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Substance Name: Streptonigrin [USAN]
RN: 3930-19-6
UNII: 261Q3JB310
InChIKey: PVYJZLYGTZKPJE-UHFFFAOYSA-N

Note

  • Complex cytotoxic antibiotic obtained from Streptomyces flocculus or S. rufochronmogenus. It is used in advanced carcinoma and causes leukopenia.

Molecular Formula

  • C25-H22-N4-O8

Molecular Weight

  • 506.4688
 

Classification Codes

  • Antibiotics, Antineoplastic
  • Antineoplastic
  • Antineoplastic Agents
  • Drug / Therapeutic Agent
  • Mutation Data
  • Natural Product
  • Reproductive Effect
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Names and Synonyms

Name of Substance

  • Rufocromomycin [INN]
  • Streptonigrin
  • Streptonigrin [USAN]

MeSH Heading

  • Streptonigrin

Synonyms

  • 5-25-17-00308 (Beilstein Handbook Reference)
  • 5-Amino-6-(7-amino-5,8-dihydro-6-methoxy-5,8-dioxo-2-quinolyl)-4-(2-hydroxy-3,4-dimethoxyphenyl)-3-methylpicolinic acid
  • 5278 R. P.
  • 5278 R.P.
  • A 050165L302
  • Abbott Crystalline antibiotic
  • AI3-52152
  • Antibiotic from Streptomyces flocculus
  • AO50165L302
  • BRN 0599390
  • Bruneomycin
  • CCRIS 1264
  • EINECS 223-501-8
  • Nigrin
  • NSC 45383
  • NSC 83950
  • Rufocromomicina
  • Rufocromomicina [INN-Spanish]
  • Rufocromomycin
  • Rufocromomycine
  • Rufocromomycine [INN-French]
  • Rufocromomycinum
  • Rufocromomycinum [INN-Latin]
  • SN
  • SN (VAN)
  • STP
  • Streptonigran
  • Streptonigrin
  • UNII-261Q3JB310
  • Valacidin

Systematic Names

  • 2-Pyridinecarboxylic acid, 5-amino-6-(7-amino-5,8-dihydro-6-methoxy-5,8-dioxo-2-quinolinyl)-4-(2-hydroxy-3,4-dimethoxyphenyl)-3-methyl-
  • Picolinic acid, 5-amino-6-(7-amino-5,8-dihydro-6-methoxy-5,8-dioxo-2-quinolyl)-4-(2-hydroxy-3,4-dimethoxyphenyl)-3-methyl-
  • Rufocromomycin
  • Streptonigrin

Registry Numbers

CAS Registry Number

  • 3930-19-6

FDA UNII

  • 261Q3JB310

System Generated Number

  • 0003930196

Structure Descriptors

InChI

InChI=1S/C25H22N4O8/c1-9-14(10-6-8-13(35-2)23(36-3)20(10)30)15(26)19(29-17(9)25(33)34)12-7-5-11-18(28-12)22(32)16(27)24(37-4)21(11)31/h5-8,30H,26-27H2,1-4H3,(H,33,34)

InChIKey

PVYJZLYGTZKPJE-UHFFFAOYSA-N

Smiles

COC1=C(N)C(=O)c2nc(ccc2C1=O)c3nc(C(=O)O)c(C)c(c3N)c4ccc(OC)c(OC)c4O

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LDLo oral 500ug/kg (0.5mg/kg) BLOOD: CHANGES IN PLATELET COUNT

BLOOD: LEUKOPENIA
Antibiotiki. Vol. 11, Pg. 1090, 1966.
mouse LD50 intraperitoneal 520ug/kg (0.52mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

BEHAVIORAL: FOOD INTAKE (ANIMAL)
Farmakologiya i Toksikologiya Vol. 37, Pg. 197, 1974.
mouse LD50 intravenous 865ug/kg (0.865mg/kg)   Antibiotiki. Vol. 12, Pg. 132, 1967.
mouse LD50 oral 2330ug/kg (2.33mg/kg)   Antibiotiki. Vol. 12, Pg. 132, 1967.
mouse LD50 subcutaneous 1000ug/kg (1mg/kg)   Comptes Rendus Hebdomadaires des Seances, Academie des Sciences. Vol. 261, Pg. 4911, 1965.
rabbit LDLo intravenous 600ug/kg (0.6mg/kg) BLOOD: LEUKOPENIA Antibiotiki. Vol. 12, Pg. 132, 1967.
rat LD50 intraperitoneal 150ug/kg (0.15mg/kg) BEHAVIORAL: FOOD INTAKE (ANIMAL)

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"
Farmakologiya i Toksikologiya Vol. 37, Pg. 197, 1974.

Physical Properties

Physical Property Value Units Temp (deg C) Source
log P (octanol-water) -0.560 (none)   EST
Atmospheric OH Rate Constant 2.34E-10 cm3/molecule-sec 25 EST

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