Drug Information

General Information
Drug ID
DR00553
Drug Name
Ceftriaxone
Synonyms
(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; Biotrakson; CEFTRIAXONE SODIUM; CTRX; Cefatriaxone; Ceftriaxon; Ceftriaxona; Ceftriaxona [INN-Spanish]; Ceftriaxone (INN); Ceftriaxone (TN); Ceftriaxone [USAN:JAN]; Ceftriaxone intravenous; Ceftriaxone, Disodium Salt; Ceftriaxone, Disodium Salt, Hemiheptahydrate; Ceftriaxonum; Ceftriaxonum [INN-Latin]; Ceftriazone; DRG-0071; Longacef; Longaceph; Ro 139904; Ro-13-9904; Ro13-9904; Rocefin; Rocephin; Rocephin (TN); Rocephine
Drug Type
Small molecular drug
Indication Pneumonia [ICD11:CA40] Approved [1]
Middle ear infections [ICD11:AB0Z] Approved [1]
Endocarditis [ICD11:1B41.1] Approved [1]
Meningitis [ICD11:1D01.Y] Approved [1]
Therapeutic Class
Antibiotics
Structure
3D MOL 2D MOL
Formula
C18H18N8O7S3
Canonical SMILES
CN1C(=NC(=O)C(=O)N1)SCC2=C(N3C(C(C3=O)NC(=O)C(=NOC)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
CAS Number
CAS 73384-59-5
Pharmaceutical Properties Molecular Weight 554.6 Topological Polar Surface Area 288
Heavy Atom Count 36 Rotatable Bond Count 8
Hydrogen Bond Donor Count 4 Hydrogen Bond Acceptor Count 13
XLogP
-1.3
PubChem CID
5479530
PubChem SID
103240795 ,103980019 ,113985965 ,11693489 ,124766008 ,126631063 ,126657477 ,134224100 ,134337467 ,134338568 ,135011808 ,137019029 ,140116145 ,141914537 ,14886134 ,14935103 ,152100037 ,15968575 ,160964545 ,162178862 ,175265409 ,176267075 ,179151046 ,179323748 ,196109964 ,210279827 ,210282150 ,223653569 ,223680127 ,223680436 ,226412100 ,241132770 ,250133954 ,252122133 ,39470230 ,46506458 ,48415733 ,50050959 ,51091963 ,57363926 ,602917 ,7978887 ,79861798 ,87322639 ,8908 ,92711237
ChEBI ID
CHEBI:3441
TTD Drug ID
D07ACT
DT(s) Transporting This Drug MRP2 Transporter Info Multidrug resistance-associated protein 2 Substrate [2]
OATP1B3 Transporter Info Organic anion transporting polypeptide 1B3 Substrate [3]
P-GP Transporter Info P-glycoprotein 1 Substrate [2]
PEPT1 Transporter Info Peptide transporter 1 Substrate [4]
References
1 Ceftriaxone was approved by FDA. The official website of the U.S. Food and Drug Administration. (2019)
2 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.
3 Screening of antibiotics that interact with organic anion-transporting polypeptides 1B1 and 1B3 using fluorescent probes. Biol Pharm Bull. 2011;34(3):389-95.
4 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.

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