Cefmetazole

Details

• Internal ID: 66c0774c-0885-4fce-a37c-810ab7c0b2b9
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Amino acids, peptides, and analogues > N-acyl-alpha amino acids and derivatives
• IUPAC Name: (6R,7S)-7-[[2-(cyanomethylsulfanyl)acetyl]amino]-7-methoxy-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• SMILES (Canonical): CN1C(=NN=N1)SCC2=C(N3C(C(C3=O)(NC(=O)CSCC#N)OC)SC2)C(=O)O
• SMILES (Isomeric): CN1C(=NN=N1)SCC2=C(N3[C@@H]([C@@](C3=O)(NC(=O)CSCC#N)OC)SC2)C(=O)O
• InChI: InChI=1S/C15H17N7O5S3/c1-21-14(18-19-20-21)30-6-8-5-29-13-15(27-2,17-9(23)7-28-4-3-16)12(26)22(13)10(8)11(24)25/h13H,4-7H2,1-2H3,(H,17,23)(H,24,25)/t13-,15+/m1/s1
• InChI Key: SNBUBQHDYVFSQF-HIFRSBDPSA-N
• Popularity: 1,192 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₇N₇O₅S₃
• Molecular Weight: 471.50 g/mol
• Exact Mass: 471.04533019 g/mol
• Topological Polar Surface Area (TPSA): 239.00 Ų
• XlogP: -0.60
• Atomic LogP (AlogP): -0.73
• H-Bond Acceptor: 12
• H-Bond Donor: 2
• Rotatable Bonds: 9

