Ceftriaxone
Identification
- Summary
Ceftriaxone is a broad-spectrum cephalosporin antibiotic used for the treatment of bacterial infections in various locations, such as in the respiratory tract, skin, soft tissue, and urinary tract.
- Brand Names
- Rocephin
- Generic Name
- Ceftriaxone
- DrugBank Accession Number
- DB01212
- Background
Ceftriaxone is a broad-spectrum third-generation cephalosporin antibiotic.1 It has a very long half-life compared to other cephalosporins and is high penetrable into the meninges1, eyes9, and inner ear6. Ceftriaxone has broader and stronger gram-negative coverage then first or second-generation cephalosporins, but worse activity against methicillin-susceptible S.aureus. Ceftriaxone is a commonly used antimicrobial due to its good activity against multi-drug resistant Enterobacteriaceae, its relatively safe adverse effect profile, and its long half-life which allows for the convenience of daily or twice-daily dosing.1
- Type
- Small Molecule
- Groups
- Approved
- Structure
- Weight
- Average: 554.58
Monoisotopic: 554.04605704 - Chemical Formula
- C18H18N8O7S3
- Synonyms
- Ceftriaxona
- Ceftriaxone
- Ceftriaxonum
- Rocephin
- External IDs
- DRG-0071
- Ro 139904
Pharmacology
- Indication
Ceftriaxone is used for the treatment of the infections (respiratory, skin, soft tissue, UTI, ENT) caused by susceptible organisms.11 Organisms that are generally susceptible to ceftriaxone include S. pneumoniae, S. pyogenes (group A beta-hemolytic streptococci), coagulase-negative staphylococci, Some Enterobacter spp, H. influenzae, N. gonorrhoeae, P. mirabilis, E. coli, Klebsiella spp, M. catarrhalis, B. burgdorferi, and some oral anaerobes.1
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Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Treatment of Acute bacterial rhinosinusitis ••• ••••• Treatment of Arthritis gonococcal ••• ••••• Treatment of Bacterial endocarditis ••• ••••• Prophylaxis of Bacterial endocarditis ••• ••••• Treatment of Bacterial infections •••••••••••• - Contraindications & Blackbox Warnings
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- Pharmacodynamics
Ceftriaxone is a cephalosporin/cephamycin beta-lactam antibiotic used in the treatment of bacterial infections caused by susceptible, usually gram-positive, organisms.11 Ceftriaxone has in vitro activity against gram-positive aerobic, gram-negative aerobic, and anaerobic bacteria.12 The bactericidal activity of ceftriaxone results from the inhibition of cell wall synthesis and is mediated through ceftriaxone binding to penicillin-binding proteins (PBPs).10 Ceftriaxone is stable against hydrolysis by a variety of beta-lactamases, including penicillinases, and cephalosporinases and extended-spectrum beta-lactamases.11 However, resistance to ceftriaxone usually occurs through beta-lactamase hydrolysis, altered PBPs, or reduced bacterial cell permeability.10 Ceftriaxone should not be mixed with or giving in the same IV line as diluents/products containing calcium as they may cause ceftriaxone to precipitate.11 Ceftriaxone use may also cause biliary sludge or gallbladder pseudolithiasis.11,2
- Mechanism of action
Ceftriaxone works by inhibiting the mucopeptide synthesis in the bacterial cell wall.10,11 The beta-lactam moiety of ceftriaxone binds to carboxypeptidases, endopeptidases, and transpeptidases in the bacterial cytoplasmic membrane. These enzymes are involved in cell-wall synthesis and cell division. Binding of ceftriaxone to these enzymes causes the enzyme to lose activity; therefore, the bacteria produce defective cell walls, causing cell death.
Target Actions Organism APenicillin-binding protein 2B inhibitorStreptococcus pneumoniae (strain ATCC BAA-255 / R6) USolute carrier family 22 member 11 Not Available Humans USolute carrier family 22 member 6 Not Available Humans USolute carrier family 22 member 8 Not Available Humans USolute carrier family 15 member 1 Not Available Humans - Absorption
Ceftriaxone is only given as an injection, either intramuscularly or intravenously.11 Ceftriaxone is less than 1% bioavailable if given orally.3
- Volume of distribution
The apparent volume of distribution of an intravenous or intramuscular dose in healthy patients is 5.78 to 13.5 L.11 The volume of distribution of an intravenous or intramuscular dose in septic patients is 6.48 to 35.2 L.4 Ceftriaxone has good enough CSF penetration to be used as an effective treatment of bacterial meningitis.5
- Protein binding
Ceftriaxone is 95% protein bound.11
- Metabolism
Metabolism of ceftriaxone is negligible.
- Route of elimination
Ceftriaxone is primarily eliminated in the urine (33-67%).11 The remainder is eliminated through secretion in the bile and removed from the body via the feces.
