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amoxicillin 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definition	Drug id	CAS RN
antibiotics, 6-aminopenicillanic acid derivatives	192	26787-78-0

Description:

Molecule	Description
Molfile Inchi Smiles Synonyms: amoxicillin trihydrate amoxicillin amocilline amoxcillin amoxycillin amoxicillin sodium amoxicillin anhydrous amoxicillin hydrate	A broad-spectrum semisynthetic antibiotic similar to AMPICILLIN except that its resistance to gastric acid permits higher serum levels with oral administration. Molecular weight: 365.40 Formula: C16H19N3O5S CLOGP: -1.87 LIPINSKI: 0 HAC: 8 HDO: 4 TPSA: 132.96 ALOGS: -2.58 ROTB: 4 Status: OFP Legend: OFP - off patent OFM - off market ONP - on patent

Molecule

Description

Molfile Inchi Smiles

Synonyms:

amoxicillin trihydrate
amoxicillin
amocilline
amoxcillin
amoxycillin
amoxicillin sodium
amoxicillin anhydrous
amoxicillin hydrate

A broad-spectrum semisynthetic antibiotic similar to AMPICILLIN except that its resistance to gastric acid permits higher serum levels with oral administration.

Molecular weight: 365.40
Formula: C16H19N3O5S
CLOGP: -1.87
LIPINSKI: 0
HAC: 8
HDO: 4
TPSA: 132.96
ALOGS: -2.58
ROTB: 4

Status: OFP

Legend:
OFP - off patent
OFM - off market
ONP - on patent

Drug dosage:

Dose	Unit	Route
1.50	g	O
3	g	P
1.50	g	O
3	g	P

ADMET properties:

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Property	Value	Reference
BA (Bioavailability)	93 %	Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
EoM (Fraction excreted unchanged in urine)	86 %	Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose)	68.42 µM/kg/day	Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
S (Water solubility)	3.50 mg/mL	Benet LZ, Broccatelli F, Oprea TI
CL (Clearance)	3.30 mL/min/kg	Lombardo F, Berellini G, Obach RS
BDDCS (Biopharmaceutical Drug Disposition Classification System)	3	Benet LZ, Broccatelli F, Oprea TI
t_half (Half-life)	1.10 hours	Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma)	0.85 %	Lombardo F, Berellini G, Obach RS
Vd (Volume of distribution)	0.25 L/kg	Lombardo F, Berellini G, Obach RS

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Approvals:

Date	Agency	Company	Orphan
Dec. 9, 1974	FDA	APOTHECON

FDA Adverse Event Reporting System (Female)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Drug hypersensitivity	822.34	9.89	1689	105015	308998	63073320
Rash maculo-papular	673.25	9.89	501	106203	31395	63350923
Drug reaction with eosinophilia and systemic symptoms	495.42	9.89	429	106275	33407	63348911
Angioedema	475.72	9.89	490	106214	47475	63334843
Urticaria	447.48	9.89	910	105794	164892	63217426
Anaphylactic shock	425.87	9.89	338	106366	23295	63359023
Pruritus	421.45	9.89	1449	105255	360004	63022314
Erythema	397.58	9.89	898	105806	174853	63207465
Acute generalised exanthematous pustulosis	344.18	9.89	221	106483	10878	63371440
Cross sensitivity reaction	317.43	9.89	124	106580	2038	63380280

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FDA Adverse Event Reporting System (Male)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Drug reaction with eosinophilia and systemic symptoms	529.79	10.15	462	65081	32550	34858838
Anaphylactic shock	519.76	10.15	341	65202	15600	34875788
Urticaria	440.23	10.15	563	64980	61814	34829574
Pruritus	415.04	10.15	858	64685	141123	34750265
Rash maculo-papular	316.20	10.15	325	65218	28126	34863262
Rash	250.56	10.15	950	64593	221802	34669586
Lip oedema	234.13	10.15	109	65434	2504	34888884
Anaphylactic reaction	233.05	10.15	295	65248	32006	34859382
Angioedema	222.98	10.15	311	65232	37063	34854325
Acute generalised exanthematous pustulosis	218.45	10.15	144	65399	6632	34884756

