Skip Navigation
ChemIDplus A TOXNET DATABASE LiteBrowseAdvanced

Substance Name: Methicillin [USAN]
RN: 61-32-5
UNII: Q91FH1328A
InChIKey: RJQXTJLFIWVMTO-TYNCELHUSA-N

Note

  • One of the PENICILLINS which is resistant to PENICILLINASE but susceptible to a penicillin-binding protein. It is inactivated by gastric acid so administered by injection.

Molecular Formula

  • C17-H20-N2-O6-S

Molecular Weight

  • 380.419
 

Classification Codes

  • Anti-Bacterial Agents
  • Anti-Infective Agents
  • Drug / Therapeutic Agent
  • Human Data
  • Mutation Data

Names and Synonyms

Results Name

  • Methicillin [USAN]

Name of Substance

  • Methicillin
  • Methicillin [USAN]
  • Meticillin [INN:BAN]

MeSH Heading

  • Methicillin

Synonyms

  • (2,6-Dimethoxyphenyl)penicillin
  • 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-((2,6-dimethoxybenzoyl)amino)-3,3-dimethyl-7-oxo-, (2S-(2alpha,5alpha,6beta))-
  • 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-(2,6-dimethoxybenzamido)-3,3-dimethyl-7-oxo-
  • 6-(2,6-Dimethoxybenzamido)penicillanic acid
  • BRL 1241
  • Dimocillin
  • EINECS 200-505-8
  • HSDB 3121
  • Metacillin
  • Methicillin
  • Methicillin [USAN]
  • Methicillinum
  • Methycillin
  • Meticilina
  • Meticilina [INN-Spanish]
  • Meticillin
  • Meticillina
  • Meticillina [DCIT]
  • Meticilline
  • Meticilline [INN-French]
  • Meticillinum
  • Meticillinum [INN-Latin]
  • Penicillin, (2,6-dimethoxyphenyl)-
  • UNII-Q91FH1328A

Systematic Names

  • 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-((2,6-dimethoxybenzoyl)amino)-3,3-dimethyl-7-oxo-, (2S-(2alpha,5alpha,6beta))-
  • 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-(2,6-dimethoxybenzamido)-3,3,-dimethyl-7-oxo-
  • 6-(2,3-Dimethoxybenzamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid

Registry Numbers

CAS Registry Number

  • 61-32-5

FDA UNII

  • Q91FH1328A

Related Registry Numbers

  • 132-92-3 (mono-hydrochloride salt, hydrate)
  • 7246-14-2 (mono-hydrochloride salt, monohydrate)

System Generated Number

  • 0000061325

Structure Descriptors

InChI

1S/C17H20N2O6S/c1-17(2)12(16(22)23)19-14(21)11(15(19)26-17)18-13(20)10-8(24-3)6-5-7-9(10)25-4/h5-7,11-12,15H,1-4H3,(H,18,20)(H,22,23)/t11-,12+,15-/m1/s1

InChIKey

RJQXTJLFIWVMTO-TYNCELHUSA-N

Smiles

CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)c3c(cccc3OC)OC)C(=O)O)C

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
man TDLo oral 11gm/kg/32D-I (11000mg/kg) KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)"

KIDNEY, URETER, AND BLADDER: INTERSTITIAL NEPHRITIS
New England Journal of Medicine. Vol. 279, Pg. 1245, 1968.
man TDLo unreported 229mg/kg/8D-I (229mg/kg) KIDNEY, URETER, AND BLADDER: URINE VOLUME INCREASED

KIDNEY, URETER, AND BLADDER: HEMATURIA
Antimicrobial Agents and Chemotherapy Vol. -, Pg. 765, 1961.
mouse LD50 intracrebral 38340ug/kg (38.34mg/kg)   Journal of Antibiotics, Series B. Vol. 16, Pg. 40, 1963.
mouse LD50 intravenous 3720mg/kg (3720mg/kg)   Antibiotiki. Vol. 10, Pg. 629, 1965.

Physical Properties

Physical Property Value Units Temp (deg C) Source
pKa Dissociation Constant 2.77 (none)   EXP
log P (octanol-water) 1.22 (none)   EXP
Water Solubility 367 mg/L 25 EST
Vapor Pressure 1.88E-13 mm Hg 25 EST
Henry's Law Constant 9.99E-17 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 2.66E-10 cm3/molecule-sec 25 EST

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