Argatroban hydrate | CAS#141396-28-3 | thrombin inhibitor

MedKoo Cat#: 319512 | Name: Argatroban hydrate

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Argatroban is an anticoagulant that is a direct thrombin inhibitor. Argatroban was approved in 2000 for prophylaxis or treatment of thrombosis in patients with heparin-induced thrombocytopenia (HIT). Argatroban is a direct thrombin inhibitor that reversibly binds to the thrombin active site. Argatroban exerts its anticoagulant effects by inhibiting thrombin-catalyzed or -induced reactions, including fibrin formation; activation of coagulation factors V, VIII, and XIII; activation of protein C; and platelet aggregation. Argatroban inhibits thrombin with an inhibition constant (Ki) of 0.04 μM.

Chemical Structure

Argatroban hydrate

CAS#141396-28-3 (hydrate)

Theoretical Analysis

MedKoo Cat#: 319512

Name: Argatroban hydrate

CAS#: 141396-28-3 (hydrate)

Chemical Formula: C23H38N6O6S

Exact Mass: 508.2468

Molecular Weight: 526.65

Elemental Analysis: C, 52.45; H, 7.27; N, 15.96; O, 18.23; S, 6.09

Price and Availability

Size	Price	Availability
50mg	USD 250.00	2 Weeks
100mg	USD 350.00	2 Weeks
200mg	USD 550.00	2 Weeks
500mg	USD 1,250.00	2 Weeks
1g	USD 2,250.00	2 Weeks
2g	USD 4,050.00	2 Weeks
5g	USD 6,950.00	2 Weeks

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Related CAS #

74863-84-6 (anhydrous) 141396-28-3 (hydrate)

Synonym

MCI-9038; MCI9038; MCI9038; MD805; MD-805; MD 805; DK-7419; DK 7419; DK7419; GN1600; GN-1600; GN 1600; MMTQAP; MPQA; Argatroban.Novastan; OM 805; Slonnon; Argipidine.

IUPAC/Chemical Name

(2R,4R)-1-[(2S)-5-(diaminomethylideneamino)-2-[[(3R)-3-methyl-1,2,3,4-tetrahydroquinolin-8-yl]sulfonylamino]pentanoyl]-4-methyl-piperidine-2-carboxylic acid hydrate

InChi Key

AIEZTKLTLCMZIA-VJCHTHLQSA-N

InChi Code

InChI=1S/C23H36N6O5S.H2O/c1-14-8-10-29(18(12-14)22(31)32)21(30)17(6-4-9-26-23(24)25)28-35(33,34)19-7-3-5-16-11-15(2)13-27-20(16)19;/h3,5,7,14-15,17-18,27-28H,4,6,8-13H2,1-2H3,(H,31,32)(H4,24,25,26);1H2/t14-,15-,17+,18-;/m1./s1

SMILES Code

O=C([C@@H]1N(C([C@@H](NS(=O)(C2=CC=CC3=C2NC[C@H](C)C3)=O)CCC/N=C(N)\N)=O)CC[C@@H](C)C1)O.[H]O[H]

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO, not in water

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Argatroban (monohydrate) (MD-805 (monohydrate)) is a direct, selective thrombin inhibitor.

In vitro activity:

To evaluate whether this small molecule compound can promote alveolar BMSC osteogenesis in vivo, this study established a periodontal disease model around the mouse maxillary 1st molar to induce bone degeneration, then injected vehicle or different doses of argatroban every other day (n = 4). After 2 weeks, alveolar bone volume was examined by micro-CT and histomorphometry. Without argatroban treatment, the alveolar bone loss volume between the first molar (M1) and second molar (M2) was larger than treated group (Fig. 1a). To evaluate the alveolar bone resorption and regeneration in vivo, relative height of alveolar crests were measured using the average distance between the cemento-enamel junction (CEJ) to the alveolar crest from the first molar and second molar (shown by green line in Fig. 1a). The distance from CEJ to bone crest was significantly longer in vehicle group than treated group (Fig. 1b). Lower dose of argatroban (1 μg) attenuated alveolar bone loss caused by periodontal disease. Reference: Life Sci. 2021 Mar 15;269:119073. https://pubmed.ncbi.nlm.nih.gov/33460666/

In vivo activity:

