(6R,7R)-7-[(2Z)-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: 1082
• Molecular Formular: C18H18N8O7S3
• Molecular Mass: 554.57992
• Monoisotopic Mass: 554.04605796
• SMILES: [C@@H]12N(C(=C(CS1)CSc1nc(=O)c(=O)[nH]n1C)C(=O)O)C(=O)[C@H]2NC(=O)/C(=N\OC)/c1csc(n1)N
• 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)/b24-8-/t9-,15-/m1/s1
• InChIKey: VAAUVRVFOQPIGI-SPQHTLEESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (6R,7R)-7-[(2Z)-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: @ceftriaxone; ceftriaxone
• Brand Name: Biotrakson; Rocephine
• Synonyms: Ceftriaxona [INN-Spanish]; Ceftriaxonum [INN-Latin]; Cefatriaxone; Ceftriazone; Ceftriaxone; (6R,7R)-7-[[(2Z)-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 Sodium Salt Hydrate; Ro-13-9904/001; Rocefin; Rocephine; Ceftriaxone Disodium Salt Hemiheptahydrate

Database IDs

• CAS Number: 104376-79-6; 73384-59-5
• PubChem SID: 46506458; 160964545
• PubChem CID: 5479530

CALCULATED PROPERTIES

JChem

• 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

ALOGPS 2.1

• Log P: -0.01
• LOG S: -3.72
• Solubility (Water): 1.05e-01 g/l

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: White to Off White Solid
• Melting Point: >190°C (dec.)
• Hydrophobicity(logP): -1.7

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

DrugBank - DB01212

• Drug Groups: approved
• Description: A broad-spectrum cephalosporin antibiotic with a very long half-life and high penetrability to meninges, eyes and inner ears. [PubChem]
• Indication: For the treatment of the infections (respiratory, skin, soft tissue, UTI, ENT) caused by S. pneumoniae, H. influenzae, staphylococci, S. pyogenes (group A beta-hemolytic streptococci), E. coli, P. mirabilis, Klebsiella sp, coagulase-negative staph
• Pharmacology: Ceftriaxone is a cephalosporin/cephamycin beta-lactam antibiotic used in the treatment of bacterial infections caused by susceptible, usually gram-positive, organisms. Ceftriaxone has in vitro activity against gram-positive and gram-negative aerobic and anaerobic bacteria. The bactericidal activity of Ceftriaxone results from the inhibition of cell wall synthesis and is mediated through Ceftriaxone binding to penicillin binding proteins (PBPs). Ceftriaxone is stable against hydrolysis by a variety of beta-lactamases, including penicillinases, and cephalosporinases and extended spectrum beta-lactamases.
• Affected Organisms: Enteric bacteria and other eubacteria
• Half Life: 5.8-8.7 hours
• Protein Binding: 95%
• Elimination: Thirty-three percent to 67% of a ceftriaxone dose was excreted in the urine as unchanged drug and the remainder was secreted in the bile and ultimately found in the feces as microbiologically inactive compounds.
• Distribution: * 5.78 to 13.5 L
• Clearance: * 0.58 - 1.45 L/h [healthy adults receiving 0.15-3 g of CEFTRIAXONE]
• External Links: Wikipedia; RxList; Drugs.com

Toronto Research Chemicals - C245000

An antibacterial, a third-generation cephalosporin.

REFERENCES

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