Cloxacillin

Details

• Internal ID: 423b2087-ee6d-4e7b-808b-ee4f90bf8493
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Amino acids, peptides, and analogues > Peptides > Dipeptides
• IUPAC Name: (2S,5R,6R)-6-[[3-(2-chlorophenyl)-5-methyl-1,2-oxazole-4-carbonyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
• InChI: InChI=1S/C19H18ClN3O5S/c1-8-11(12(22-28-8)9-6-4-5-7-10(9)20)15(24)21-13-16(25)23-14(18(26)27)19(2,3)29-17(13)23/h4-7,13-14,17H,1-3H3,(H,21,24)(H,26,27)/t13-,14+,17-/m1/s1
• InChI Key: LQOLIRLGBULYKD-JKIFEVAISA-N
• Popularity: 5,548 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₁₈ClN₃O₅S
• Molecular Weight: 435.90 g/mol
• Exact Mass: 435.0655696 g/mol
• Topological Polar Surface Area (TPSA): 138.00 Ų
• XlogP: 2.40
• Atomic LogP (AlogP): 2.55
• H-Bond Acceptor: 6
• H-Bond Donor: 2
• Rotatable Bonds: 4

Synonyms

• 61-72-3
• Cloxacilline
• Cloxacillinum
• Cloxacilina
• Methocillin S
• Syntarpen
• Clossacillina
• Chloroxacillin
• O6X5QGC2VB
• (3-(o-Chlorophenyl)-5-methyl-4-isoxazolyl)penicillin
• CHEBI:49566
• 6-(3-(o-Chlorophenyl)-5-methyl-4-isoxazolecarboxamido)penicillanic acid
• 6-(((3-(2-Chlorophenyl)-5-methyl-4-isoxazolyl)carbonyl)amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid
• 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-(3-(O-chlorophenyl)-5-methyl-4-isoxazolecarboxamido)-3,3-dimethyl-7-oxo-
• (2S,5R,6R)-6-[3-(2-chlorophenyl)-5-methyl-1,2-oxazole-4-amido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
• 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-(((3-(2-chlorophenyl)-5-methyl-4-isoxazolyl)carbonyl)amino)-3,3-dimethyl-7-oxo-, (2S-(2alpha,5alpha,6beta))-
• [3-(O-CHLOROPHENYL)-5-METHYL-4-ISOXAZOLYL]PENICILLIN
• (2S,5R,6R)-6-({[3-(2-chlorophenyl)-5-methylisoxazol-4-yl]carbonyl}amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
• 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-(3-(o-chlorophenyl)-S-methyl-4-isoxazolecarboxamido)-3,3-dimethyl-7-oxo-
• cloxacillina
• (2S,5R,6R)-6-(((3-(2-chlorophenyl)-5-methylisoxazol-4-yl)carbonyl)amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid
• (2S,5R,6R)-6-(3-(2-chlorophenyl)-5-methyl-1,2-oxazole-4-amido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid
• Cloxacillin, Sodium
• Sodium, Cloxacillin
• cloxacillinum natricum
• RefChem:54862
• J01CF02
• 200-514-7
• Tegopen
• Clossacillina [DCIT]
• Cloxacillin (INN)
• (2S,5R,6R)-6-[[3-(2-chlorophenyl)-5-methyl-1,2-oxazole-4-carbonyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
• CHEMBL891
• CLOXACILLIN [INN]
• Cloxacillin [INN:BAN]
• Cloxacilina [INN-Spanish]
• Cloxacilline [INN-French]
• Cloxacillinum [INN-Latin]
• BRL 1621
• Methylchlorphenylisoxazoryl-penicillin
• Tegopen (sodium monohydrate)
• (2S,5R,6R)-6-[[3-(2-chlorophenyl)-5-methyl-isoxazole-4-carbonyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
• 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-[[[3-(2-chlorophenyl)-5-methyl-4-isoxazolyl]carbonyl]amino]-3,3-dimethyl-7-oxo-, (2S,5R,6R)-
• CXN
• Orbenin (TN)
• HSDB 3042
• EINECS 200-514-7
• UNII-O6X5QGC2VB
• P-25 (sodium monohydrate)
• CloxacillinNa
• Cloxapen (sodium monohydrate)
• BRL-1621 (sodium monohydrate)
• Cloxacilline-13c4
• Spectrum_001345
• CLOXACILLIN [MI]
• Prestwick0_000186
• Prestwick1_000186
• Prestwick2_000186
• Prestwick3_000186
• Spectrum2_001143
• Spectrum3_000360
• Spectrum4_000296
• Spectrum5_000783
• CLOXACILLIN [HSDB]
• Epitope ID:120363
• CLOXACILLIN [VANDF]
• SCHEMBL2953
• CLOXACILLIN [MART.]
• BSPBio_000111
• BSPBio_002059
• CLOXACILLIN [WHO-DD]
• KBioGR_000852
• KBioSS_001825
• DivK1c_000736
• SPBio_001065
• SPBio_002032
• BPBio1_000123
• orb1744466
• DTXSID5022853
• GTPL11126
• HY-B0466A
• KBio1_000736
• KBio2_001825
• KBio2_004393
• KBio2_006961
• KBio3_001279
• BRL1621
• NINDS_000736
• BDBM50022788
• EBC-27091
• DB01147
• IDI1_000736
• FC175020
• SBI-0051319.P003
• Cloxacillin 1000 microg/mL in Acetonitrile
• CS-0028411
• NS00000114
• C06923
• D07733
• EN300-708784
