Dabigatran etexilate mesylate | CAS#872728-81-9 | 211915-06-9 | 211914-51-1 | thrombin inhibitor

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

MedKoo CAT#: 329452

CAS#: 872728-81-9 (mesylate)

Description: Dabigatran etexilate, also known as BIBR 1048MS, is a direct thrombin inhibitor. Dabigatran is used to prevent strokes in those with atrial fibrillation not caused by heart valve issues, as well as deep vein thrombosis and pulmonary embolism in persons who have been treated for 5–10 days with parenteral anticoagulant (usually low molecular weight heparin), and to prevent deep vein thrombosis and pulmonary embolism in some circumstances. It appears to be as effective as warfarin in preventing nonhemorrhagic strokes and embolic events in those with atrial fibrillation not due to valve problems.

Chemical Structure

Dabigatran etexilate mesylate

CAS# 872728-81-9 (mesylate)

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 329452
Name: Dabigatran etexilate mesylate
CAS#: 872728-81-9 (mesylate)
Chemical Formula: C35H45N7O8S
Exact Mass: 0.00
Molecular Weight: 723.846
Elemental Analysis: C, 58.08; H, 6.27; N, 13.55; O, 17.68; S, 4.43

Price and Availability

Size	Price	Availability
50mg	USD 250	2 Weeks
100mg	USD 450	2 Weeks
200mg	USD 750	2 Weeks
500mg	USD 1650	2 Weeks
1g	USD 2950	2 Weeks
2g	USD 5250	2 Weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Related CAS #: 872728-81-9 (Dabigatran etexilate mesylate) 211915-06-9 (Dabigatran etexilate) 211914-51-1 (Dabigatran)

Synonym: Dabigatran etexilate mesylate; BIBR 1048MS; BIBR1048MS; BIBR-1048MS; BIBR 1048; BIBR1048; BIBR-1048; band name: Pradaxa.

IUPAC/Chemical Name: Ethyl 3-(((2-(((4-(((hexyloxy)carbonyl)carbamimidoyl)phenyl)amino)methyl)-1-methyl-1h-benzimidazol-5-yl)carbonyl)(pyridin-2-yl)amino)propanoate, methanesulfonate

InChi Key: XETBXHPXHHOLOE-UHFFFAOYSA-N

InChi Code: InChI=1S/C34H41N7O5.CH4O3S/c1-4-6-7-10-21-46-34(44)39-32(35)24-12-15-26(16-13-24)37-23-30-38-27-22-25(14-17-28(27)40(30)3)33(43)41(20-18-31(42)45-5-2)29-11-8-9-19-36-29;1-5(2,3)4/h8-9,11-17,19,22,37H,4-7,10,18,20-21,23H2,1-3H3,(H2,35,39,44);1H3,(H,2,3,4)

SMILES Code: O=C(OCC)CCN(C(C1=CC=C2C(N=C(CNC3=CC=C(C(NC(OCCCCCC)=O)=N)C=C3)N2C)=C1)=O)C4=NC=CC=C4.CS(=O)(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: Related CAS# CAS#872728-81-9 (Dabigatran etexilate mesylate) CAS#211915-06-9 (Dabigatran etexilate) CAS#211914-51-1 (Dabigatran)

Product Data:

Product Data

Instruction:

