Details of the Drug

General Information of Drug (ID: DMUYNEI)

Drug Name

Amoxicillin

Synonyms

AMPC; Actimoxi; Amoclen; Amolin; Amopen; Amopenixin; Amoxi; Amoxibiotic; Amoxicaps; Amoxicilina; Amoxicillanyl; Amoxicilline; Amoxicillinum; Amoxiden; Amoxil; Amoxivet; Amoxycillin; Anemolin; Aspenil; Biomox; Bristamox; Cemoxin; Clamoxyl; Delacillin; DisperMox; Efpenix; Flemoxin; Hiconcil; Histocillin; Hydroxyampicillin; Ibiamox; Imacillin; Lamoxy; Larotid; Moxacin; Moxal; Moxatag; Ospamox; Pamoxicillin; Piramox; Polymox; Robamox; Sumox; Tolodina; Trimox; Unicillin; Utimox; Vetramox; Wymox; AMOXICILLIN CRYSTALLINE; AMOXICILLIN PEDIATRIC; Amoxicillin anhydrous; Amoxicilline [INN]; Amoxycillin Trihydrate; Metafarma capsules; Metifarma capsules; Sawamox PM; BLP 1410; AMK (TN); Actimoxi (TN); Alphamox (TN); Amoksibos (TN); Amoksiklav (TN); Amoxi-Mast; Amoxibiotic (TN); Amoxicilina (TN); Amoxicilina [INN-Spanish]; Amoxicillin (INN); Amoxicillin (TN); Amoxicillin (anhydrous); Amoxicilline [INN-French]; Amoxicillinum [INN-Latin]; Amoxiclav (TN); Amoxidal (TN); Amoxil (TN); Amoxin (TN); Apo-Amoxi; Augmentin (TN); BL-P 1410; BRL-2333; Bactox (TN); Betalaktam (TN); Cilamox (TN); Clamoxyl (TN); Curam (TN); D-Amoxicillin; Dedoxil (TN); Dispermox (TN); Duomox (TN); Enhancin (TN); Geramox (TN); Gimalxina (TN); Hiconcil (TN); Isimoxin (TN); Klavox (TN); Lamoxy (TN); Moxatag (TN); Moxilen (TN); Moxypen (TN); Moxyvit (TN); Nobactam (TN); Novamoxin (TN); Ospamox (TN); P-Hydroxyampicillin; Pamoxicillin (TN); Panamox (TN); Panklav (TN); Polymox (TN); Ro 10-8756; Samthongcillin (TN); Sandoz (TN); Senox (TN); Sinacilin (TN); Tolodina (TN); Trimox (TN); Wymox (TN); Yucla (TN); Zerrsox (TN); Zimox (TN); Apo-Amoxi (TN); Alpha-Amino-p-hydroxybenzylpenicillin; D-2-Amino-2-(4-hydroxyphenyl)acetamidopenicillanic acid; D-(-)-alpha-Amino-p-hydroxybenzylpenicillin; (-)-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; 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-(2-amino-2-(p-hydroxyphenyl)acetamido)-3,3-dimethyl-7-oxo-, D-(8CI); 6-(D-(-)-alpha-Amino-p-hydroxyphenylacetamido)penicillanic acid; 6-(D-(-)-p-Hydroxy-alpha-aminobenzyl)penicillin; 6-(p-Hydroxy-alpha-aminophenylacetamido)penicillanic acid; 6beta-[(2R)-2-amino-2-(4-hydroxyphenyl)acetamido]-2,2-dimethylpenam-3alpha-carbonyl; 6beta-[(2R)-2-amino-2-(4-hydroxyphenyl)acetamido]-2,2-dimethylpenam-3alpha-carboxylic acid

Indication

Disease Entry	ICD 11	Status	REF
Acute otitis media	AB00	Approved	[1]
Bacterial infection	1A00-1C4Z	Approved	[2]
Staphylococcus aureus infection	N.A.	Approved	[1]
Streptococcal pneumonia	N.A.	Approved	[1]
Urinary tract infection	GC08	Approved	[1]
Pneumonia due to Klebsiella pneumoniae	CA40.03	Investigative	[1]
Sinusitis	CA0A.Z	Investigative	[1]
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⏷ Show the Full List of Indication(s)

Therapeutic Class

Antibiotics

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

365.4

Logarithm of the Partition Coefficient (xlogp)

-2

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

ADMET Property

Absorption AUC: The area under the plot of plasma concentration (AUC) of drug is 27.29 +/- 4.72 mgh/L [3]
Absorption Cmax: The maximum plasma concentration (Cmax) of drug is 3.93 +/- 1.13 mg/L [3]
Absorption Tmax: The time to maximum plasma concentration (Tmax) is 1.31 +/- 0.33 h [3]
BDDCS Class: Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 3: high solubility and low permeability [4]
Bioavailability: The bioavailability of drug is 60% [3]
Clearance: The clearance of drug is 21.3 L/h [5]
Elimination: 125mg to 1g doses are 70-78% eliminated in the urine after 6 hours [6]
Half-life: The concentration or amount of drug in body reduced by one-half in 61.3 minutes [3]
Metabolism: The drug is metabolized via the liver [7]
MRTD: The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 68.41612 micromolar/kg/day [8]
Unbound Fraction: The unbound fraction of drug in plasma is 0.85% [9]
Vd: The volume of distribution (Vd) of drug is 27.7 L [5]
Water Solubility: The ability of drug to dissolve in water is measured as 3.5 mg/mL [4]

Adverse Drug Reaction (ADR)

ADR Term	Variation	Related DOT	DOT ID	REF
Liver injury	HLA-A*30:02	HLA-A	OTAH14LU	[10]
Liver injury	Not Available	CCR9 GPR28	OT5FSOD8	[11]
Liver injury	Not Available	CCR4 CMKBR4	OT68KZ9B	[11]
Liver injury	Not Available	CXCR3 GPR9	OTIGS220	[11]
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Chemical Identifiers

Formula: C16H19N3O5S
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
Canonical SMILES: 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
InChIKey: LSQZJLSUYDQPKJ-NJBDSQKTSA-N

Cross-matching ID

PubChem CID: 33613
ChEBI ID: CHEBI:2676
CAS Number: 26787-78-0
DrugBank ID: DB01060
TTD ID: D0F6EO
VARIDT ID: DR00190
INTEDE ID: DR0104
ACDINA ID: D00035

Combinatorial Drugs (CBD)

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Repurposed Drugs (RPD)

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Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Bacterial Cell membrane (Bact CM)	TTXT4D5	NOUNIPROTAC	Modulator	[12]

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Drug Transporter (DTP)

DTP Name	DTP ID	UniProt ID	MOA	REF
Peptide transporter 2 (SLC15A2)	DT8QKNP	S15A2_HUMAN	Substrate	[13]
Peptide transporter 1 (SLC15A1)	DT9G7XN	S15A1_HUMAN	Substrate	[13]
Organic anion transporter 1 (SLC22A6)	DTQ23VB	S22A6_HUMAN	Substrate	[14]
P-glycoprotein 1 (ABCB1)	DTUGYRD	MDR1_HUMAN	Substrate	[15]

