Ceftriaxone

Details

• Internal ID: 75599c3d-11b0-4e3d-bbaa-0016b8e1cdfc
• Taxonomy: Organoheterocyclic compounds > Lactams > Beta lactams > Cephalosporins
• 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
• 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
• InChI Key: VAAUVRVFOQPIGI-SPQHTLEESA-N
• Popularity: 7,451 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₁₈N₈O₇S₃
• Molecular Weight: 554.60 g/mol
• Exact Mass: 554.04605846 g/mol
• Topological Polar Surface Area (TPSA): 288.00 Ų
• XlogP: -1.30
• Atomic LogP (AlogP): -1.61
• H-Bond Acceptor: 14
• H-Bond Donor: 4
• Rotatable Bonds: 8

Synonyms

• Biotrakson
• Rocephin
• Ceftriaxon
• 73384-59-5
• Ceftriaxona
• Ceftriaxonum
• Ceftriazone
• Rocefin
• Ceftriaxonum [INN-Latin]
• Ceftriaxona [INN-Spanish]
• Rocephine
• CEFTRIAXONE SODIUM
• DRG-0071
• CHEBI:29007
• EINECS 277-405-6
• Rocephalin
• Ceftriaxone (INN)
• UNII-75J73V1629
• CHEMBL161
• CTRX
• (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
• 75J73V1629
• DTXSID0022773
• 5-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 7-(((2-amino-4-thiazolyl)(methoxyimino)acetyl)amino)-8-oxo-3-(((1,2,5,6-tetrahydro-2-methyl-5,6-dioxo-1,2,4-triazin-3-yl)thio)methyl)-, (6R-(6alpha,7beta(Z)))-
• CEFTRIAXONE [INN]
• Ceftriaxonum (INN-Latin)
• Ceftriaxona (INN-Spanish)
• (E)-Ceftriaxone
• 74578-69-1
• Ro 139904
• Rophex
• Ceftriaxone (TN)
• (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
• (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
• 5-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 7-(((2Z)-(2-amino-4-thiazolyl)(methoxyimino)acetyl)amino)-8-oxo-3-(((1,2,5,6-tetrahydro-2-methyl-5,6-dioxo-1,2,4-triazin-3-yl)thio)methyl)-, (6R,7R)-
• 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
• Ceftriaxone [USAN:INN:JAN]
• (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
• ceftriaxonum natricum
• CEFTRIAXONE [MI]
• CEFTRIAXONE [VANDF]
• SCHEMBL23354
• CEFTRIAXONE [WHO-DD]
• DTXCID902773
• J01DA13
• HY-B0712
• BDBM50049707
• BDBM50103601
• AKOS015960618
• AC-1592
• DB01212
• (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-aminothiazol-4-yl)-2-methoxyimino-acetyl]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
• AS-56320
• C06683
• D07659
• A899928
• EN300-23582312
• Cefatriaxone, Antibiotic for Culture Media Use Only
• W-104454
• (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
• (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, 7^2-(Z)-(O-
• (6R,7R)-7-{2-(2-Amino-thiazol-4-yl)-2-[(Z)-methoxyimino]-acetylamino}-3-(2-methyl-5,6-dioxo-1,2,5,6-tetrahydro-[1,2,4]triazin-3-ylsulfanylmethyl)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• (6R,7R)-7-{2-(2-Amino-thiazol-4-yl)-2-[(Z)-methoxyimino]-acetylamino}-3-(6-hydroxy-2-methyl-5-oxo-2,5-dihydro-[1,2,4]triazin-3-ylsulfanylmethyl)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• (6R,7R,)-7-(2-(2-aminothiazol-4-yl)-2-(methoxyimino)acetamido)-3-((2-methyl-5,6-dioxo-1,2,5,6-tetrahydro-1,2,4-triazin-3-ylthio)methyl)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• (6R,7R,Z)-7-(2-(2-aminothiazol-4-yl)-2-(methoxyimino)acetamido)-3-((2-methyl-5,6-dioxo-1,2,5,6-tetrahydro-1,2,4-triazin-3-ylthio)methyl)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• (6R,7R,Z)-7-(2-(2-aminothiazol-4-yl)-2-(methoxyimino)acetamido)-3-((6-hydroxy-2-methyl-5-oxo-2,5-dihydro-1,2,4-triazin-3-ylthio)methyl)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• 5-THIA-1-AZABICYCLO(4.2.0)OCT-2-ENE-2-CARBOXYLIC ACID, 7-(((2-AMINO-4-THIAZOLYL)(METHOXYIMINO)ACETYL)AMINO)-8-OXO-3-(((1,2,5,6-TETRAHYDRO-2-METHYL-5,6-DIOXO-1,2,4-TRIAZIN-3-YL)THIO)METHYL)-, (6R-(6.ALPHA.,7.BETA.(Z)))-
• 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 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]-, (6R,7R)-
• 7-[2-(2-Amino-thiazol-4-yl)-2-methoxyimino-acetylamino]-3-(6-hydroxy-2-methyl-5-oxo-2,5-dihydro-[1,2,4]triazin-3-ylsulfanylmethyl)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid (Ceftriaxone)
• 7-[2-(2-Amino-thiazol-4-yl)-2-methoxyimino-acetylamino]-3-(6-hydroxy-2-methyl-5-oxo-2,5-dihydro-[1,2,4]triazin-3-ylsulfanylmethyl)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid(Ceftriaxone)