- Half-life
The elimination half-life of ceftriaxone is 5.8-8.7 hours.11 The half-life of ceftriaxone in the middle ear fluid has been estimated to be 25 hours.11,6
- Clearance
The plasma clearance of ceftriaxone in healthy adults receiving a 0.15-3g dose is 0.58 to 1.45 L/hour.11 The renal clearance of ceftriaxone is 0.32 to 0.73 L/hour.11 In intensive care unit patients, ceftriaxone's total drug clearance was 0.96L/h (0.55-1.28 L/h), and unbound drug clearance was 1.91 L/h (1.46-6.20 L/h).7
- Adverse Effects
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- Toxicity
Ceftriaxone overdose may increase the risk of urolithiasis and subsequent post-renal acute renal failure (PARF).8 Other symptoms of overdose unavailable in the literature. However, they are likely similar to the adverse effects of the medication. If overdose of ceftriaxone occurs, treat with symptomatic and supportive treatment, as ceftriaxone levels will not be reduced by dialysis.11
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAbacavir Ceftriaxone may decrease the excretion rate of Abacavir which could result in a higher serum level. Abciximab The therapeutic efficacy of Abciximab can be decreased when used in combination with Ceftriaxone. Acamprosate The excretion of Acamprosate can be decreased when combined with Ceftriaxone. Aceclofenac The risk or severity of nephrotoxicity can be increased when Ceftriaxone is combined with Aceclofenac. Acemetacin The risk or severity of nephrotoxicity can be increased when Ceftriaxone is combined with Acemetacin. - Food Interactions
- No interactions found.
Products
- Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.
- Product Ingredients
Ingredient UNII CAS InChI Key Ceftriaxone sodium 023Z5BR09K 104376-79-6 PMRZKYOXTPBIQF-MAODNAKNSA-J - International/Other Brands
- Acantex (Roche) / Biotrakson (Bioton) / Rocephine (Roche)
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Ceftriaxone and Dextrose Injection, solution 2 g/50mL Intravenous B. Braun Medical Inc. 2005-04-20 Not applicable US Ceftriaxone and Dextrose Injection, solution 1 g/50mL Intravenous B. Braun Medical Inc. 2005-04-20 Not applicable US Ceftriaxone for Injection Powder, for solution 500 mg / vial Intramuscular; Intravenous Fresenius Kabi Not applicable Not applicable Canada Ceftriaxone for Injection Powder, for solution 10 g / vial Intramuscular; Intravenous Fresenius Kabi Not applicable Not applicable Canada Ceftriaxone for Injection Powder, for solution 100 g / bag Intravenous Fresenius Kabi 2014-06-05 Not applicable Canada - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Ceftriaxone Injection, powder, for solution 250 mg/1 Intramuscular; Intravenous Pfizer Laboratories, Division of Pfizer Inc 2008-07-31 2012-05-31 US Ceftriaxone Injection, powder, for solution 1 g/1 Intramuscular; Intravenous Lupin Pharmaceuticals, Inc. 2009-06-01 Not applicable US Ceftriaxone Injection, powder, for solution 1 g/1 Intramuscular; Intravenous Baxter Healthcare Corporation 2003-09-30 2017-12-31 US Ceftriaxone Injection, powder, for solution 10 g/1 Intravenous Xellia Pharmaceuticals USA LLC 2022-01-06 Not applicable US Ceftriaxone Injection, powder, for solution 1 g/1 Intramuscular; Intravenous Fresenius Kabi USA, LLC 2011-06-20 Not applicable US - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image AXTAR®1G POLVO ESTERIL PARA INYECCION Ceftriaxone (1.106 g) + Lidocaine (12.33 mg) Injection, powder, for solution Intramuscular GRUPO UNIPHARM S.A. Y/O LABORATORIOS UNI S.A. 2006-11-10 Not applicable Colombia Easy-Ceft 1g Ceftriaxone sodium (1 g/1) + Isopropyl alcohol (0.7 mL/1mL) Kit Intramuscular; Intravenous; Topical American Health RX, LLC 2021-06-15 Not applicable US ROCEPHIN VIAL 1G IM Ceftriaxone (1 g) + Lidocaine hydrochloride (1 %) Injection, solution Intramuscular ROCHE (MALAYSIA) SDN. BHD. 2020-09-08 Not applicable Malaysia ROCEPHIN VIAL 250MG IM Ceftriaxone (250 mg) + Lidocaine (1 %) Injection Intramuscular ROCHE (MALAYSIA) SDN. BHD. 2020-09-08 Not applicable Malaysia SEFABEL 0.5 G I.M. ENJEKSIYONLUK ÇÖZELTI HAZIRLAMAK IÇIN KURU TOZ IÇEREN FLAKON ,1 ADET Ceftriaxone sodium (500 mg) + Lidocaine hydrochloride (1 %) Injection, solution Intramuscular NOBEL İLAÇ PAZARLAMA VE SAN. LTD. ŞTİ. 2014-04-01 Not applicable Turkey
Categories
- ATC Codes
- J01DD04 — Ceftriaxone
- J01DD — Third-generation cephalosporins
- J01D — OTHER BETA-LACTAM ANTIBACTERIALS
- J01 — ANTIBACTERIALS FOR SYSTEMIC USE
- J — ANTIINFECTIVES FOR SYSTEMIC USE
- Drug Categories
- Amides
