Ceforanide

Details

• Internal ID: 178d21cc-429a-4042-958d-bf38f3ae5c42
• Taxonomy: Organoheterocyclic compounds > Lactams > Beta lactams > Cephalosporins
• IUPAC Name: (6R,7R)-7-[[2-[2-(aminomethyl)phenyl]acetyl]amino]-3-[[1-(carboxymethyl)tetrazol-5-yl]sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• SMILES (Canonical): C1C(=C(N2C(S1)C(C2=O)NC(=O)CC3=CC=CC=C3CN)C(=O)O)CSC4=NN=NN4CC(=O)O
• SMILES (Isomeric): C1C(=C(N2[C@H](S1)[C@@H](C2=O)NC(=O)CC3=CC=CC=C3CN)C(=O)O)CSC4=NN=NN4CC(=O)O
• InChI: InChI=1S/C20H21N7O6S2/c21-6-11-4-2-1-3-10(11)5-13(28)22-15-17(31)27-16(19(32)33)12(8-34-18(15)27)9-35-20-23-24-25-26(20)7-14(29)30/h1-4,15,18H,5-9,21H2,(H,22,28)(H,29,30)(H,32,33)/t15-,18-/m1/s1
• InChI Key: SLAYUXIURFNXPG-CRAIPNDOSA-N
• Popularity: 226 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₁N₇O₆S₂
• Molecular Weight: 519.60 g/mol
• Exact Mass: 519.09947376 g/mol
• Topological Polar Surface Area (TPSA): 244.00 Ų
• XlogP: -3.20
• Atomic LogP (AlogP): -0.71
• H-Bond Acceptor: 11
• H-Bond Donor: 4
• Rotatable Bonds: 10

