maytansine

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Names

[ CAS No. ]:
35846-53-8

[ 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

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

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

  • (2Z,4E)-2-formyl-5-methoxypenta-2,4-dienenitrile
  • (14S,16S,2R,3E,5E,12S,13E,15S)-84-chloro-12-hydroxy-14,85,2-trimethoxy-6,9,13,15-tetramethyl-9-aza-1(4,6)-oxazinana-8(1,3)-benzenacyclopentadecaphane-3,5,13-triene-12,10-dione
  • (5S,6E,8S,9S,12R,13E,15E)-5-((tert-butyldimethylsilyl)oxy)-6-chloro-9-hydroxy-5,12-dimethoxy-2,6,8,16-tetramethylspiro[2-aza-1(1,3)-benzenacycloheptadecaphanene-11,2'-[1,3]dithiane]-6,13,15-trien-3-one
  • (5S,6E,8S,9S,12R,13E,15E)-5-((tert-butyldimethylsilyl)oxy)-6-chloro-5,12-dimethoxy-2,6,8,16-tetramethyl-3-oxospiro[2-aza-1(1,3)-benzenacycloheptadecaphanene-11,2'-[1,3]dithiane]-6,13,15-trien-9-yl carbamate
  • (-)-maytansinol

DownStream

Related Compounds

  • Normaytansine
  • Maytansine, 2-de(acetylmethylamino)-
  • O3-de-(N-acetyl-N-methyl-L-alanyl)-maytansine
  • Maytansine, 2-de(acetylmethylamino)-30-hydroxy-
  • Maytansine,N2'-deacetyl-N2'-(1-oxopropyl)- (9CI)
  • Maytansine, 2-de(acetylmethylamino)-22-demethyl-
  • 4-((Cyclohexylamino)methyl)benzoic acid hydrochloride
  • 1-[(2,4-Dichlorophenyl)methyl]-N-(1,1-dimethylethyl)-2-methyl-1H-indole-3-methanamine
  • 2-Methoxy-6-(pyrazol-1-yl)-benzonitrile
  • 1H-3-Benzazepin-7-ol, 8-chloro-2,3,4,5-tetrahydro-5-(3-iodophenyl)-3-methyl-, (S)-
  • (4-Methyl-tetrahydro-furan-2-yl)-methanol
  • N-(1-cyanocyclopentyl)-2-[4-(4-fluorobenzenesulfonyl)-1,4-diazepan-1-yl]acetamide
  • 4,5,6,7-Tetrahydrobenzo[d]isoxazole-3-carbaldehyde
  • tert-Butyl-DL-alanine
  • (2S)-2,3-dimethoxypropan-1-amine
  • 4-amino-N-[2-tert-butyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazol-5-yl]-N-ethylbenzenesulfonamide