• 242C583
• Q422219
• BRD-K01244426-236-05-5
• BRD-K01244426-236-08-9
• BRD-K01244426-236-12-1
• BRD-K01244426-323-07-7
• Oxacillin Sodium Monohydrate EP Impurity E; Cloxacillin
• OXACILLIN SODIUM MONOHYDRATE IMPURITY E [EP IMPURITY]
• 6-(3-o-Chlorophenyl-5-methylisoxazol-4-ylamido) penicillanic acid
• 6-(3-o-Chlorophenyl-5-methylisoxazol-4-ylamido)penicillanic acid
• (2S,5R,6R)-6-(3-(2-chlorophenyl)-5-methylisoxazole-4-carboxamido)-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid
• (2S,5R,6R)-6-(3-(2-chlorophenyl)-5-methylisoxazole-4-carboxamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
• (2S,5R,6R)-6-[3-(2-Chlorophenyl)-5-methyl-1,2-oxazole-4-carboxamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
• (2S,5R,6R)-6-{[3-(2-Chloro-phenyl)-5-methyl-isoxazole-4-carbonyl]-amino}-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid
• 6-{[3-(2-Chloro-phenyl)-5-methyl-isoxazole-4-carbonyl]-amino}-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5516	55.16%
Caco-2	-	0.5711	57.11%
Blood Brain Barrier	-	1.0000	100.00%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Lysosomes	0.4793	47.93%
OATP2B1 inhibitior	-	0.7269	72.69%
OATP1B1 inhibitior	-	0.5217	52.17%
OATP1B3 inhibitior	-	0.2906	29.06%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.9317	93.17%
P-glycoprotein inhibitior	-	0.6467	64.67%
P-glycoprotein substrate	+	0.5801	58.01%
CYP3A4 substrate	+	0.7376	73.76%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9020	90.20%
CYP3A4 inhibition	-	0.8190	81.90%
CYP2C9 inhibition	-	0.8910	89.10%
CYP2C19 inhibition	-	0.8832	88.32%
CYP2D6 inhibition	-	0.9180	91.80%
CYP1A2 inhibition	+	0.8592	85.92%
CYP2C8 inhibition	-	0.6997	69.97%
CYP inhibitory promiscuity	-	0.9186	91.86%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.5100	51.00%
Carcinogenicity (trinary)	Non-required	0.5685	56.85%
Eye corrosion	-	0.9845	98.45%
Eye irritation	-	0.9864	98.64%
Skin irritation	+	0.6503	65.03%
Skin corrosion	-	0.9215	92.15%
Ames mutagenesis	-	0.6700	67.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4919	49.19%
Micronuclear	+	0.8600	86.00%
Hepatotoxicity	+	0.9875	98.75%
skin sensitisation	-	0.8191	81.91%
Respiratory toxicity	+	0.9778	97.78%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	+	0.9875	98.75%
Nephrotoxicity	+	0.8703	87.03%
Acute Oral Toxicity (c)	III	0.4590	45.90%
Estrogen receptor binding	-	0.7816	78.16%
Androgen receptor binding	-	0.8511	85.11%
Thyroid receptor binding	+	0.5620	56.20%
Glucocorticoid receptor binding	+	0.8970	89.70%
Aromatase binding	+	0.5425	54.25%
PPAR gamma	+	0.7276	72.76%
Honey bee toxicity	-	0.9033	90.33%
Biodegradation	-	0.9500	95.00%
Crustacea aquatic toxicity	+	0.5500	55.00%
Fish aquatic toxicity	+	0.9896	98.96%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1951	P21397	Monoamine oxidase A	96.88%	91.49%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	96.71%	81.11%
CHEMBL221	P23219	Cyclooxygenase-1	96.36%	90.17%
CHEMBL1293294	P51151	Ras-related protein Rab-9A	96.11%	87.67%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.21%	85.14%
CHEMBL2581	P07339	Cathepsin D	92.63%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.47%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.50%	91.11%
CHEMBL1966	Q02127	Dihydroorotate dehydrogenase	91.38%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.38%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.81%	96.09%
CHEMBL2553	Q15418	Ribosomal protein S6 kinase alpha 1	87.10%	85.11%
CHEMBL3401	O75469	Pregnane X receptor	86.00%	94.73%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.62%	99.23%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	84.50%	100.00%
CHEMBL5028	O14672	ADAM10	83.59%	97.50%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	83.32%	96.77%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	81.24%	94.08%
CHEMBL2095226	P05556	Integrin alpha-5/beta-1	80.19%	96.39%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 6098
• LOTUS: LTS0221894
• wikiData: Q422219