maytansine

Names

[ Name ]:
maytansine

[Synonym ]:
maitansine
(3E,5E,7R,84S)-12c-(N-acetyl-N-methyl-L-alanyloxy)-14-chloro-10t,11c-epoxy-84-hydroxy-15,7r-dimethoxy-3,9c,11t,15-tetramethyl-(84r'H,86c'H)-15-aza-1(1,3)-benzena-8(4,6)-[1,3]oxazinana-cyclopentadecaphane-3,5-diene-82,14-dione
Maytansine

Biological Activity

[Description]:

Maytansine is a highly potent microtubule-targeted compound that induces mitotic arrest and kills tumor cells at subnanomolar concentrations[1].

[Related Catalog]:

Research Areas >> Cancer

Signaling Pathways >> Others >> Others

[In Vitro]

Maytansine, at 6x10-8 M, irreversibly inhibits cell division in eggs of sea urchins and clams. Maytansine causes the disappearance of a mitotic apparatus or prevents one from forming if added at early stages. Maytansine does inhibit in vitro polymerization of tubulin. Maytansine inhibits in vitro polymerization of tubulin[2].

[References]

[1]. Lopus M, et al. Maytansine and cellular metabolites of antibody-maytansinoid conjugates strongly suppress microtubule dynamics by binding to microtubules. Mol Cancer Ther. 2010;9(10):2689-2699.

[2]. Remillard S, et al. Antimitotic activity of the potent tumor inhibitor maytansine. Science. 1975;189(4207):1002-1005.

Chemical & Physical Properties

[ Density]:
1.32g/cm3

[ Boiling Point ]:
895.1ºC at 760mmHg

[ Molecular Formula ]:
C₃₄H₄₆ClN₃O₁₀

[ Molecular Weight ]:
692.19600

[ Flash Point ]:
495.1ºC

[ Exact Mass ]:
691.28700

[ PSA ]:
156.47000

[ LogP ]:
3.92820

[ Index of Refraction ]:
1.59

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: OQ2290000

CHEMICAL NAME :: Maytansine

CAS REGISTRY NUMBER :: 35846-53-8

LAST UPDATED :: 199801

DATA ITEMS CITED :: 16

MOLECULAR FORMULA :: C34-H46-Cl-N3-O10

MOLECULAR WEIGHT :: 692.28

WISWESSER LINE NOTATION :: T D3 K6-19-6 A K- EO IVN WNVO QU SUTJ C1 GOVY1&N1&V1 J1 LG MO1 Q1 UO1 VQ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Human

DOSE/DURATION :: 190 ug/kg/5D

TOXIC EFFECTS :: Behavioral - hallucinations, distorted perceptions Behavioral - changes in motor activity (specific assay) Gastrointestinal - nausea or vomiting

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 480 ug/kg

TOXIC EFFECTS :: Lungs, Thorax, or Respiration - dyspnea 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 :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 245 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 :: 1530 ug/kg

TOXIC EFFECTS :: Blood - leukopenia Blood - thrombocytopenia Skin and Appendages - hair

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 1305 ug/kg/7W-I

TOXIC EFFECTS :: Behavioral - changes in motor activity (specific assay) Nutritional and Gross Metabolic - weight loss or decreased weight gain Nutritional and Gross Metabolic - body temperature increase

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 700 ug/kg/5D-I

TOXIC EFFECTS :: Behavioral - muscle contraction or spasticity Blood - pigmented or nucleated red blood cells Blood - leukopenia

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 200 ug/kg

SEX/DURATION :: female 7 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Effects on Embryo or Fetus - fetal death 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 7 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - Central Nervous System Reproductive - Specific Developmental Abnormalities - eye/ear Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 200 ug/kg

SEX/DURATION :: female 7 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - urogenital system

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 250 ug/kg

SEX/DURATION :: female 8 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - cytological changes (including somatic cell genetic material)

MUTATION DATA

TYPE OF TEST :: Cytogenetic analysis

TEST SYSTEM :: Rodent - mouse Ascites tumor

DOSE/DURATION :: 100 ug/kg

REFERENCE :: JNCIAM Journal of the National Cancer Institute. (Washington, DC) V.1-60, 1940-78. For publisher information, see JJIND8. Volume(issue)/page/year: 60,649,1978

maytansine

Names

Biological Activity

Chemical & Physical Properties

Toxicological Information

CHEMICAL IDENTIFICATION

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

MUTATION DATA

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Related Compounds