Details of the Drug

General Information of Drug (ID: DMCEW64)

Drug Name
Ceftriaxone
Synonyms
Biotrakson; CTRX; Cefatriaxone; Ceftriaxon; Ceftriaxona; Ceftriaxonum; Ceftriazone; Longacef; Longaceph; Rocefin; Rocephin; Rocephine; CEFTRIAXONE SODIUM; Ceftriaxone intravenous; Ro 139904; Ceftriaxona [INN-Spanish]; Ceftriaxone (INN); Ceftriaxone (TN); Ceftriaxone [USAN:JAN]; Ceftriaxone, Disodium Salt; Ceftriaxonum [INN-Latin]; DRG-0071; Ro13-9904; Rocephin (TN); Ceftriaxone, Disodium Salt, Hemiheptahydrate; Ro-13-9904; (6R,7R)-7-(2-(2-Amino-4-thiazolyl)glyoxylamido)-8-oxo-3-(((1,2,5,6-tetrahydro-2-methyl-5,6-dioxo-as-triazin-3-yl)thio)methyl)-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 7(sup 2)-(Z)-(O-methyloxime), sesquaterhydrate; (6R,7R)-7-({(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-[(methyloxy)imino]acetyl}amino)-3-{[(6-hydroxy-2-methyl-5-oxo-2,5-dihydro-1,2,4-triazin-3-yl)thio]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; (6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-[(2-methyl-5,6-dioxo-1H-1,2,4-triazin-3-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; (6R,7R)-7-{[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]amino}-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; 7beta-{[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]amino}-3-{[(2-methyl-5,6-dioxo-1,2,5,6-tetrahydro-1,2,4-triazin-3-yl)sulfanyl]methyl}-3,4-didehydrocepham-4-carboxylic acid
Indication
Disease Entry ICD 11 Status REF
Acute gonococcal cervicitis N.A. Approved [1]
Bacteremia 1A73 Approved [1]
Bacterial arthritis N.A. Approved [1]
Bacterial infection 1A00-1C4Z Approved [2]
Chancroid N.A. Approved [1]
Endometritis N.A. Approved [1]
Escherichia coli meningitis N.A. Approved [1]
Gonococcal infection of joint N.A. Approved [1]
Meningococcal meningitis N.A. Approved [1]
Pneumococcal meningitis N.A. Approved [1]
Staphylococcal pneumonia N.A. Approved [1]
Pelvic inflammatory disease GA05 Investigative [1]
⏷ Show the Full List of Indication(s)
Therapeutic Class
Antibiotics
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 2 Molecular Weight (mw) 554.6
Logarithm of the Partition Coefficient (xlogp) -1.3
Rotatable Bond Count (rotbonds) 8
Hydrogen Bond Donor Count (hbonddonor) 4
Hydrogen Bond Acceptor Count (hbondacc) 13
ADMET Property
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 3: high solubility and low permeability [3]
Bioavailability
The bioavailability of drug is 1% [4]
Clearance
The renal clearance of drug is 0.32-0.73 L/h [4]
Elimination
Ceftriaxone is primarily eliminated in the urine (33-67%), and the remainder is eliminated through secretion in the bile and removed from the body via the feces [4]
Half-life
The concentration or amount of drug in body reduced by one-half in 5.8 - 8.7 hours [4]
Metabolism
The drug is not metabolised []
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 120.26999 micromolar/kg/day [5]
Unbound Fraction
The unbound fraction of drug in plasma is 0.1% [6]
Vd
The volume of distribution (Vd) of drug is 5.78-13.5 L [4]
Water Solubility
The ability of drug to dissolve in water is measured as 400 mg/mL [3]
Chemical Identifiers
Formula
C18H18N8O7S3
IUPAC Name
(6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-[(2-methyl-5,6-dioxo-1H-1,2,4-triazin-3-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Canonical SMILES
CN1C(=NC(=O)C(=O)N1)SCC2=C(N3[C@@H]([C@@H](C3=O)NC(=O)/C(=N\\OC)/C4=CSC(=N4)N)SC2)C(=O)O
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
Cross-matching ID
PubChem CID
5479530
ChEBI ID
CHEBI:29007
CAS Number
73384-59-5
DrugBank ID
DB01212
TTD ID
D07ACT
VARIDT ID
DR00553
INTEDE ID
DR2655
Combinatorial Drugs (CBD) Click to Jump to the Detailed CBD Information of This Drug
Repurposed Drugs (RPD) Click to Jump to the Detailed RPD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Bacterial Penicillin binding protein (Bact PBP) TTJP4SM NOUNIPROTAC Modulator [7]