- Anti-Bacterial Agents
- Anti-Infective Agents
- Antibacterials for Systemic Use
- Antiinfectives for Systemic Use
- beta Lactam Antibiotics
- beta-Lactams
- Cephalosporins
- Drugs that are Mainly Renally Excreted
- Heterocyclic Compounds, Fused-Ring
- Lactams
- Nephrotoxic agents
- OAT1/SLC22A6 inhibitors
- OAT3/SLC22A8 Inhibitors
- P-glycoprotein inhibitors
- Sulfur Compounds
- Thiazines
- Third-Generation Cephalosporins
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as cephalosporins. These are compounds containing a 1,2-thiazine fused to a 2-azetidinone to for a oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid moiety or a derivative thereof.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Lactams
- Sub Class
- Beta lactams
- Direct Parent
- Cephalosporins
- Alternative Parents
- N-acyl-alpha amino acids and derivatives / 2,4-disubstituted thiazoles / Alkylarylthioethers / 1,2,4-triazines / 1,3-thiazines / 2-amino-1,3-thiazoles / Tertiary carboxylic acid amides / Heteroaromatic compounds / Secondary carboxylic acid amides / Amino acids show 12 more
- Substituents
- 1,2,4-triazine / 1,3-thiazol-2-amine / 2,4-disubstituted 1,3-thiazole / Alkylarylthioether / Alpha-amino acid or derivatives / Amine / Amino acid / Amino acid or derivatives / Aromatic heteropolycyclic compound / Aryl thioether show 29 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- cephalosporin, 1,3-thiazole, oxime O-ether, 1,2,4-triazines (CHEBI:29007) / Cephems (C06683)
- Affected organisms
- Enteric bacteria and other eubacteria
- Neisseria meningitidis
- Haemophilus influenzae
- Neisseria gonorrhoeae
- Escherichia coli
- Salmonella typhi
Chemical Identifiers
- UNII
- 75J73V1629
- CAS number
- 73384-59-5
- InChI Key
- VAAUVRVFOQPIGI-SPQHTLEESA-N
- 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
- 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
- SMILES
- [H][C@]12SCC(CSC3=NC(=O)C(=O)NN3C)=C(N1C(=O)[C@H]2NC(=O)C(=N/OC)\C1=CSC(N)=N1)C(O)=O
References
- Synthesis Reference
Monguzzi Riccardo, Menaspace Silvano, Anzaghi Piergiorgio, "Process for the preparation of ceftriaxone." U.S. Patent US5026843, issued November, 1984.
US5026843- General References
- Richards DM, Heel RC, Brogden RN, Speight TM, Avery GS: Ceftriaxone. A review of its antibacterial activity, pharmacological properties and therapeutic use. Drugs. 1984 Jun;27(6):469-527. doi: 10.2165/00003495-198427060-00001. [Article]
- Park HZ, Lee SP, Schy AL: Ceftriaxone-associated gallbladder sludge. Identification of calcium-ceftriaxone salt as a major component of gallbladder precipitate. Gastroenterology. 1991 Jun;100(6):1665-70. doi: 10.1016/0016-5085(91)90667-a. [Article]
- Lee S, Kim SK, Lee DY, Chae SY, Byun Y: Pharmacokinetics of a new, orally available ceftriaxone formulation in physical complexation with a cationic analogue of bile acid in rats. Antimicrob Agents Chemother. 2006 May;50(5):1869-71. doi: 10.1128/AAC.50.5.1869-1871.2006. [Article]
- Garot D, Respaud R, Lanotte P, Simon N, Mercier E, Ehrmann S, Perrotin D, Dequin PF, Le Guellec C: Population pharmacokinetics of ceftriaxone in critically ill septic patients: a reappraisal. Br J Clin Pharmacol. 2011 Nov;72(5):758-67. doi: 10.1111/j.1365-2125.2011.04005.x. [Article]
- Rockowitz J, Tunkel AR: Bacterial meningitis. Practical guidelines for management. Drugs. 1995 Nov;50(5):838-53. doi: 10.2165/00003495-199550050-00005. [Article]
- Gudnason T, Gudbrandsson F, Barsanti F, Kristinsson KG: Penetration of ceftriaxone into the middle ear fluid of children. Pediatr Infect Dis J. 1998 Mar;17(3):258-60. doi: 10.1097/00006454-199803000-00022. [Article]
- Schleibinger M, Steinbach CL, Topper C, Kratzer A, Liebchen U, Kees F, Salzberger B, Kees MG: Protein binding characteristics and pharmacokinetics of ceftriaxone in intensive care unit patients. Br J Clin Pharmacol. 2015 Sep;80(3):525-33. doi: 10.1111/bcp.12636. Epub 2015 Jun 11. [Article]
- Shen-Hua W, Fan-Yi M, Qing-Ling Z, Li-Na Z, Li-Jun M: Ceftriaxone-associated renal toxicity in adults: a case report and recommendations for the management of such cases. J Clin Pharm Ther. 2016 Jun;41(3):348-350. doi: 10.1111/jcpt.12358. Epub 2016 Feb 23. [Article]
- Gobeaux D, Ambart L, Couderc JL, Renard PH, De Charnace B, Lokiec F: Ceftriaxone diffusion from blood to aqueous humour in man. Br J Ophthalmol. 1989 Jul;73(7):574-5. doi: 10.1136/bjo.73.7.574. [Article]
- Sivapalasingam S., Steigbigel N. (2015). Mandell, Douglas and Bennett's Principles and practice of infectious diseases (8th ed.). Elsevier.
