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Streptonigrin

Streptonigrin structure

CAS No:
3930-19-6
Formula:
C25H22N4O8
Chemical Name:
Streptonigrin
Synonyms:
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-,(4R)-;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-;(4R)-5-Amino-6-(7-amino-5,8-dihydro-6-methoxy-5,8-dioxo-2-quinolinyl)-4-(2-hydroxy-3,4-dimethoxyphenyl)-3-methyl-2-pyridinecarboxylic acid;NSC 45383;5-Amino-6-(7-amino-5,8-dihydro-6-methoxy-5,8-dioxo-2-quinolyl)-4-(2-hydroxy-3,4-dimethoxyphenyl)-3-methylpicolinic acid;Nigrin;SN;Streptonigrin;Bruneomycin;Rufocromomycin;5278RP;AO 50165L302;Abbott Crystalline antibiotic;Streptonigran;STP;NSC 56748;NSC 83950;(R)-Streptonigrin;11011-76-0;80206-29-7;197730-36-2
Categories:
Active Pharmaceutical Ingredients > Antineoplastic Agents

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].

Streptonigrin is complex cytotoxic antibiotic obtained from Streptomyces flocculus or S. rufochronmogenus. It is used in advanced carcinoma and causes leukopenia. It has a role as an antimicrobial agent and an antineoplastic agent. It is a quinolone and a member of pyridines.|Streptonigrin is an aminoquinone antineoplastic antibiotic isolated from the bacterium Streptomyces flocculus. Streptonigrin complexes with DNA and topoisomerase II, resulting in DNA cleavage and inhibition of DNA replication and RNA synthesis. This agent also acts as a reverse transcriptase inhibitor and causes free radical-mediated cellular damage. (NCI04)|Complex cytotoxic antibiotic obtained from Streptomyces flocculus or S. rufochronmogenus. It is used in advanced carcinoma and causes leukopenia.

Streptonigrin Basic Attributes

Molecular Weight：

506.46

Exact Mass：

506.46

EC Number：

223-501-8

UNII：

261Q3JB310

NSC Number：

83950|56748|45383

NCI Thesaurus Code：

C844

Characteristics

PSA：

197.18000

XLogP3：

3.59940

Density：

1.54g/cm3

Melting Point：

262-263 °C

Boiling Point：

719ºC at 760mmHg

Flash Point：

388.7ºC

Refractive Index：

1.716

Water Solubility：

74.9 [ug/mL]

Storage Conditions：

2-8°C

Toxicity：

LD50 oral in mouse: 2330ug/kg

Safety Information

Packing level：

Hazard category：

6.1(a)

Transport codes：

UN 3462 6.1/PG 1

wgk germany：

hazard class code：

safety instructions：

53-28-36/37/39-45

RTECS Number：

TJ7350000

Marks：

T+

Precautionary statement(s)：

P264-P301 + P310

Hazard Statements：

H300

GHS Classification：

|Danger|H300 (100%): Fatal if swallowed [Danger Acute toxicity, oral]|P264, P270, P301+P310, P321, P330, P405, and P501|Aggregated GHS information provided by 38 companies from 1 notifications to the ECHA C&L Inventory.

Drug Information

MeSH：

Chemical substances, produced by microorganisms, inhibiting or preventing the proliferation of neoplasms. (See all compounds classified as Antibiotics, Antineoplastic.)

MeSH Entry Terms：

Brunemycin

Streptonigrin Use and Manufacturing

Streptonigrin is an unusual aminoquinone with broad biological activity against bacteria, fungi, nematodes, viruses and tumor cells. Streptonigrin acts as a bioreductive agent, highly dependent on interactions with metal ions, notably iron, and plays an important role in free radical production through redox cycling of NAD(P)H:quinone oxidoreductase (NQO1).

Computed Properties

Molecular Weight:506.5
XLogP3:1.8
Hydrogen Bond Donor Count:4
Hydrogen Bond Acceptor Count:12
Rotatable Bond Count:6
Exact Mass:506.14376367
Monoisotopic Mass:506.14376367
Topological Polar Surface Area:197
Heavy Atom Count:37
Complexity:944
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes