Amoxicillin

Details

• Internal ID: 257f3a76-9ecf-4bce-831b-8c7e77be5eca
• Taxonomy: Organoheterocyclic compounds > Lactams > Beta lactams > Penams > Penicillins
• IUPAC Name: (2S,5R,6R)-6-[[(2R)-2-amino-2-(4-hydroxyphenyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
• SMILES (Canonical): CC1(C(N2C(S1)C(C2=O)NC(=O)C(C3=CC=C(C=C3)O)N)C(=O)O)C
• SMILES (Isomeric): CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)[C@@H](C3=CC=C(C=C3)O)N)C(=O)O)C
• InChI: InChI=1S/C16H19N3O5S/c1-16(2)11(15(23)24)19-13(22)10(14(19)25-16)18-12(21)9(17)7-3-5-8(20)6-4-7/h3-6,9-11,14,20H,17H2,1-2H3,(H,18,21)(H,23,24)/t9-,10-,11+,14-/m1/s1
• InChI Key: LSQZJLSUYDQPKJ-NJBDSQKTSA-N
• Popularity: 15,970 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₁₉N₃O₅S
• Molecular Weight: 365.40 g/mol
• Exact Mass: 365.10454189 g/mol
• Topological Polar Surface Area (TPSA): 158.00 Ų
• XlogP: -2.00
• Atomic LogP (AlogP): 0.02
• H-Bond Acceptor: 6
• H-Bond Donor: 4
• Rotatable Bonds: 4