Four-week treatment of argatroban (0.3 and 1 mg/kg) significantly reduced plasma glucose, cholesterol, and glycated hemoglobin level when compared with T2DM animals whereas plasma insulin level was improved significantly with argatroban 1 mg/kg. Argatroban did not significantly affect the body weight of the diabetic rats. There was even no significant change in any of the parameters in the argatroban per se group (Fig. 1a–e). Reference: Cardiovasc Drugs Ther. 2017 Jun;31(3):255-267. https://pubmed.ncbi.nlm.nih.gov/28695302/

	Solvent	mg/mL	mM
Solubility
	DMSO	100.0	189.88
	Ethanol	40.0	75.95

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 526.65 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Song J, Jiang N, Gan X, Zhi W, Zhu Z. Thrombin inhibitor argatroban modulates bone marrow stromal cells behaviors and promotes osteogenesis through canonical Wnt signaling. Life Sci. 2021 Mar 15;269:119073. doi: 10.1016/j.lfs.2021.119073. Epub 2021 Jan 15. PMID: 33460666. 2. Raaz U, Kaeberich A, Maegdefessel L, Buerke M, Busshardt M, Schubert S, Russ M, Plehn A, Ebelt H, Werdan K, Schlitt A. The direct thrombin inhibitor argatroban effectively prevents cardiac catheter thrombosis in vitro. Thromb Haemost. 2010 Apr;103(4):808-14. doi: 10.1160/TH09-07-0456. Epub 2010 Feb 19. PMID: 20174756. 3. Bulani Y, Sharma SS. Argatroban Attenuates Diabetic Cardiomyopathy in Rats by Reducing Fibrosis, Inflammation, Apoptosis, and Protease-Activated Receptor Expression. Cardiovasc Drugs Ther. 2017 Jun;31(3):255-267. doi: 10.1007/s10557-017-6732-3. PMID: 28695302. 4. Lyden P, Pereira B, Chen B, Zhao L, Lamb J, Lei IF, Rajput P. Direct thrombin inhibitor argatroban reduces stroke damage in 2 different models. Stroke. 2014 Mar;45(3):896-9. doi: 10.1161/STROKEAHA.113.004488. Epub 2014 Jan 28. PMID: 24473182; PMCID: PMC3995814.

In vitro protocol:

In vivo protocol:

1. Bulani Y, Sharma SS. Argatroban Attenuates Diabetic Cardiomyopathy in Rats by Reducing Fibrosis, Inflammation, Apoptosis, and Protease-Activated Receptor Expression. Cardiovasc Drugs Ther. 2017 Jun;31(3):255-267. doi: 10.1007/s10557-017-6732-3. PMID: 28695302. 2. Lyden P, Pereira B, Chen B, Zhao L, Lamb J, Lei IF, Rajput P. Direct thrombin inhibitor argatroban reduces stroke damage in 2 different models. Stroke. 2014 Mar;45(3):896-9. doi: 10.1161/STROKEAHA.113.004488. Epub 2014 Jan 28. PMID: 24473182; PMCID: PMC3995814.

