(6R,7R)-7-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetamido]-3-[(furan-2-carbonylsulfanyl)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid hydrochloride

• ChemBase ID: 70338
• Molecular Formular: C19H18ClN5O7S3
• Molecular Mass: 560.02352
• Monoisotopic Mass: 559.00568862
• SMILES: N12C(=C(CS[C@@H]1[C@@H](C2=O)NC(=O)/C(=N\OC)/c1nc(sc1)N)CSC(=O)c1occc1)C(=O)O.Cl
• Canonical SMILES: CO/N=C(/c1csc(n1)N)\C(=O)N[C@@H]1C(=O)N2[C@@H]1SCC(=C2C(=O)O)CSC(=O)c1ccco1.Cl
• InChI: InChI=1S/C19H17N5O7S3.ClH/c1-30-23-11(9-7-34-19(20)21-9)14(25)22-12-15(26)24-13(17(27)28)8(5-32-16(12)24)6-33-18(29)10-3-2-4-31-10;/h2-4,7,12,16H,5-6H2,1H3,(H2,20,21)(H,22,25)(H,27,28);1H/b23-11-;/t12-,16-;/m1./s1
• InChIKey: KEQFDTJEEQKVLM-JUODUXDSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (6R,7R)-7-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetamido]-3-[(furan-2-carbonylsulfanyl)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid hydrochloride; (6R,7R)-7-[2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetamido]-3-[(furan-2-carbonylsulfanyl)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid hydrochloride
• IUPAC Traditional name: ceftiofur hydrochloride; (6R,7R)-7-[2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetamido]-3-[(furan-2-carbonylsulfanyl)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid hydrochloride
• Synonyms: Ceftiofur hydrochloride; (6R,7R)-7-[[(2Z)-2-(2-Amino-4-thiazolyl)-2-(methoxyimino)acetyl]amino]-3-[[(2-furanylcarbonyl)thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid; Excenel; Excenel RTU; U 64279A; U 67279A; (6R,7R)-7-{[(2Z)-2-(2-Amino-4-thiazolyl)-2-(methoxyimino)acetyl]amino}-3-{[(2-furanylcarbonyl)thio]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid hydrochloride; 3-[(2-Furylcarbonyl)thio]methyl]-7-[2-(2-amino-4-thiazolyl)-2-(methoxyiminoacetamido)-3-cephem-4-carboxylic acid hydrochloride; Ceftiofur hydrochloride; (6R,7R)-7-{[(2Z)-2-(2-氨基-4-噻唑基)-2-(甲氧亚氨基)乙酰基]氨基}-3-{[(2-呋喃甲酰基)硫代]甲基}-8-氧-5-硫杂-1-氮杂双环[4.2.0]辛-2-烯-2-羧酸 盐酸盐; 3-[(2-呋喃羰基)硫代]甲基]-7-[2-(2-氨基-4-噻唑基)-2-(甲氧基亚氨基乙酰胺基)-3-头孢烯-4-羧酸 盐酸盐; 头孢噻呋 盐酸盐

Database IDs

• CAS Number: 103980-44-5
• MDL Number: MFCD04038020
• PubChem SID: 162036058
• PubChem CID: 9937686

CALCULATED PROPERTIES

• Acid pKa: 2.8336954
• H Acceptors: 9
• H Donor: 3
• LogD (pH = 5.5): -1.4857522
• LogD (pH = 7.4): -2.4443562
• Log P: -0.4283595
• Molar Refractivity: 124.5146 cm^3
• Polarizability: 47.04454 Å^3
• Polar Surface Area: 177.42 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: Off-White Solid
• Melting Point: >184°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer
• Storage Warning: IRRITANT
• German water hazard class: 3
• TSCA Listed: false

Product Information

• Purity: 95+%
• Grade: VETRANAL™, analytical standard
• Empirical Formula (Hill Notation): C19H17N5O7S3 · HCl

DETAILS

Sigma Aldrich - 32422

Legal Information
VETRANAL is a trademark of Sigma-Aldrich Co. LLC

Toronto Research Chemicals - C244700

An antibacterial.

REFERENCES

• Yancey, R.J., et al.: Am. J. Vet. Res., 48, 1050 (1987)