID
Systematic Name English
BCX4161
Code English
Avoralstat [WHO-DD]
Common Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 457114
Created by admin on Fri Dec 15 17:27:01 GMT 2023 , Edited by admin on Fri Dec 15 17:27:01 GMT 2023
Code System Code Type Description
EU-Orphan Drug
EU/3/15/1431(WITHDRAWN)
Created by admin on Fri Dec 15 17:27:01 GMT 2023 , Edited by admin on Fri Dec 15 17:27:01 GMT 2023
PRIMARY Please note that this product was withdrawn from the Community Register of designated Orphan Medicinal Products in March 2017 on request of the Sponsor. On 12 February 2015, orphan designation (EU/3/15/1431) was granted by the European Commission to BioCryst UK Ltd., the United Kingdom, for 3-[2-(4-carbamimidoyl-phenylcarbamoyl)-5-methoxy-4-vinyl-phenyl]-6-(cyclopropylmethyl-carbamoyl)-pyridine-2-carboxylic acid for the treatment of hereditary angioedema. This medicine is now known as avoralstat.
CAS
918407-35-9
Created by admin on Fri Dec 15 17:27:01 GMT 2023 , Edited by admin on Fri Dec 15 17:27:01 GMT 2023
PRIMARY
SMS_ID
100000183842
Created by admin on Fri Dec 15 17:27:01 GMT 2023 , Edited by admin on Fri Dec 15 17:27:01 GMT 2023
PRIMARY
FDA UNII
UX17773O15
Created by admin on Fri Dec 15 17:27:01 GMT 2023 , Edited by admin on Fri Dec 15 17:27:01 GMT 2023
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PUBCHEM
86566678
Created by admin on Fri Dec 15 17:27:01 GMT 2023 , Edited by admin on Fri Dec 15 17:27:01 GMT 2023
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INN
10052
Created by admin on Fri Dec 15 17:27:01 GMT 2023 , Edited by admin on Fri Dec 15 17:27:01 GMT 2023
PRIMARY
NCI_THESAURUS
C169799
Created by admin on Fri Dec 15 17:27:01 GMT 2023 , Edited by admin on Fri Dec 15 17:27:01 GMT 2023
PRIMARY
DRUG BANK
DB12120
Created by admin on Fri Dec 15 17:27:01 GMT 2023 , Edited by admin on Fri Dec 15 17:27:01 GMT 2023
PRIMARY