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FDA Adverse Event Reporting System (Geriatric)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Drug reaction with eosinophilia and systemic symptoms	970.42	9.63	859	144756	63385	79535388
Rash maculo-papular	917.89	9.63	785	144830	55293	79543480
Anaphylactic shock	894.87	9.63	645	144970	35351	79563422
Pruritus	849.67	9.63	2078	143537	392570	79206203
Urticaria	800.01	9.63	1306	144309	183895	79414878
Angioedema	628.30	9.63	734	144881	75301	79523472
Erythema	569.57	9.63	1258	144357	222032	79376741
Acute generalised exanthematous pustulosis	534.23	9.63	354	145261	16900	79581873
Rash	529.76	9.63	2272	143343	576086	79022687
Anaphylactic reaction	457.49	9.63	659	144956	83084	79515689

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FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

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Source	Code	Description
ATC	A02BD01	ALIMENTARY TRACT AND METABOLISM DRUGS FOR ACID RELATED DISORDERS DRUGS FOR PEPTIC ULCER AND GASTRO-OESOPHAGEAL REFLUX DISEASE (GORD) Combinations for eradication of Helicobacter pylori
ATC	A02BD03	ALIMENTARY TRACT AND METABOLISM DRUGS FOR ACID RELATED DISORDERS DRUGS FOR PEPTIC ULCER AND GASTRO-OESOPHAGEAL REFLUX DISEASE (GORD) Combinations for eradication of Helicobacter pylori
ATC	A02BD04	ALIMENTARY TRACT AND METABOLISM DRUGS FOR ACID RELATED DISORDERS DRUGS FOR PEPTIC ULCER AND GASTRO-OESOPHAGEAL REFLUX DISEASE (GORD) Combinations for eradication of Helicobacter pylori
ATC	A02BD05	ALIMENTARY TRACT AND METABOLISM DRUGS FOR ACID RELATED DISORDERS DRUGS FOR PEPTIC ULCER AND GASTRO-OESOPHAGEAL REFLUX DISEASE (GORD) Combinations for eradication of Helicobacter pylori
ATC	A02BD06	ALIMENTARY TRACT AND METABOLISM DRUGS FOR ACID RELATED DISORDERS DRUGS FOR PEPTIC ULCER AND GASTRO-OESOPHAGEAL REFLUX DISEASE (GORD) Combinations for eradication of Helicobacter pylori
ATC	A02BD07	ALIMENTARY TRACT AND METABOLISM DRUGS FOR ACID RELATED DISORDERS DRUGS FOR PEPTIC ULCER AND GASTRO-OESOPHAGEAL REFLUX DISEASE (GORD) Combinations for eradication of Helicobacter pylori
ATC	A02BD10	ALIMENTARY TRACT AND METABOLISM DRUGS FOR ACID RELATED DISORDERS DRUGS FOR PEPTIC ULCER AND GASTRO-OESOPHAGEAL REFLUX DISEASE (GORD) Combinations for eradication of Helicobacter pylori
ATC	A02BD11	ALIMENTARY TRACT AND METABOLISM DRUGS FOR ACID RELATED DISORDERS DRUGS FOR PEPTIC ULCER AND GASTRO-OESOPHAGEAL REFLUX DISEASE (GORD) Combinations for eradication of Helicobacter pylori
ATC	A02BD12	ALIMENTARY TRACT AND METABOLISM DRUGS FOR ACID RELATED DISORDERS DRUGS FOR PEPTIC ULCER AND GASTRO-OESOPHAGEAL REFLUX DISEASE (GORD) Combinations for eradication of Helicobacter pylori
ATC	A02BD13	ALIMENTARY TRACT AND METABOLISM DRUGS FOR ACID RELATED DISORDERS DRUGS FOR PEPTIC ULCER AND GASTRO-OESOPHAGEAL REFLUX DISEASE (GORD) Combinations for eradication of Helicobacter pylori

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Drug Use | Suggest Off label Use Form| |View source of the data|

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Disease	Relation	SNOMED_ID	DOID
Acute otitis media	indication	3110003
Staphylococcal tonsillitis	indication	11461005
Haemophilus Influenzae Acute Otitis Media	indication	19021002
Infection of skin AND/OR subcutaneous tissue	indication	19824006
Pneumonia due to Streptococcus	indication	34020007
Streptococcal tonsillitis	indication	41582007
Lower respiratory tract infection	indication	50417007
Bacterial pneumonia	indication	53084003	DOID:874
Klebsiella cystitis	indication	60867007
Pneumonia due to Klebsiella pneumoniae	indication	64479007

