Argatroban | CAS#74863-84-6 | thrombin inhibitor

MedKoo Cat#: 540027 | Name: Argatroban

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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

CAS#74863-84-6 (anhydrous)

Theoretical Analysis

MedKoo Cat#: 540027

Name: Argatroban

CAS#: 74863-84-6 (anhydrous)

Chemical Formula: C23H36N6O5S

Exact Mass: 508.2468

Molecular Weight: 508.63

Elemental Analysis: C, 54.31; H, 7.13; N, 16.52; O, 15.73; S, 6.30

Price and Availability

Size	Price	Availability
250mg	USD 750.00	2 Weeks
500mg	USD 1,250.00	2 Weeks
1g	USD 2,250.00	2 Weeks
2g	USD 4,050.00	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)-4-methyl-1-(((3-methyl-1,2,3,4-tetrahydroquinolin-8-yl)sulfonyl)-L-arginyl)piperidine-2-carboxylic acid

InChi Key

KXNPVXPOPUZYGB-IOVMHBDKSA-N

InChi Code

InChI=1S/C23H36N6O5S/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)/t14-,15?,17+,18-/m1/s1

SMILES Code

O=C(O)[C@H]1C[C@H](C)CCN1C([C@H](CCCNC(N)=N)NS(=O)(C2=CC=CC3=C2NCC(C)C3)=O)=O

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

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 (MD-805) 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	21.0	41.19
	DMF	20.0	39.32
	Ethanol	5.0	9.83
	PBS (pH 7.2)	0.1	0.20

