Ceftazidime

Details

• Internal ID: 8b5d2819-c56f-4812-ac79-8cb45fdc1bb9
• Taxonomy: Organoheterocyclic compounds > Lactams > Beta lactams > Cephalosporins
• IUPAC Name: (6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(2-carboxypropan-2-yloxyimino)acetyl]amino]-8-oxo-3-(pyridin-1-ium-1-ylmethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
• SMILES (Canonical): CC(C)(C(=O)O)ON=C(C1=CSC(=N1)N)C(=O)NC2C3N(C2=O)C(=C(CS3)C[N+]4=CC=CC=C4)C(=O)[O-]
• SMILES (Isomeric): CC(C)(C(=O)O)O/N=C(/C1=CSC(=N1)N)\C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)C[N+]4=CC=CC=C4)C(=O)[O-]
• InChI: InChI=1S/C22H22N6O7S2/c1-22(2,20(33)34)35-26-13(12-10-37-21(23)24-12)16(29)25-14-17(30)28-15(19(31)32)11(9-36-18(14)28)8-27-6-4-3-5-7-27/h3-7,10,14,18H,8-9H2,1-2H3,(H4-,23,24,25,29,31,32,33,34)/b26-13-/t14-,18-/m1/s1
• InChI Key: ORFOPKXBNMVMKC-DWVKKRMSSA-N
• Popularity: 16,109 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₂N₆O₇S₂
• Molecular Weight: 546.60 g/mol
• Exact Mass: 546.09913941 g/mol
• Topological Polar Surface Area (TPSA): 245.00 Ų
• XlogP: 0.40
• Atomic LogP (AlogP): -1.30
• H-Bond Acceptor: 11
• H-Bond Donor: 3
• Rotatable Bonds: 9

Synonyms

• 72558-82-8
• Tazidime
• Fortaz
• Ceftazidime anhydrous
• Pentacef
• Tazicef
• Ceptaz
• ceftazidima
• ceftazidimum
• GR 20263
• CHEBI:3508
• Fortaz (TN)
• (6R,7R)-7-[[2-(2-Amino-1,3-thiazol-4-yl)-2-(2-carboxypropan-2-yloxyimino)acetyl]amino]-8-oxo-3-(pyridin-1-ium-1-ylmethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
• 7-[[(2E)-2-(2-amino-1,3-thiazol-4-yl)-2-(2-carboxypropan-2-yloxyimino)acetyl]amino]-8-oxo-3-(pyridin-1-ium-1-ylmethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
• GR-20263
• LY-139381
• 78439-06-2
• (6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(2-carboxypropan-2-yloxyimino)acetyl]amino]-8-oxo-3-(pyridin-1-ium-1-ylmethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
• CAZ
• J01DD07
• 1-{[(6R,7R)-7-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-[(1-carboxy-1-methylethoxy)imino]acetamido]-2-carboxylato-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl}pyridin-1-ium
• NSC-759260
• Ceftazidime (TN)
• Ceptaz (TN)
• SCHEMBL36849
• BIDD:GT0734
• CHEMBL44354
• DTXSID5022770
• HMS2090M13
• (6R,7R)-7-{[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-{[(2-carboxypropan-2-yl)oxy]imino}acetyl]amino}-8-oxo-3-(pyridinium-1-ylmethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
• HY-B0593
• BDBM50420259
• AKOS015951273
• CCG-269983
• DB00438
• NCGC00179584-05
• CEFTAZIDIME (ARGININE FORMULATION)
• AB00513848
• C06889
• D07654
• AB00513848-02
• Cefprozil, Antibiotic for Culture Media Use Only
• A839420
• EN300-22411480
• Q-200811
• (6R,7R)-7-((Z)-2-(2-Aminothiazol-4-yl)-2-(((2-carboxypropan-2-yl)oxy)imino)acetamido)-8-oxo-3-(pyridin-1-ium-1-ylmethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate (contains ca. 10% Na2CO3)
• (6R,7R)-7-((Z)-2-(2-Aminothiazol-4-yl)-2-(((2-carboxypropan-2-yl)oxy)imino)acetamido)-8-oxo-3-(pyridin-1-ium-1-ylmethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate(containsca.10%Na2CO3)
• (6R,7R)-7-({(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-[(1-carboxy-1-methylethoxy)imino]acetyl}amino)-8-oxo-3-(pyridinium-1-ylmethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
• 7beta-{[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-{[(2-carboxypropan-2-yl)oxy]imino}acetyl]amino}-3-(pyridinium-1-ylmethyl)-3,4-didehydrocepham-4-carboxylate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.9659	96.59%
Caco-2	-	0.8863	88.63%
Blood Brain Barrier	-	0.9750	97.50%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Lysosomes	0.3777	37.77%
OATP2B1 inhibitior	-	0.8589	85.89%
OATP1B1 inhibitior	+	0.8596	85.96%
OATP1B3 inhibitior	+	0.9323	93.23%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.7612	76.12%
P-glycoprotein inhibitior	+	0.6811	68.11%
P-glycoprotein substrate	+	0.6106	61.06%
CYP3A4 substrate	+	0.6737	67.37%
CYP2C9 substrate	-	0.8034	80.34%
CYP2D6 substrate	-	0.8789	87.89%
CYP3A4 inhibition	-	0.8354	83.54%
CYP2C9 inhibition	-	0.7396	73.96%
CYP2C19 inhibition	-	0.7009	70.09%
CYP2D6 inhibition	-	0.8758	87.58%
CYP1A2 inhibition	-	0.8112	81.12%
CYP2C8 inhibition	+	0.5208	52.08%
CYP inhibitory promiscuity	-	0.7222	72.22%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.7500	75.00%
Carcinogenicity (trinary)	Non-required	0.4679	46.79%
Eye corrosion	-	0.9849	98.49%
Eye irritation	-	0.9502	95.02%
Skin irritation	-	0.7528	75.28%
Skin corrosion	-	0.9166	91.66%
Ames mutagenesis	-	0.7082	70.82%
Human Ether-a-go-go-Related Gene inhibition	-	0.5793	57.93%
Micronuclear	+	0.9100	91.00%
Hepatotoxicity	+	0.9253	92.53%
skin sensitisation	-	0.8279	82.79%
Respiratory toxicity	+	1.0000	100.00%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	1.0000	100.00%
Nephrotoxicity	+	0.7709	77.09%
Acute Oral Toxicity (c)	IV	0.5470	54.70%
Estrogen receptor binding	+	0.6964	69.64%
Androgen receptor binding	-	0.5473	54.73%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	+	0.6465	64.65%
Aromatase binding	+	0.6344	63.44%
PPAR gamma	+	0.6858	68.58%
Honey bee toxicity	-	0.7993	79.93%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	0.9834	98.34%

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	98.28%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.21%	95.56%
CHEMBL2581	P07339	Cathepsin D	93.25%	98.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	90.67%	99.23%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.01%	86.33%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	88.29%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	87.83%	91.11%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	84.86%	97.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.45%	99.17%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	83.61%	93.00%
CHEMBL3384	Q16512	Protein kinase N1	82.62%	80.71%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.03%	97.09%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 5481173
• LOTUS: LTS0253707
• wikiData: Q808845