- DailyMed Label: ceftriaxone sodium injection, powder for solution [Link]
- FDA: Ceftriaxone - Injection products [Link]
- External Links
- Human Metabolome Database
- HMDB0015343
- KEGG Drug
- D07659
- KEGG Compound
- C06683
- PubChem Compound
- 5479530
- PubChem Substance
- 46506458
- ChemSpider
- 4586394
- BindingDB
- 50103601
- 2193
- ChEBI
- 29007
- ChEMBL
- CHEMBL161
- ZINC
- ZINC000028467879
- Therapeutic Targets Database
- DAP000145
- PharmGKB
- PA448866
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Ceftriaxone
- FDA label
- Download (211 KB)
- MSDS
- Download (53.3 KB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Completed Health Services Research Meningitis / Neurological Infections 1 4 Completed Other Acute Tubulo-Interstitial Nephritis 1 4 Completed Prevention Cirrhosis of the Liver 1 4 Completed Prevention Gastric and Esophageal Varices / Gastrointestinal Hemorrhage 1 4 Completed Prevention Kidney Stones / Urinary Tract Infection 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- American Regent
- Apotex Inc.
- APP Pharmaceuticals
- A-S Medication Solutions LLC
- Aurobindo Pharma Ltd.
- B. Braun Melsungen AG
- Baxter International Inc.
- Bedford Labs
- Biopharma SRL
- Cardinal Health
- Cephazone Pharma LLC
- Cura Pharmaceutical Co. Inc.
- Dispensing Solutions
- F Hoffmann La Roche Ltd.
- F Hoffmann-La Roche Ltd.
- GlaxoSmithKline Inc.
- Hanmi Fine Chemical Co. Ltd.
- Hikma Pharmaceuticals
- Hospira Inc.
- Lupin Pharmaceuticals Inc.
- Medisca Inc.
- Orchid Healthcare
- Patheon Inc.
- PD-Rx Pharmaceuticals Inc.
- Pfizer Inc.
- Physicians Total Care Inc.
- Preferred Pharmaceuticals Inc.
- Rebel Distributors Corp.
- Sagent Pharmaceuticals
- Sandoz
- Teva Pharmaceutical Industries Ltd.
- West-Ward Pharmaceuticals
- Wockhardt Ltd.
- Dosage Forms
Form Route Strength Solution Parenteral 596.490 mg Solution Parenteral 596.487 mg Solution Intravenous 1.000 g Powder, for solution 2 G Injection, powder, for solution Intravenous 1 g Injection, powder, for solution Intramuscular 0.5 g Injection, powder, for solution Intramuscular; Parenteral 1 G/3.5ML Injection, powder, for solution Intramuscular; Parenteral 500 MG/2ML Injection, powder, for solution Intravenous; Parenteral 1000 MG/10ML Injection, powder, for solution 1000 mg Injection, solution Intramuscular; Intravenous 0.5 g Injection, solution Intramuscular; Intravenous 1 g Injection, powder, for solution Intramuscular 1 G/3.5ML Injection, powder, for solution Intravenous; Parenteral 1 G/10ML Injection, powder, for solution Intramuscular; Intravenous 500 mg/5ml Injection, powder, for solution Intramuscular Injection, powder, for solution Intramuscular 1 gr Injection, powder, for solution Intravenous 1 gr Injection, powder, for solution Intramuscular 250 mg Injection, powder, for solution Intravenous 250 mg Injection, powder, for solution Intravenous 500 mg Injection, solution Intramuscular; Intravenous Injection, powder, for solution Intravenous 0.5 g Solution Intramuscular Solution Intravenous 0.500 g Injection, powder, for solution Intramuscular 1 g Injection, powder, for solution 250 MG Injection, powder, for solution Intramuscular; Intravenous 250 mg Injection, powder, for solution Intramuscular; Intravenous 500 mg Injection, powder, for solution Parenteral 0.5 g Injection, powder, for solution Intravenous 2 gr Injection, powder, for solution Parenteral 250 mg Injection, powder, for solution Intramuscular; Intravenous 100000 g Injection, powder, for solution Intravenous 1.184 g Injection, powder, for solution Intramuscular; Intravenous Injection, powder, for suspension Parenteral 1 g Injection, powder, lyophilized, for solution Intramuscular; Intravenous 1 g Injection, powder, for solution Intramuscular 1 g/1 Injection, powder, for solution Intramuscular 250 mg/1 Injection, powder, for solution Intramuscular; Intravenous 1 g/10mL Injection, powder, for solution Intramuscular; Intravenous 2 g/1 Injection, powder, for solution Intramuscular; Intravenous 250 mg/1 Injection, powder, for solution Intravenous 1 g/1 Injection, powder, for solution Intravenous 10 g/100mL Injection, powder, for solution Intravenous 10 g/1 Injection, powder, for solution Intravenous 100 g/1 Injection, powder, for solution Intravenous 100 mg/1mL Injection, powder, for solution Intravenous 2 g/1 Injection, powder, lyophilized, for solution Intravenous 