(6R,7R)-7-[(2E)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetamido]-3-{[(2-methyl-5,6-dioxo-1,2,5,6-tetrahydro-1,2,4-triazin-3-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

• ChemBase ID: 126463
• Molecular Formular: C18H18N8O7S3
• Molecular Mass: 554.57992
• Monoisotopic Mass: 554.04605796
• SMILES: O=C1N2C(=C(CS[C@@H]2[C@@H]1NC(=O)/C(=N/OC)/c1nc(sc1)N)CSc1nc(=O)c(=O)[nH]n1C)C(=O)O
• Canonical SMILES: CO/N=C(\c1csc(n1)N)/C(=O)N[C@@H]1C(=O)N2[C@@H]1SCC(=C2C(=O)O)CSc1nc(=O)c(=O)[nH]n1C
• InChI: InChI=1S/C18H18N8O7S3/c1-25-18(22-12(28)13(29)23-25)36-4-6-3-34-15-9(14(30)26(15)10(6)16(31)32)21-11(27)8(24-33-2)7-5-35-17(19)20-7/h5,9,15H,3-4H2,1-2H3,(H2,19,20)(H,21,27)(H,23,29)(H,31,32)/t9-,15-/m1/s1
• InChIKey: VAAUVRVFOQPIGI-RFAUZJTJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (6R,7R)-7-[(2E)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetamido]-3-{[(2-methyl-5,6-dioxo-1,2,5,6-tetrahydro-1,2,4-triazin-3-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; (6R,7R)-7-[2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetamido]-3-{[(2-methyl-5,6-dioxo-1,2,5,6-tetrahydro-1,2,4-triazin-3-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• IUPAC Traditional name: ceftriazone; (6R,7R)-7-[2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetamido]-3-{[(2-methyl-5,6-dioxo-1H-1,2,4-triazin-3-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• Brand Name: Rocephin, Arixon
• Synonyms: (6R,7R)-7-[[(2E)-2-(2-Amino-4-thiazolyl)-2-(methoxyimino)acetyl]amino]-8-oxo-3-[[(1,2,5,6-tetrahydro-2-methyl-5,6-dioxo-1,2,4-triazin-3-yl)thio]methyl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid; Ro 15-2254; (E)-Ceftriaxone; Ceftriaxone

Database IDs

• CAS Number: 92143-31-2; 73384-59-5
• PubChem SID: 162220797
• PubChem CID: 5479530; 5361919
• CHEBI ID: 29007
• ATC CODE: J01DD04
• CHEMBL: 161
• Chemspider ID: 4586394
• DrugBank ID: DB01212
• KEGG ID: D07659
• Unique Ingredient Identifier: 75J73V1629
• Wikipedia Title: Ceftriaxone

CALCULATED PROPERTIES

• Acid pKa: 3.1880236
• H Acceptors: 12
• H Donor: 4
• LogD (pH = 5.5): -3.2965198
• LogD (pH = 7.4): -4.674165
• Log P: -2.2233887
• Molar Refractivity: 128.4667 cm^3
• Polarizability: 48.594624 Å^3
• Polar Surface Area: 208.98 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Pharmacology Properties

• Admin Routes: Intravenous, intramuscular
• Bioavailability: n/a
• Excretion: 33–67% renal, 35–45% biliary
• Half Life: 5.8–8.7 hours
• Metabolism: Negligible
• Legal Status: S4 (Australia)
• Pregnancy Category: B (US); B1 (Australia)

DETAILS

Toronto Research Chemicals - C244990

The E-isomer of Ceftriaxone (C245000), a third-generation cephalosporin. An antibacterial.

REFERENCES

• Reiner, R., et al.: J. Antibiot., 33, 783 (1980)