Cefadroxil

Details

• Internal ID: 287437db-5694-45ea-881e-99d2e97490a7
• Taxonomy: Organoheterocyclic compounds > Lactams > Beta lactams > Cephalosporins
• IUPAC Name: (6R,7R)-7-[[(2R)-2-amino-2-(4-hydroxyphenyl)acetyl]amino]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• InChI: InChI=1S/C16H17N3O5S/c1-7-6-25-15-11(14(22)19(15)12(7)16(23)24)18-13(21)10(17)8-2-4-9(20)5-3-8/h2-5,10-11,15,20H,6,17H2,1H3,(H,18,21)(H,23,24)/t10-,11-,15-/m1/s1
• InChI Key: BOEGTKLJZSQCCD-UEKVPHQBSA-N
• Popularity: 2,096 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₁₇N₃O₅S
• Molecular Weight: 363.40 g/mol
• Exact Mass: 363.08889182 g/mol
• Topological Polar Surface Area (TPSA): 158.00 Ų
• XlogP: -2.10
• Atomic LogP (AlogP): 0.15
• H-Bond Acceptor: 6
• H-Bond Donor: 4
• Rotatable Bonds: 4

Synonyms

• 50370-12-2
• Cefadroxil anhydrous
• Cephadroxil
• Cefadroxilo
• Cefadroxilum
• D-Cefadroxil
• Cefadroxil [INN]
• BL-S 578
• BL-S578
• Anhydrous cefadroxil
• CHEBI:3479
• (6R,7R)-7-{[(2R)-2-amino-2-(4-hydroxyphenyl)acetyl]amino}-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• CDX
• Q525PA8JJB
• (6R,7R)-7-[[(2R)-2-amino-2-(4-hydroxyphenyl)acetyl]amino]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• DTXSID8022749
• Duracef
• NSC-756664
• MJF-11567-3
• (6R,7R)-7-((R)-2-amino-2-(4-hydroxyphenyl)acetamido)-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• (6R,7R)-7-[(2R)-2-amino-2-(4-hydroxyphenyl)acetamido]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• DTXCID402749
• Cefadroxil (as monohydrate)
• Cefadroxilum [INN-Latin]
• Cefadroxilo [INN-Spanish]
• 5-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 7-(((2R)-amino(4-hydroxyphenyl)acetyl)amino)-3-methyl-8-oxo-, (6R,7R)-
• Sumacef (TN)
• CEFADROXIL/CEFADROXIL HEMIHYDRATE
• S 578
• S-578
• UNII-Q525PA8JJB
• Cefradroxil
• Cefadrops
• NCGC00016858-01
• (6R,7R)-7-(((2R)-2-AMINO-2-(4-HYDROXYPHENYL)ACETYL)AMINO)-3-METHYL-8-OXO-5-THIA-1-AZABICYCLO(4.2.0)OCT-2-ENE-2-CARBOXYLIC ACID
• EINECS 256-555-6
• CAS-50370-12-2
• Cefadroxil (JP17)
• Spectrum_000104
• CEFADROXIL [MI]
• CEFADROXIL [JAN]
• (6R,7R)-7-[[(2R)-2-azaniumyl-2-(4-hydroxyphenyl)acetyl]amino]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
• Prestwick0_000434
• Prestwick1_000434
• Prestwick2_000434
• Prestwick3_000434
• Spectrum2_000087
• Spectrum4_000266
• Spectrum5_000663
• Epitope ID:117131
• CEFADROXIL [WHO-DD]
• CHEMBL1644
• BSPBio_000448
• KBioGR_000732
• KBioSS_000544
• (6R,7R)-7-((R)-2-Amino-2-(p-hydroxyphenyl)acetamido)-3-methyl-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid
• MLS002207219
• DivK1c_000409
• SCHEMBL151320
• SPBio_000014
• SPBio_002387
• Cefadroxil, analytical standard
• BPBio1_000494
• GTPL4831
• HMS501E11
• KBio1_000409
• KBio2_000544
• KBio2_003112
• KBio2_005680
• BOEGTKLJZSQCCD-UEKVPHQBSA-N
• NINDS_000409
• HMS1569G10
• HMS2096G10
• HMS3713G10
• Pharmakon1600-01500163
• 5-THIA-1-AZABICYCLO(4.2.0)OCT-2-ENE-2-CARBOXYLIC ACID, 7-(((2R)-2-AMINO-2-(4-HYDROXYPHENYL)ACETYL)AMINO)-3-METHYL-8-OXO-, (6R,7R)-
• HY-B1190
• Tox21_110651
• BDBM50350467
• MFCD00865091
• NSC756664
• AKOS005622555
• Tox21_110651_1
• CCG-220434
• CS-4696
• DB01140
• IDI1_000409
• NCGC00179556-01
• NCGC00179556-03
• AS-11655
• SMR001306770
• CEFPROZIL IMPURITY B [EP IMPURITY]
• SBI-0051305.P003
• AB00513838
• CEFPROZIL E IMPURITY B [EP IMPURITY]
• C-2462
• C06878
• D00257
• D81830
• EN300-6733479
• Q2319020
