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Substance Name: Amoxicillin [INN]
RN: 26787-78-0
UNII: 9EM05410Q9
InChIKey: LSQZJLSUYDQPKJ-NJBDSQKTSA-N

Note

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

Molecular Formula

  • C16-H19-N3-O5-S

Molecular Weight

  • 365.4081
 

Classification Codes

  • Anti-Bacterial Agents
  • Anti-Infective Agents
  • Antimicrobial
  • Drug / Therapeutic Agent
  • Human Data
  • Reproductive Effect

Names and Synonyms

Results Name

  • Amoxicillin [INN]

Name of Substance

  • Amopen
  • Amoxicillin
  • Amoxicillin anhydrous

MeSH Heading

  • Amoxicillin

Synonyms

  • (-)-6-(2-Amino-2-(P-hydroxyphenyl)acetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo-(3.2.0)heptane-2-carboxylic acid
  • 6-(D-(-)-alpha-Amino-p-hydroxyphenylacetamido)penicillanic acid
  • 6-(D-(-)-p-Hydroxy-alpha-aminobenzyl)penicillin
  • 6-(p-Hydroxy-alpha-aminophenylacetamido)penicillanic acid
  • alpha-Amino-p-hydroxybenzylpenicillin
  • Amoclen
  • Amolin
  • Amopenixin
  • Amoxi
  • Amoxi-Mast
  • Amoxicaps
  • Amoxicilina
  • Amoxicilina [INN-Spanish]
  • Amoxicillin
  • Amoxicillin pediatric
  • Amoxicilline
  • Amoxicilline [INN-French]
  • Amoxicillinum
  • Amoxicillinum [INN-Latin]
  • Amoxiden
  • Amoxil
  • Amoxivet
  • Amoxycillin
  • AMPC
  • Ampy-Penyl
  • Anemolin
  • Apo-Amoxi
  • Aspenil
  • BLP 1410
  • Bristamox
  • Cemoxin
  • Clamoxyl
  • D-(-)-alpha-Amino-p-hydroxybenzylpenicillin
  • D-2-Amino-2-(4-hydroxyphenyl)acetamidopenicillanic acid
  • D-Amoxicillin
  • Delacillin
  • Dispermox
  • EC 248-003-8
  • Efpenix
  • EINECS 248-003-8
  • Flemoxin
  • Hiconcil
  • Histocillin
  • HSDB 3204
  • Ibiamox
  • Imacillin
  • Larotid
  • Metafarma capsules
  • Metifarma capsules
  • Moxacin
  • Moxal
  • Moxatag
  • NSC 277174
  • Ospamox
  • p-Hydroxyampicillin
  • Piramox
  • Polymox
  • Ro 10-8756
  • Robamox
  • Sawamox PM
  • Sumox
  • Trimox
  • Unicillin
  • UNII-9EM05410Q9
  • Utimox
  • Vetramox
  • Wymox

Systematic Names

  • 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- (8CI)
  • 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)))-
  • Amopen
  • Amoxicillin
  • BL-P 1410

Registry Numbers

CAS Registry Number

  • 26787-78-0

FDA UNII

  • 9EM05410Q9

Other Registry Numbers

  • 1236363-38-4
  • 33911-69-2
  • 71447-36-4
  • 81030-75-3

Related Registry Numbers

  • 34642-77-8 (mono-hydrochloride salt)
  • 61336-70-7 (trihydrate)

System Generated Number

  • 0026787780

Structure Descriptors

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

Smiles

CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)[C@@H](c3ccc(cc3)O)N)C(=O)O)C

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
child TDLo oral 300mg/kg (300mg/kg) KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)"

KIDNEY, URETER, AND BLADDER: HEMATURIA

KIDNEY, URETER, AND BLADDER: OTHER CHANGES IN URINE COMPOSITION
Clinical Pediatrics Vol. 32, Pg. 735, 1993.
child TDLo oral 682mg/kg (682mg/kg) KIDNEY, URETER, AND BLADDER: HEMATURIA

KIDNEY, URETER, AND BLADDER: URINE VOLUME DECREASED

KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)"
Clinical Pediatrics Vol. 32, Pg. 735, 1993.
man TDLo oral 7143ug/kg (7.143mg/kg) SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE" Allergy. Vol. 52(Suppl,
man TDLo oral 40mg/kg/4D (40mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

GASTROINTESTINAL: OTHER CHANGES
Lancet. Vol. 2, Pg. 707, 1978.
mouse LD50 intracrebral > 500mg/kg (500mg/kg) BRAIN AND COVERINGS: RECORDINGS FROM SPECIFIC AREAS OF CNS Chemotherapy Vol. 26, Pg. 196, 1980.
mouse LD50 intraperitoneal 3590mg/kg (3590mg/kg)   Drugs in Japan Vol. -, Pg. 59, 1990.
mouse LD50 oral > 25gm/kg (25000mg/kg)   Drugs in Japan Vol. 6, Pg. 38, 1982.
mouse LD50 subcutaneous > 20mg/kg (20mg/kg)   Drugs in Japan Vol. -, Pg. 59, 1990.
rat LD50 intraperitoneal 2870mg/kg (2870mg/kg)   Drugs in Japan Vol. -, Pg. 59, 1990.
rat LD50 oral > 15gm/kg (15000mg/kg)   Drugs in Japan Vol. 6, Pg. 38, 1982.
rat LD50 subcutaneous > 8gm/kg (8000mg/kg)   Drugs in Japan Vol. -, Pg. 59, 1990.

Physical Properties

Physical Property Value Units Temp (deg C) Source
log P (octanol-water) 0.87 (none)   EXP
Water Solubility 3430 mg/L 25 EST
Vapor Pressure 4.69E-17 mm Hg 25 EST
Henry's Law Constant 2.49E-21 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 1.39E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.