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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

Molecular Formula C22H48N12O2
Molecular Weight 512.6957
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Secondary
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
634 ng/mL
15 mg single, intravenous
dose: 15 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
CIRAPARANTAG serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
10570 ng/mL
300 mg single, intravenous
dose: 300 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
CIRAPARANTAG serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
173 ng/mL
5 mg single, intravenous
dose: 5 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
CIRAPARANTAG serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
3860 ng/mL
100 mg single, intravenous
dose: 100 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
CIRAPARANTAG serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
7755 ng/mL
200 mg single, intravenous
dose: 200 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
CIRAPARANTAG serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
861 ng/mL
25 mg single, intravenous
dose: 25 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
CIRAPARANTAG serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
861 ng/mL
50 mg single, intravenous
dose: 50 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
CIRAPARANTAG serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
151 ng × h/mL
15 mg single, intravenous
dose: 15 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
CIRAPARANTAG serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
3800 ng × h/mL
300 mg single, intravenous
dose: 300 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
CIRAPARANTAG serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
0.2 h
15 mg single, intravenous
dose: 15 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
CIRAPARANTAG serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
0.32 h
300 mg single, intravenous
dose: 300 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
CIRAPARANTAG serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
0.24 h
100 mg single, intravenous
dose: 100 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
CIRAPARANTAG serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
0.33 h
200 mg single, intravenous
dose: 200 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
CIRAPARANTAG serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
0.19 h
25 mg single, intravenous
dose: 25 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
CIRAPARANTAG serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
0.24 h
50 mg single, intravenous
dose: 50 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
CIRAPARANTAG serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
100%
300 mg single, intravenous
dose: 300 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
CIRAPARANTAG serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer


Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
no
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
no
PubMed

PubMed

TitleDatePubMed
Reversal agents in development for the new oral anticoagulants.
2014 Nov
Use of PER977 to reverse the anticoagulant effect of edoxaban.
2014 Nov 27
Patents

Sample Use Guides

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
Substance Class Chemical
Created
by admin
on Thu Jul 06 13:54:45 UTC 2023
Edited
by admin
on Thu Jul 06 13:54:45 UTC 2023
Record UNII
U2R67KV65Q
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CIRAPARANTAG
INN   USAN   WHO-DD  
INN   USAN  
Official Name English
PER977
Code English
CIRAPARANTAG [USAN]
Common Name English
PER-977
Code English
Ciraparantag [WHO-DD]
Common Name English
N1,N1'-(PIPERAZINE-1,4-DIYLBIS(PROPANE-1,3-DIYL))BIS-L-ARGININAMIDE
Systematic Name English
ciraparantag [INN]
Common Name English
PENTANAMIDE, N,N'-(1,4-PIPERAZINEDIYLDI-3,1-PROPANEDIYL)BIS(2-AMINO-5-((AMINOIMINOMETHYL)AMINO)-, (2S,2'S)-
Systematic Name English
Code System Code Type Description
ChEMBL
CHEMBL3544919
Created by admin on Thu Jul 06 13:54:45 UTC 2023 , Edited by admin on Thu Jul 06 13:54:45 UTC 2023
PRIMARY
PUBCHEM
71576543
Created by admin on Thu Jul 06 13:54:45 UTC 2023 , Edited by admin on Thu Jul 06 13:54:45 UTC 2023
PRIMARY
FDA UNII
U2R67KV65Q
Created by admin on Thu Jul 06 13:54:45 UTC 2023 , Edited by admin on Thu Jul 06 13:54:45 UTC 2023
PRIMARY
INN
10164
Created by admin on Thu Jul 06 13:54:45 UTC 2023 , Edited by admin on Thu Jul 06 13:54:45 UTC 2023
PRIMARY
SMS_ID
300000034035
Created by admin on Thu Jul 06 13:54:45 UTC 2023 , Edited by admin on Thu Jul 06 13:54:45 UTC 2023
PRIMARY
NCI_THESAURUS
C169854
Created by admin on Thu Jul 06 13:54:45 UTC 2023 , Edited by admin on Thu Jul 06 13:54:45 UTC 2023
PRIMARY
WIKIPEDIA
Ciraparantag
Created by admin on Thu Jul 06 13:54:45 UTC 2023 , Edited by admin on Thu Jul 06 13:54:45 UTC 2023
PRIMARY
EPA CompTox
DTXSID701045783
Created by admin on Thu Jul 06 13:54:45 UTC 2023 , Edited by admin on Thu Jul 06 13:54:45 UTC 2023
PRIMARY
USAN
BC-147
Created by admin on Thu Jul 06 13:54:45 UTC 2023 , Edited by admin on Thu Jul 06 13:54:45 UTC 2023
PRIMARY
CAS
1438492-26-2
Created by admin on Thu Jul 06 13:54:45 UTC 2023 , Edited by admin on Thu Jul 06 13:54:45 UTC 2023
PRIMARY
DRUG BANK
DB15199
Created by admin on Thu Jul 06 13:54:45 UTC 2023 , Edited by admin on Thu Jul 06 13:54:45 UTC 2023
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR
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ACTIVE MOIETY