View handling instruction

Biological target:	Dabigatran etexilate mesylate (BIBR 1048MS) is an active prodrug of Dabigatran that has anticoagulant effects and is used for the prophylaxis of venousthromboembolism and stroke due to atrial fibrillation.
In vitro activity:	Apoptosis of liver specimens after IRI was evaluated by TUNEL staining in the IRI + vehicle (Fig. 3A‐a) and IRI + dabigatran groups (Fig. 3A‐b). Dabigatran treatment markedly reduced the number of TUNEL‐positive cells compared with vehicle (84.20 [IQR, 69.00101.57] in IRI + vehicle, 5.15 [IQR, 3.85‐9.67] in IRI + dabigatran, P = 0.004; Fig. 3B). In addition, compared with vehicle, dabigatran treatment attenuated activation of caspase 9, one of the proapoptotic mediators evaluated by Western blot analysis (cleaved‐caspase 9/pro‐caspase 9: 1.04 [IQR, 0.96‐1.09] in IRI + vehicle, 0.69 [IQR, 0.54‐0.86] in IRI + dabigatran, P = 0.01; Fig. 3C), and upregulated generation of bcl‐2, an antiapoptotic gene evaluated by real‐time PCR (bcl‐2/β‐actin: 0.97 [IQR, 0.87‐1.01] in IRI + vehicle, 1.61 [IQR, 1.45‐1.79] in IRI + dabigatran, P = 0.006; Fig. 3D).The number of Ly6G‐positive cells was significantly lower in the IRI + dabigatran group than in the IRI + vehicle group (5.80 [IQR, 5.40‐7.10] in IRI + dabigatran, 38.30 [IQR, 24.6042.55] in IRI + vehicle, P = 0.004; Fig. 3F). Gene expression evaluated by real‐time PCR showed that dabigatran treatment significantly reduced VCAM‐1 compared with vehicle (VCAM‐1/β‐actin: 0.35 [IQR, 0.32‐0.39] in IRI + dabigatran, 1.10 [IQR, 0.561.32] in IRI + vehicle, P = 0.01; Fig. 3G). As shown in Fig. 3H,I, dabigatran treatment markedly reduced generation of inflammatory cytokines such as TNF‐α and IL6 compared with vehicle (TNF‐α/β‐actin: 0.21 [IQR, 0.10‐0.29] in IRI + dabigatran, 0.96 [IQR, 0.441.51] in IRI + vehicle, P = 0.02; IL6/β‐actin: 0.02 [IQR, 0.01‐0.03] in IRI + dabigatran, 0.24 [IQR, 0.18‐1.90] in IRI + vehicle, P = 0.006). Reference: Liver Transpl. 2021 Mar; 27(3): 363–384. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7984054/
In vivo activity:	This study was undertaken to test whether dabigatran etexilate attenuates lung injury in a murine model of interstitial lung disease. Lung injury was induced in female C57BL/6 mice by a single intratracheal instillation of bleomycin. Dabigatran etexilate was given as supplemented chow beginning on day 1 of bleomycin instillation (early treatment, study of antiinflammatory effect) or on day 8 following bleomycin instillation (late treatment, study of antifibrotic effect). Both early treatment and late treatment with dabigatran etexilate attenuated the development of bleomycin-induced pulmonary fibrosis. Dabigatran etexilate significantly reduced thrombin activity and levels of transforming growth factor β1 in BAL fluid, while simultaneously reducing the number of inflammatory cells and protein concentrations. Histologically evident lung inflammation and fibrosis were significantly decreased in dabigatran etexilatetreated mice. Additionally, dabigatran etexilate reduced collagen, connective tissue growth factor, and α-smooth muscle actin expression in mice with bleomycin-induced lung fibrosis, whereas it had no effect on basal levels of these proteins. This data provides preclinical information about the feasibility and efficacy of dabigatran etexilate as a new therapeutic approach for the treatment of interstitial lung disease. Reference: Arthritis Rheum. 2011 May;63(5):1416-25. https://pubmed.ncbi.nlm.nih.gov/21312187/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMSO	75.0	103.61

