5-chloro-2-(13C,2H3)methoxy-N-(2-{4-[({[(1r,4r)-4-hydroxycyclohexyl]carbamoyl}amino)sulfonyl]phenyl}ethyl)benzamide

• ChemBase ID: 170624
• Molecular Formular: C23H28ClN3O6S
• Molecular Mass: 510.99557484
• Monoisotopic Mass: 510.14208915
• SMILES: c1(ccc(c(c1)C(=O)NCCc1ccc(cc1)S(=O)(=O)NC(=O)N[C@@H]1CC[C@H](CC1)O)O[13CH3])Cl
• Canonical SMILES: [13CH3]Oc1ccc(cc1C(=O)NCCc1ccc(cc1)S(=O)(=O)NC(=O)N[C@@H]1CC[C@H](CC1)O)Cl
• InChI: InChI=1S/C23H28ClN3O6S/c1-33-21-11-4-16(24)14-20(21)22(29)25-13-12-15-2-9-19(10-3-15)34(31,32)27-23(30)26-17-5-7-18(28)8-6-17/h2-4,9-11,14,17-18,28H,5-8,12-13H2,1H3,(H,25,29)(H2,26,27,30)/t17-,18-/i1+1
• InChIKey: IUWSGCQEWOOQDN-UOBXQHSMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-chloro-2-(^1^3C,^2H₃)methoxy-N-(2-{4-[({[(1r,4r)-4-hydroxycyclohexyl]carbamoyl}amino)sulfonyl]phenyl}ethyl)benzamide
• IUPAC Traditional name: 5-chloro-2-(^1^3C,^2H₃)methoxy-N-{2-[4-({[(1r,4r)-4-hydroxycyclohexyl]carbamoyl}aminosulfonyl)phenyl]ethyl}benzamide
• Synonyms: 5-Chloro-N-[2-[4-[[[[(trans-4-hydroxycyclohexyl)amino]carbonyl]amino]sulfonyl]phenyl]ethyl]-2-(methoxy-13C,d3)benzamide; trans-1-[[p-[2-(5-Chloro-o-anisamido)ethyl]phenyl]sulfonyl]-3-(4-hydroxycyclohexyl)urea-13C,d3; 4-trans-Hydroxycyclohexyl Glyburide-13C,d3; 4-trans-Hydroxyglibenclamide-13C,d3; N-[4-[β-(2-(Methoxy-13C,d3)-5-chlorobenzamido)ethyl]benzenesulfonyl]-N'-(trans-4-hydroxycyclohexyl)urea; trans-4-Hydroxyglyburide-13C,d3; rac trans-4-Hydroxy Glyburide-13C,d3

Database IDs

• PubChem SID: 164226534
• PubChem CID: 46781812

CALCULATED PROPERTIES

• Acid pKa: 4.3201733
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): 1.6321936
• LogD (pH = 7.4): 1.4642429
• Log P: 2.4043915
• Molar Refractivity: 128.6496 cm^3
• Polarizability: 50.200527 Å^3
• Polar Surface Area: 133.83 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White to Off-White Solid

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - H942627

Labelled rac trans-4-Hydroxy Glyburide (H942625). rac trans-4-Hydroxy Glyburide is a metabolite of Glyburide which is used as an antidiabetic.

REFERENCES

• Heptner, W., et al.: Pharmaceut. Res., 5, 215 (1984)
• Rydberg, T., et al.: Br. J. Clin. Pharm., 43, 373 (1984)