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 508.63 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: Bain J, Meyer A. Comparison of bivalirudin to lepirudin and argatroban in patients with heparin-induced thrombocytopenia. Am J Health Syst Pharm. 2015 Sep 1;72(17 Suppl 2):S104-9. doi: 10.2146/sp150018. PubMed PMID: 26272889. 2: Tardy-Poncet B, Nguyen P, Thiranos JC, Morange PE, Biron-Andréani C, Gruel Y, Morel J, Wynckel A, Grunebaum L, Villacorta-Torres J, Grosjean S, de Maistre E. Argatroban in the management of heparin-induced thrombocytopenia: a multicenter clinical trial. Crit Care. 2015 Nov 11;19:396. doi: 10.1186/s13054-015-1109-0. PubMed PMID: 26556106; PubMed Central PMCID: PMC4641392. 3: McAlister RK, Ito S. Minimal Prolongation of Prothrombin Time with Extended Exposure to Argatroban. Pharmacotherapy. 2015 Jul;35(7):e122-6. doi: 10.1002/phar.1613. Epub 2015 Jul 3. PubMed PMID: 26147471. 4: Zhou L, Liu D, Li Y, Zhu W, Sun W, Li Y, Xiong Y, Chen Z, Wang Q, Cai Q, Wang Z, Wang X, Sun W, Ge L, Ma M, Li M, Li H, Fan X, Yin Q, Xu G, Liu G, Fan X, Liu X. Argatroban for preventing occlusion and restenosis after extracranial artery stenting. Eur Neurol. 2014;71(5-6):319-25. doi: 10.1159/000357866. Epub 2014 Apr 8. PubMed PMID: 24732894. 5: Treichl B, Bachler M, Lorenz I, Friesenecker B, Oswald E, Schlimp CJ, Pedross F, Fries D. Efficacy of argatroban in critically ill patients with heparin resistance: a retrospective analysis. Semin Thromb Hemost. 2015 Feb;41(1):61-7. doi: 10.1055/s-0034-1398382. Epub 2015 Jan 16. PubMed PMID: 25594496. 6: Kim SC, Tran N, Schewe JC, Boehm O, Wittmann M, Graeff I, Hoeft A, Baumgarten G. Safety and economic considerations of argatroban use in critically ill patients: a retrospective analysis. J Cardiothorac Surg. 2015 Feb 7;10:19. doi: 10.1186/s13019-015-0214-0. PubMed PMID: 25879883; PubMed Central PMCID: PMC4332969. 7: Wada T, Yasunaga H, Horiguchi H, Matsubara T, Fushimi K, Nakajima S, Yahagi N. Outcomes of Argatroban Treatment in Patients With Atherothrombotic Stroke: Observational Nationwide Study in Japan. Stroke. 2016 Feb;47(2):471-6. doi: 10.1161/STROKEAHA.115.011250. Epub 2015 Dec 15. PubMed PMID: 26670085. 8: Vo QA, Lin JK, Tong LM. Efficacy and safety of argatroban and bivalirudine in patients with suspected heparin-induced thrombocytopenia. Ann Pharmacother. 2015 Feb;49(2):178-84. doi: 10.1177/1060028014562949. Epub 2014 Dec 16. PubMed PMID: 25515865. 9: Klingele M, Bomberg H, Lerner-Gräber A, Fliser D, Poppleton A, Schäfers HJ, Groesdonk HV. Use of argatroban: experiences in continuous renal replacement therapy in critically ill patients after cardiac surgery. J Thorac Cardiovasc Surg. 2014 Jun;147(6):1918-24. doi: 10.1016/j.jtcvs.2013.11.051. Epub 2013 Dec 31. PubMed PMID: 24485959. 10: 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. 11: Argatroban: for a few selected patients. Prescrire Int. 2013 Feb;22(135):33-5. Review. PubMed PMID: 23444494. 12: Jakimczuk PJ, Churchwell MD, Howard MS, Mauro VF, Alexander KS, Boddu SH. Compatibility of argatroban injection with select antiarrhythmic drugs. Am J Health Syst Pharm. 2014 Nov 1;71(21):1831-2. doi: 10.2146/ajhp140258. Erratum in: Am J Health Syst Pharm. 2017 May 15;74(10 ):629. PubMed PMID: 25320130. 13: Treschan TA, Schaefer MS, Geib J, Bahlmann A, Brezina T, Werner P, Golla E, Greinacher A, Pannen B, Kindgen-Milles D, Kienbaum P, Beiderlinden M. Argatroban versus Lepirudin in critically ill patients (ALicia): a randomized controlled trial. Crit Care. 2014 Oct 25;18(5):588. doi: 10.1186/s13054-014-0588-8. PubMed PMID: 25344113; PubMed Central PMCID: PMC4234853. 14: Guy S, Kitchen S, Maclean R, Van Veen JJ. Limitation of the activated partial thromboplastin time as a monitoring method of the direct thrombin inhibitor argatroban. Int J Lab Hematol. 2015 Dec;37(6):834-43. doi: 10.1111/ijlh.12414. Epub 2015 Aug 25. PubMed PMID: 26305560. 15: Vianello F, Furian L, Nordio M, Treleani M, Fabris F. Concomitant use of argatroban and warfarin during hemodialysis in heparin-induced thrombocytopenia. Hematology. 2015 Jan;20(1):48-9. doi: 10.1179/1607845414Y.0000000157. Epub 2014 Feb 28. PubMed PMID: 24580134. 16: Tardy-Poncet B, Combe M, Piot M, Chapelle C, Akrour M, Tardy B. Effects of argatroban, danaparoid, and fondaparinux on trombin generation in heparin-induced thrombocytopenia. Thromb Haemost. 2013 Mar;109(3):504-9. doi: 10.1160/TH12-05-0321. Epub 2013 Jan 17. PubMed PMID: 23328916. 17: Eller T, Busse J, Dittrich M, Flieder T, Alban S, Knabbe C, Birschmann I. Dabigatran, rivaroxaban, apixaban, argatroban and fondaparinux and their effects on coagulation POC and platelet function tests. Clin Chem Lab Med. 2014 Jun;52(6):835-44. doi: 10.1515/cclm-2013-0936. PubMed PMID: 24406289. 18: 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. PubMed PMID: 24473182; PubMed Central PMCID: PMC3995814. 19: Jing R, Cui M, Wang H, Xu L, Chen W. Evaluation of Argatroban as a Potential Anticoagulant for Clinical Laboratory Analysis: Precision, Stability and Interference Study. Clin Lab. 2016;62(4):621-30. PubMed PMID: 27215081. 20: Li G, Fan RM, Chen JL, Wang CM, Zeng YC, Han C, Jiao S, Xia XP, Chen W, Yao ST. Neuroprotective effects of argatroban and C5a receptor antagonist (PMX53) following intracerebral haemorrhage. Clin Exp Immunol. 2014 Feb;175(2):285-95. doi: 10.1111/cei.12220. PubMed PMID: 24117111; PubMed Central PMCID: PMC3892419.