100 mg/1mL Powder, for solution Intramuscular; Intravenous 1 g/1 Powder, for solution Intramuscular; Intravenous 2 g/1 Powder, for solution Intramuscular; Intravenous 250 mg/1 Powder, for solution Intramuscular; Intravenous 500 mg/1 Injection, powder, for solution Intramuscular; Parenteral 250 MG/2ML Injection, powder, for solution Intramuscular; Intravenous 1.0 g Injection, powder, for solution Intramuscular; Intravenous 2.0 g Injection, powder, for solution Parenteral 1 G/10ML Powder, for solution Parenteral 2 G Injection, powder, for solution Intramuscular Injection, powder, for solution Intramuscular; Parenteral 250 MG Injection, powder, for solution Intramuscular; Parenteral 500 MG Powder, for solution Intravenous 100 g / bag Injection, powder, for solution Intramuscular 250 MG/2ML Injection, powder, for solution Intramuscular 500 MG/2ML Injection, powder, for solution Intravenous 1 G/10ML Solution Intravenous 1000 mg / 50 mL Solution Intravenous 2000 mg / 50 mL Injection, powder, for solution Intravenous 2000 mg/bottle Injection, powder, for solution Intramuscular; Intravenous 500 mg/vial Injection, powder, for solution Intramuscular; Intravenous 1000 mg/vial Injection, powder, for solution Parenteral 1 G Injection, powder, for solution Parenteral 2 G Injection, powder, for solution Intramuscular; Intravenous 1 g/1 Injection, powder, for solution Intramuscular; Intravenous 500 mg/1 Injection, powder, for solution Intravenous 500 mg/1 Powder, for solution Intramuscular; Intravenous 0.25 g / vial Powder, for solution Intramuscular; Intravenous 10 g / vial Powder, for solution Intramuscular; Intravenous 1 g / vial Powder, for solution Intramuscular; Intravenous 2 g / vial Powder, for solution Intramuscular; Intravenous 250 mg / vial Powder, for solution Intramuscular; Intravenous 500 mg / vial Powder, for solution Intravenous 10 g / vial Injection, powder, for solution Intravenous 2 g Injection Injection, powder, for solution Intramuscular; Intravenous 1 g Injection, powder, for solution Injection, powder, for solution Intravenous Powder, for solution Injection, solution Intramuscular 0.5 g Injection Intravenous 0.5 g Solution Intravenous 2 g Injection, powder, for solution Intramuscular 100000 g Injection, powder, for solution Intramuscular 500 mg Kit Intramuscular; Intravenous; Topical Injection Intramuscular; Intravenous Injection, powder, for solution Intramuscular 0.5 gr Injection, powder, for solution Intravenous 0.5 gr Injection; injection, powder, for solution 1 g Injection, powder, for solution 1 g Injection, powder, for solution Intramuscular; Intravenous 1000.0 mg Injection, powder, for solution Intramuscular; Intravenous 2000.0 mg Injection, powder, for solution Parenteral Injection, powder, for solution Intramuscular; Intravenous 1000 mg Injection, powder, for solution Intramuscular; Intravenous 2000 mg Injection Intramuscular 1000 mg Injection Intravenous 1000 mg Injection Intramuscular 250 mg Injection Intramuscular 500 mg Injection Intramuscular 0.5 g/2ml Injection Intravenous 0.5 g/5ml Injection Intravenous 1 g/10ml Injection Intramuscular 1 g/3.5ml Injection Intravenous 2 g Powder 2 G Injection, powder, for solution Intravenous; Parenteral 500 MG/5ML Injection 1 g Injection, powder, for solution Intramuscular; Parenteral 1 MG/3.5ML Injection, powder, for solution Intravenous Injection, powder, for solution Intramuscular; Parenteral 1 G Injection, powder, for solution Intravenous; Parenteral 250 MG/5ML Powder 1 G Injection, powder, for solution Parenteral 500 mg Injection, solution Intravenous 1 g/50mL Injection, solution Intravenous 2 g/50mL Injection, powder, for solution Intramuscular 1 g/vial Injection, powder, for solution Intravenous 1 g/vial Solution Intramuscular 1.000 g Powder, for solution Intravenous 1 g / vial Injection, solution Intramuscular Injection Intravenous 1 g Injection Intravenous 250 mg Injection Intravenous Injection Intramuscular Injection, powder, for solution Intramuscular; Intravenous Injection, solution Intramuscular 1 g Injection, solution Intravenous 2 g Injection, solution Intravenous 0.5 g Injection, solution Intravenous 1 g Injection, powder, for solution Intravenous; Parenteral 1 G Powder Solution Intramuscular 500.00 g Solution Intravenous 500 mg Solution Parenteral 1.000 g Injection, solution Intramuscular Injection, solution Intravenous