disodium bis((6R,7R)-7-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetamido]-3-{[(2-methyl-5,6-dioxo-1-sodio-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-carboxylate) heptahydrate

• ChemBase ID: 133894
• Molecular Formular: C36H46N16Na4O21S6
• Molecular Mass: 1323.19412
• Monoisotopic Mass: 1322.0938457
• SMILES: Cn1n(c(=O)c(=O)nc1SCC1=C(N2C(=O)[C@H]([C@H]2SC1)NC(=O)/C(=N\OC)/c1nc(sc1)N)C(=O)[O-])[Na].Cn1n(c(=O)c(=O)nc1SCC1=C(N2C(=O)[C@H]([C@H]2SC1)NC(=O)/C(=N\OC)/c1nc(sc1)N)C(=O)[O-])[Na].O.O.O.O.O.O.O.[Na+].[Na+]
• 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)n(n1C)[Na].CO/N=C(/c1csc(n1)N)\C(=O)N[C@@H]1C(=O)N2[C@@H]1SCC(=C2C(=O)[O-])CSc1nc(=O)c(=O)n(n1C)[Na].O.O.O.O.O.O.O.[Na+].[Na+]
• InChI: InChI=1S/2C18H18N8O7S3.4Na.7H2O/c2*1-25-18(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;;;;;;;;;;;/h2*5,9,15H,3-4H2,1-2H3,(H5,19,20,21,23,27,29,31,32);;;;;7*1H2/q;;4*+1;;;;;;;/p-4/b2*24-8-;;;;;;;;;;;/t2*9-,15-;;;;;;;;;;;/m11.........../s1
• InChIKey: PMRZKYOXTPBIQF-MAODNAKNSA-J

NAMES AND DATABASE IDS

Names

• IUPAC name: disodium bis((6R,7R)-7-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetamido]-3-{[(2-methyl-5,6-dioxo-1-sodio-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-carboxylate) heptahydrate
• IUPAC Traditional name: disodium bis((6R,7R)-7-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetamido]-3-{[(2-methyl-5,6-dioxo-1-sodio-1,2,4-triazin-3-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate) heptahydrate
• Synonyms: Ceftriaxone disodium salt hemi(heptahydrate)

Database IDs

• CAS Number: 104376-79-6
• EC Number: 277-930-0
• MDL Number: MFCD01750405
• PubChem SID: 162228171; 24278322
• PubChem CID: 71307090

CALCULATED PROPERTIES

• Acid pKa: 3.0745335
• H Acceptors: 12
• H Donor: 2
• LogD (pH = 5.5): -4.576532
• LogD (pH = 7.4): -5.778621
• Log P: -3.4913027
• Molar Refractivity: 138.5038 cm^3
• Polarizability: 50.143932 Å^3
• Polar Surface Area: 203.02 Å^2
• Rotatable Bonds: 16
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 1
• Risk Statements: 36/37/38-42/43
• Safety Statements: 26-36
• GHS Pictograms: GHS07; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H315-H317-H319-H334-H335
• GHS Precautionary statements: P261-P280-P305 + P351 + P338-P342 + P311
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• Storage Temperature: 2-8°C

DETAILS

Sigma Aldrich - C5793

Application
Ceftriaxone is used to study drug-induced immune hemolytic anemias 1, prophylactic strategies to reduce neonatal encephalopathy 2, pentylenetetrazole-evoked convulsions 3, the effect of expression, binding, and inhibition of PDP1 and other penicillin-binding proteins (PBPs) on bacterial cell wall mucopeptide synthesis.
Biochem/physiol Actions
Ceftriaxone is a third-generation cephalosporin antibiotic that disrupts the synthesis of the peptidoglycan layer of bacterial cell walls. It is effective against gram-positive and gram-negative bacteria. Ceftriaxone is thought to increase EAAT2 pump expression in the central nervous system and to reduce glutamatergic toxicity4.