sodium (2R,3R)-2-ethyl-4-hydroxy-3-[(1-methyl-1H-imidazol-5-yl)methyl]butanoate

• ChemBase ID: 171611
• Molecular Formular: C11H17N2NaO3
• Molecular Mass: 248.25405
• Monoisotopic Mass: 248.1136867
• SMILES: n1cc(n(c1)C)C[C@H]([C@@H](CC)C(=O)[O-])CO.[Na+]
• Canonical SMILES: OC[C@@H]([C@H](C(=O)[O-])CC)Cc1cncn1C.[Na+]
• InChI: InChI=1S/C11H18N2O3.Na/c1-3-10(11(15)16)8(6-14)4-9-5-12-7-13(9)2;/h5,7-8,10,14H,3-4,6H2,1-2H3,(H,15,16);/q;+1/p-1/t8-,10+;/m0./s1
• InChIKey: YGXGGGNCVNXKBE-KXNXZCPBSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium (2R,3R)-2-ethyl-4-hydroxy-3-[(1-methyl-1H-imidazol-5-yl)methyl]butanoate
• IUPAC Traditional name: sodium (2R,3R)-2-ethyl-4-hydroxy-3-[(3-methylimidazol-4-yl)methyl]butanoate
• Synonyms: [R-(R*,R*)]-α-Ethyl-β-(hydroxymethyl)-1-methyl-1H-imidazole-5-butanoic Acid Monosodium Salt; Isopilocarpinate Sodium Salt; Isopilocarpinic Acid Sodium Salt; (αR,βR)-α-Ethyl-β-(hydroxymethyl)-1-methyl-1H-imidazole-5-butanoic Acid Sodium Salt; 1,2-Seco-3-isopilocarpin-2-oic Acid Sodium Salt; Isopilocarpic Acid Sodium Salt; [S-(R*,S*)]-α-Ethyl-β-(hydroxymethyl)-1-methyl-1H-Imidazole-5-butanoic Acid Monosodium Salt; Sodium Pilocarpate; Pilocarpic Acid Sodium Salt

Database IDs

• CAS Number: 101769-87-3; 92598-79-3
• PubChem SID: 164227521
• PubChem CID: 71749484

CALCULATED PROPERTIES

• Acid pKa: 4.339911
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): -0.53404164
• LogD (pH = 7.4): -1.3701233
• Log P: -0.4824863
• Molar Refractivity: 70.8635 cm^3
• Polarizability: 22.858503 Å^3
• Polar Surface Area: 78.18 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - P441450

An imidazole derivative used in the preparation of novel sequentially labile pilocarpine prodrugs for improved ocular delivery.

Toronto Research Chemicals - I821960

Isopilocarpic Acid is a degradation product of Pilocarpine (P441500).

REFERENCES

• Bungaard, H. et al.: J. Med. Chem., 28, 978 (1985)
• Jarvinen, T.e t al.: Int. J. Pharmac., 79, 233 (1985)
• Szepesi, G. et al.: Pharmazie, 38, 94 (1983)
• Bundgaard, H. et al.: Int. J. Pharmac., 10, 281 (1983)