Synonyms

• Amoxycillin
• 26787-78-0
• Amoxicillin anhydrous
• Amoxicilline
• p-Hydroxyampicillin
• Amopenixin
• Amolin
• Moxal
• D-Amoxicillin
• Amoxil
• Amoxicillinum
• Amoxicilina
• Clamoxyl
• Amoxiden
• Amoxivet
• Anemolin
• Bristamox
• Delacillin
• Flemoxin
• Hiconcil
• Histocillin
• Imacillin
• Unicillin
• Vetramox
• Amoclen
• Aspenil
• Cemoxin
• Efpenix
• Piramox
• Amoxi
• Sumox
• Amoxi-Mast
• Sawamox PM
• Metafarma capsules
• Metifarma capsules
• Moxatag
• Ospamox
• Amopen
• Amoxicillin (anhydrous)
• Amoxicaps
• Robamox
• alpha-Amino-p-hydroxybenzylpenicillin
• Amoxicilina [INN-Spanish]
• Amoxicilline [INN-French]
• Amoxicillinum [INN-Latin]
• Apo-Amoxi
• AMOXICILLIN PEDIATRIC
• Amoxycillin Trihydrate
• BRL-2333
• Amoxicillin [INN]
• 6-(p-Hydroxy-alpha-aminophenylacetamido)penicillanic acid
• BLP 1410
• AMOXICILLIN CRYSTALLINE
• amoxycilin
• D-(-)-alpha-Amino-p-hydroxybenzylpenicillin
• Topramoxin
• Amoxyke
• Atoksilin
• CHEBI:2676
• Demoksil
• Largopen
• Moksilin
• Promoxil
• Remoxil
• Damoxy
• HSDB 3204
• Ro 10-8756
• EINECS 248-003-8
• BL-P 1410
• D-2-Amino-2-(4-hydroxyphenyl)acetamidopenicillanic acid
• Amoxicillin (INN)
• NSC 277174
• NSC-277174
• 6-(D-(-)-p-Hydroxy-alpha-aminobenzyl)penicillin
• AMOX
• DTXSID3037044
• UNII-9EM05410Q9
• Amoxicillinum trihydricum
• Amoxicillin hydrate
• 6-(D-(-)-alpha-Amino-p-hydroxyphenylacetamido)penicillanic acid
• 9EM05410Q9
• Amoxicillin (as trihydrate)
• (-)-6-(2-Amino-2-(P-hydroxyphenyl)acetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo-(3.2.0)heptane-2-carboxylic acid
• (2S,5R,6R)-6-[[(2R)-2-amino-2-(4-hydroxyphenyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
• (2S,5R,6R)-6-{[(2R)-2-amino-2-(4-hydroxyphenyl)acetyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
• DTXCID1017044
• EC 248-003-8
• Amoksicillin
• Kentrocyllin
• Matasedrin
• Paradroxil
• Zamocillin
• Zamocilline
• Alfamox
• Amophar
• Amoxidal
• Amoxillat
• Amoxina
• Amoxine
• Flemoxine
• Galenamox
• Gramidil
• Himinomax
• Izoltil
• Metifarma
• Pacetocin
• Pamocil
• Pasetocin
• Siganopen
• Simplamox
• Sintopen
• Velamox
• Amoran
• Ciblor
• NSC277174
• Amoxi-wolff
• Uro-clamoxyl
• Amoxi-Diolan
• AX
• Amoksicillin forte
• A-Gram
• Dura AX
• co-amoxiclav (amoxicillin + clavulanic acid)
• Amoxicillin-ratiopharm
• AMOXICILLIN (MART.)
• AMOXICILLIN [MART.]
• (2S,5R,6R)-6-((R)-2-Amino-2-(4-hydroxyphenyl)acetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
• (2S,5R,6R)-6-[(2R)-2-amino-2-(4-hydroxyphenyl)acetamido]-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-(((2R)-amino(4-hydroxyphenyl)acetyl)amino)-3,3-dimethyl-7-oxo-, (2S,5R,6R)-
• 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-(2-amino-2-(p-hydroxyphenyl)acetamido)-3,3-dimethyl-7-oxo-, D-
• 4-Thia-1-azobicyclo(3.2.0)heptane-2-carboxylic acid, 6-((amino(4-hydroxyphenyl)acetyl)amino)-3,3-dimethyl-7-oxo-, (2S-(2alpha,5alpha,6beta(S)))-
• amoxicillanyl
• Drg-0075
• 6beta-[(2R)-2-amino-2-(4-hydroxyphenyl)acetamido]-2,2-dimethylpenam-3alpha-carboxylic acid
• UNII-804826J2HU
• CHEBI:51254
• Amoxicillin (TN)
• (2S,5R,6R)-6-((R)-(-)-2-AMINO-2-(P-HYDROXYPHENYL)ACETAMIDO)-3,3-DIMETHYL-7-OXO-4-THIA-1-AZABICYCLO(3.2.0)HEPTANE-2-CARBOXYLIC ACID
• SMR000058707
• Amoxicillin (trihydrate)
• AMOXICILLIN (USP IMPURITY)
• Amoxycillin (trihydrate)
• AMOXICILLIN (USP MONOGRAPH)
• PREVPAC COMPONENT AMOXICILLIN
• TALICIA COMPONENT AMOXICILLIN
• Amoxicillin (Amoxycillin)
• AUGMENTIN COMPONENT AMOXICILLIN
• AMOXICILLIN TRIHYDRATE (MART.)
• AMOXICILLIN COMPONENT OF PREVPAC
• AMOXICILLIN COMPONENT OF TALICIA
• (2S,5R,6R)-6-(2-Amino-2-(4-hydroxyphenyl)acetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
• AMOXICILLIN COMPONENT OF AUGMENTIN
• 61336-70-7
• AMOXICILLIN TRIHYDRATE (EP MONOGRAPH)
• amoxicillina
• alpha-Amino-p-hydroxybenzylpenicillin trihydrate
• CLAVULOX COMPONENT AMOXICILLIN TRIHYDRATE
• AMOXICILLINTRIHYDRATE
• Amoxi-Inject
• AMOXICILLIN TRIHYDRATE COMPONENT OF CLAVULOX
• Amoxi-Tabs
• notoginsenoside-fe
• 6beta-((2R)-2-amino-2-(4-hydroxyphenyl)acetamido)-2,2-dimethylpenam-3alpha-carboxylic acid
• NCGC00016797-02
• NCGC00094586-01
• (2S,5R,6R)-6-(((2R)-2-amino-2-(4-hydroxyphenyl)acetyl)amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid
• Prestwick_713
• CAS-26787-78-0
• Amoxicillinum (Latin)
• MFCD00056860
• AMOXICILLIN [MI]
• (2S,5R,6R)-6-((R)-(-)-2-AMINO-2-(P-HYDROXYPHENYL)ACETAMIDO)-3,3-DIMETHYL-7-OXO-4-THIA-1-AZABICYCL(3.2.0)HEPTANE-2-CARBOXYLIC ACID TRIHYDRATE
• 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-(((2R)-amino(4-hydroxyphenyl)acetyl)amino)-3,3-dimethyl-7-oxo-, trihydrate, (2S,5R,6R)-
