Ciraparantag

File:Ciraparantag skeletal.svg
Systematic (IUPAC) name
N,N'-(1,4-piperazinediyldi-3,1-propanediyl)bis[2-amino-5-[(aminoiminomethyl)amino]-, (2S,2'S)-pentanamide
Clinical data
Legal status	Investigational
Routes of administration	Intravenous
Pharmacokinetic data
Onset of action	10 min
Duration of action	24 hrs
Identifiers
CAS Number	1438492-26-2
ATC code	none
PubChem	CID: 71576543
ChemSpider	33427375
UNII	U2R67KV65Q
Synonyms	PER977
Chemical data
Formula	C22H48N12O2
Molecular mass	512.71 g·mol−1
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 (INN/USAN, or 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, low molecular weight heparins and unfractionated heparin.

Mechanism of action

According to in vitro studies, the substance binds directly to anticoagulants via hydrogen bonds 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

Chemical properties

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

See also

Other anticoagulant antidotes

• Andexanet alfa
• Idarucizumab
• Vitamin K