CIRAPARANTAG

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 Search

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25387210 | https://journals.prous.com/journals/servlet/xmlxsl/pk_journals.xml_summary_pr?p_JournalId=2&p_RefId=2490311&p_IsPs=N

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 Target	Pharmacology	Condition	Potency
Coagulation factor X 20 Target ID: CHEMBL244 Sources: http://adisinsight.springer.com/drugs/800037993	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Hemorrhage 11 Sources: http://adisinsight.springer.com/drugs/800037993	Secondary		Phase II 1132	Unknown Approved Use Unknown

C_max

Value	Dose	Analyte	Population
634 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/33205809/	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/33205809/	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/33205809/	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/33205809/	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/33205809/	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/33205809/	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/33205809/	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

Value	Dose	Co-administered	Analyte	Population
151 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/33205809/	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/33205809/	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

T_1/2

Value	Dose	Analyte	Population
0.2 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/33205809/	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/33205809/	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/33205809/	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/33205809/	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/33205809/	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/33205809/	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

F_unbound

Value	Dose	Co-administered	Analyte	Population
100% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/33205809/	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

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYPs 22	CYPs 33

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
CYPs 28	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/27548686/	no

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
CYPs 33	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/27548686/	no

Sourcing

Vendor/Aggregator	ID	URL
Compound Cloud	71576543
Compound Cloud	90659771
MuseChem	I006142	https://www.musechem.com/product/I006142.html
ShangHai Biochempartner	BCP18453	http://www.biochempartner.com/search_BCP18453
eMolecules	92488456	https://orderbb.emolecules.com/search/#?query=92488456

PubMed

Title	Date	PubMed
Reversal agents in development for the new oral anticoagulants.	2014 Nov	25387210
Use of PER977 to reverse the anticoagulant effect of edoxaban.	2014 Nov 27	25371966

Patents

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

Substance Class	Chemical Created by `admin` on `Sat Dec 16 08:28:30 GMT 2023` Edited by `admin` on `Sat Dec 16 08:28:30 GMT 2023`
Record UNII	U2R67KV65Q
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CIRAPARANTAG

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