Injection, powder, for solution Intramuscular; Intravenous 0.25 g Injection, powder, for solution Intramuscular; Intravenous 0.5 g Injection, powder, for solution Intramuscular; Intravenous 2 g Solution Parenteral 1.079 g Injection Intramuscular; Intravenous 1 g Solution Intramuscular 500 mg Injection Intramuscular; Intravenous 250 MG Injection Intramuscular; Intravenous 1 gr Injection Intramuscular; Intravenous 0.5 gr Injection 1000 MG Injection 500 MG Injection, powder, for solution 2 G Injection, powder, for solution 500 MG Solution Intravenous 595.000 mg Solution Parenteral Injection, powder, for solution 250 mg/1vial Injection, powder, for solution 500 mg/1vial Powder 500 mg/1vial Powder 250 mg/1vial Powder - Prices
Unit description Cost Unit Rocephin 10 gm vial 478.32USD vial Rocephin 2 gm vial 97.5USD vial Ceftriaxone 2 gm piggyback 94.17USD each Rocephin 1 gm Solution Vial 65.53USD vial Rocephin 1 gm vial 62.02USD vial Ceftriaxone For Injection Usp 2 g/vial 49.13USD vial Ceftriaxone 1 gm piggyback 47.91USD each Rocephin 1 g/vial 40.2USD vial Ceftriaxone 10 gm vial 36.25USD vial Ceftriaxone 2 gm-d5w bag 27.84USD each Ceftriaxone For Injection Usp 1 g/vial 24.93USD vial Chloromycetin 1 g/vial 20.33USD vial Ceftriaxone 2 gm vial 17.04USD vial Ceftriaxone 1 gm-d5w bag 13.92USD each Rocephin 0.25 g/vial 12.71USD vial Ceftriaxone For Injection Usp 0.25 g/vial 7.88USD vial Ceftriaxone 1 gm vial 7.56USD vial Ceftriaxone sodium powder 1.84USD g DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) >155 °C Not Available logP -1.7 Not Available Caco2 permeability -6.88 ADME Research, USCD - Predicted Properties
Property Value Source Water Solubility 0.105 mg/mL ALOGPS logP -0.01 ALOGPS logP -1.9 Chemaxon logS -3.7 ALOGPS pKa (Strongest Acidic) 2.7 Chemaxon pKa (Strongest Basic) 3.36 Chemaxon Physiological Charge -2 Chemaxon Hydrogen Acceptor Count 12 Chemaxon Hydrogen Donor Count 4 Chemaxon Polar Surface Area 208.98 Å2 Chemaxon Rotatable Bond Count 8 Chemaxon Refractivity 128.47 m3·mol-1 Chemaxon Polarizability 51.47 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption - 0.952 Blood Brain Barrier - 0.9748 Caco-2 permeable - 0.8957 P-glycoprotein substrate Substrate 0.726 P-glycoprotein inhibitor I Non-inhibitor 0.8942 P-glycoprotein inhibitor II Inhibitor 0.5293 Renal organic cation transporter Non-inhibitor 0.8024 CYP450 2C9 substrate Non-substrate 0.7943 CYP450 2D6 substrate Non-substrate 0.8172 CYP450 3A4 substrate Substrate 0.5374 CYP450 1A2 substrate Non-inhibitor 0.7538 CYP450 2C9 inhibitor Non-inhibitor 0.7088 CYP450 2D6 inhibitor Non-inhibitor 0.8666 CYP450 2C19 inhibitor Non-inhibitor 0.7034 CYP450 3A4 inhibitor Inhibitor 0.6432 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.5509 Ames test Non AMES toxic 0.7336 Carcinogenicity Non-carcinogens 0.8392 Biodegradation Not ready biodegradable 0.9968 Rat acute toxicity 2.1681 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9865 hERG inhibition (predictor II) Non-inhibitor 0.6145
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 231.4101087 predictedDarkChem Lite v0.1.0 [M-H]- 214.6093087 predictedDarkChem Lite v0.1.0 [M-H]- 218.3416 predictedDeepCCS 1.0 (2019) [M+H]+ 230.9318087 predictedDarkChem Lite v0.1.0 [M+H]+ 213.4504087 predictedDarkChem Lite v0.1.0 [M+H]+ 220.73717 predictedDeepCCS 1.0 (2019) [M+Na]+ 230.9912087 predictedDarkChem Lite v0.1.0 [M+Na]+ 215.0078087 predictedDarkChem Lite v0.1.0 [M+Na]+ 226.64981 predictedDeepCCS 1.0 (2019)
Targets
- Kind
- Protein
- Organism
- Streptococcus pneumoniae (strain ATCC BAA-255 / R6)
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Not Available
- Specific Function
- Penicillin binding
- Gene Name
- penA
- Uniprot ID
- P0A3M6
- Uniprot Name
- Penicillin-binding protein 2B
- Molecular Weight
- 73872.305 Da
References
- Tomberg J, Unemo M, Davies C, Nicholas RA: Molecular and structural analysis of mosaic variants of penicillin-binding protein 2 conferring decreased susceptibility to expanded-spectrum cephalosporins in Neisseria gonorrhoeae: role of epistatic mutations. Biochemistry. 2010 Sep 21;49(37):8062-70. doi: 10.1021/bi101167x. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Sodium-independent organic anion transmembrane transporter activity
- Specific Function
- Mediates saturable uptake of estrone sulfate, dehydroepiandrosterone sulfate and related compounds.