1: Grouzi E. Update on argatroban for the prophylaxis and treatment of heparin-induced thrombocytopenia type II. J Blood Med. 2014 Aug 13;5:131-41. doi: 10.2147/JBM.S38762. eCollection 2014. Review. PubMed PMID: 25152637; PubMed Central PMCID: PMC4140228. 2: Rozec B, Boissier E, Godier A, Cinotti R, Stephan F, Blanloeil Y. [Argatroban, a new antithrombotic treatment for heparin-induced thrombocytopenia application in cardiac surgery and in intensive care]. Ann Fr Anesth Reanim. 2014 Sep-Oct;33(9-10):514-23. doi: 10.1016/j.annfar.2014.06.006. Epub 2014 Aug 20. Review. French. PubMed PMID: 25148720. 3: Badiye A, Hernandez GA, Chaparro S. Argatroban as novel therapy for suspected thrombosis in patients with continuous-flow left ventricle assist device and hemolysis. ASAIO J. 2014 May-Jun;60(3):361-5. doi: 10.1097/MAT.0000000000000067. Review. PubMed PMID: 24614354. 4: Argatroban: for a few selected patients. Prescrire Int. 2013 Feb;22(135):33-5. Review. PubMed PMID: 23444494. 5: Cruz-González I, López-Jiménez R, Perez-Rivera A, Yan BP. Pharmacokinetic evaluation of argatroban for the treatment of acute coronary syndrome. Expert Opin Drug Metab Toxicol. 2012 Nov;8(11):1483-93. doi: 10.1517/17425255.2012.722621. Epub 2012 Sep 13. Review. PubMed PMID: 22970706. 6: Alatri A, Armstrong AE, Greinacher A, Koster A, Kozek-Langenecker SA, Lancé MD, Link A, Nielsen JD, Sandset PM, Spanjersberg AJ, Spannagl M. Results of a consensus meeting on the use of argatroban in patients with heparin-induced thrombocytopenia requiring antithrombotic therapy - a European Perspective. Thromb Res. 2012 Apr;129(4):426-33. doi: 10.1016/j.thromres.2011.11.041. Epub 2011 Dec 16. Review. PubMed PMID: 22178575. 7: Jeske WP, Fareed J, Hoppensteadt DA, Lewis B, Walenga JM. Pharmacology of argatroban. Expert Rev Hematol. 2010 Oct;3(5):527-39. doi: 10.1586/ehm.10.53. Review. PubMed PMID: 21083469. 8: Babuin L, Pengo V. Argatroban in the management of heparin-induced thrombocytopenia. Vasc Health Risk Manag. 2010 Sep 7;6:813-9. Review. PubMed PMID: 20859550; PubMed Central PMCID: PMC2941792. 9: Follis F, Filippone G, Montalbano G, Floriano M, Lobianco E, D'Ancona G, Follis M. Argatroban as a substitute of heparin during cardiopulmonary bypass: a safe alternative? Interact Cardiovasc Thorac Surg. 2010 Apr;10(4):592-6. doi: 10.1510/icvts.2009.215848. Epub 2010 Jan 8. Review. PubMed PMID: 20061338. 10: Dhillon S. Argatroban: a review of its use in the management of heparin-induced thrombocytopenia. Am J Cardiovasc Drugs. 2009;9(4):261-82. doi: 10.2165/1120090-000000000-00000. Review. PubMed PMID: 19655821. 11: Hursting MJ, Soffer J. Reducing harm associated with anticoagulation: practical considerations of argatroban therapy in heparin-induced thrombocytopenia. Drug Saf. 2009;32(3):203-18. doi: 10.2165/00002018-200932030-00003. Review. PubMed PMID: 19338378. 12: Taimeh Z, Weksler B. Review: recent advances in argatroban-warfarin transition in patients with heparin-induced thrombocytopenia. Clin Appl Thromb Hemost. 2010 Feb;16(1):5-12. doi: 10.1177/1076029608327862. Epub 2008 Dec 2. Review. PubMed PMID: 19054792. 13: Young SK, Al-Mondhiry HA, Vaida SJ, Ambrose A, Botti JJ. Successful use of argatroban during the third trimester of pregnancy: case report and review of the literature. Pharmacotherapy. 2008 Dec;28(12):1531-6. doi: 10.1592/phco.28.12.1531. Review. PubMed PMID: 19025434. 14: Boggio LN, Oza VM. Argatroban use in heparin-induced thrombocytopenia. Expert Opin Pharmacother. 2008 Aug;9(11):1963-7. doi: 10.1517/14656566.9.11.1963 . Review. PubMed PMID: 18627333. 15: Ohtani R, Tomimoto H, Takahashi R, Tsukahara T, Hatano T. [Argatroban]. Nihon Rinsho. 2006 Oct 28;64 Suppl 7:581-4. Review. Japanese. PubMed PMID: 17461209. 16: Martin ME, Kloecker GH, Laber DA. Argatroban for anticoagulation during cardiac surgery. Eur J Haematol. 2007 Feb;78(2):161-6. Review. PubMed PMID: 17328717. 17: Schönfeld H, Hein OV. [Pharmacotherapy: argatroban--alternative to heparin in case of heparin-induced thrombocytopenia type II (HIT II)]. Anasthesiol Intensivmed Notfallmed Schmerzther. 2006 Jun;41(6):376-7. Review. German. PubMed PMID: 16804787. 18: Yeh RW, Jang IK. Argatroban: update. Am Heart J. 2006 Jun;151(6):1131-8. Review. PubMed PMID: 16781211. 19: Escolar G, Bozzo J, Maragall S. Argatroban: a direct thrombin inhibitor with reliable and predictable anticoagulant actions. Drugs Today (Barc). 2006 Apr;42(4):223-36. Review. PubMed PMID: 16703119. 20: Matthai WH Jr. Safety and efficacy of argatroban in patients with heparin-induced thrombocytopenia. Curr Hematol Rep. 2006 Mar;5(1):95-9. Review. PubMed PMID: 16537053.