PRALNACASAN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C26H29N5O7
Molecular Weight	523.5378
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCO[C@@H]1OC(=O)C[C@@H]1NC(=O)[C@@H]2CCCN3N2C(=O)[C@H](CCC3=O)NC(=O)C4=C5C=CC=CC5=CC=N4

InChI

InChIKey=CXAGHAZMQSCAKJ-WAHHBDPQSA-N

InChI=1S/C26H29N5O7/c1-2-37-26-18(14-21(33)38-26)29-23(34)19-8-5-13-30-20(32)10-9-17(25(36)31(19)30)28-24(35)22-16-7-4-3-6-15(16)11-12-27-22/h3-4,6-7,11-12,17-19,26H,2,5,8-10,13-14H2,1H3,(H,28,35)(H,29,34)/t17-,18-,19-,26+/m0/s1

HIDE SMILES / InChI

Molecular Formula	C26H29N5O7
Molecular Weight	523.5378
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	4 / 4
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.drugbank.ca/drugs/DB04875 | https://www.ncbi.nlm.nih.gov/pubmed/17845807 | https://www.ncbi.nlm.nih.gov/pubmed/14610233 | http://drugprofiles.informa.com/drug_profiles/49-pralnacasan | https://clinicaltrials.gov/ct2/show/NCT01501383

Pralnacasan is a potent, non-peptide inhibitor of interleukin-1beta converting enzyme (ICE, aka Caspase-1). It was originally discovered by Vertex Pharmaceuticals and licensed for development to Aventis Pharma. In 2003 Aventis and Vertex Pharmaceuticals agreed to voluntarily discontinue development based on results from a 9-month animal toxicity trial that showed liver abnormalities due to chronic high doses of pralnacasan. Pralnacasan has also been investigated for the treatment of Partial Epilepsy; advancing to Phase II clinical trials.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Caspase-1 5 Target ID: P29466 Gene ID: 834.0 Gene Symbol: CASP1 Target Organism: Homo sapiens (Human) Sources: https://www.drugbank.ca/drugs/DB04875	Inhibitor 8504

Conditions

Condition	Modality	Highest Phase	Product
Inflammatory bowel disease 24 Sources: https://www.ncbi.nlm.nih.gov/pubmed/14610233	Primary	Basic research	Unknown Approved Use Unknown
Osteoarthritis 157 Sources: https://www.ncbi.nlm.nih.gov/pubmed/13129693	Primary	Phase II 1147	Unknown Approved Use Unknown
Rheumatoid arthritis 320 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11772244	Primary	Phase II 1147	Unknown Approved Use Unknown
Treatment resistant partial epilepsy 1 Sources: https://clinicaltrials.gov/ct2/show/NCT01501383	Primary	Phase II 1147	Unknown Approved Use Unknown

F_unbound

Value	Dose	Co-administered	Analyte	Population
0.6% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/20229566/			PRALNACASAN plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

Sourcing

Vendor/Aggregator	ID	URL
Angene	AGN-PC-0QLH8J	http://www.angenechemical.com/productshow/AGN-PC-0QLH8J.html
Compound Cloud	153270
eMolecules	36367262	https://orderbb.emolecules.com/search/#?query=36367262
eMolecules	43295170	https://orderbb.emolecules.com/search/#?query=43295170
Innovapharm	VT-00687902
MuseChem	M034379	https://www.musechem.com/product/M034379.html

PubMed

Title	Date	PubMed
A selective, non-peptide caspase-1 inhibitor, VRT-018858, markedly reduces brain damage induced by transient ischemia in the rat.	2007-10	17845807
Influence of the interleukin-converting enzyme inhibitor HMR-3480 on myocardial stunning in pigs in vivo.	2007	18650993
Inactivation of caspase-1 in rodent brain: a novel anticonvulsive strategy.	2006-07	16886979
Caspase inhibitors: a pharmaceutical industry perspective.	2005	16375749
The interleukin-1 beta-converting enzyme inhibitor pralnacasan reduces dextran sulfate sodium-induced murine colitis and T helper 1 T-cell activation.	2004-02	14610233
Pralnacasan, an inhibitor of interleukin-1beta converting enzyme, reduces joint damage in two murine models of osteoarthritis.	2003-10	13129693

Patents

Sample Use Guides

In Vivo Use Guide

In a Phase-IIa clinical trial patients suffering from rheumatoid arthritis received up to 1200 mg/day orally of pralnacasan for 12 weeks. Patients receiving 1200 mg/day had statistically significant reductions in the inflammatory biomarkers C-reactive protein, erythrocyte sedimentation rate, and serum amyloid A. PAtients receiving pralnacasan were also able to reduce their concomitant corticosteroid therapy.

Route of Administration: Oral

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:14:04 GMT 2025` Edited by `admin` on `Mon Mar 31 18:14:04 GMT 2025`
Record UNII	N986NI319S
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

HMR-3480

Preferred Name

English

PRALNACASAN

Official Name

English

PRALNACASAN [USAN]

Common Name

English

HMR-3480/VX-740

Code

English

VX-740

Code

English

HMR3480

Code

English

pralnacasan [INN]

Common Name

English

HMR3480/VX-740

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C257