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Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
Mephenytoin 4-hydroxylase (CYP2C19)	DEGTFWK	CP2CJ_HUMAN	Substrate	[16]
Metallo-beta-lactamase (blaM)	DEK9VG2	BLAN1_KLEPN	Substrate	[17]
Beta-lactamase (blaB)	DEW193R	BLA1_KLEPN	Substrate	[17]
New delhi metallo-beta-lactamase NDM-1 (blaNDM)	DEBGCYQ	A0A345N7K5_SALET	Substrate	[18]
Beta-lactamase (blaB)	DE7IH52	AMPC_CITFR	Substrate	[19]
Metallo-beta-lactamase (blaM)	DEPCQ12	Q68K11_ALCXX	Substrate	[17]
Beta-lactamase (blaB)	DEV0KWQ	Q8KT52_9BACT	Substrate	[19], [20]
Beta-lactamase (blaB)	DEACNTL	Q2F4C6_SHISO	Substrate	[21]
N-acylhomoserine lactone acylase (lacA)	DEIU0XN	A0A0A1VBK6_9BURK	Substrate	[22]
Beta-lactamase (blaB)	DET9I1W	BLAC_BACUN	Substrate	[23]
Beta-lactamase (blaB)	DENJ2SQ	BLAB_BACFG	Substrate	[23]
Beta-lactamase (blaB)	DED0TBR	A0A414M273_9BACE	Substrate	[24]
Beta-lactamase (blaB)	DEX8KJO	A6NX15_9FIRM	Substrate	[25]
Beta-lactamase (blaB)	DEAYSTX	C0W968_9FIRM	Substrate	[26]
Beta-lactamase (blaB)	DERGEVU	C3WC84_FUSMR	Substrate	[27], [28]
Beta-lactamase (blaB)	DEQMISO	F9Z530_ODOSD	Substrate	[27], [28]
Beta-lactamase (blaB)	DEHFJ4G	Q8KT51_9BACT	Substrate	[27], [28]
Beta-lactamase (blaB)	DEHPJRC	Q8KT60_9BACT	Substrate	[27], [28]
Beta-lactamase (blaB)	DEITMS0	Q9XBM2_ACIFE	Substrate	[29]
Beta-lactamase (blaB)	DE5HV8P	A0A4Q5I6I2_9BACE	Substrate	[23]
Beta-lactamase (blaB)	DE47ARF	B5WXV2_9BACT	Substrate	[30]
Beta-lactamase (blaB)	DEG2PK9	B5WXV3_BACOV	Substrate	[23]
Beta-lactamase (blaB)	DEWHJ7A	B5WXV7_BACT4	Substrate	[23]
Beta-lactamase (blaB)	DEU1RXB	BLAC_BACVU	Substrate	[23], [31]
Beta-lactamase (blaB)	DETDS7E	A0A2S0LB67_9FLAO	Substrate	[19]
Beta-lactamase (blaB)	DE37FJH	C6JIU1_FUSVA	Substrate	[27]
Beta-lactamase (blaB)	DEC7JEF	A0A1S1G219_9NEIS	Substrate	[19]
Beta-lactamase (blaB)	DEP7MN1	Q9X4S7_PREIN	Substrate	[32]
Beta-lactamase (blaB)	DEAILCM	A0A246EJV2_9BACT	Substrate	[32], [19]
Beta-lactamase (blaB)	DET4XFN	Q8KT59_9BACT	Substrate	[19]
Beta-lactamase (blaB)	DEE8742	O32372_CAPOC	Substrate	[33]
Beta-lactamase (blaB)	DEY09SU	C9MN73_9BACT	Substrate	[19]
Beta-lactamase (blaB)	DEQLVCA	C9LD75_9BACT	Substrate	[32]
Beta-lactamase (blaB)	DE2IL34	C2M7J0_CAPGI	Substrate	[33]
Beta-lactamase (blaB)	DE1NJIW	B6VMJ3_PHOAA	Substrate	[34], [35]
Beta-lactamase (blaB)	DEDIMN9	A0A413GBG0_9BACE	Substrate	[23]
Beta-lactamase (blaB)	DEJ8X2W	A0A412YFL9_9BACE	Substrate	[23]
Beta-lactamase (blaB)	DEFEVNH	A0A381DV31_9FLAO	Substrate	[33]
Beta-lactamase (blaB)	DEAPGXV	A0A347B2J2_9BACT	Substrate	[19]
Beta-lactamase (blaB)	DE0PDVC	A0A2A3N1K0_CAPSP	Substrate	[33]
Beta-lactamase (blaB)	DEQL32N	A0A250F962_9FLAO	Substrate	[33]
Beta-lactamase (blaB)	DE9HF0I	A0A120A1C6_BACSE	Substrate	[23]
Beta-lactamase (blaB)	DESHI6O	A0A108T9G3_9BACE	Substrate	[23]
Beta-lactamase (blaB)	DEZS3N4	A0A069QS91_PRELO	Substrate	[19]
Beta-lactamase (blaB)	DE5NSUX	A0A095XPV0_9FIRM	Substrate	[19]
Beta-lactamase (blaB)	DEQ1CTE	A0A2T4TNV5_9BACT	Substrate	[36]