Synonyms

• 60925-61-3
• Precef
• Ceforanido
• Ceforanidum
• Ceforanidum [INN-Latin]
• Ceforanido [INN-Spanish]
• BL-S786
• (6R,7R)-7-[[2-[2-(aminomethyl)phenyl]acetyl]amino]-3-[[1-(carboxymethyl)tetrazol-5-yl]sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• UNII-8M1YF8951V
• CHEBI:3495
• DTXSID1022760
• 8M1YF8951V
• (6R,7R)-7-{2-[2-(aminomethyl)phenyl]acetamido}-3-({[1-(carboxymethyl)-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-(o-(Aminomethyl)phenylacetamido)-3-(((1-(carboxymethyl)-1H-tetrazol-5-yl)thio)methyl)-3-cephem-4-carboxylic acid
• NSC-760049
• DTXCID402760
• (6R,7R)-7-(2-(alpha-Amino-o-tolyl)acetamido)-3-(((1-(carboxymethyl)-1H-tetrazol-5-yl)thio)methyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid
• Ceforanide [USAN:USP:INN:BAN]
• NSC 760049
• (6R-trans)-7-(((2-(Aminomethyl)phenyl)acetyl)amino)-3-(((1-(carboxymethyl)-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-(((2-(aminomethyl)phenyl)acetyl)amino)-3-(((1-(carboxymethyl)-1H-tetrazol-5-yl)thio)methyl)-8-oxo-, (6R-trans)-
• Ceforanidum (INN-Latin)
• Ceforanido (INN-Spanish)
• CEFORANIDE (MART.)
• CEFORANIDE [MART.]
• CEFORANIDE (USP-RS)
• CEFORANIDE [USP-RS]
• 7-[O-(aminomethyl)phenylacetamido]-3-[[[1-(carboxymethyl)-1H-tetrazol-5-yl]thio]methyl]-3-cephem-4-carboxylic acid
• 7beta-[2-(aminomethyl)phenyl]acetamido-3-{[1-(carboxymethyl)-1H-tetrazol-5-yl]sulfanyl}methyl-3,4-didehydrocepham-4-carboxylic acid
• CEFORANIDE (USP IMPURITY)
• CEFORANIDE [USP IMPURITY]
• Ceforanide (USAN:USP:INN:BAN)
• BL-S 786
• (6R,7R)-7-({[2-(aminomethyl)phenyl]acetyl}amino)-3-({[1-(carboxymethyl)-1H-tetrazol-5-yl]sulfanyl}methyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• Precef (TN)
• Ceforanide (USP/INN)
• SR-01000872614
• cefaronide
• ceforanida
• NCGC00016897-01
• (6R,7R)-7-(((2-(aminomethyl)phenyl)acetyl)amino)-3-(((1-(carboxymethyl)-1H-tetrazol-5-yl)sulfanyl)methyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid
• (6R,7R)-7-((2-(2-(aminomethyl)phenyl)acetyl)amino)-3-((1-(carboxymethyl)tetrazol-5-yl)sulfanylmethyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid
• (6R,7R)-7-[2-(alpha-Amino-O-tolyl)acetamido]-3-[[[1-(carboxymethyl)-1H-tetrazol-5-yl]thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• 7beta-(2-(aminomethyl)phenyl)acetamido-3-((1-(carboxymethyl)-1H-tetrazol-5-yl)sulfanyl)methyl-3,4-didehydrocepham-4-carboxylic acid
• CAS-60925-61-3
• CEFORANIDE [MI]
• CEFORANIDE [INN]
• Prestwick0_000470
• Prestwick1_000470
• Prestwick2_000470
• Prestwick3_000470
• CEFORANIDE [USAN]
• CEFORANIDE [VANDF]
• CEFORANIDE(200MG)
• CEFORANIDE [WHO-DD]
• BSPBio_000580
• SCHEMBL122072
• SPBio_002519
• BPBio1_000638
• CEFORANIDE [ORANGE BOOK]
• CHEMBL1201046
• GTPL12218
• J01DC11
• HMS1569M22
• HMS2096M22
• HMS3713M22
• (6R,7R)-7-(2-(2-(Aminomethyl)phenyl)acetamido)-3-(((1-(carboxymethyl)-1H-tetrazol-5-yl)thio)methyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• HY-B1297
• Tox21_110670
• AKOS027427040
• CCG-220470
• DB00923
• NCGC00179514-05
• (6R,7R)-7-({[2-(aminomethyl)phenyl]acetyl}amino)-3-({[1-(carboxymethyl)-1H-tetrazol-5-yl]thio}methyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• AS-15783
• AB00513845
• CS-0013066
• S5081
• C06884
• D00259
• D81832
• EN300-7408761
• A913663
• Q5057287
• SR-01000872614-2
• SR-01000872614-3
• BRD-K37848908-001-03-1
• (6R,7R)-7-(2-(2-(Aminomethyl)phenyl)acetamido)-3-(((1-(carboxymethyl)-1H-tetrazol-5-yl)thio)methyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylicacid
• 7-(alpha-(2-aminomethylphenyl)acetamido)-3-((1-carboxymethyltetrazol-5-ylthio)methyl)-3-cephem-4-carboxylic acid
• 7-[[2-[2-(aminomethyl)phenyl]acetyl]amino]-3-[[1-(carboxymethyl)tetrazol-5-yl]sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6214	62.14%
Caco-2	-	0.9249	92.49%
Blood Brain Barrier	-	1.0000	100.00%
Human oral bioavailability	+	0.5857	58.57%
Subcellular localzation	Mitochondria	0.6348	63.48%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9058	90.58%
OATP1B3 inhibitior	+	0.9261	92.61%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	-	0.5753	57.53%
P-glycoprotein inhibitior	-	0.5782	57.82%
P-glycoprotein substrate	+	0.6650	66.50%
CYP3A4 substrate	+	0.6242	62.42%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8507	85.07%
CYP3A4 inhibition	-	0.8308	83.08%
CYP2C9 inhibition	-	0.9070	90.70%
CYP2C19 inhibition	-	0.9026	90.26%
CYP2D6 inhibition	-	0.9231	92.31%
CYP1A2 inhibition	-	0.9045	90.45%
CYP2C8 inhibition	+	0.5000	50.00%
CYP inhibitory promiscuity	-	0.5770	57.70%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Non-required	0.4705	47.05%
Eye corrosion	-	0.9886	98.86%
Eye irritation	-	0.9622	96.22%
Skin irritation	-	0.7539	75.39%
Skin corrosion	-	0.9187	91.87%
Ames mutagenesis	-	0.5800	58.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6621	66.21%
Micronuclear	+	0.9700	97.00%
Hepatotoxicity	+	0.9625	96.25%
skin sensitisation	-	0.8271	82.71%
Respiratory toxicity	+	0.9778	97.78%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.9875	98.75%
Nephrotoxicity	+	0.9027	90.27%
Acute Oral Toxicity (c)	III	0.5724	57.24%
Estrogen receptor binding	-	0.5234	52.34%
Androgen receptor binding	-	0.6908	69.08%
Thyroid receptor binding	-	0.5776	57.76%
Glucocorticoid receptor binding	-	0.6076	60.76%
Aromatase binding	+	0.5336	53.36%
PPAR gamma	+	0.5378	53.78%
Honey bee toxicity	-	0.7960	79.60%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.7100	71.00%
Fish aquatic toxicity	+	0.9707	97.07%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293235	P02545	Prelamin-A/C	56.2 nM	Potency	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	96.37%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.36%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.16%	95.56%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	89.11%	93.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.25%	97.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	86.66%	85.14%
CHEMBL1741221	Q9Y4P1	Cysteine protease ATG4B	86.34%	87.50%
CHEMBL1293294	P51151	Ras-related protein Rab-9A	86.02%	87.67%
CHEMBL3891	P07384	Calpain 1	85.42%	93.04%
CHEMBL3769292	Q9H773	dCTP pyrophosphatase 1	82.98%	94.40%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	82.81%	90.71%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	82.17%	81.11%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.94%	99.23%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.57%	99.17%
CHEMBL221	P23219	Cyclooxygenase-1	80.46%	90.17%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	80.32%	95.50%

Plants that contains it

• Platycodon grandiflorus

Cross-Links

• PubChem: 43507
• LOTUS: LTS0032873
• wikiData: Q105176556