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🐶 Veterinary Drug Use

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Species	Use	Relation
Cats	Upper respiratory tract infections caused by Staphylococcus aureus	Indication
Cats	Upper respiratory tract infections caused by Streptococcus spp	Indication
Cats	Upper respiratory tract infections caused by Escherichia coli	Indication
Cats	Gastrointestinal tract infections caused by Escherichia coli	Indication
Cats	Genitourinary tract infections caused by Staphylococcus aureus	Indication
Cats	Genitourinary tract infections caused by Streptococcus spp	Indication
Cats	Genitourinary tract infections caused by Escherichia coli	Indication
Cats	Genitourinary tract infections caused by Proteus species	Indication
Cats	Skin and soft tissue infections caused by Staphylococcus spp	Indication
Cats	Skin and soft tissue infections caused by Streptococcus spp	Indication

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🐶 Veterinary products

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Product	Applicant	Ingredients
Amoxi-Bol	Zoetis Inc.	1
Amoxi-Doser	Zoetis Inc.	1
Amoxi-Drop Oral Suspension	Zoetis Inc.	1
Amoxi-Inject (Cattle)	Zoetis Inc.	1
Amoxi-Inject (Dogs and Cats)	Zoetis Inc.	1
Amoxi-Mast	Intervet Inc.	1
Amoxi-Sol	Zoetis Inc.	1
Amoxi-Tabs	Zoetis Inc.	1
Amoxi-Tabs	Zoetis Inc.	1
Amoxicillin and Clavulanate Potassium for Oral Suspension	Dechra Veterinary Products LLC	2

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Acid dissociation constants calculated using MoKa v3.0.0

Dissociation level	Dissociation constant	Type (acidic/basic)
pKa1	2.79	acidic
pKa2	9.72	acidic
pKa3	7.63	Basic

Orange Book patent data (new drug applications)

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Formulation strength	Trade name	Applicant	Application number	Approval date	Type	Dose form	Route	Patent number	Patent expiration date	Patent use
250MG;EQ 10MG BASE;12.5MG	TALICIA	REDHILL	N213004	Nov. 1, 2019	RX	CAPSULE, DELAYED RELEASE	ORAL	11135172	Feb. 12, 2034	TREATMENT OF H. PYLORI INFECTION IN ADULTS
250MG;EQ 10MG BASE;12.5MG	TALICIA	REDHILL	N213004	Nov. 1, 2019	RX	CAPSULE, DELAYED RELEASE	ORAL	9050263	Feb. 12, 2034	TREATMENT OF H. PYLORI INFECTION IN ADULTS
250MG;EQ 10MG BASE;12.5MG	TALICIA	REDHILL	N213004	Nov. 1, 2019	RX	CAPSULE, DELAYED RELEASE	ORAL	9498445	Feb. 12, 2034	TREATMENT OF H. PYLORI INFECTION IN ADULTS
250MG;EQ 10MG BASE;12.5MG	TALICIA	REDHILL	N213004	Nov. 1, 2019	RX	CAPSULE, DELAYED RELEASE	ORAL	9603806	Feb. 12, 2034	TREATMENT OF H. PYLORI INFECTION IN ADULTS
775MG	MOXATAG	PRAGMA	N050813	Jan. 23, 2008	DISCN	TABLET, EXTENDED RELEASE	ORAL	8778924	Dec. 8, 2026	METHOD OF TREATING TONSILLITIS AND/OR PHARYNGITIS SECONDARY TO STREPTOCOCCUS PYOGENES IN A ONCE-A-DAY AMOXICILLIN PRODUCT
775MG	MOXATAG	PRAGMA	N050813	Jan. 23, 2008	DISCN	TABLET, EXTENDED RELEASE	ORAL	8299052	May 7, 2027	USE OF ONCE-A-DAY AMOXICILLIN PRODUCT TO TREAT TONSILLITIS AND/OR PHARYNGITIS SECONDARY TO STREPTOCOCCUS PYOGENES

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Orange Book exclusivity data (new drug applications)