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.9724	97.24%
Caco-2	-	0.9373	93.73%
Blood Brain Barrier	-	1.0000	100.00%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.4446	44.46%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9070	90.70%
OATP1B3 inhibitior	+	0.9376	93.76%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.7783	77.83%
P-glycoprotein inhibitior	+	0.5823	58.23%
P-glycoprotein substrate	+	0.7362	73.62%
CYP3A4 substrate	+	0.6665	66.65%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8683	86.83%
CYP3A4 inhibition	+	0.6432	64.32%
CYP2C9 inhibition	-	0.7088	70.88%
CYP2C19 inhibition	-	0.7034	70.34%
CYP2D6 inhibition	-	0.8666	86.66%
CYP1A2 inhibition	-	0.7538	75.38%
CYP2C8 inhibition	+	0.5082	50.82%
CYP inhibitory promiscuity	+	0.5509	55.09%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.7700	77.00%
Carcinogenicity (trinary)	Non-required	0.5045	50.45%
Eye corrosion	-	0.9876	98.76%
Eye irritation	-	0.9549	95.49%
Skin irritation	-	0.7600	76.00%
Skin corrosion	-	0.9171	91.71%
Ames mutagenesis	-	0.8000	80.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6558	65.58%
Micronuclear	+	0.9600	96.00%
Hepatotoxicity	+	0.9699	96.99%
skin sensitisation	-	0.8339	83.39%
Respiratory toxicity	+	1.0000	100.00%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	+	0.9930	99.30%
Nephrotoxicity	+	0.8985	89.85%
Acute Oral Toxicity (c)	III	0.4938	49.38%
Estrogen receptor binding	-	0.5655	56.55%
Androgen receptor binding	-	0.5470	54.70%
Thyroid receptor binding	-	0.5832	58.32%
Glucocorticoid receptor binding	-	0.6264	62.64%
Aromatase binding	+	0.6442	64.42%
PPAR gamma	+	0.5683	56.83%
Honey bee toxicity	-	0.7694	76.94%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5400	54.00%
Fish aquatic toxicity	+	0.9864	98.64%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	99.23%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	96.70%	85.14%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	92.83%	99.23%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	91.30%	93.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.95%	95.56%
CHEMBL1293294	P51151	Ras-related protein Rab-9A	86.55%	87.67%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	85.61%	94.42%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.54%	97.09%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	85.48%	90.71%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.63%	99.17%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	83.62%	81.11%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	83.32%	96.67%
CHEMBL4208	P20618	Proteasome component C5	83.06%	90.00%
CHEMBL3384	Q16512	Protein kinase N1	82.48%	80.71%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	82.36%	89.34%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.85%	94.45%
CHEMBL2443	P49862	Kallikrein 7	80.29%	94.00%
CHEMBL2581	P07339	Cathepsin D	80.24%	98.95%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 5479530
• LOTUS: LTS0116489
• wikiData: Q421713