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Substance Name: Cephradine [USAN:BAN]
RN: 38821-53-3
UNII: 9YA6SX5S4D
InChIKey: RDLPVSKMFDYCOR-UEKVPHQBSA-N

Note

  • A semi-synthetic cephalosporin antibiotic.

Molecular Formula

  • C16-H19-N3-O4-S

Molecular Weight

  • 349.409
 

Classification Codes

  • Anti-Bacterial Agents
  • Anti-Infective Agents
  • Antibacterial
  • Antibiotics
  • Drug / Therapeutic Agent
  • Human Data
  • Reproductive Effect
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Names and Synonyms

Name of Substance

  • Cefradine [INN]
  • Cephradine
  • Cephradine [USAN:BAN]

MeSH Heading

  • Cephradine

Synonyms

  • (6R,7R)-7-((R)-2-Amino-2-(1,4-cyclohexadien-1-yl)acetamido)-3-methyl-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid
  • 5-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 7-((amino-1,4-cyclohexadien-1-ylacetyl)amino)-3-methyl-8-oxo-, (6R-(6alpha,7beta(R*)))-
  • 7-(D-2-Amino-2-(1,4-cyclohexadien-1-yl)acetamido)-3-methyl-8-oxo-5-thia-1-azabicyclo(4.2.0)-oct-2-ene-2-caboxylic acid
  • 7-(D-2-Amino-2-(1,4-cyclohexadienyl)acetamide)desacetoxycephalosporanicacid
  • Anspor
  • BRN 6075388
  • Cefradina
  • Cefradina [INN-Spanish]
  • Cefradine
  • Cefradinum
  • Cefradinum [INN-Latin]
  • Cekodin
  • Cephradin
  • Cephradine
  • EINECS 254-137-8
  • Eskacef
  • HSDB 3216
  • Megace f
  • Megacef
  • NSC 756672
  • Sefril
  • SKF D 39304
  • SQ 11436
  • UNII-9YA6SX5S4D
  • Velosef
  • Velosef '125'
  • Velosef '250'
  • Velosef '500'

Systematic Names

  • 5-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 7-((amino-1,4-cyclohexadien-1-ylacetyl)amino)-3-methyl-8-oxo-, (6R-(6alpha,7beta(R*)))-
  • Cefradine

Registry Numbers

CAS Registry Number

  • 38821-53-3

FDA UNII

  • 9YA6SX5S4D

Related Registry Number

  • 58456-86-3 (dihydrate)

System Generated Number

  • 0038821533

Structure Descriptors

InChI

InChI=1S/C16H19N3O4S/c1-8-7-24-15-11(14(21)19(15)12(8)16(22)23)18-13(20)10(17)9-5-3-2-4-6-9/h2-3,6,10-11,15H,4-5,7,17H2,1H3,(H,18,20)(H,22,23)/t10-,11-,15-/m1/s1

InChIKey

RDLPVSKMFDYCOR-UEKVPHQBSA-N

Smiles

CC1=C(N2[C@H](SC1)[C@H](NC(=O)[C@H](N)C3=CCC=CC3)C2=O)C(=O)O

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 597mg/kg (597mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 8, Pg. 680, 1977.
mouse LD50 intravenous 3539mg/kg (3539mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 8, Pg. 680, 1977.
mouse LD50 oral 3549mg/kg (3549mg/kg)   Chemotherapy Vol. 23, Pg. 37, 1975.
mouse LD50 subcutaneous 2890mg/kg (2890mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 8, Pg. 680, 1977.
rat LD50 intraperitoneal > 5gm/kg (5000mg/kg)   Chemotherapy Vol. 23, Pg. 37, 1975.
rat LD50 intravenous > 2500mg/kg (2500mg/kg)   Chemotherapy Vol. 23, Pg. 37, 1975.
rat LD50 oral > 12gm/kg (12000mg/kg)   Chemotherapy Vol. 23, Pg. 37, 1975.
rat LD50 subcutaneous > 7500mg/kg (7500mg/kg)   Chemotherapy Vol. 23, Pg. 37, 1975.
women TDLo oral 5mg/kg (5mg/kg) SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE" CUTIS; Cutaneous Medicine for the Practitioner. Vol. 38, Pg. 58, 1986.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 140 deg C   EXP
log P (octanol-water) 0.410 (none)   EST
Water Solubility 2.13E+04 mg/L   EXP
Atmospheric OH Rate Constant 2.94E-10 cm3/molecule-sec 25 EST

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