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Formulation strength	Trade name	Applicant	Application number	Approval date	Type	Dose form	Route	Exclusivity date	Description
500MG;500MG;EQ 20MG BASE	VOQUEZNA TRIPLE PAK	PHATHOM	N215152	May 3, 2022	DISCN	CAPSULE, TABLET, TABLET	ORAL	May 3, 2027	NEW CHEMICAL ENTITY
500MG;500MG;EQ 20MG BASE	VOQUEZNA TRIPLE PAK	PHATHOM	N215152	May 3, 2022	DISCN	CAPSULE, TABLET, TABLET	ORAL	May 3, 2032	GENERATING ANTIBIOTIC INCENTIVES NOW
500MG;EQ 20MG BASE	VOQUEZNA DUAL PAK	PHATHOM	N215153	May 3, 2022	DISCN	CAPSULE, TABLET	ORAL	May 3, 2027	NEW CHEMICAL ENTITY
500MG;EQ 20MG BASE	VOQUEZNA DUAL PAK	PHATHOM	N215153	May 3, 2022	DISCN	CAPSULE, TABLET	ORAL	May 3, 2032	GENERATING ANTIBIOTIC INCENTIVES NOW

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Bioactivity Summary:

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Target	Class	Pharos	UniProt	Action	Type	Activity value (-log[M])	Bioact source	MoA source
5-hydroxytryptamine receptor 2A	GPCR	P28223	5HT2A_HUMAN		IC50	6.22	WOMBAT-PK
5-hydroxytryptamine receptor 2B	GPCR	P41595	5HT2B_HUMAN		IC50	5.96	WOMBAT-PK
5-hydroxytryptamine receptor 2C	GPCR	P28335	5HT2C_HUMAN		IC50	5.80	WOMBAT-PK
Bacterial penicillin-binding protein	Enzyme		PBPA_ECOLI PBPB_ECOLI DACC_ECOLI PBP2_ECOLI FTSI_ECOLI DACA_ECOLI DACB_ECOLI	INHIBITOR			CHEMBL	CHEMBL
Penicillin-binding protein 1A	Enzyme		PBPA_CLOPE				WOMBAT-PK

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External reference:

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ID	Source
002707	NDDF
003675	NDDF
003718	NDDF
10895	IUPHAR_LIGAND_ID
11786	MMSL
1297882	RXNORM
27658006	SNOMEDCT_US
3230	INN_ID
33613	PUBCHEM_CID
34642-77-8	SECONDARY_CAS_RN

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Pharmaceutical products:

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Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
Amoxicillin	HUMAN PRESCRIPTION DRUG LABEL	1	0093-2263	TABLET, FILM COATED	500 mg	ORAL	ANDA	26 sections
Amoxicillin	HUMAN PRESCRIPTION DRUG LABEL	1	0093-2263	TABLET, FILM COATED	500 mg	ORAL	ANDA	26 sections
Amoxicillin	HUMAN PRESCRIPTION DRUG LABEL	1	0093-2263	TABLET, FILM COATED	500 mg	ORAL	ANDA	26 sections
Amoxicillin	HUMAN PRESCRIPTION DRUG LABEL	1	0093-2264	TABLET, FILM COATED	875 mg	ORAL	ANDA	26 sections
Amoxicillin	HUMAN PRESCRIPTION DRUG LABEL	1	0093-2264	TABLET, FILM COATED	875 mg	ORAL	ANDA	26 sections
Amoxicillin	HUMAN PRESCRIPTION DRUG LABEL	1	0093-2264	TABLET, FILM COATED	875 mg	ORAL	ANDA	26 sections
Amoxicillin	HUMAN PRESCRIPTION DRUG LABEL	1	0093-2267	TABLET, CHEWABLE	125 mg	ORAL	ANDA	27 sections
Amoxicillin	HUMAN PRESCRIPTION DRUG LABEL	1	0093-2267	TABLET, CHEWABLE	125 mg	ORAL	ANDA	27 sections
Amoxicillin	HUMAN PRESCRIPTION DRUG LABEL	1	0093-2267	TABLET, CHEWABLE	125 mg	ORAL	ANDA	27 sections
Amoxicillin	HUMAN PRESCRIPTION DRUG LABEL	1	0093-2268	TABLET, CHEWABLE	250 mg	ORAL	ANDA	27 sections

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