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Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
Aldo-keto reductase family 1 member B10 (AKR1B10)	OTOA4HTH	AK1BA_HUMAN	Gene/Protein Processing	[37]
Aromatase (CYP19A1)	OTZ6XF74	CP19A_HUMAN	Gene/Protein Processing	[38]
C-C chemokine receptor type 4 (CCR4)	OT68KZ9B	CCR4_HUMAN	Drug Response	[11]
C-C chemokine receptor type 9 (CCR9)	OT5FSOD8	CCR9_HUMAN	Drug Response	[11]
C-X-C chemokine receptor type 3 (CXCR3)	OTIGS220	CXCR3_HUMAN	Drug Response	[11]
C-X-C motif chemokine 10 (CXCL10)	OTTLQ6S0	CXL10_HUMAN	Gene/Protein Processing	[39]
Cytochrome P450 11B2, mitochondrial (CYP11B2)	OTIOLWYN	C11B2_HUMAN	Gene/Protein Processing	[38]
Cytochrome P450 2C8 (CYP2C8)	OTHCWT42	CP2C8_HUMAN	Gene/Protein Processing	[40]
HLA class I histocompatibility antigen, A alpha chain (HLA-A)	OTAH14LU	HLAA_HUMAN	Drug Response	[10]
HLA class I histocompatibility antigen, B alpha chain (HLA-B)	OTNXFWY2	HLAB_HUMAN	Gene/Protein Processing	[41]

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Molecular Interaction Atlas (MIA)

MIA Detail

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Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Disease Different from Amoxicillin (Comorbidity)

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Comorbidity	REF
Anisindione	DM2C48U	Moderate	Increased risk of bleeding by the combination of Amoxicillin and Anisindione.	Coagulation defect [3B10]	[42]
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Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG

DIG Name	DIG ID	PubChem CID	Functional Classification
Allura red AC dye	E00338	33258	Colorant
Aspartame	E00402	134601	Flavoring agent
D&C red no. 28	E00491	6097185	Colorant
D&C red no. 30	E00456	3000709	Colorant
D&C red no. 33	E00261	19116	Colorant
FD&C blue no. 1	E00263	19700	Colorant
FD&C blue no. 2	E00446	2723854	Colorant
Isopropyl alcohol	E00070	3776	Antimicrobial preservative; Solvent
Mannitol	E00103	6251	Diluent; Flavoring agent; Lyophilization aid; Plasticizing agent; Tonicity agent
methylparaben	E00149	7456	Antimicrobial preservative
Propyl 4-hydroxybenzoate	E00141	7175	Antimicrobial preservative
Quinoline yellow WS	E00309	24671	Colorant
Sodium citrate anhydrous	E00102	6224	Alkalizing agent; Buffering agent; Complexing agent; Emulsifying agent
Sodium lauryl sulfate	E00464	3423265	Emulsifying agent; Modified-release agent; Penetration agent; Solubilizing agent; Surfactant; lubricant
Sunset yellow FCF	E00255	17730	Colorant
Ammonia	E00007	222	Alkalizing agent
Beta-D-lactose	E00099	6134	Diluent; Dry powder inhaler carrier; Lyophilization aid
Butyl alcohol	E00011	263	Flavoring agent; Solvent
Carmellose sodium	E00625	Not Available	Disintegrant
Citric acid monohydrate	E00271	22230	Acidulant; Antioxidant; Buffering agent; Complexing agent; Flavoring agent
Crospovidone	E00626	Not Available	Disintegrant
Eisenoxyd	E00585	56841934	Colorant
FD&C red no. 3	E00629	Not Available	Colorant
Ferric hydroxide oxide yellow	E00539	23320441	Colorant
Ferrosoferric oxide	E00231	14789	Colorant
Lactose monohydrate	E00393	104938	Binding agent; Diluent; Dry powder inhaler carrier; Lyophilization aid
Magnesium stearate	E00208	11177	lubricant
Polyethylene glycol 3350	E00652	Not Available	Coating agent; Diluent; Ointment base; Plasticizing agent; Solvent; Suppository base; lubricant
Polyethylene glycol 400	E00653	Not Available	Coating agent; Diluent; Ointment base; Plasticizing agent; Solvent; Suppository base; lubricant
Polyoxyl 35 castor oil	E00660	Not Available	Emulsifying agent; Solubilizing agent; Surfactant
Polyvinyl alcohol	E00666	Not Available	Coating agent; Emulsion stabilizing agent; Film/Membrane-forming agent
Potassium hydroxide	E00233	14797	Alkalizing agent
Povidone	E00667	Not Available	Binding agent; Coating agent; Disintegrant; Film/membrane-forming agent; Solubilizing agent; Suspending agent
Propylene glycol	E00040	1030	Antimicrobial preservative; Humectant; Plasticizing agent; Solvent
Saccharose	E00091	5988	Binding agent; Coating agent; Cryoprotectant; Diluent; Flavoring agent; Suspending agent; Viscosity-controlling agent
Silicon dioxide	E00670	Not Available	Anticaking agent; Opacifying agent; Viscosity-controlling agent
Soybean lecithin	E00637	Not Available	Other agent
Talc	E00520	16211421	Anticaking agent; Diluent; Glidant; lubricant
Titanium dioxide	E00322	26042	Coating agent; Colorant; Opacifying agent
Triacetin	E00080	5541	Humectant; Plasticizing agent; Solvent
Triethyl citrate	E00128	6506	Plasticizing agent; Solvent
Water	E00035	962	Solvent
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⏷ Show the Full List of 42 Pharmaceutical Excipients of This Drug