Drug Transporter (DTP)
DTP Name DTP ID UniProt ID MOA REF
Peptide transporter 1 (SLC15A1) DT9G7XN S15A1_HUMAN Substrate [8]
Multidrug resistance-associated protein 2 (ABCC2) DTFI42L MRP2_HUMAN Substrate [9]
Organic anion transporting polypeptide 1B3 (SLCO1B3) DT9C1TS SO1B3_HUMAN Substrate [10]
P-glycoprotein 1 (ABCB1) DTUGYRD MDR1_HUMAN Substrate [9]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Beta-lactamase (blaB) DEEAL81 BLA2_KLEPO Substrate [11]
Beta-lactamase (blaB) DEYIEO5 AMPC_SERMA Substrate [12], [13]
Beta-lactamase (blaB) DEBKS91 A0A1B1FBM9_ACIBA Substrate [14]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Dihydrofolate reductase (DHFR) OT3DVIGM DYR_HUMAN Gene/Protein Processing [15]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Disease Different from Ceftriaxone (Comorbidity)
DDI Drug Name DDI Drug ID Severity Mechanism Comorbidity REF
Plazomicin DMKMBES Moderate Increased risk of nephrotoxicity by the combination of Ceftriaxone and Plazomicin. Urinary tract infection [GC08] [16]

References

1 Ceftriaxone FDA Label
2 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 5326).
3 BDDCS applied to over 900 drugs
4 DailyMed Label: ceftriaxone sodium injection, powder for solution
5 Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
6 Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
7 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services.
8 Intestinal transport of beta-lactam antibiotics: analysis of the affinity at the H+/peptide symporter (PEPT1), the uptake into Caco-2 cell monolayers and the transepithelial flux. Pharm Res. 1999 Jan;16(1):55-61.
9 Mammalian drug efflux transporters of the ATP binding cassette (ABC) family in multidrug resistance: A review of the past decade. Cancer Lett. 2016 Jan 1;370(1):153-64.
10 Screening of antibiotics that interact with organic anion-transporting polypeptides 1B1 and 1B3 using fluorescent probes. Biol Pharm Bull. 2011;34(3):389-95.
11 Antibiotic resistance and production of extended-spectrum beta-lactamases amongst Klebsiella spp. from intensive care units in Europe. J Antimicrob Chemother. 1996 Sep;38(3):409-24.
12 Determination of the antibiotic resistance rates of Serratia marcescens isolates obtained from various clinical specimens. Niger J Clin Pract. 2019 Jan;22(1):125-130.
13 Serratia marcescens is injurious to intestinal epithelial cells. Gut Microbes. 2014;5(6):729-36.
14 Drug-resistant genes carried by Acinetobacter baumanii isolated from patients with lower respiratory tract infection. Chin Med J (Engl). 2010 Sep;123(18):2571-5.
15 Investigation of the effects of some drugs and phenolic compounds on human dihydrofolate reductase activity. J Biochem Mol Toxicol. 2015 Mar;29(3):135-9.
16 Agencia Espaola de Medicamentos y Productos Sanitarios Healthcare "Centro de informacion online de medicamentos de la AEMPS - CIMA.".