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Substance Name: Teniposide [USAN:INN:BAN]
RN: 29767-20-2
UNII: 957E6438QA
InChIKey: NRUKOCRGYNPUPR-QBPJDGROSA-N

Note

  • A semisynthetic derivative of PODOPHYLLOTOXIN that exhibits antitumor activity. Teniposide inhibits DNA synthesis by forming a complex with topoisomerase II and DNA. This complex induces breaks in double stranded DNA and prevents repair by topoisomerase II binding. Accumulated breaks in DNA prevent cells from entering into the mitotic phase of the cell cycle, and lead to cell death. Teniposide acts primarily in the G2 and S phases of the cycle.

Molecular Formula

  • C32-H32-O13-S

Molecular Weight

  • 656.6578
 

Classification Codes

Classification Codes

  • Antineoplastic
  • Antineoplastic Agents
  • DNA Topoisomerase II Inhibitors
  • Drug / Therapeutic Agent
  • Enzyme Inhibitors
  • Human Data
  • Mutation Data
  • Nucleic Acid Synthesis Inhibitors
  • Reproductive Effect
  • Topoisomerase II Inhibitors

Superlist Classification Code

  • Overall Carcinogenic Evaluation: Group 2A
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Names and Synonyms

Name of Substance

  • Teniposide
  • Teniposide [USAN:INN:BAN]

MeSH Heading

  • Teniposide

Synonyms

  • (5R-(5alpha,5abeta,8aalpha,9beta(R*)))-5,8,8a,9-Tetrahydro-5-(4-hydroxy-3,5-dimethoxyphenyl)-9-((4-6-O-(2-thienylmethylene)-beta-D-glucopyranosyl)oxy)furo(3',4':6,7)naphtho(2,3-d)-1,3-dioxol-6(5aH)-one
  • 4'-Demethyl 1-O-(4,6-O,O-(2-thenylidene)-beta-D-glucopyranosyl)epipodophyllotoxin
  • 4'-Demethyl-epipodophyllotoxin-beta-D-thenylidene-glucoside
  • 4'-Demethylepipodophyllotoxin 9-(4,6-O-(R)-2-thenylidene-beta-D-glucopyranoside)
  • 4'-Demethylepipodophyllotoxin 9-(4,6-O-2-thenylidene-beta-D-glucopyranoside)
  • 4'-Demethylepipodophyllotoxin-beta-D-thenylidine glucoside
  • 4'-Dimethyl-9-(4,6-O-2-thenyid)-epipodophyllotoxin
  • CCRIS 2058
  • EINECS 249-831-2
  • Epipodophyllotoxin, 4'-demethyl-, 9-(4,6-O-2-thenylidene-beta-D-glucopyranoside)
  • Epipodophyllotoxin-beta-D-thenylidene-glucoside, 4'-demethyl-
  • EPT
  • Furo(3',4':6,7)naphtho(2,3-d)-1,3-dioxol-6(5aH)-one, 5,8,8a,9-tetrahydro-5-(4-hydroxy-3,5-dimethoxyphenyl)-9-((4,6-O-(2-thienylmethylene)-beta-D-glucopyranosyl)-oxy)-, (5R-(5alpha,5abeta,8aalpha,9beta(R*)))-
  • HSDB 6546
  • NSC 122819
  • NSC-122819
  • Teniposide
  • Teniposido
  • Teniposido [INN-Spanish]
  • Teniposidum
  • Teniposidum [INN-Latin]
  • UNII-957E6438QA
  • Vee M-26
  • Vehem
  • VM 26
  • VM-26
  • Vumon

Systematic Names

  • Epipodophyllotoxin, 4'-demethyl-, 9-(4,6-O-2-thenylidene-beta-D-glucopyranoside)
  • Furo(3',4':6,7)naphtho(2,3-d)-1,3-dioxol-6(5aH)-one, 5,8,8a,9-tetrahydro-5-(4-hydroxy-3,5-dimethoxyphenyl)-9-((4,6-O-((R)-2-thienylmethylene)-beta-D-glucopyranosyl)oxy)-, (5R,5aR,8aR,9S)-
  • Furo(3',4':6,7)naphtho(2,3-d)-1,3-dioxol-6(5aH)-one, 5,8,8a,9-tetrahydro-5-(4-hydroxy-3,5-dimethoxyphenyl)-9-((4,6-O-(2-thienylmethylene)-beta-D-glucopyranosyl)-oxy)-, (5R-(5alpha,5abeta,8aalpha,9beta(R*)))-
  • Teniposide

Superlist Name

  • Teniposide

Registry Numbers

CAS Registry Number

  • 29767-20-2

FDA UNII

  • 957E6438QA

Other Registry Numbers

  • 23362-13-2
  • 31514-29-1
  • 35317-44-3

System Generated Number

  • 0029767202

Structure Descriptors

InChI

InChI=1S/C32H32O13S/c1-37-19-6-13(7-20(38-2)25(19)33)23-14-8-17-18(42-12-41-17)9-15(14)28(16-10-39-30(36)24(16)23)44-32-27(35)26(34)29-21(43-32)11-40-31(45-29)22-4-3-5-46-22/h3-9,16,21,23-24,26-29,31-35H,10-12H2,1-2H3/t16-,21+,23+,24-,26+,27+,28+,29+,31+,32-/m0/s1

InChIKey

NRUKOCRGYNPUPR-QBPJDGROSA-N

Smiles

COc1cc(cc(OC)c1O)[C@H]2[C@@H]3[C@H](COC3=O)[C@H](O[C@@H]4O[C@@H]5CO[C@H](O[C@H]5[C@H](O)[C@H]4O)c6cccs6)c7cc8OCOc8cc27

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
human TDLo intravenous 26mg/kg/10D-I (26mg/kg) BLOOD: CHANGES IN BONE MARROW NOT INCLUDED ABOVE

BLOOD: APLASTIC ANEMIA

BLOOD: AGRANULOCYTOSIS		 Cancer Vol. 34, Pg. 985, 1974.
human TDLo intravenous 132mg/kg/7W-I (132mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING

BLOOD: LEUKOPENIA		 Cancer Treatment Reports. Vol. 63, Pg. 7, 1979.
human TDLo oral 9579mg/kg (9579mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING

SKIN AND APPENDAGES (SKIN): HAIR: OTHER

BEHAVIORAL: ANOREXIA (HUMAN		 European Journal of Cancer. Vol. 14, Pg. 1395, 1978.
mouse LD50 intraperitoneal 29570ug/kg (29.57mg/kg)   National Cancer Institute Screening Program Data Summary, Developmental Therapeutics Program. Vol. JAN1986,
mouse LD50 subcutaneous 31560ug/kg (31.56mg/kg)   National Cancer Institute Screening Program Data Summary, Developmental Therapeutics Program. Vol. JAN1986,
rat LD17 intraperitoneal 50mg/kg (50mg/kg)   Cancer Treatment Reports. Vol. 60, Pg. 1127, 1976.
rat LDLo intravenous 15mg/kg (15mg/kg) BLOOD: LEUKOPENIA

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

LUNGS, THORAX, OR RESPIRATION: DYSPNEA		 Proceedings of the European Society of Toxicology. Vol. 17, Pg. 171, 1976.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 242-246 deg C   EXP
log P (octanol-water) 1.24 (none)   EXP
Water Solubility 5.940 mg/L 25 EST
Vapor Pressure 6.80E-26 mm Hg 25 EST
Henry's Law Constant 5.78E-32 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 3.05E-10 cm3/molecule-sec 25 EST

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