Ciraparantag

Chemical compound From Wikipedia, the free encyclopedia

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).[1][2]

Other namesPER977; N1,N1′-[Piperazine-1,4-diylbis(propane-1,3-diyl)]bis-L-argininamide
Routes of
administrationIntravenous
ATC code
  • None
Legal status
  • Investigational
Quick facts Clinical data, Other names ...
Ciraparantag
Clinical data
Other namesPER977; 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 action10 min
Duration of action24 hours
Identifiers
  • (2S)-2-Amino-N-[3-[4-[3-[[(2S)-2-amino-5-(diaminomethylideneamino)pentanoyl]amino]propyl]piperazin-1-yl]propyl]-5-(diaminomethylideneamino)pentanamide
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC22H48N12O2
Molar mass512.708 g·mol−1
3D model (JSmol)
  • C1CN(CCN1CCCNC(=O)[C@H](CCCNC(=N)N)N)CCCNC(=O)[C@H](CCCNC(=N)N)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
  • Key:HRDUUSCYRPOMSO-ROUUACIJSA-N
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Medical uses

Ciraparantag significantly reverses anticoagulation induced by a therapeutic dose of edoxaban within 10 minutes following injection.[3] This return to normal haemostasis persists over 24 hours following a single intravenous dose of the drug.[4] In addition to edoxaban, it also reverses the actions of LMWH and dabigatran.[5]

Pharmacology

Mechanism of action

According to in vitro studies, the substance binds directly to anticoagulants via hydrogen bonds and charge-charge interactions [3] from or to various parts of the molecule:[1]

More information Hydrogen bonds, Rivaroxaban ...
Hydrogen bonds Rivaroxaban Apixaban Edoxaban Dabigatran Heparins
Guanidine part checkY checkY checkY checkY
α-Amino group checkY checkY checkY checkY
Amide nitrogen checkY checkY checkY
Amide oxygen checkY checkY
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Chemistry

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

See also

References

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