- Gene Name
- SLC22A11
- Uniprot ID
- Q9NSA0
- Uniprot Name
- Solute carrier family 22 member 11
- Molecular Weight
- 59970.945 Da
References
- Takeda M, Babu E, Narikawa S, Endou H: Interaction of human organic anion transporters with various cephalosporin antibiotics. Eur J Pharmacol. 2002 Mar 8;438(3):137-42. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Sodium-independent organic anion transmembrane transporter activity
- Specific Function
- Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one ...
- Gene Name
- SLC22A6
- Uniprot ID
- Q4U2R8
- Uniprot Name
- Solute carrier family 22 member 6
- Molecular Weight
- 61815.78 Da
References
- Takeda M, Babu E, Narikawa S, Endou H: Interaction of human organic anion transporters with various cephalosporin antibiotics. Eur J Pharmacol. 2002 Mar 8;438(3):137-42. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Sodium-independent organic anion transmembrane transporter activity
- Specific Function
- Plays an important role in the excretion/detoxification of endogenous and exogenous organic anions, especially from the brain and kidney. Involved in the transport basolateral of steviol, fexofenad...
- Gene Name
- SLC22A8
- Uniprot ID
- Q8TCC7
- Uniprot Name
- Solute carrier family 22 member 8
- Molecular Weight
- 59855.585 Da
References
- Takeda M, Babu E, Narikawa S, Endou H: Interaction of human organic anion transporters with various cephalosporin antibiotics. Eur J Pharmacol. 2002 Mar 8;438(3):137-42. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Proton-dependent oligopeptide secondary active transmembrane transporter activity
- Specific Function
- Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides. May constitute a major route for the absorption of protein digestion end-products.
- Gene Name
- SLC15A1
- Uniprot ID
- P46059
- Uniprot Name
- Solute carrier family 15 member 1
- Molecular Weight
- 78805.265 Da
References
- Luckner P, Brandsch M: Interaction of 31 beta-lactam antibiotics with the H+/peptide symporter PEPT2: analysis of affinity constants and comparison with PEPT1. Eur J Pharm Biopharm. 2005 Jan;59(1):17-24. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inducer
- General Function
- Manganese ion binding
- Specific Function
- This enzyme has 2 functions: it catalyzes the production of glutamine and 4-aminobutanoate (gamma-aminobutyric acid, GABA), the latter in a pyridoxal phosphate-independent manner (By similarity). E...
- Gene Name
- GLUL
- Uniprot ID
- P15104
- Uniprot Name
- Glutamine synthetase
- Molecular Weight
- 42064.15 Da
References
- Tumani H, Smirnov A, Barchfeld S, Olgemoller U, Maier K, Lange P, Bruck W, Nau R: Inhibition of glutamine synthetase in rabbit pneumococcal meningitis is associated with neuronal apoptosis in the dentate gyrus. Glia. 2000 Mar;30(1):11-8. [Article]
- Verma R, Mishra V, Sasmal D, Raghubir R: Pharmacological evaluation of glutamate transporter 1 (GLT-1) mediated neuroprotection following cerebral ischemia/reperfusion injury. Eur J Pharmacol. 2010 Jul 25;638(1-3):65-71. doi: 10.1016/j.ejphar.2010.04.021. Epub 2010 Apr 24. [Article]
Carriers
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Other/unknown
- General Function
- Toxic substance binding
- Specific Function
- Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
- Gene Name
- ALB
- Uniprot ID
- P02768
- Uniprot Name
- Serum albumin
- Molecular Weight
- 69365.94 Da
References
- Gulian JM, Dalmasso C, Gonard V: Interaction of beta-lactam antibiotics on bilirubin-albumin complex: comparison by three methods, total bilirubin, unbound bilirubin and erythrocyte-bound bilirubin. Chemotherapy. 1990;36(2):91-7. [Article]
- Nerli B, Farruggia B, Pico G: A comparative study of the binding characteristics of ceftriaxone, cefoperazone and cefsulodin to human serum albumin. Biochem Mol Biol Int. 1996 Nov;40(4):823-31. [Article]
- Robertson A, Fink S, Karp W: Effect of cephalosporins on bilirubin-albumin binding. J Pediatr. 1988 Feb;112(2):291-4. [Article]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Proton-dependent oligopeptide secondary active transmembrane transporter activity
- Specific Function
- Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides. May constitute a major route for the absorption of protein digestion end-products.
