Cefamandole

Details

• Internal ID: 3f202677-7451-4d79-bed0-552ea64f3208
• Taxonomy: Organoheterocyclic compounds > Lactams > Beta lactams > Cephalosporins
• IUPAC Name: (6R,7R)-7-[[(2R)-2-hydroxy-2-phenylacetyl]amino]-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• InChI: InChI=1S/C18H18N6O5S2/c1-23-18(20-21-22-23)31-8-10-7-30-16-11(15(27)24(16)12(10)17(28)29)19-14(26)13(25)9-5-3-2-4-6-9/h2-6,11,13,16,25H,7-8H2,1H3,(H,19,26)(H,28,29)/t11-,13-,16-/m1/s1
• InChI Key: OLVCFLKTBJRLHI-AXAPSJFSSA-N
• Popularity: 3,125 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₁₈N₆O₅S₂
• Molecular Weight: 462.50 g/mol
• Exact Mass: 462.07801004 g/mol
• Topological Polar Surface Area (TPSA): 201.00 Ų
• XlogP: -0.90
• Atomic LogP (AlogP): -0.23
• H-Bond Acceptor: 10
• H-Bond Donor: 3
• Rotatable Bonds: 7

Synonyms

• Cefadole
• 34444-01-4
• CEPHAMANDOLE
• Cefamandol
• Cephadole
• Cefamandolum
• L-Cefamandole
• Compound 83405
• CHEBI:3480
• 5CKP8C2LLI
• (6R,7R)-7-(R)-Mandelamido-3-(((1-methyl-1H-tetrazol-5-yl)thio)methyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-carboxylic acid
• (6R,7R)-7-{[(2R)-2-hydroxy-2-phenylacetyl]amino}-3-{[(1-methyl-1H-tetrazol-5-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• COMPOUND-83405
• (6R,7R)-7-[[(2R)-2-hydroxy-2-phenylacetyl]amino]-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• J01DC03
• Kefdole
• 7-D-Mandelamido-3-(((1-methyl-1H-tetrazol-5-yl)thio)methyl)-3-cephem-4-carboxylic acid
• Kefamandol
• Mancef
• (6R,7R)-7-((R)-2-hydroxy-2-phenylacetamido)-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,7R)-7-[(2R)-2-hydroxy-2-phenylacetamido]-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
• 7-[(2-hydroxy-2-phenylacetyl)amino]-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• 30034-03-8
• UNII-5CKP8C2LLI
• Cefamandol [INN-Spanish]
• Cefamandole (USAN/INN)
• Cefamandolum [INN-Latin]
• Cefamandole [USAN:INN:BAN]
• free form'
• (6R,7R)-7-(R)-Mandelamido-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-carboxylic acid
• 5-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 7-((hydroxyphenylacetyl)amino)-3-(((1-methyl-1H-tetrazol-5-yl)thio)methyl)-8-oxo-, (6R-(6alpha,7beta(R*)))-
• EINECS 252-030-0
• BRN 0598510
• CEFAMANDOLE [MI]
• Prestwick0_000747
• Prestwick1_000747
• Prestwick2_000747
• Prestwick3_000747
• CEFAMANDOLE [INN]
• CEFAMANDOLE [USAN]
• Epitope ID:141490
• CEFAMANDOLE [VANDF]
• CEFAMANDOLE [MART.]
• CHEMBL1146
• SCHEMBL37287
• BSPBio_000734
• CEFAMANDOLE [WHO-DD]
• SPBio_002673
• BPBio1_000808
• DTXSID7022750
• GTPL12210
• OLVCFLKTBJRLHI-AXAPSJFSSA-N
• HY-B1128
• BDBM50350468
• AKOS025401365
• AC-1294
• CS-4724
• DB01326
• (6R,7R)-7-[[(2R)-2-hydroxy-2-phenyl-acetyl]amino]-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• (6R,7R)-7-{[(2R)-2-hydroxy-2-phenylacetyl]amino}-3-{[(1-methyl-1H-tetrazol-5-yl)thio]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• 7beta-[(2R)-2-hydroxy-2-phenylacetamido]-3-{[(1-methyl-1H-tetrazol-5-yl)sulfanyl]methyl}ceph-3-em-4-carboxylic acid
• C06879
• D02344
• Cefamandole, Antibiotic for Culture Media Use Only
• EN300-19734690
• Q2601530
• W-106736
• BRD-K27130738-236-03-4
• (6R,7R)-7-((R)-2-hydroxy-2-phenylacetamido)-3-((1-methyl-1H-tetrazol-5-ylthio)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-((HYDROXYPHENYLACETYL)AMINO)-3-(((1-METHYL-1H-TETRAZOL-5-YL)THIO)METHYL)-8-OXO-, (6R-(6.ALPHA.,7.BETA.(R*)))-
• 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 7-[[(2R)-2-hydroxy-2-phenylacetyl]amino]-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-8-oxo-, (6R,7R)-
• 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 7-[[(2R)-2-hydroxy-2-phenylacetyl]amino]-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-8-oxo-, 6R,7R)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.9394	93.94%
Caco-2	-	0.8846	88.46%
Blood Brain Barrier	-	1.0000	100.00%
Human oral bioavailability	+	0.8429	84.29%
Subcellular localzation	Mitochondria	0.6283	62.83%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9387	93.87%
OATP1B3 inhibitior	+	0.9398	93.98%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.4549	45.49%
P-glycoprotein inhibitior	-	0.7477	74.77%
P-glycoprotein substrate	+	0.7527	75.27%
CYP3A4 substrate	+	0.6230	62.30%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8714	87.14%
CYP3A4 inhibition	-	0.7111	71.11%
CYP2C9 inhibition	-	0.7509	75.09%
CYP2C19 inhibition	-	0.7454	74.54%
CYP2D6 inhibition	-	0.8653	86.53%
CYP1A2 inhibition	-	0.8336	83.36%
CYP2C8 inhibition	-	0.8001	80.01%
CYP inhibitory promiscuity	+	0.5818	58.18%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.5072	50.72%
Eye corrosion	-	0.9886	98.86%
Eye irritation	-	0.9779	97.79%
Skin irritation	-	0.7581	75.81%
Skin corrosion	-	0.9191	91.91%
Ames mutagenesis	-	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5347	53.47%
Micronuclear	+	0.9600	96.00%
Hepatotoxicity	+	0.9952	99.52%
skin sensitisation	-	0.8369	83.69%
Respiratory toxicity	+	0.9889	98.89%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	+	0.9750	97.50%
Nephrotoxicity	+	0.7766	77.66%
Acute Oral Toxicity (c)	III	0.5103	51.03%
Estrogen receptor binding	-	0.5000	50.00%
Androgen receptor binding	-	0.8512	85.12%
Thyroid receptor binding	+	0.5178	51.78%
Glucocorticoid receptor binding	-	0.6451	64.51%
Aromatase binding	-	0.6141	61.41%
PPAR gamma	-	0.5347	53.47%
Honey bee toxicity	-	0.8136	81.36%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.6400	64.00%
Fish aquatic toxicity	+	0.9693	96.93%

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	99.01%	96.09%
CHEMBL2581	P07339	Cathepsin D	98.29%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.24%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.17%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	90.25%	99.23%
CHEMBL1293294	P51151	Ras-related protein Rab-9A	89.32%	87.67%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	85.66%	93.00%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	85.20%	90.71%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	84.44%	81.11%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	81.58%	96.67%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	81.43%	97.50%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 456255
• LOTUS: LTS0252717
• wikiData: Q2601530