Ciraparantag

Ciraparantag

Clinical data
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 N,N′-(1,4-Piperazinediyldi-3,1-propanediyl)bis[2-amino-5-[(aminoiminomethyl)amino]-, (2S,2S)-pentanamide
Synonyms	PER977 N^1,N^1′-[Piperazine-1,4-diylbis(propane-1,3-diyl)]bis-L-argininamide
CAS Number	1438492-26-2
PubChem (CID)	71576543
ChemSpider	33427375
UNII	U2R67KV65Q
Chemical and physical data
Formula	C22H48N12O2
Molar mass	512.71 g·mol^−1
3D model (Jmol)	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 (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.^[1][2]

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:^[1]

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

Chemical properties

Ciraparantag consists of two L-arginine units connected with a piperazine containing linker chain.^[1]

See also

Other anticoagulant antidotes

• Andexanet alfa
• Idarucizumab
• Vitamin K

References

1. Schubert-Zsilavecz, M, Wurglics, M, Neue Arzneimittel Herbst 2015 (German)
2. Ansell, J. E. (2015). "Universal, class-specific and drug-specific reversal agents for the new oral anticoagulants". Journal of Thrombosis and Thrombolysis. doi:10.1007/s11239-015-1288-1. PMID 26449414.