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Details

Stereochemistry ABSOLUTE
Molecular Formula C22H48N12O2
Molecular Weight 512.6957
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CIRAPARANTAG

SMILES

N[C@@H](CCCNC(N)=N)C(=O)NCCCN1CCN(CCCNC(=O)[C@@H](N)CCCNC(N)=N)CC1

InChI

InChIKey=HRDUUSCYRPOMSO-ROUUACIJSA-N
InChI=1S/C22H48N12O2/c23-17(5-1-7-31-21(25)26)19(35)29-9-3-11-33-13-15-34(16-14-33)12-4-10-30-20(36)18(24)6-2-8-32-22(27)28/h17-18H,1-16,23-24H2,(H,29,35)(H,30,36)(H4,25,26,31)(H4,27,28,32)/t17-,18-/m0/s1

HIDE SMILES / InChI

Description

Ciraparantag (PER-977, aripazine), developed by Perosphere Inc., is a small, synthetic, water-soluble, cationic molecule and can reverse the anticoagulation mediated by unfractionated heparin, low-molecular-weight heparin, factor Xa and factor IIa inhibitors, and fondaparinux. It has the potential to be a universal antidote, inhibiting nearly all anticoagulants except vitamin K antagonists and argatroban. In April 2015, ciraparantag received FDA fast-track designation as an investigational anticoagulant reversal agent. Phase I/II trials are currently underway to evaluate the safety and efficacy of PER977 in reversing anticoagulation of edoxaban, LMWH, and UFH.2.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Secondary
Unknown

Cmax

ValueDoseCo-administeredAnalytePopulation
634 ng/mL
15 mg single, intravenous
CIRAPARANTAG serum
Homo sapiens
10570 ng/mL
300 mg single, intravenous
CIRAPARANTAG serum
Homo sapiens
173 ng/mL
5 mg single, intravenous
CIRAPARANTAG serum
Homo sapiens
3860 ng/mL
100 mg single, intravenous
CIRAPARANTAG serum
Homo sapiens
7755 ng/mL
200 mg single, intravenous
CIRAPARANTAG serum
Homo sapiens
861 ng/mL
25 mg single, intravenous
CIRAPARANTAG serum
Homo sapiens
861 ng/mL
50 mg single, intravenous
CIRAPARANTAG serum
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
151 ng × h/mL
15 mg single, intravenous
CIRAPARANTAG serum
Homo sapiens
3800 ng × h/mL
300 mg single, intravenous
CIRAPARANTAG serum
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
0.2 h
15 mg single, intravenous
CIRAPARANTAG serum
Homo sapiens
0.32 h
300 mg single, intravenous
CIRAPARANTAG serum
Homo sapiens
0.24 h
100 mg single, intravenous
CIRAPARANTAG serum
Homo sapiens
0.33 h
200 mg single, intravenous
CIRAPARANTAG serum
Homo sapiens
0.19 h
25 mg single, intravenous
CIRAPARANTAG serum
Homo sapiens
0.24 h
50 mg single, intravenous
CIRAPARANTAG serum
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
100%
300 mg single, intravenous
CIRAPARANTAG serum
Homo sapiens

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer


Drug as perpetrator​

Drug as victim

PubMed

Sample Use Guides

In Vivo Use Guide
Single intravenous doses of Ciraparantag (100–300 mg) that completelyreversed anticoagulation associated with a single doseof edoxaban (60 mg) in healthy volunteers within 10 minutesand maintained reversal over 24 hours with no rebound andno need for infusions or repeat administration.
Route of Administration: Intravenous
In Vitro Use Guide
Unknown