Pharmaceutical Formulation

Formulation Name	Drug Dosage	Dosage Form	Route
Amoxicillin 775 mg tablet	775 mg	Extended Release Tablet	Oral
Amoxicillin 250 mg tablet	250 mg	Chewable Tablet	Oral
Amoxicillin 775 mg tablet	775 mg	Extended Release Oral Tablet	Oral
Amoxicillin 200 mg/5 ml suspension	200 mg/5 ml	Oral Suspension	Oral
Amoxicillin 400 mg/5 ml suspension	400 mg/5 ml	Oral Suspension	Oral
Amoxicillin 250 mg capsule	250 mg	Oral Capsule	Oral
Amoxicillin 500 mg capsule	500 mg	Oral Capsule	Oral
Amoxicillin 125 mg tablet	125 mg	Chewable Tablet	Oral
Amoxicillin 500 mg tablet	500 mg	Oral Tablet	Oral
Amoxicillin 875 mg tablet	875 mg	Oral Tablet	Oral

Jump to Detail Pharmaceutical Formulation Page of This Drug

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4	BDDCS applied to over 900 drugs
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18	Genomic characterization of an extensively-drug resistance Salmonella enterica serotype Indiana strain harboring bla NDM-1 gene isolated from a chicken carcass in China. Microbiol Res. 2017 Nov;204:48-54.
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21	IncU plasmid harbouring bla CTX-M-8 in multidrug-resistant Shigella sonnei in Brazil. J Glob Antimicrob Resist. 2018 Sep;14:99-100.
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23	Prevalence of antimicrobial resistance genes in Bacteroides spp. and Prevotella spp. Dutch clinical isolates. Clin Microbiol Infect. 2019 Sep;25(9):1156.e9-1156.e13.
24	Major phenylpropanoid-derived metabolites in the human gut can arise from microbial fermentation of protein. Mol Nutr Food Res. 2013 Mar;57(3):523-35.
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27	Beta-lactamase production and susceptibilities to amoxicillin, amoxicillin-clavulanate, ticarcillin, ticarcillin-clavulanate, cefoxitin, imipenem, and metronidazole of 320 non-Bacteroides fragilis Bacteroides isolates and 129 fusobacteria from 28 U.S. centers. Antimicrob Agents Chemother. 1990 Aug;34(8):1546-50.
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29	ACI-1 from Acidaminococcus fermentans: characterization of the first beta-lactamase in Anaerobic cocci. Antimicrob Agents Chemother. 2000 Nov;44(11):3144-9.
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32	Prevotella strains and lactamic resistance gene distribution in different oral environments of children with pulp necrosis. Int Endod J. 2018 Nov;51(11):1196-1204.
33	High prevalence of beta-lactam and macrolide resistance genes in human oral Capnocytophaga species. J Antimicrob Chemother. 2014 Feb;69(2):381-4.
34	Yersinia enterocolitica and Photorhabdus asymbiotica beta-lactamases BlaA are exported by the twin-arginine translocation pathway. Int J Med Microbiol. 2013 Jan;303(1):16-24.
35	Xenorhabdus luminescens (DNA hybridization group 5) from human clinical specimens. J Clin Microbiol. 1989 Jul;27(7):1594-600. Case Reports
36	High prevalence of cfxA beta-lactamase in aminopenicillin-resistant Prevotella strains isolated from periodontal pockets. Oral Microbiol Immunol. 2002 Apr;17(2):85-8.
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