Amoxicillin anhydrous

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C16H19N3O5S
Molecular Weight	365.404
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

CC1(C)S[C@@H]2[C@H](NC(=O)[C@H](N)C3=CC=C(O)C=C3)C(=O)N2[C@H]1C(O)=O

InChI

InChIKey=LSQZJLSUYDQPKJ-NJBDSQKTSA-N

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

HIDE SMILES / InChI

Molecular Formula	C16H19N3O5S
Molecular Weight	365.404
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	4 / 4
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description

Amoxicillin is one of the widely prescribed antibacterial agents, which was discovered by scientists at Beecham Research Laboratories in 1972. In the US GlaxoSmithKline markets it under the original brand name Amoxil. It is the first line treatment for middle ear infections. It is also used for strep throat, pneumonia, skin infections, and urinary tract infections it is taken by mouth. Amoxicillin inhibits the third and final stage of bacterial cell wall synthesis by preferentially binding to specific penicillin-binding proteins (PBPs) that are located inside the bacterial cell wall. This results in a formation of defective cell wall and a cell death. Common side effects include nausea and rash. It may also increase the risk of yeast infections and, when used in combination with clavulanic acid, diarrhea. It should not be used in those who are allergic to penicillin.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Bacterial penicillin-binding protein 234	Inhibitor 8,504

Conditions

Condition	Modality	Highest Phase	Product
Infections of the ear, nose, and throat 5	Curative	Approved 8,583	AMOXIL
Infections of the genitourinary tract 3	Curative	Approved 8,583	AMOXIL
Skin and skin structure infections 81	Curative	Approved 8,583	AMOXIL
Gonorrhea, acute uncomplicated 3	Curative	Approved 8,583	AMOXIL
Helicobacter pylori infection and duodenal ulcer disease 3	Curative	Approved 8,583	AMOXIL

C_max

Value	Dose	Co-administered	Analyte	Population
11.8 μg/mL	500 mg single, oral		AMOXICILLIN plasma	Homo sapiens

AUC

Value	Dose	Co-administered	Analyte	Population
37.6 μg × h/mL	500 mg single, oral		AMOXICILLIN plasma	Homo sapiens

T_1/2

Value	Dose	Co-administered	Analyte	Population
0.5 h	500 mg single, oral		AMOXICILLIN plasma	Homo sapiens

Doses

Show entries

Dose	Population	Adverse events
775 mg 1 times / day steady, oral	unhealthy, > 12 years	Disc. AE: Pharyngolaryngeal pain... Other AEs: Nausea, Pharyngotonsillitis...

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AEs

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AE	Significance	Dose	Population
Abdominal pain	0.5%	775 mg 1 times / day steady, oral	unhealthy, > 12 years
Diarrhea	0.5%	775 mg 1 times / day steady, oral	unhealthy, > 12 years
Headache	0.7%	775 mg 1 times / day steady, oral	unhealthy, > 12 years
Pharyngotonsillitis	0.9%	775 mg 1 times / day steady, oral	unhealthy, > 12 years
Vulvovaginal candidiasis	0.9%	775 mg 1 times / day steady, oral	unhealthy, > 12 years

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Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2,252	inhibitor 2,438	inhibitor 2,507	inhibitor 2,217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP3A5 136 CYP2C8 1,057 BSEP 550 CYP2A6 879 PEPT1 27 PEPT2 13 OAT1 725 CYP2C19 2,057 MRP2 499 P-gp 1,741 OATP1B1 1,079 CYP2J2 33 CYP2E1 1,060 BCRP 910 OATP1B3 961 MRP3 246 CYP19A1 429 CYP1A2 2,153 OATP2B1 157 ABCB6 3 MRP4 290	OCT2 434 chicken BCRP 3 OAT1 395 chicken P-gp 3 OAT3 391 PEPT1 60 OATP1B1 503 PEPT2 37 OATP2B1 122 OATP1B3 435 OCT1 393

Drug as perpetrator

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Target	Modality	Activity
CYP2J2 36	inhibitor 4,027	inconclusive [IC50 50 uM]
CYP1A2 2,333	inhibitor 4,027	no [IC50 >10 uM]
CYP2A6 911	inhibitor 4,027	no [IC50 >10 uM]
CYP2C19 2,141	inhibitor 4,027	no [IC50 >10 uM]
CYP2E1 1,146	inhibitor 4,027	no [IC50 >10 uM]

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Drug as victim

Show entries

Target	Modality	Activity
OATP1B1 503	substrate 4,014	likely
OCT1 393	substrate 4,014	likely
OCT2 434	substrate 4,014	likely
OAT1 395	substrate 4,014	no
OATP1B3 435	substrate 4,014	no

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Tox targets

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Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2,263	inhibitor 2,237

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Sourcing

Sourcing

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Vendor/Aggregator	ID	URL
3B Scientific (Wuhan) Corp	3B2-0028	http://www.3bsc.com/index/pro_info.php?id=19384
Aaron Chemicals	AR006UMZ	http://www.aaronchem.com/26787-78-0
abcr GmbH	AB439985	http://www.abcr.com/shop/en/AB439985
AbMole Bioscience	M4095	http://www.abmole.com/products/notoginsenoside-fe.html
Achemtek	0104-023910	http://www.achemtek.com/26787-78-0

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PubMed

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Title	Date	PubMed
[Amoxicillin caused aseptic meningoencephalitis].	1999 Jan 20	10068320
Adverse reaction to amoxicillin: a case report.	2000 Sep-Oct	11048309
Use of antibiotics to treat bacteriuria of pregnancy in the Nordic countries. Which antibiotics are appropriate to treat bacteriuria of pregnancy?	2001 Apr	11295409
A prospective observational study of 5-, 7-, and 10-day antibiotic treatment for acute otitis media.	2001 Apr	11283494
Efficacy, safety and tolerability of 3 day azithromycin versus 10 day co-amoxiclav in the treatment of children with acute lower respiratory tract infections.	2001 Apr	11266417

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Patents

Sample Use Guides

In Vivo Use Guide

In adults, 750-1750 mg/day in divided doses every 8-12 hours. In Pediatric Patients > 3 Months of Age, 20-45 mg/kg/day in divided doses every 8-12 hours. Treatment of gonorrhea is 3 grams as a single oral dose. The upper dose for neonates and infants ≤ 3 months is 30 mg/kg/day divided every 12 hours. Dosing for H. pylori Infection: Triple therapy: 1 gram AMOXIL, 500 mg clarithromycin, and 30 mg lansoprazole, all given twice daily (every 12 hours) for 14 days. Dual therapy: 1 gram AMOXIL and 30 mg lansoprazole, each given three times daily (every 8 hours) for 14 days.

Route of Administration: Oral

In Vitro Use Guide

Unknown