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Dabigatran

Athanor · official

C25H25N7O3 · 471.5 g/mol

IUPAC name: 3-[[2-[(4-carbamimidoylanilino)methyl]-1-methylbenzimidazole-5-carbonyl]-pyridin-2-ylamino]propanoic acid

Also called Pradaxa, direct thrombin inhibitor, DOAC, anticoagulant

Drugs
Open in Athanor
The structure of Dabigatran
Drawn from its SMILES with RDKit
Harmful or irritantWarningHarmful if swallowed · Causes skin irritation · Causes serious eye irritation · May cause respiratory irritation

Names and identifiers

IUPAC name
3-[[2-[(4-carbamimidoylanilino)methyl]-1-methylbenzimidazole-5-carbonyl]-pyridin-2-ylamino]propanoic acid
Synonyms
Pradaxa, direct thrombin inhibitor, DOAC
+ 39 more

anticoagulant, BIBR-953, Pradaxa (dabigatran), BIBR 953 ZW, 3-[[2-[(4-carbamimidoylanilino)methyl]-1-methylbenzimidazole-5-carbonyl]-pyridin-2-ylamino]propanoic acid, I0VM4M70GC, BIBR-953-ZW, CHEBI:70752, DTXSID50175419, N-((2-((p-Amidinoanilino)methyl)-1-methyl-5-benzimidazolyl)carbonyl)-N-2-pyridyl-beta-alanine, 3-[[2-[[(4-carbamimidoylphenyl)amino]methyl]-1-methylbenzimidazole-5-carbonyl]-pyridin-2-ylamino]propanoic acid, beta-Alanine, N-((2-(((4-(aminoiminomethyl)phenyl)amino)methyl)-1-methyl-1H-benzimidazol-5-yl)carbonyl)-N-2-pyridinyl-, 3-((2-(((4-carbamimidoylphenyl)amino)methyl)-1-methylbenzimidazole-5-carbonyl)-pyridin-2-ylamino)propanoic acid, 3-((2-((4-carbamimidoylanilino)methyl)-1-methylbenzimidazole-5-carbonyl)-pyridin-2-ylamino)propanoic acid, BETA-ALANINE, N-[[2-[[[4-(AMINOIMINOMETHYL)PHENYL]AMINO]METHYL]-1-METHYL-1H-BENZIMIDAZOL-5-YL]CARBONYL]-N-2-PYRIDINYL-, RefChem:54923, Etexilate Mesylate, Dabigatran, Mesylate, Dabigatran Etexilate, DTXCID4097910, N-((2-(((4-(aminoiminomethyl)phenyl)amino)methyl)-1-methyl-1H-benzimidazol-5-yl)carbonyl)-N-2-pyridinyl-beta-alanine, 859-177-5, BIBR 953, MFCD09837830, 3-(2-(((4-carbamimidoylphenyl)amino)methyl)-1-methyl-N-(pyridin-2-yl)-1H-benzo[d]imidazole-5-carboxamido)propanoic acid, Dabigatran (BIBR 953), CHEMBL48361, 3-[1-(2-{[(4-carbamimidoylphenyl)amino]methyl}-1-methyl-1H-1,3-benzodiazol-5-yl)-N-(pyridin-2-yl)formamido]propanoic acid, C25H25N7O3, b-Alanine,N-[[2-[[[4-(aminoiminomethyl)phenyl]amino]methyl]-1-methyl-1H-benzimidazol-5-yl]carbonyl]-N-2-pyridinyl-, N-[(2-{[(4-Carbamimidoylphenyl)amino]methyl}-1-Methyl-1h-Benzimidazol-5-Yl)carbonyl]-N-Pyridin-2-Yl-Beta-Alanine, 1-Methyl-2-[(4-amidinophenyl)aminomethyl]benzimidazol-5-yl-carboxylic acid-N-(2-pyridyl)-N-(2-hydroxycarbonylethyl)amide, BIBR-953ZW, 3-[[2-[[(4-CARBAMIMIDOYLPHENYL)AMINO]METHYL]-1-METHYL-BENZOIMIDAZOLE-5-CARBONYL]-PYRIDIN-2-YL-AMINO]PROPANOIC ACID, Dabigatran Standard, 3-(((2-(((4-Carbamimidoylphenyl)amino)methyl)-1-methyl-1H-benzimidazol-5-yl)carbonyl)(pyridin-2-yl)amino)propanoic acid, 3-{[(2-{[(4-Carbamimidoylphenyl)amino]methyl}-1-methyl-1H-benzimidazol-5-yl)carbonyl](pyridin-2-yl)amino}propanoic acid, BIBR 953; BIBR 953ZW; Dabigatran; N-[[2-[[[4-(aminoiminomethyl)phenyl]amino]methyl]-1-methyl-1H-benzimidazol-5-yl]carbonyl]-N-2-pyridinyl-beta-Alanine; N-[[2-[[[4-(Aminoiminomethyl)phenyl]amino]methyl]-1-methyl-1H-benzimidazol-5-yl]carbonyl]-N-2-pyridinyl-beta-alanine, Dabigatran [INN], DABIGATRAN [MI]

