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Ciraparantag

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Chemical compound Pharmaceutical compound
Ciraparantag
Clinical data
Other namesPER977; N,N-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
IUPAC name
  • (2S)-2-Amino-N-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
3D model (JSmol)
SMILES
  • C1CN(CCN1CCCNC(=O)(CCCNC(=N)N)N)CCCNC(=O)(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 checkY checkY checkY checkY
α-Amino group checkY checkY checkY checkY
Amide nitrogen checkY checkY checkY
Amide oxygen checkY checkY

Chemistry

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

See also

References

  1. ^ Schubert-Zsilavecz M, Wurglics M (Fall 2015). Neue Arzneimittel (in German).
  2. Ansell JE (February 2016). "Universal, class-specific and drug-specific reversal agents for the new oral anticoagulants". Journal of Thrombosis and Thrombolysis. 41 (2): 248–52. doi:10.1007/s11239-015-1288-1. PMID 26449414. S2CID 7364744.
  3. ^ Ansell JE, Bakhru SH, Laulicht BE, Steiner SS, Grosso MA, Brown K, et al. (January 2017). "Single-dose ciraparantag safely and completely reverses anticoagulant effects of edoxaban". Thrombosis and Haemostasis. 117 (2): 238–245. doi:10.1160/TH16-03-0224. PMC 6260118. PMID 27853809.
  4. Laulicht B, Bakhru S, Jiang X, Chen L, Pan D, Grosso M, Morishima Y, Brown K, Masumoto H, Costin J, Steiner S (June 2013). "Antidote for new oral anticoagulants: mechanism of action and binding specificity of PER977". J Thromb Haemost. 11 (suppl 2): 1–84.
  5. Costin JC, Laulicht B, Bakhru S, Steiner S (March 2015). "PER977 reverses low molecular weight heparin in addition to IIa and Xa new oral anticoagulants". Journal of the American College of Cardiology. 65 (10): A2056. doi:10.1016/S0735-1097(15)62056-3.
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