• 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-((amino(4-hydroxyphenyl)acetyl)amino)-3,3-dimethyl-7-oxo-, trihydrate (2S-(2alpha,5alpha,6beta(S*)))-
• 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-((amino(4-hydroxyphenyl)acetyl)amino)-3,3-dimethyl-7-oxo-, trihydrate(2S-(2alpha,5alpha,6beta(S*)))-
• Prestwick0_000357
• Prestwick1_000357
• Prestwick2_000357
• Prestwick3_000357
• Epitope ID:114241
• Epitope ID:116054
• SCHEMBL3427
• CHEMBL1082
• AMOXICILLIN [WHO-DD]
• BSPBio_000453
• MLS000028632
• MLS002222248
• SPBio_002374
• BPBio1_000499
• CHEBI:53712
• GTPL10895
• HY-B0467A
• J01CA04
• LSQZJLSUYDQPKJ-NJBDSQKTSA-N
• HMS1569G15
• HMS2096G15
• HMS2231K23
• HMS3259P17
• HMS3713G15
• 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-[[(2R)-2-amino-2-(4-hydroxyphenyl)acetyl]amino]-3,3-dimethyl-7-oxo-, (2S,5R,6R)-
• AMOXICILLIN ANHYDROUS [HSDB]
• Tox21_111302
• BDBM50350464
• s3015
• AKOS025395540
• Tox21_111302_1
• CCG-220357
• DB01060
• DS-3835
• NC00670
• NCGC00179554-01
• AC-12263
• Amoxicillin, potency: >=900 mug per mg
• C06827
• D07452
• EN300-118704
• A877139
• Q201928
• SR-01000721886
• SR-01000721886-2
• BRD-K55044200-001-03-9
• BRD-K55044200-001-15-3
• Z1515385072
• (2S,5R,6R)-6-((R)-2-Amino-2-(4-hydroxyphenyl)acetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylicacid
• 4-THIA-1-AZABICYCLO(3.2.0)HEPTANE-2-CARBOXYLIC ACID, 6-((AMINO(4-HYDROXYPHENYL)ACETYL)AMINO)-3,3-DIMETHYL-7-OXO-(2S-(2.ALPHA.,5.ALPHA.,6.BETA.(S*)))-
• 4-Thia-1-Azabicyclo(3.2.0)Heptane-2-Carboxylic Acid, 6-((Amino(4-Hydroxyphenyl)Acetyl)Amino)-3,3-Dimethyl-7-Oxo-(2S-(2Alpha,5Alpha,6Beta(S*)))-
• 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-[[amino (4-hydroxyphenyl)acetyl]amino]-3,3-dimethyl-7-oxo-, [2S-[2.alpha.,5.alpha.,6.beta.(S*)]]-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.8790	87.90%
Caco-2	-	0.9249	92.49%
Blood Brain Barrier	-	1.0000	100.00%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Lysosomes	0.4840	48.40%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9413	94.13%
OATP1B3 inhibitior	+	0.9480	94.80%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.8681	86.81%
P-glycoprotein inhibitior	-	0.9167	91.67%
P-glycoprotein substrate	+	0.5750	57.50%
CYP3A4 substrate	+	0.5477	54.77%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8298	82.98%
CYP3A4 inhibition	-	0.8309	83.09%
CYP2C9 inhibition	-	0.9070	90.70%
CYP2C19 inhibition	-	0.9150	91.50%
CYP2D6 inhibition	-	0.9231	92.31%
CYP1A2 inhibition	-	0.9045	90.45%
CYP2C8 inhibition	-	0.9882	98.82%
CYP inhibitory promiscuity	-	0.9767	97.67%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	+	0.6977	69.77%
Carcinogenicity (trinary)	Non-required	0.6829	68.29%
Eye corrosion	-	0.9897	98.97%
Eye irritation	-	0.9872	98.72%
Skin irritation	-	0.7402	74.02%
Skin corrosion	-	0.9216	92.16%
Ames mutagenesis	-	0.8800	88.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7668	76.68%
Micronuclear	+	0.9000	90.00%
Hepatotoxicity	+	0.9875	98.75%
skin sensitisation	-	0.7693	76.93%
Respiratory toxicity	+	0.9778	97.78%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	+	1.0000	100.00%
Nephrotoxicity	+	0.4889	48.89%
Acute Oral Toxicity (c)	IV	0.5992	59.92%
Estrogen receptor binding	-	0.5725	57.25%
Androgen receptor binding	-	0.7253	72.53%
Thyroid receptor binding	-	0.5145	51.45%
Glucocorticoid receptor binding	-	0.6684	66.84%
Aromatase binding	-	0.8514	85.14%
PPAR gamma	-	0.7379	73.79%
Honey bee toxicity	-	0.8715	87.15%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.8700	87.00%
Fish aquatic toxicity	+	0.9203	92.03%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293235	P02545	Prelamin-A/C	8.9 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	97.17%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.64%	91.11%
CHEMBL2581	P07339	Cathepsin D	95.63%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.03%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.63%	95.56%
CHEMBL2553	Q15418	Ribosomal protein S6 kinase alpha 1	87.73%	85.11%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.43%	99.23%
CHEMBL340	P08684	Cytochrome P450 3A4	87.31%	91.19%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	84.78%	85.14%
CHEMBL5600	P27448	Serine/threonine-protein kinase c-TAK1	82.82%	88.81%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	82.74%	93.10%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	82.26%	90.93%
CHEMBL4208	P20618	Proteasome component C5	81.52%	90.00%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	80.40%	94.62%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	80.01%	99.15%

Plants that contains it

• Arundo donax

Cross-Links

• PubChem: 33613
• LOTUS: LTS0146314
• wikiData: Q201928