• CEFPROZIL MONOHYDRATE IMPURITY B [EP IMPURITY]
• Z2587996508
• Cefadroxil monohydrate, Antibiotic for Culture Media Use Only
• (7R)-7-((R)-2-amino-2-(4-hydroxyphenyl)acetamido)-3-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-((amino(4-hydroxyphenyl)acetyl)amino)-3-methyl-8-oxo-, (6R-(6-alpha,7-beta(R*)))-
• 7beta-{[(2R)-2-amino-2-(4-hydroxyphenyl)acetyl]amino}-3-methyl-3,4-didehydrocepham-4-carboxylic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8272	82.72%
Caco-2	-	0.9219	92.19%
Blood Brain Barrier	-	1.0000	100.00%
Human oral bioavailability	+	0.9143	91.43%
Subcellular localzation	Mitochondria	0.5294	52.94%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9414	94.14%
OATP1B3 inhibitior	+	0.9479	94.79%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.8666	86.66%
P-glycoprotein inhibitior	-	0.8677	86.77%
P-glycoprotein substrate	-	0.7210	72.10%
CYP3A4 substrate	+	0.5232	52.32%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8570	85.70%
CYP3A4 inhibition	-	0.8421	84.21%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	-	0.9025	90.25%
CYP2D6 inhibition	-	0.9231	92.31%
CYP1A2 inhibition	-	0.9045	90.45%
CYP2C8 inhibition	-	0.9759	97.59%
CYP inhibitory promiscuity	-	0.8730	87.30%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.8550	85.50%
Carcinogenicity (trinary)	Non-required	0.5643	56.43%
Eye corrosion	-	0.9889	98.89%
Eye irritation	-	0.9788	97.88%
Skin irritation	-	0.7611	76.11%
Skin corrosion	-	0.9259	92.59%
Ames mutagenesis	-	0.7100	71.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4226	42.26%
Micronuclear	+	0.9100	91.00%
Hepatotoxicity	+	0.9685	96.85%
skin sensitisation	-	0.8960	89.60%
Respiratory toxicity	+	1.0000	100.00%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	1.0000	100.00%
Nephrotoxicity	+	0.8053	80.53%
Acute Oral Toxicity (c)	IV	0.6156	61.56%
Estrogen receptor binding	+	0.5736	57.36%
Androgen receptor binding	-	0.5561	55.61%
Thyroid receptor binding	-	0.5572	55.72%
Glucocorticoid receptor binding	-	0.5529	55.29%
Aromatase binding	-	0.5664	56.64%
PPAR gamma	-	0.5920	59.20%
Honey bee toxicity	-	0.9081	90.81%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.7400	74.00%
Fish aquatic toxicity	+	0.9638	96.38%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293235	P02545	Prelamin-A/C	12.6 nM	Potency	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.68%	96.09%
CHEMBL2581	P07339	Cathepsin D	95.84%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.45%	95.56%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	90.43%	93.00%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	90.32%	90.71%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.79%	99.23%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	85.59%	90.93%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	85.44%	91.11%
CHEMBL340	P08684	Cytochrome P450 3A4	85.31%	91.19%
CHEMBL4208	P20618	Proteasome component C5	84.88%	90.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.43%	94.45%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	83.39%	85.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.35%	97.09%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	82.21%	89.62%
CHEMBL2553	Q15418	Ribosomal protein S6 kinase alpha 1	82.05%	85.11%
CHEMBL4578	Q14680	Maternal embryonic leucine zipper kinase	82.01%	81.58%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 47965
• LOTUS: LTS0207227
• wikiData: Q2319020