BIBR 1087 SE (BIBR-1087SE; Desethyl Dabigatran Etexilate) is a metabolite of dabigatran etexilate (BIBR-1048), which is the prodrug of dabigatran (an anticoagulant drug and blood thinner).

Physicochemical Properties

Molecular Formula	C₃₂H₃₇N₇O₅
Molecular Weight	599.68
Exact Mass	599.285
CAS #	212321-78-3
Related CAS #	Dabigatran etexilate;211915-06-9
PubChem CID	135565549
Appearance	Typically exists as solid at room temperature
Density	1.3±0.1 g/cm3
Boiling Point	853.4±75.0 °C at 760 mmHg
Flash Point	469.9±37.1 °C
Vapour Pressure	0.0±0.3 mmHg at 25°C
Index of Refraction	1.636
LogP	4.14
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	9
Rotatable Bond Count	16
Heavy Atom Count	44
Complexity	959
Defined Atom Stereocenter Count	0
SMILES	CCCCCCOC(=O)NC(=N)c1ccc(NCc2nc3cc(ccc3n2C)C(=O)N(CCC(O)=O)c2ccccn2)cc1
InChi Key	UGEWTLXHMYKLCO-UHFFFAOYSA-N
InChi Code	InChI=1S/C32H37N7O5/c1-3-4-5-8-19-44-32(43)37-30(33)22-10-13-24(14-11-22)35-21-28-36-25-20-23(12-15-26(25)38(28)2)31(42)39(18-16-29(40)41)27-9-6-7-17-34-27/h6-7,9-15,17,20,35H,3-5,8,16,18-19,21H2,1-2H3,(H,40,41)(H2,33,37,43)
Chemical Name	3-[[2-[[4-(N-hexoxycarbonylcarbamimidoyl)anilino]methyl]-1-methylbenzimidazole-5-carbonyl]-pyridin-2-ylamino]propanoic acid
Synonyms	Desethyl Dabigatran Etexilate; BIBR 1087 SE; 212321-78-3; Desethyl Dabigatran Etexilate; BIBR-1087SE; Desethyldabigatran Etexilate; BIBR 1087; BIBR-1087; 441X78E2Z0; (E)-3-(2-(((4-(N'-((Hexyloxy)carbonyl)carbamimidoyl)phenyl)amino)methyl)-1-methyl-N-(pyridin-2-yl)-1H-benzo[d]imidazole-5-carboxamido)propanoic acid; BIBR-1087 SE
HS Tariff Code	2934.99.9001
Storage	Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month
Shipping Condition	Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity

Targets

Dabigatran etexilate metabolite/intermediate

Additional Infomation

The impact of moderate hepatic impairment on the pharmacokinetics (PK) and pharmacodynamics (PD) of dabigatran etexilate was evaluated in an open, parallel-group study. Healthy volunteers (n = 12) and patients with hepatic impairment (Child-Pugh classification B; n = 12) received a single oral dose of 150 mg dabigatran etexilate. The mean values for area under the concentration-time curve, terminal half-life, and renal clearance of dabigatran were comparable between patients with hepatic impairment and healthy volunteers. Conversion of the dabigatran intermediate BIBR1087 to active dabigatran was slower in patients with hepatic impairment, indicating that the liver is partly involved in bioconversion of dabigatran etexilate. However, total drug exposure was comparable between groups; therefore, this observation is of no clinical relevance with respect to the anticoagulant activity of dabigatran. The extent of dabigatran glucuronidation was unchanged by liver disease; glucuronidation capacity was maintained in moderate liver disease. The activated partial thromboplastin time, ecarin clotting time, and thrombin time relationships were essentially identical in both groups. This study shows that moderate hepatic impairment does not affect the PK/PD or safety profile of dabigatran. Therefore, patients with moderate hepatic impairment can be given dabigatran etexilate without the need for dose adjustment. [1]

Solubility Data

Solubility (In Vitro)

DMSO : ~250 mg/mL (~416.89 mM)

Solubility (In Vivo)

Solubility in Formulation 1: ≥ 2.08 mg/mL (3.47 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.08 mg/mL (3.47 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Solubility in Formulation 3: ≥ 2.08 mg/mL (3.47 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	1.6676 mL	8.3378 mL	16.6756 mL
	5 mM	0.3335 mL	1.6676 mL	3.3351 mL
	10 mM	0.1668 mL	0.8338 mL	1.6676 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.