- Gene Name
- SLC15A1
- Uniprot ID
- P46059
- Uniprot Name
- Solute carrier family 15 member 1
- Molecular Weight
- 78805.265 Da
References
- Luckner P, Brandsch M: Interaction of 31 beta-lactam antibiotics with the H+/peptide symporter PEPT2: analysis of affinity constants and comparison with PEPT1. Eur J Pharm Biopharm. 2005 Jan;59(1):17-24. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Peptide:proton symporter activity
- Specific Function
- Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides.
- Gene Name
- SLC15A2
- Uniprot ID
- Q16348
- Uniprot Name
- Solute carrier family 15 member 2
- Molecular Weight
- 81782.77 Da
References
- Luckner P, Brandsch M: Interaction of 31 beta-lactam antibiotics with the H+/peptide symporter PEPT2: analysis of affinity constants and comparison with PEPT1. Eur J Pharm Biopharm. 2005 Jan;59(1):17-24. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Sodium-independent organic anion transmembrane transporter activity
- Specific Function
- Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one ...
- Gene Name
- SLC22A6
- Uniprot ID
- Q4U2R8
- Uniprot Name
- Solute carrier family 22 member 6
- Molecular Weight
- 61815.78 Da
References
- Takeda M, Babu E, Narikawa S, Endou H: Interaction of human organic anion transporters with various cephalosporin antibiotics. Eur J Pharmacol. 2002 Mar 8;438(3):137-42. [Article]
- Jung KY, Takeda M, Shimoda M, Narikawa S, Tojo A, Kim DK, Chairoungdua A, Choi BK, Kusuhara H, Sugiyama Y, Sekine T, Endou H: Involvement of rat organic anion transporter 3 (rOAT3) in cephaloridine-induced nephrotoxicity: in comparison with rOAT1. Life Sci. 2002 Mar 8;70(16):1861-74. [Article]
- Jariyawat S, Sekine T, Takeda M, Apiwattanakul N, Kanai Y, Sophasan S, Endou H: The interaction and transport of beta-lactam antibiotics with the cloned rat renal organic anion transporter 1. J Pharmacol Exp Ther. 1999 Aug;290(2):672-7. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Sodium-independent organic anion transmembrane transporter activity
- Specific Function
- Plays an important role in the excretion/detoxification of endogenous and exogenous organic anions, especially from the brain and kidney. Involved in the transport basolateral of steviol, fexofenad...
- Gene Name
- SLC22A8
- Uniprot ID
- Q8TCC7
- Uniprot Name
- Solute carrier family 22 member 8
- Molecular Weight
- 59855.585 Da
References
- Takeda M, Babu E, Narikawa S, Endou H: Interaction of human organic anion transporters with various cephalosporin antibiotics. Eur J Pharmacol. 2002 Mar 8;438(3):137-42. [Article]
- Jung KY, Takeda M, Shimoda M, Narikawa S, Tojo A, Kim DK, Chairoungdua A, Choi BK, Kusuhara H, Sugiyama Y, Sekine T, Endou H: Involvement of rat organic anion transporter 3 (rOAT3) in cephaloridine-induced nephrotoxicity: in comparison with rOAT1. Life Sci. 2002 Mar 8;70(16):1861-74. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Sodium-independent organic anion transmembrane transporter activity
- Specific Function
- Mediates saturable uptake of estrone sulfate, dehydroepiandrosterone sulfate and related compounds.
- Gene Name
- SLC22A11
- Uniprot ID
- Q9NSA0
- Uniprot Name
- Solute carrier family 22 member 11
- Molecular Weight
- 59970.945 Da
References
- Takeda M, Babu E, Narikawa S, Endou H: Interaction of human organic anion transporters with various cephalosporin antibiotics. Eur J Pharmacol. 2002 Mar 8;438(3):137-42. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Xenobiotic-transporting atpase activity
- Specific Function
- Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
- Gene Name
- ABCB1
- Uniprot ID
- P08183
- Uniprot Name
- Multidrug resistance protein 1
- Molecular Weight
- 141477.255 Da
References
- Hanko E, Tommarello S, Watchko JF, Hansen TW: Administration of drugs known to inhibit P-glycoprotein increases brain bilirubin and alters the regional distribution of bilirubin in rat brain. Pediatr Res. 2003 Oct;54(4):441-5. doi: 10.1203/01.PDR.0000085169.87948.B6. Epub 2003 Aug 6. [Article]
Drug created at June 13, 2005 13:24 / Updated at May 10, 2024 22:29