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87-11-6

87-11-6 structure
87-11-6 structure
  • Name: Thiolutin
  • Chemical Name: N-(4-methyl-5-oxodithiolo[4,3-b]pyrrol-6-yl)acetamide
  • CAS Number: 87-11-6
  • Molecular Formula: C8H8N2O2S2
  • Molecular Weight: 228.291
  • Catalog: API Antibiotics Other antibiotics
  • Create Date: 2018-09-23 13:11:01
  • Modify Date: 2024-01-04 16:12:29
  • Thiolutin (Acetopyrrothin) is a disulfide-containing antibiotic and anti-angiogenic compound produced by Streptomyces. Thiolutin inhibits the JAMM metalloproteases Csn5, Associated-molecule-with-the-SH3-Domain-of-STAM (AMSH) and Brcc36[1]. Thiolutin is a potent and selective inhibitor of endothelial cell adhesion accompanied by rapid induction of Heat-shock protein beta-1 (Hsp27) phosphorylation[2].

Name N-(4-methyl-5-oxodithiolo[4,3-b]pyrrol-6-yl)acetamide
Synonyms acetopyrrothine
N-(4-Methyl-5-oxo-4,5-dihydro[1,2]dithiolo[4,3-b]pyrrol-6-yl)acetamide
N-(4-methyl-5-oxo-4,5-dihydro-[1,2]dithiolo[4,3-b]pyrrol-6-yl)-acetamide
6-(Acetylamino)-4-methyl-1,2-dithiolo(4,3-b)pyrrol-5(4H)-one
6-Acetamido-4-methyl-1,2-dithiolo<4,3-b>pyrrol-5(4H)-on
Acetopyrrothin
6-Acetamido-4-methyl-1,2-dithiolo(4,3-b)pyrrol-5(4H)-one
6-(Acetamido)-4-methyl-1,2-dithiolo[4,3-b]pyrrol-5(4H)-one
MFCD07370147
3-Acetamido-5-methylpyrrolin-4-one[4,3-d]-1,2-dithiole
Acetamide, N-(4,5-dihydro-4-methyl-5-oxo-1,2-dithiolo[4,3-b]pyrrol-6-yl)-
Thiolutin
N-(4-Methyl-5-oxo-4,5-dihydro-[1,2]dithiolo[4,3-b]pyrrol-6-yl)-acetamid
3-Acetamido-5-methylpyrrolin-4-one(4,3-d)-1,2-dithiole
6-acetylamino-4-methyl-4H-[1,2]dithiolo[4,3-b]pyrrol-5-one
Description Thiolutin (Acetopyrrothin) is a disulfide-containing antibiotic and anti-angiogenic compound produced by Streptomyces. Thiolutin inhibits the JAMM metalloproteases Csn5, Associated-molecule-with-the-SH3-Domain-of-STAM (AMSH) and Brcc36[1]. Thiolutin is a potent and selective inhibitor of endothelial cell adhesion accompanied by rapid induction of Heat-shock protein beta-1 (Hsp27) phosphorylation[2].
Related Catalog
References

[1]. Lauinger L, et al. Thiolutin is a zinc chelator that inhibits the Rpn11 and other JAMM metalloproteases. Nat Chem Biol. 2017 Jul;13(7):709-714.

[2]. Jia Y, et al. Thiolutin inhibits endothelial cell adhesion by perturbing Hsp27 interactions with components of the actin and intermediate filament cytoskeleton. Cell Stress Chaperones. 2010 Mar;15(2):165-81.

Density 1.6±0.1 g/cm3
Boiling Point 478.6±45.0 °C at 760 mmHg
Melting Point 273-276℃
Molecular Formula C8H8N2O2S2
Molecular Weight 228.291
Flash Point 243.3±28.7 °C
Exact Mass 228.002716
PSA 107.58000
LogP 0.99
Vapour Pressure 0.0±1.2 mmHg at 25°C
Index of Refraction 1.721
Water Solubility DMSO: 5 mg/mL

CHEMICAL IDENTIFICATION

RTECS NUMBER :
JP1355000
CHEMICAL NAME :
1,2-Dithiolo(4.3-b)pyrrol-5(4H)-one, 6-acetamido-4-methyl-
CAS REGISTRY NUMBER :
87-11-6
BEILSTEIN REFERENCE NO. :
0209485
LAST UPDATED :
199612
DATA ITEMS CITED :
3
MOLECULAR FORMULA :
C8-H8-N2-O2-S2
MOLECULAR WEIGHT :
228.30
WISWESSER LINE NOTATION :
T55 BNV FSSJ B1 DMV1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
25 mg/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 :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
25 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value

MUTATION DATA

TYPE OF TEST :
Mutation test systems - not otherwise specified
TEST SYSTEM :
Yeast - Saccharomyces cerevisiae
DOSE/DURATION :
4 mg/L
REFERENCE :
AMACCQ Antimicrobial Agents and Chemotherapy. (American Soc. for Microbiology, 1913 I St., NW, Washington, DC 20006) V.1- 1972- Volume(issue)/page/year: 3,729,1973
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;T: Toxic;
Risk Phrases 28
Safety Phrases S45
RIDADR UN 2811 6.1/PG 2
WGK Germany 3
RTECS JP1355000
HS Code 2933990090
HS Code 2933990090
Summary 2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%