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Substance Name: Maytansine [USAN]
RN: 35846-53-8
UNII: 14083FR882
InChIKey: WKPWGQKGSOKKOO-RSFHAFMBSA-N

Note

  • An ansa macrolide isolated from the MAYTENUS genus of East African shrubs.

Molecular Formula

  • C34-H46-Cl-N3-O10

Molecular Weight

  • 692.2014
 

Classification Codes

  • Antimitotic Agents
  • Antineoplastic
  • Antineoplastic Agents
  • Antineoplastic Agents, Phytogenic
  • Drug / Therapeutic Agent
  • Human Data
  • Mitosis Modulators
  • Mutation Data
  • Natural Product
  • Reproductive Effect
  • Tubulin Modulators
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Names and Synonyms

Name of Substance

  • Maitansine [INN]
  • Maytansine
  • Maytansine [USAN]

MeSH Heading

  • Maytansine

Synonyms

  • BRN 5417399
  • EINECS 252-754-7
  • Maitansina
  • Maitansina [INN-Spanish]
  • Maitansine
  • Maitansinum
  • Maitansinum [INN-Latin]
  • Maytansin
  • Maytansine
  • N-Acetyl-N-methyl-L-alanine(1S-(1R*,2S*,3R*,5R*,6R*,16E,18E,20S*,21R*))-11-chloro-21-hydroxy-12,20-dimethoxy-2,5,9,16-tetramethy-8,23-dioxo-4,24-dioxa-9,22-diazatetracyclo(19.3.1.1(sup 10,14).0(sup 3,5))hexacosa-10,12,14(26),16,18-pentaen-6-yl ester
  • NSC 153858
  • NSC-153858
  • UNII-14083FR882

Systematic Names

  • L-Alanine, N-acetyl-N-methyl-, 11-chloro-21-hydroxy-12,20-dimethoxy-2,5,9,16-tetramethyl-8,23-dioxo-4,24-dioxa-9,22-diazatetracyclo(19.3.1.110,14.03,5)hexacosa-10,12,14(26),16,18-pentaen-6-yl ester, (1S-(1R*,2S*,3R*,5R*,6R*,16E,18E,20S*,21R*))-
  • Maitansine
  • Maytansine

Registry Numbers

CAS Registry Number

  • 35846-53-8

FDA UNII

  • 14083FR882

System Generated Number

  • 0035846538

Structure Descriptors

InChI

1S/C34H46ClN3O10/c1-18-11-10-12-26(45-9)34(43)17-25(46-32(42)36-34)19(2)30-33(5,48-30)27(47-31(41)20(3)37(6)21(4)39)16-28(40)38(7)23-14-22(13-18)15-24(44-8)29(23)35/h10-12,14-15,19-20,25-27,30,43H,13,16-17H2,1-9H3,(H,36,42)/b12-10+,18-11+/t19-,20+,25+,26-,27+,30+,33+,34+/m1/s1

InChIKey

WKPWGQKGSOKKOO-RSFHAFMBSA-N

Smiles

C[C@@H]1[C@@H]2C[C@]([C@@H](/C=C/C=C(/Cc3cc(c(c(c3)OC)Cl)N(C(=O)C[C@@H]([C@]4([C@H]1O4)C)OC(=O)[C@H](C)N(C)C(=O)C)C)\C)OC)(NC(=O)O2)O

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
human TDLo intravenous 190ug/kg/5D (0.19mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING

BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"

BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)
Journal of the National Cancer Institute. Vol. 60, Pg. 93, 1978.
mouse LD50 intraperitoneal 245ug/kg (0.245mg/kg)   National Cancer Institute Screening Program Data Summary, Developmental Therapeutics Program. Vol. JAN1986,
mouse LD50 intravenous 1530ug/kg (1.53mg/kg) BLOOD: THROMBOCYTOPENIA

BLOOD: LEUKOPENIA

SKIN AND APPENDAGES (SKIN): HAIR: OTHER
National Technical Information Service. Vol. PB82-165507,
rat LD50 subcutaneous 480ug/kg (0.48mg/kg)   Cancer Treatment Reports. Vol. 61, Pg. 1333, 1977.
rat LD50 subcutaneous 480ug/kg (0.48mg/kg) LUNGS, THORAX, OR RESPIRATION: DYSPNEA

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"
Cancer Treatment Reports. Vol. 61, Pg. 1333, 1977.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 171-172 deg C   EXP
log P (octanol-water) 1.99 (none)   EXP
Water Solubility 0.790 mg/L 25 EST
Vapor Pressure 3.72E-25 mm Hg 25 EST
Henry's Law Constant 4.23E-26 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 4.25E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.