1-{[(cyclohexyloxy)carbonyl]oxy}ethyl (6R,7R)-7-[2-(2-amino-1,3-thiazol-4-yl)acetamido]-3-[({1-[2-(dimethylamino)ethyl]-1H-1,2,3,4-tetrazol-5-yl}sulfanyl)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

• ChemBase ID: 163922
• Molecular Formular: C27H37N9O7S3
• Molecular Mass: 695.83378
• Monoisotopic Mass: 695.19780757
• SMILES: [C@H]1(C(=O)N2[C@@H]1SCC(=C2C(=O)OC(OC(=O)OC1CCCCC1)C)CSc1nnnn1CCN(C)C)NC(=O)Cc1csc(n1)N
• Canonical SMILES: CN(CCn1nnnc1SCC1=C(C(=O)OC(OC(=O)OC2CCCCC2)C)N2[C@H](SC1)[C@@H](C2=O)NC(=O)Cc1csc(n1)N)C
• InChI: InChI=1S/C27H37N9O7S3/c1-15(42-27(40)43-18-7-5-4-6-8-18)41-24(39)21-16(13-46-26-31-32-33-35(26)10-9-34(2)3)12-44-23-20(22(38)36(21)23)30-19(37)11-17-14-45-25(28)29-17/h14-15,18,20,23H,4-13H2,1-3H3,(H2,28,29)(H,30,37)/t15?,20-,23-/m1/s1
• InChIKey: VVFDMWZLBPUKTD-ZKRNHDOASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-{[(cyclohexyloxy)carbonyl]oxy}ethyl (6R,7R)-7-[2-(2-amino-1,3-thiazol-4-yl)acetamido]-3-[({1-[2-(dimethylamino)ethyl]-1H-1,2,3,4-tetrazol-5-yl}sulfanyl)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
• IUPAC Traditional name: cefotiam hexetil
• Synonyms: (6R,7R)-7-[[(2-Amino-4-thiazolyl)acetyl]amino]-3-[[[1-[2-(dimethylamino)ethyl]-1H-tetrazol-5-yl]thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid 1-[[(Cyclohexyloxy)carbonyl]oxy]ethyl Ester Dihydrochloride; Pansporin T; SCE 2174; Cefotiam Hexetil Hydrochloride

Database IDs

• CAS Number: 95789-30-3
• PubChem SID: 162258057
• PubChem CID: 125846

CALCULATED PROPERTIES

• Acid pKa: 11.209347
• H Acceptors: 11
• H Donor: 2
• LogD (pH = 5.5): -0.2671245
• LogD (pH = 7.4): 1.5411539
• Log P: 2.549302
• Molar Refractivity: 184.839 cm^3
• Polarizability: 66.35578 Å^3
• Polar Surface Area: 196.99 Å^2
• Rotatable Bonds: 16
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Dmso; Methanol
• Apperance: Off-White to Pale Yellow Solid
• Melting Point: 120-130°C

Safety Information

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

DETAILS

Toronto Research Chemicals - C243000

A semi-synthetic cephalosporin antibiotic. Antibacterial.

REFERENCES

• Goodhart, F., et al.: J. Pharamac. Sci., 62, 133 (1973)
• Maier, H., et al.: Arzneim.-Forsch., 42, 980 (1973)