Cefuroxime Axetil

Details

• Internal ID: 9c25cc5b-676e-42d3-b8d2-624b4767f319
• Taxonomy: Organoheterocyclic compounds > Lactams > Beta lactams > Cephalosporins > Cephalosporin 3-carbamates
• IUPAC Name: 1-acetyloxyethyl (6R,7R)-3-(carbamoyloxymethyl)-7-[[(2Z)-2-(furan-2-yl)-2-methoxyiminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
• SMILES (Canonical): CC(OC(=O)C)OC(=O)C1=C(CSC2N1C(=O)C2NC(=O)C(=NOC)C3=CC=CO3)COC(=O)N
• SMILES (Isomeric): CC(OC(=O)C)OC(=O)C1=C(CS[C@H]2N1C(=O)[C@H]2NC(=O)/C(=N\OC)/C3=CC=CO3)COC(=O)N
• InChI: InChI=1S/C20H22N4O10S/c1-9(25)33-10(2)34-19(28)15-11(7-32-20(21)29)8-35-18-14(17(27)24(15)18)22-16(26)13(23-30-3)12-5-4-6-31-12/h4-6,10,14,18H,7-8H2,1-3H3,(H2,21,29)(H,22,26)/b23-13-/t10?,14-,18-/m1/s1
• InChI Key: KEJCWVGMRLCZQQ-YJBYXUATSA-N
• Popularity: 792 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₂N₄O₁₀S
• Molecular Weight: 510.50 g/mol
• Exact Mass: 510.10566408 g/mol
• Topological Polar Surface Area (TPSA): 214.00 Ų
• XlogP: 0.90
• Atomic LogP (AlogP): -0.17
• H-Bond Acceptor: 12
• H-Bond Donor: 2
• Rotatable Bonds: 9

