Inosine,6-S-methyl-6-thio-

Names

[ CAS No. ]:
342-69-8

[ Name ]:
Inosine,6-S-methyl-6-thio-

[Synonym ]:
EINECS 206-442-2
6-MethylmercaptopurineRiboside
MFCD00022826
6-Methylthioinosine
METHYLTHIOINOSINE
6-Methylmercaptopurinribosid
6-methylmp-riboside
6-MMPR
6-METHYLTHIOPURINE RIBOSIDE
6-Methylmercaptopurine riboside

Biological Activity

[Description]:

6-Methylmercaptopurine riboside is a purine nucleoside analog. Purine nucleoside analogs have broad antitumor activity targeting indolent lymphoid malignancies. Anticancer mechanisms in this process rely on inhibition of DNA synthesis, induction of apoptosis, etc[1].

[Related Catalog]:

Research Areas >> Cancer

Signaling Pathways >> Cell Cycle/DNA Damage >> Nucleoside Antimetabolite/Analog

[References]

[1]. Robak T, Robak P. Purine nucleoside analogs in the treatment of rarer chronic lymphoid leukemias. Curr Pharm Des. 2012;18(23):3373-88.

Chemical & Physical Properties

[ Density]:
1.85g/cm3

[ Boiling Point ]:
636.3ºC at 760mmHg

[ Melting Point ]:
166°C

[ Molecular Formula ]:
C₁₁H₁₄N₄O₄S

[ Molecular Weight ]:
298.32

[ Flash Point ]:
338.6ºC

[ Exact Mass ]:
298.07400

[ PSA ]:
138.82000

[ Index of Refraction ]:
1.822

[ Storage condition ]:
−20°C

[ Stability ]:
Incompatible with strong oxidizing agents.

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: UO8985000

CHEMICAL NAME :: 9H-Purine, 6-(methylthio)-9-beta-D-ribofuranosyl-

CAS REGISTRY NUMBER :: 342-69-8

BEILSTEIN REFERENCE NO. :: 0042871

LAST UPDATED :: 199612

DATA ITEMS CITED :: 10

MOLECULAR FORMULA :: C11-H14-N4-O4-S

MOLECULAR WEIGHT :: 298.35

WISWESSER LINE NOTATION :: T56 BN DN FN HNJ IS1 D- BT5OTJ CQ DQ E1Q

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 :: 65 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 :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 137 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD10 - Lethal Dose

ROUTE OF EXPOSURE :: Unreported

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 20 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 44 mg/kg/7W-I

TOXIC EFFECTS :: Tumorigenic - equivocal tumorigenic agent by RTECS criteria Lungs, Thorax, or Respiration - tumors Endocrine - tumors

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 780 mg/kg/26W-I

TOXIC EFFECTS :: Tumorigenic - equivocal tumorigenic agent by RTECS criteria Lungs, Thorax, or Respiration - tumors Endocrine - adrenal cortex tumors

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 65 mg/kg

SEX/DURATION :: female 11 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - fetal death

MUTATION DATA

TYPE OF TEST :: Mutation test systems - not otherwise specified

TEST SYSTEM :: Rodent - mouse Lymphocyte

DOSE/DURATION :: 3 umol/L

REFERENCE :: CNREA8 Cancer Research. (Public Ledger Building, Suit 816, 6th & Chestnut Sts., Philadelphia, PA 19106) V.1- 1941- Volume(issue)/page/year: 43,1587,1983

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Safety Phrases ]:
S22-S24/25

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
UO8985000

[ HS Code ]:
29349990

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Articles

The role of inosine-5'-monophosphate dehydrogenase in thiopurine metabolism in patients with inflammatory bowel disease.

Ther. Drug Monit. 33 , 200-208, (2011)

There is a large interindividual variability in thiopurine metabolism. High concentrations of methylthioinosine-5'-monophosphate (meTIMP) and low concentrations of 6-thioguanine nucleotides (6-TGNs) h...

Methylthioadenosine deaminase in an alternative quorum sensing pathway in Pseudomonas aeruginosa.

Biochemistry 51(45) , 9094-103, (2012)

Pseudomonas aeruginosa possesses an unusual pathway for 5'-methylthioadenosine (MTA) metabolism involving deamination to 5'-methylthioinosine (MTI) followed by N-ribosyl phosphorolysis to hypoxanthine...

A prospective, open-label trial of 6-thioguanine in patients with ulcerative or indeterminate colitis.

Scand. J. Gastroenterol. 40(10) , 1205-13, (2005)

6-thioguanine (6-TG) has emerged as a promising therapeutic alternative in patients with Crohn's disease intolerant or resistant to azathioprine (AZA) and/or 6-mercaptopurine (6-MP). The aim of the pr...