Preparing Stock Solutions

The following data is based on the product molecular weight 723.85 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. Noguchi D, Kuriyama N, Hibi T, Maeda K, Shinkai T, Gyoten K, Hayasaki A, Fujii T, Iizawa Y, Tanemura A, Murata Y, Kishiwada M, Sakurai H, Mizuno S. The Impact of Dabigatran Treatment on Sinusoidal Protection Against Hepatic Ischemia/Reperfusion Injury in Mice. Liver Transpl. 2021 Feb;27(3):363-384. doi: 10.1002/lt.25929. Epub 2020 Dec 9. PMID: 33108682; PMCID: PMC7984054. 2. Bastiaans J, Mulder VC, van Meurs JC, Smits-Te Nijenhuis M, van Holten-Neelen C, van Hagen PM, Dik WA. Dabigatran inhibits intravitreal thrombin activity. Acta Ophthalmol. 2018 Aug;96(5):452-458. doi: 10.1111/aos.13630. Epub 2017 Nov 30. PMID: 29193875. 3. Bogatkevich GS, Ludwicka-Bradley A, Nietert PJ, Akter T, van Ryn J, Silver RM. Antiinflammatory and antifibrotic effects of the oral direct thrombin inhibitor dabigatran etexilate in a murine model of interstitial lung disease. Arthritis Rheum. 2011 May;63(5):1416-25. doi: 10.1002/art.30255. PMID: 21312187; PMCID: PMC3086970.
In vitro protocol:	1. Noguchi D, Kuriyama N, Hibi T, Maeda K, Shinkai T, Gyoten K, Hayasaki A, Fujii T, Iizawa Y, Tanemura A, Murata Y, Kishiwada M, Sakurai H, Mizuno S. The Impact of Dabigatran Treatment on Sinusoidal Protection Against Hepatic Ischemia/Reperfusion Injury in Mice. Liver Transpl. 2021 Feb;27(3):363-384. doi: 10.1002/lt.25929. Epub 2020 Dec 9. PMID: 33108682; PMCID: PMC7984054. 2. Bastiaans J, Mulder VC, van Meurs JC, Smits-Te Nijenhuis M, van Holten-Neelen C, van Hagen PM, Dik WA. Dabigatran inhibits intravitreal thrombin activity. Acta Ophthalmol. 2018 Aug;96(5):452-458. doi: 10.1111/aos.13630. Epub 2017 Nov 30. PMID: 29193875.
In vivo protocol:	1. Noguchi D, Kuriyama N, Hibi T, Maeda K, Shinkai T, Gyoten K, Hayasaki A, Fujii T, Iizawa Y, Tanemura A, Murata Y, Kishiwada M, Sakurai H, Mizuno S. The Impact of Dabigatran Treatment on Sinusoidal Protection Against Hepatic Ischemia/Reperfusion Injury in Mice. Liver Transpl. 2021 Feb;27(3):363-384. doi: 10.1002/lt.25929. Epub 2020 Dec 9. PMID: 33108682; PMCID: PMC7984054. 2. Bogatkevich GS, Ludwicka-Bradley A, Nietert PJ, Akter T, van Ryn J, Silver RM. Antiinflammatory and antifibrotic effects of the oral direct thrombin inhibitor dabigatran etexilate in a murine model of interstitial lung disease. Arthritis Rheum. 2011 May;63(5):1416-25. doi: 10.1002/art.30255. PMID: 21312187; PMCID: PMC3086970.

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1: Douxfils J, Mullier F, Dogné JM. Dose tailoring of dabigatran etexilate: obvious or excessive? Expert Opin Drug Saf. 2015 Aug;14(8):1283-9. doi: 10.1517/14740338.2015.1049995. Review. PubMed PMID: 25994994.

2: Dzeshka MS, Lip GY. Warfarin versus dabigatran etexilate: an assessment of efficacy and safety in patients with atrial fibrillation. Expert Opin Drug Saf. 2015 Jan;14(1):45-62. doi: 10.1517/14740338.2015.973847. Review. PubMed PMID: 25341529.

3: Greig SL, McKeage K. Dabigatran etexilate: a review of its use in the treatment of acute venous thromboembolism and prevention of venous thromboembolism recurrence. Drugs. 2014 Oct;74(15):1785-800. doi: 10.1007/s40265-014-0304-7. Review. PubMed PMID: 25270377.

4: Tabata E, Yasaka M, Wakugawa Y, Okada Y. Recombinant tissue-type plasminogen activator (rt-PA) therapy in an acute stroke patient taking dabigatran etexilate: a case report and literature review. Intern Med. 2014;53(14):1515-7. Review. PubMed PMID: 25030563.

5: Vora A. Dabigatran etexilate in atrial fibrillation. J Assoc Physicians India. 2013 Dec;61(12):900-2. Review. PubMed PMID: 24968547.

6: Douxfils J, Buckinx F, Mullier F, Minet V, Rabenda V, Reginster JY, Hainaut P, Bruyère O, Dogné JM. Dabigatran etexilate and risk of myocardial infarction, other cardiovascular events, major bleeding, and all-cause mortality: a systematic review and meta-analysis of randomized controlled trials. J Am Heart Assoc. 2014 Jun 6;3(3):e000515. doi: 10.1161/JAHA.113.000515. Review. PubMed PMID: 24906369; PubMed Central PMCID: PMC4309041.

7: Brown R, Lip GY, Gallego P. Dabigatran etexilate for venous thromboembolism: a safety evaluation. Expert Opin Drug Saf. 2014 May;13(5):639-47. doi: 10.1517/14740338.2014.895321. Review. PubMed PMID: 24598005.