Synonyms

• 56796-20-4
• Cefmetazolo
• Cefmetazolum
• Cefmetazolum [INN-Latin]
• Cefmetazolo [INN-Spanish]
• (6R,7S)-7-[[2-(cyanomethylsulfanyl)acetyl]amino]-7-methoxy-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• CHEBI:3489
• U-72791
• 3J962UJT8H
• (6R,7S)-7-({[(cyanomethyl)sulfanyl]acetyl}amino)-7-methoxy-3-{[(1-methyl-1H-tetrazol-5-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• 56796-20-4 (free)
• (6R,7S)-7-(2-((Cyanomethyl)thio)acetamido)-7-methoxy-3-(((1-methyl-1H-tetrazol-5-yl)thio)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-((((cyanomethyl)thio)acetyl)amino)-7-methoxy-3-(((1-methyl-1H-tetrazol-5-yl)thio)methyl)-8-oxo-, (6R-cis)-
• 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid,7-[[[(cyanomethyl)thio]acetyl]amino]-7-methoxy-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-8-oxo-, (6R,7S)-
• SKF 83088
• CS 1170
• (6R,7S)-7-{2-[(cyanomethyl)sulfanyl]acetamido}-7-methoxy-3-{[(1-methyl-1H-1,2,3,4-tetrazol-5-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• U 72791
• Cefmetazole (USP/INN)
• EINECS 260-384-2
• BRN 0634647
• UNII-3J962UJT8H
• Cefmetazole [USAN:USP:INN]
• Cefmetazolesodium
• (6R,7S)-7-[2-[(Cyanomethyl)thio]acetamido]-7-methoxy-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• CefmetaZole, 95%
• CEFMETAZOLE [MI]
• Prestwick0_000700
• Prestwick1_000700
• Prestwick2_000700
• Prestwick3_000700
• CEFMETAZOLE [INN]
• CEFMETAZOLE [USAN]
• Epitope ID:116204
• CEFMETAZOLE [VANDF]
• CEFMETAZOLE [MART.]
• CS 1170;SKF 83088;U 72791;U 72791a
• Lopac0_000266
• BSPBio_000859
• CEFMETAZOLE [USP-RS]
• CEFMETAZOLE [WHO-DD]
• SCHEMBL147832
• SPBio_002780
• BPBio1_000945
• CEFMETAZOLE SODIUM [JAN]
• CHEMBL1201195
• DTXSID7022756
• GTPL12215
• CEFMETAZOLE [USP IMPURITY]
• CEFMETAZOLE [USP MONOGRAPH]
• BCP11998
• HY-B1595
• BDBM50350471
• MFCD00865068
• AKOS015896219
• DB00274
• SDCCGSBI-0050254.P002
• (6R,7S)-7-({[(cyanomethyl)thio]acetyl}amino)-7-(methyloxy)-3-{[(1-methyl-1H-tetrazol-5-yl)thio]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• (6R,7S)-7-(2-((Cyanomethyl)thio)acetamido)-7-methoxy-3-(((1-methyl-1H-tetrazol-5-yl)thiomethyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, sodium salt
• AC-13154
• BS-42476
• 2,6-DIFLUORO-4-METHOXYACETOPHENONE
• CS-0013513
• C08103
• D00910
• A831178
• EN300-19766367
• -1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• J-700159
• Q5057238
• (6R,7S)-7-({[(cyanomethyl)sulfanyl]acetyl}amino)-7-methoxy-3-{[(1-methyl-1H-tetrazol-5-yl)sulfanyl]methyl}-8-oxo-5-thia
• (6R,7S)-7-(2-(cyanomethylthio)acetamido)-7-methoxy-3-((1-methyl-1H-tetrazol-5-ylthio)methyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• (6R,7S)-7-[[2-(cyanomethylthio)-1-oxoethyl]amino]-7-methoxy-3-[[(1-methyl-5-tetrazolyl)thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• (6R,7S)-7-[2-(cyanomethylsulfanyl)ethanoylamino]-7-methoxy-3-[(1-methyl-1,2,3,4-tetrazol-5-yl)sulfanylmethyl]-8-oxidanylidene-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• 7beta-{[(cyanomethyl)sulfanyl]acetamido}-7alpha-methoxy-3-{[(1-methyl-1H-tetrazol-5-yl)sulfanyl]methyl}ceph-3-em-4-carboxylic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.8751	87.51%
Caco-2	-	0.9373	93.73%
Blood Brain Barrier	-	1.0000	100.00%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.4975	49.75%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9109	91.09%
OATP1B3 inhibitior	+	0.9404	94.04%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.8847	88.47%
P-glycoprotein inhibitior	-	0.9167	91.67%
P-glycoprotein substrate	+	0.7808	78.08%
CYP3A4 substrate	+	0.6737	67.37%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8771	87.71%
CYP3A4 inhibition	-	0.8551	85.51%
CYP2C9 inhibition	-	0.8200	82.00%
CYP2C19 inhibition	-	0.8093	80.93%
CYP2D6 inhibition	-	0.8950	89.50%
CYP1A2 inhibition	-	0.8575	85.75%
CYP2C8 inhibition	+	0.6018	60.18%
CYP inhibitory promiscuity	-	0.6417	64.17%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.5000	50.00%
Eye corrosion	-	0.9861	98.61%
Eye irritation	-	0.9691	96.91%
Skin irritation	-	0.7572	75.72%
Skin corrosion	-	0.9160	91.60%
Ames mutagenesis	-	0.5800	58.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7274	72.74%
Micronuclear	+	0.9300	93.00%
Hepatotoxicity	+	0.9803	98.03%
skin sensitisation	-	0.8219	82.19%
Respiratory toxicity	+	0.9222	92.22%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	1.0000	100.00%
Nephrotoxicity	+	0.9391	93.91%
Acute Oral Toxicity (c)	III	0.4864	48.64%
Estrogen receptor binding	+	0.6543	65.43%
Androgen receptor binding	+	0.5453	54.53%
Thyroid receptor binding	+	0.6697	66.97%
Glucocorticoid receptor binding	-	0.5111	51.11%
Aromatase binding	+	0.6235	62.35%
PPAR gamma	+	0.5956	59.56%
Honey bee toxicity	-	0.6329	63.29%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	+	0.8033	80.33%

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	98.79%	96.09%
CHEMBL2581	P07339	Cathepsin D	93.17%	98.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	90.97%	99.23%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.54%	94.45%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	90.42%	93.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	88.59%	85.14%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	86.25%	94.42%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	83.82%	97.50%
CHEMBL1744525	P43490	Nicotinamide phosphoribosyltransferase	83.70%	96.25%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	83.00%	97.33%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	82.95%	96.90%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	82.77%	96.77%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	82.61%	89.34%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.57%	95.56%
CHEMBL5255	O00206	Toll-like receptor 4	80.90%	92.50%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 42008
• LOTUS: LTS0014131
• wikiData: Q5057238