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Ciraparantag

January 01, 1970

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]

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
  • 1438492-26-2
PubChem CID
  • 71576543
ChemSpider
  • 33427375
UNII
  • U2R67KV65Q
KEGG
  • D10868 Y
Chemical and physical data
FormulaC22H48N12O2
Molar mass512.708 g·mol−1
3D model (JSmol)
  • Interactive image
  • 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

Medical uses edit

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 edit

Mechanism of action edit

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]

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 edit

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

See also edit

References edit

  1. ^ a b c 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. ^ a b 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.
 

This drug article relating to the blood and blood forming organs is a stub. You can help Wikipedia by expanding it.

January 01, 1970
ciraparantag, aripazine, drug, under, investigation, antidote, number, anticoagulant, anti, blood, clotting, drugs, including, factor, inhibitors, rivaroxaban, apixaban, edoxaban, dabigatran, heparins, including, fondaparinux, molecular, weight, heparins, lmwh. 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 CiraparantagClinical dataOther namesPER977 N1 N1 Piperazine 1 4 diylbis propane 1 3 diyl bis L argininamideRoutes ofadministrationIntravenousATC codeNoneLegal statusLegal statusInvestigationalPharmacokinetic dataOnset of action10 minDuration of action24 hoursIdentifiersIUPAC name 2S 2 Amino N 3 4 3 2S 2 amino 5 diaminomethylideneamino pentanoyl amino propyl piperazin 1 yl propyl 5 diaminomethylideneamino pentanamideCAS Number1438492 26 2PubChem CID71576543ChemSpider33427375UNIIU2R67KV65QKEGGD10868 YChemical and physical dataFormulaC 22H 48N 12O 2Molar mass512 708 g mol 13D model JSmol Interactive imageSMILES C1CN CCN1CCCNC O C H CCCNC N N N CCCNC O C H CCCNC N N NInChI 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 s1Key HRDUUSCYRPOMSO ROUUACIJSA N Contents 1 Medical uses 2 Pharmacology 2 1 Mechanism of action 3 Chemistry 4 See also 5 ReferencesMedical uses editCiraparantag 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 editMechanism of action edit 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 Hydrogen bonds Rivaroxaban Apixaban Edoxaban Dabigatran Heparins Guanidine part nbsp Y nbsp Y nbsp Y nbsp Y a Amino group nbsp Y nbsp Y nbsp Y nbsp Y Amide nitrogen nbsp Y nbsp Y nbsp Y Amide oxygen nbsp Y nbsp YChemistry editCiraparantag consists of two L arginine units connected with a piperazine containing linker chain 1 See also editAndexanet alfa Idarucizumab Prothrombin complex concentrate Vitamin KReferences edit a b c Schubert Zsilavecz M Wurglics M Fall 2015 Neue Arzneimittel in German 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 a b 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 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 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 nbsp This drug article relating to the blood and blood forming organs is a stub You can help Wikipedia by expanding it vte Retrieved from https en wikipedia org w index php title Ciraparantag amp oldid 1188122568, wikipedia, wiki, book, books, library,

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