Synonyms

• Elobact
• Zinat
• Ceftin
• Cepazine
• Cetoxil
• Cefuroxime 1-acetoxyethyl ester
• Cefurax
• Oraxim
• Zinnat
• Bioracef
• CXM-AX
• 64544-07-6
• Cethixim
• Coliofossim
• Furoxime
• Celocid
• Kalcef
• Medoxm
• Nivador
• Novador
• Novocef
• Zoref
• CCI 15641
• CCI-15641
• Curocef
• Sharox-500
• DRG-0157
• SN 407
• Cefuroxime (as axetil)
• UNII-Z49QDT0J8Z
• Z49QDT0J8Z
• BRN 6854419
• CHEBI:3516
• HSDB 8150
• NSC-758677
• NSC 758677
• Cefuroxime axetil [USAN:USP:BAN:JAN]
• 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid,3-[[(aminocarbonyl)oxy]methyl]-7-[[(2Z)-2-furanyl(methoxyimino)acetyl]amino]-8-oxo-, 1-(acetyloxy)ethyl ester, (6R,7R)-
• CEFUROXIME AXETIL (MART.)
• CEFUROXIME AXETIL [MART.]
• CEFUROXIME AXETIL (USP-RS)
• CEFUROXIME AXETIL [USP-RS]
• CEFUROXIME AXETIL (EP MONOGRAPH)
• CEFUROXIME AXETIL [EP MONOGRAPH]
• Cefuroxime axetil (USAN:USP:BAN:JAN)
• CEFUROXIME AXETIL (USP MONOGRAPH)
• CEFUROXIME AXETIL [USP MONOGRAPH]
• DTXSID0022775
• Cefuroximaxetil
• Maxitil
• Ceftin (TN)
• (E)-Cefuroxime Axetil
• (RS)-1-Hydroxyethyl (6R,7R)-7-(2-(2-furyl)glyoxylamido)-3-(hydroxymethyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylate, 7(sup 2)-(Z)-(O-methyloxime), 1-acetate 3-carbamate
• SCHEMBL721709
• DTXCID702775
• CEFUROXIME AXETIL [JAN]
• CEFUROXIME AXETIL [USAN]
• CHEMBL1095930
• CEFUROXIME AXETIL [VANDF]
• HMS3715J04
• CEFUROXIME AXETIL [WHO-DD]
• HY-B1325
• BDBM50248197
• Cefuroxime axetil (JP17/USP/INN)
• MFCD00864991
• s4813
• SN-407
• Cefuroxime Axetil for Oral Suspension
• AKOS015896220
• CCG-221241
• CEFUROXIME AXETIL [ORANGE BOOK]
• 5-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 3-(((aminocarbonyl)oxy)methyl)-7-((2-furanyl(methoxyimino)acetyl)amino)-8-oxo-, 1-(acetyloxy)ethyl ester, (6R-(6alpha,7beta(Z)))-
• CEFUROXIME 1-ACETOXYETHYL ESTER [MI]
• CS-0013084
• C08107
• D00914
• A830563
• A834806
• Q27293978
• Cefuroxime Axetil, European Pharmacopoeia (EP) Reference Standard
• Cefuroxime Axetil, United States Pharmacopeia (USP) Reference Standard
• (1RS)-1-Acetoxyethyl (6R,7R)-3-carbamoyloxymethyl-7-((Z)-2-furan-2-yl-2-(methoxyimino)acetylamino)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylate
• (6R,7R)-3-(carbamoyloxymethyl)-7-[[(2Z)-2-(2-furyl)-2-methoxyimino-acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid;Cefuroxime
• (RS)-1-Hydroxyethyl (6R,7R)-7-(2-(2-furyl)glyoxylamido)-3- (hydroxymethyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2- carboxylate, 7(sup 2)-(Z)-(O-methyloxime), 1-acetate 3- carbamate
• [6R-[6alpha,7beta(Z)]]-3-[[(Aminocarbonyl)oxy]methyl]-7-[[2-furanyl(methoxyimino)acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid 1-(acetyloxy)ethyl ester
• 1-acetoxyethyl (6R,7R)-3-(carbamoyloxymethyl)-7-[[(2Z)-2-(2-furyl)-2-methoxyimino-acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate;Cefuroxime axetil
• 5-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 3- (((aminocarbonyl)oxy)methyl)-7-((2- furanyl(methoxyimino)acetyl)amino)-8-oxo-, 1- (acetyloxy)ethyl ester, (6R-(6alpha,7beta(Z)))-
• 5-THIA-1-AZABICYCLO(4.2.0)OCT-2-ENE-2-CARBOXYLIC ACID, 3-(((AMINOCARBONYL)OXY)METHYL)-7-((2-FURANYL(METHOXYIMINO)ACETYL)AMINO)-8-OXO-, 1-(ACETYLOXY)ETHYL ESTER, (6R-(6.ALPHA.,7.BETA.(Z)))-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6341	63.41%
Caco-2	-	0.8210	82.10%
Blood Brain Barrier	-	0.9750	97.50%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Lysosomes	0.4690	46.90%
OATP2B1 inhibitior	-	0.8556	85.56%
OATP1B1 inhibitior	+	0.9070	90.70%
OATP1B3 inhibitior	+	0.9415	94.15%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.9437	94.37%
P-glycoprotein inhibitior	+	0.7609	76.09%
P-glycoprotein substrate	-	0.6284	62.84%
CYP3A4 substrate	+	0.6936	69.36%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8736	87.36%
CYP3A4 inhibition	+	0.5147	51.47%
CYP2C9 inhibition	-	0.7234	72.34%
CYP2C19 inhibition	-	0.6421	64.21%
CYP2D6 inhibition	-	0.8705	87.05%
CYP1A2 inhibition	-	0.6659	66.59%
CYP2C8 inhibition	+	0.5000	50.00%
CYP inhibitory promiscuity	-	0.8132	81.32%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8200	82.00%
Carcinogenicity (trinary)	Non-required	0.4917	49.17%
Eye corrosion	-	0.9838	98.38%
Eye irritation	-	0.9582	95.82%
Skin irritation	-	0.7538	75.38%
Skin corrosion	-	0.9175	91.75%
Ames mutagenesis	-	0.6154	61.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.5721	57.21%
Micronuclear	+	0.9200	92.00%
Hepatotoxicity	-	0.9000	90.00%
skin sensitisation	-	0.8260	82.60%
Respiratory toxicity	+	0.9111	91.11%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	+	0.9500	95.00%
Nephrotoxicity	+	0.7951	79.51%
Acute Oral Toxicity (c)	IV	0.6091	60.91%
Estrogen receptor binding	+	0.6907	69.07%
Androgen receptor binding	+	0.6622	66.22%
Thyroid receptor binding	+	0.5334	53.34%
Glucocorticoid receptor binding	+	0.6035	60.35%
Aromatase binding	-	0.5368	53.68%
PPAR gamma	-	0.5568	55.68%
Honey bee toxicity	-	0.8090	80.90%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	0.9629	96.29%

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	99.34%	96.09%
CHEMBL2581	P07339	Cathepsin D	98.09%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.02%	94.45%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	96.46%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.94%	91.11%
CHEMBL3060	Q9Y345	Glycine transporter 2	92.67%	99.17%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	88.59%	95.89%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.42%	95.89%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.88%	97.09%
CHEMBL3830	Q2M2I8	Adaptor-associated kinase	84.01%	83.10%
CHEMBL3891	P07384	Calpain 1	83.79%	93.04%
CHEMBL340	P08684	Cytochrome P450 3A4	83.37%	91.19%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.81%	95.56%
CHEMBL3401	O75469	Pregnane X receptor	82.69%	94.73%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	81.76%	95.50%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	81.38%	89.62%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	80.80%	93.00%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.45%	90.71%
CHEMBL4208	P20618	Proteasome component C5	80.31%	90.00%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 6321416
• LOTUS: LTS0060308
• wikiData: Q3604308