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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
- All
- Classifications
- Links to Resources
- Names & Synonyms
- Registry Numbers
- Structure Descriptors
- Toxicity
- Physical Properties
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/s1InChIKey
NRUKOCRGYNPUPR-QBPJDGROSA-NSmiles
COc1cc(cc(OC)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.