8: Chin PK, Wright DF, Patterson DM, Doogue MP, Begg EJ. A proposal for dose-adjustment of dabigatran etexilate in atrial fibrillation guided by thrombin time. Br J Clin Pharmacol. 2014 Sep;78(3):599-609. doi: 10.1111/bcp.12364. Review. PubMed PMID: 24592851; PubMed Central PMCID: PMC4243910.

9: Hohnloser SH, Camm AJ. Safety and efficacy of dabigatran etexilate during catheter ablation of atrial fibrillation: a meta-analysis of the literature. Europace. 2013 Oct;15(10):1407-11. doi: 10.1093/europace/eut241. Review. PubMed PMID: 23954917.

10: Ellis CR, Kaiser DW. The clinical efficacy of dabigatran etexilate for preventing stroke in atrial fibrillation patients. Vasc Health Risk Manag. 2013;9:341-52. doi: 10.2147/VHRM.S28271. Review. PubMed PMID: 23874100; PubMed Central PMCID: PMC3711881.

11: Huber K, Connolly SJ, Kher A, Christory F, Dan GA, Hatala R, Kiss RG, Meier B, Merkely B, Pieske B, Potpara T, Stępińska J, Klun NV, Vinereanu D, Widimský P. Practical use of dabigatran etexilate for stroke prevention in atrial fibrillation. Int J Clin Pract. 2013 Jun;67(6):516-26. doi: 10.1111/ijcp.12147. Review. PubMed PMID: 23557519; PubMed Central PMCID: PMC3712459.

12: Croft PE, Cabral KP, Strout TD, Baumann MR, Gibbs MA, Delaney MC. Managing blunt trauma in patients receiving dabigatran etexilate: case study and review of the literature. J Emerg Nurs. 2013 May;39(3):302-8. doi: 10.1016/j.jen.2013.01.016. Review. PubMed PMID: 23541336.

13: Marshall S, Fearon P, Dawson J, Quinn TJ. Stop the clots, but at what cost? Pharmacoeconomics of dabigatran etexilate for the prevention of stroke in subjects with atrial fibrillation: a systematic literature review. Expert Rev Pharmacoecon Outcomes Res. 2013 Feb;13(1):29-42. doi: 10.1586/erp.12.79. Review. PubMed PMID: 23402443.

14: Sarah S. The pharmacology and therapeutic use of dabigatran etexilate. J Clin Pharmacol. 2013 Jan;53(1):1-13. doi: 10.1177/0091270011432169. Review. PubMed PMID: 23400738.

15: Graff J, Harder S. Anticoagulant therapy with the oral direct factor Xa inhibitors rivaroxaban, apixaban and edoxaban and the thrombin inhibitor dabigatran etexilate in patients with hepatic impairment. Clin Pharmacokinet. 2013 Apr;52(4):243-54. doi: 10.1007/s40262-013-0034-0. Review. PubMed PMID: 23389892.

16: Táborský M, Heinc P, Hrčková Y. [Dabigatran etexilate in clinical practice for prevention of thromboembolic events in patients with atrial fibrillation]. Vnitr Lek. 2012 Oct;58(10):769-77. Review. Czech. PubMed PMID: 23121065.

17: McKeage K. Dabigatran etexilate: a pharmacoeconomic review of its use in the prevention of stroke and systemic embolism in patients with atrial fibrillation. Pharmacoeconomics. 2012 Sep 1;30(9):841-55. doi: 10.2165/11209130-000000000-00000. Review. PubMed PMID: 22734683.

18: Burness CB, McKeage K. Dabigatran etexilate: a review of its use for the prevention of venous thromboembolism after total hip or knee replacement surgery. Drugs. 2012 May 7;72(7):963-86. doi: 10.2165/11209080-000000000-00000. Review. PubMed PMID: 22564134.

19: Cheng JW, Vu H. Dabigatran etexilate: an oral direct thrombin inhibitor for the management of thromboembolic disorders. Clin Ther. 2012 Apr;34(4):766-87. doi: 10.1016/j.clinthera.2012.02.022. Review. PubMed PMID: 22444784.

20: Huisman MV, Lip GY, Diener HC, Brueckmann M, van Ryn J, Clemens A. Dabigatran etexilate for stroke prevention in patients with atrial fibrillation: resolving uncertainties in routine practice. Thromb Haemost. 2012 May;107(5):838-47. doi: 10.1160/TH11-10-0718. Review. PubMed PMID: 22318514.

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