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3930-19-6

3930-19-6 structure
3930-19-6 structure
  • Name: bruneomycin
  • Chemical Name: streptonigrin
  • CAS Number: 3930-19-6
  • Molecular Formula: C25H22N4O8
  • Molecular Weight: 506.46400
  • Catalog: API Antineoplastic agents Antibiotic antineoplastic agents
  • Create Date: 2018-09-21 12:50:47
  • Modify Date: 2025-08-26 00:04:09
  • Streptonigrin (Bruneomycin), a natural product produced by Streptomyces flocculus, possesses both anti-tumor and anti-bacterial activity. Streptonigrin acts as a pan-PAD inhibitor with IC50s of 48.3±34.2 µM, 26.1±0.3 µM, 0.43±0.03 µM, and 2.5±0.4 µM for PAD1, PAD2, PAD3, and PAD4, respectively[1].
Name streptonigrin
Synonyms Rufocromomycinum
Valacidin
Rufocromomycine
Bruneomycin
Streptonigran
(4Z)-5-amino-6-(7-amino-6-methoxy-5,8-dioxoquinolin-2-yl)-4-(4,5-dimethoxy-6-oxocyclohexa-2,4-dien-1-ylidene)-3-methyl-1H-pyridine-2-carboxylic acid
Nigrin
Rufocromomicina
Rufocromomycin
Description Streptonigrin (Bruneomycin), a natural product produced by Streptomyces flocculus, possesses both anti-tumor and anti-bacterial activity. Streptonigrin acts as a pan-PAD inhibitor with IC50s of 48.3±34.2 µM, 26.1±0.3 µM, 0.43±0.03 µM, and 2.5±0.4 µM for PAD1, PAD2, PAD3, and PAD4, respectively[1].
Related Catalog
Target

Anti-bacterial[1] IC50: 48.3±34.2 µM (PAD1), 26.1±0.3 µM, (PAD2), 0.43±0.03 µM (PAD3), 2.5±0.4 µM (PAD4)[1]

References

[1]. Dreyton CJ, et al. Insights into the mechanism of Streptonigrin-induced protein arginine deiminase inactivation. Bioorg Med Chem. 2014 Feb 15;22(4):1362-9.
Density 1.54g/cm3
Boiling Point 719ºC at 760mmHg
Melting Point 301-303℃
Molecular Formula C25H22N4O8
Molecular Weight 506.46400
Flash Point 388.7ºC
Exact Mass 506.14400
PSA 197.18000
LogP 3.59940
Index of Refraction 1.716
Storage condition 2-8°C

CHEMICAL IDENTIFICATION

RTECS NUMBER :
TJ7350000
CHEMICAL NAME :
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-
CAS REGISTRY NUMBER :
3930-19-6
BEILSTEIN REFERENCE NO. :
0599390
LAST UPDATED :
199806
DATA ITEMS CITED :
64
MOLECULAR FORMULA :
C25-H22-N4-O8
MOLECULAR WEIGHT :
506.51
WISWESSER LINE NOTATION :
T66 BV EV GNJ CO1 DZ H- BT6NJ CZ DR BQ CO1 DO1& E1 FVQ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
150 ug/kg
TOXIC EFFECTS :
Behavioral - food intake (animal) Gastrointestinal - hypermotility, diarrhea Nutritional and Gross Metabolic - weight loss or decreased weight gain
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
2330 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
520 ug/kg
TOXIC EFFECTS :
Behavioral - food intake (animal) Gastrointestinal - hypermotility, diarrhea Nutritional and Gross Metabolic - weight loss or decreased weight gain
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
1000 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
865 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
500 ug/kg
TOXIC EFFECTS :
Blood - leukopenia Blood - changes in platelet count
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
600 ug/kg
TOXIC EFFECTS :
Blood - leukopenia
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
50 mg/kg/10D-I
TOXIC EFFECTS :
Blood - other changes Endocrine - changes in spleen weight Nutritional and Gross Metabolic - weight loss or decreased weight gain
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
1710 ug/kg/7D-I
TOXIC EFFECTS :
Kidney, Ureter, Bladder - urine volume decreased
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
800 ug/kg/10D-I
TOXIC EFFECTS :
Gastrointestinal - other changes Liver - hepatitis (hepatocellular necrosis), zonal Liver - fatty liver degeneration
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
250 ug/kg/10D-I
TOXIC EFFECTS :
Blood - leukopenia Blood - changes in bone marrow (not otherwise specified) Blood - changes in platelet count
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
500 ug/kg/10D-I
TOXIC EFFECTS :
Blood - leukopenia Related to Chronic Data - death
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
100 ug/kg
SEX/DURATION :
female 10 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - fetal death
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
100 ug/kg
SEX/DURATION :
female 9 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - Central Nervous System Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue) Reproductive - Specific Developmental Abnormalities - musculoskeletal system
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
200 ug/kg
SEX/DURATION :
female 9 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - body wall Reproductive - Specific Developmental Abnormalities - endocrine system Reproductive - Specific Developmental Abnormalities - urogenital system
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Parenteral
DOSE :
250 ug/kg
SEX/DURATION :
female 11 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - cytological changes (including somatic cell genetic material)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Unreported
DOSE :
100 ug/kg
SEX/DURATION :
female 11 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Unreported
DOSE :
100 ug/kg
SEX/DURATION :
female 2 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - other developmental abnormalities
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
DOSE :
90 ug/kg
SEX/DURATION :
female 1 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Fertility - other measures of fertility
TYPE OF TEST :
Cytogenetic analysis
TYPE OF TEST :
Cytogenetic analysis
TYPE OF TEST :
Sister chromatid exchange
TYPE OF TEST :
Cytogenetic analysis
TYPE OF TEST :
Cytogenetic analysis
TYPE OF TEST :
Sister chromatid exchange

MUTATION DATA

TEST SYSTEM :
Rodent - rabbit
DOSE/DURATION :
30 ug/kg
REFERENCE :
ENMUDM Environmental Mutagenesis. (New York, NY) V.1-9, 1979-87. For publisher information, see EMMUEG. Volume(issue)/page/year: 7(Suppl 3),48,1985 *** REVIEWS *** TOXICOLOGY REVIEW ARVPAX Annual Review of Pharmacology. (Palo Alto, CA) V.1-15, 1961-75. For publisher information, see ARPTDI. Volume(issue)/page/year: 5,447,1965
Symbol GHS06
GHS06
Signal Word Danger
Hazard Statements H300
Precautionary Statements P264-P301 + P310
Personal Protective Equipment Eyeshields;Faceshields;full-face particle respirator type N100 (US);Gloves;respirator cartridge type N100 (US);type P1 (EN143) respirator filter;type P3 (EN 143) respirator cartridges
Hazard Codes T+: Very toxic;
Risk Phrases 28
Safety Phrases 53-28-36/37/39-45
RIDADR UN 3462 6.1/PG 1
WGK Germany 3
RTECS TJ7350000
Packaging Group II
Hazard Class 6.1(a)
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