Ciraparantag

Ciraparantag

Clinical data
Other names	PER977; N1,N1′-[Piperazine-1,4-diylbis(propane-1,3-diyl)]bis-L-argininamide
Routes of administration	Intravenous
ATC code	None
Legal status
Legal status	Investigational
Pharmacokinetic data
Onset of action	10 min
Duration of action	24 hours
Identifiers
IUPAC name (2S)-2-Amino-N-[3-[4-[3-[[(2S)-2-amino-5-(diaminomethylideneamino)pentanoyl]amino]propyl]piperazin-1-yl]propyl]-5-(diaminomethylideneamino)pentanamide
CAS Number	1438492-26-2
PubChem CID	71576543
ChemSpider	33427375
UNII	U2R67KV65Q
KEGG	D10868 Y
Chemical and physical data
Formula	C22H48N12O2
Molar mass	512.708 g·mol−1
3D model (JSmol)	Interactive image
SMILES C1CN(CCN1CCCNC(=O)[C@H](CCCNC(=N)N)N)CCCNC(=O)[C@H](CCCNC(=N)N)N
InChI 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 Key:HRDUUSCYRPOMSO-ROUUACIJSA-N

Ciraparantag (aripazine) is a drug under investigation as an antidote for a number of anticoagulant (anti-blood clotting) drugs, including factor Xa inhibitors (rivaroxaban, apixaban and edoxaban), dabigatran, and heparins (including fondaparinux, low molecular weight heparins (LMWH), and unfractionated heparin).

Medical uses

Ciraparantag significantly reverses anticoagulation induced by a therapeutic dose of edoxaban within 10 minutes following injection. This return to normal haemostasis persists over 24 hours following a single intravenous dose of the drug. In addition to edoxaban, it also reverses the actions of LMWH and dabigatran.

Pharmacology

Mechanism of action

According to in vitro studies, the substance binds directly to anticoagulants via hydrogen bonds and charge-charge interactions from or to various parts of the molecule:

Hydrogen bonds	Rivaroxaban	Apixaban	Edoxaban	Dabigatran	Heparins
Guanidine part	Y		Y	Y	Y
α-Amino group	Y	Y		Y	Y
Amide nitrogen	Y			Y	Y
Amide oxygen		Y	Y

Chemistry

Ciraparantag consists of two L-arginine units connected with a piperazine containing linker chain.

See also

• Andexanet alfa
• Idarucizumab
• Prothrombin complex concentrate
• Vitamin K