Molecular formula
C25H25N7O3
Empirical formula
C25H25N7O3
Molecular weight
471.5 g/mol
Exact mass
471.20189
CAS number
211914-51-1
PubChem CID
216210
Canonical SMILES
CN1C2=C(C=C(C=C2)C(=O)N(CCC(=O)O)C3=CC=CC=N3)N=C1CNC4=CC=C(C=C4)C(=N)N
Isomeric SMILES
CN1C2=C(C=C(C=C2)C(=O)N(CCC(=O)O)C3=CC=CC=N3)N=C1CNC4=CC=C(C=C4)C(=N)N
InChI
InChI=1S/C25H25N7O3/c1-31-20-10-7-17(25(35)32(13-11-23(33)34)21-4-2-3-12-28-21)14-19(20)30-22(31)15-29-18-8-5-16(6-9-18)24(26)27/h2-10,12,14,29H,11,13,15H2,1H3,(H3,26,27)(H,33,34)
InChIKey
YBSJFWOBGCMAKL-UHFFFAOYSA-N
Molfile

Names, InChI and the identifiers from PubChem, retrieved 2026-10-14.

Calculated

Heavy atoms
35
Rings
4
Aromatic rings
4
Fraction sp³ carbons (Fsp3)
0.16
H-bond donors
4
H-bond acceptors
6 computed here · PubChem 7
Rotatable bonds
9
TPSA (Ų)
150.2 computed here · PubChem 150
Formal charge
0
XLogP3
1.7 PubChem
Complexity
757 PubChem
Stereocenters
None
Double-bond geometry
None specified
Point group
C1 of one 3D conformer with its hydrogens, by Athanor’s engine (as in the app)

Elemental analysis

  • C63.68%
  • H5.34%
  • N20.79%
  • O10.18%

Isotope pattern

100%471.20230%472.2055.0%473.207474.210

Each peak is a nominal mass with its abundance-weighted exact mass, as a percentage of the tallest, from IUPAC natural isotope abundances.

Computed from the structure with RDKit 2026.09 when this page was built, beside PubChem's own computed values from its record; where the two differ, both are shown.

Predicted

log P
2.99 Crippen (Wildman and Crippen 1999)
log S (water solubility)
-4.49 ESOL (Delaney 2004), log mol/L
Synthetic accessibility
2.61 SA score, 1 easy to 10 hard (Ertl and Schuffenhauer 2009)

Drug-likeness: Lipinski’s rule of five

  • Molecular weight ≤ 500: 471.52
  • log P ≤ 5 (Crippen): 2.99
  • H-bond donors ≤ 5: 4
  • H-bond acceptors ≤ 10: 6

Passes all four rules.

¹³C NMR shifts, predicted

Predictions, not measurements; each names its method. A measured log P, where a source reports one, is under Physical properties.

Safety

Warning

Most widely reported: 2 company reports to ECHA. Source [2].

  • Harmful or irritant
  • H302Harmful if swallowed (50% of reports)
  • H315Causes skin irritation (50% of reports)
  • H319Causes serious eye irritation (50% of reports)
  • H335May cause respiratory irritation (50% of reports)

Precautionary statements: P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, P501

View all classifications (2)
  • [2] European Chemicals Agency (ECHA)This chemical does not meet GHS hazard criteria for 50% (1 of 2) of reports.
  • [2] European Chemicals Agency (ECHA) · 2 reports · WarningH302, H315, H319, H335

Storage

  • Store blisters (packs) at 25 °C (77 °F); excursions permitted to 15-30 °C (59-86 °F). Store in the original package to protect from moisture.[1]
  • Store bottles at 25 °C (77 °F); excursions permitted to 15-30 °C (59-86 °F). Once opened, the product must be used within 4 months. Keep the bottle tightly closed. Store in the original package to protect from moisture.[1]

Safety data sheets on the supplier’s page: Angel Pharmatech Ltd., AstaTech, Inc., AiFChem, an XtalPi Company.

Always read the supplier’s safety data sheet before working with it.

Literature

Reading PubChem, OpenAlex and GSRS…

Bioactivity

Reading ChEMBL…

References

  1. [1]Hazardous Substances Data Bank (HSDB) · Public domain (US NLM) · via PubChem · retrieved 2026-10-14
  2. [2]European Chemicals Agency (ECHA) · ECHA legal notice: reuse with acknowledgement · via PubChem · retrieved 2026-10-14
  3. ·Calculated values: computed by Athanor with RDKit 2026.09 from the structure.
  4. ·Literature on PubChem

Data last updated 2026-10-14.