CAS 865-21-4|Vinblastine
Introduction：Basic information about CAS 865-21-4|Vinblastine, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
| Common Name | Vinblastine | ||
|---|---|---|---|
| CAS Number | 865-21-4 | Molecular Weight | 810.974 |
| Density | 1.4±0.1 g/cm3 | Boiling Point | / |
| Molecular Formula | C46H58N4O9 | Melting Point | 211 - 216ºC |
| MSDS | / | Flash Point | / |
Names
| Name | vincaleukoblastine |
|---|---|
| Synonym | More Synonyms |
Vinblastine BiologicalActivity
| Description | Vinblastine is a cytotoxic alkaloid used against various cancer types. Vinblastine inhibits the formation of microtubule and suppresses nAChR with an IC50 of 8.9 μM. |
|---|---|
| Related Catalog | Signaling Pathways >>Cell Cycle/DNA Damage >>Microtubule/TubulinSignaling Pathways >>Cytoskeleton >>Microtubule/TubulinSignaling Pathways >>Membrane Transporter/Ion Channel >>nAChRSignaling Pathways >>Neuronal Signaling >>nAChRResearch Areas >>Cancer |
| Target | IC50: 8.9 μM(nAChR)[1] |
| In Vitro | Vinblastine does not depolymerize spindle microtubules, yet it powerfully blocks mitosis (for example, IC50 0.8 nM in HeLa cells) and cells die by apoptosis[2]. In NB4 cells, vinblastine produces alteration of p53 and DNA fragmentation. Vinblastine treatment has an antiproliferative effect via the induction of apoptosis producing Bax/Bcl-2 imbalance. Vinblastine treatment suppresses NFκB expression and depresses NFκB-DNA binding activity while maintaining JNK activation that subsequently results in apoptotic response through caspase-dependent pathway[3]. Vinblastine is found to trigger apoptosis as evidenced by the loss of mitochondrial membrane potential, the release of both cytochrome c and apoptosis inducing factor, activation of caspase-9 and 3, and cleavage of Poly (ADP-ribose)-Polymerase[4]. |
| In Vivo | Vinblastine is a widely used anticancer drug with undesired side effects. Its conjugation with carrier molecules could be an efficient strategy to reduce these side effects[5]. |
| References | [1]. McKay DB, et al. Nicotinic and nonnicotinic receptor-mediated actions of vinblastine. Proc Soc Exp Biol Med. 1993 Jul;203(3):372-6. [2]. Pandya P, et al. Molecular recognition pattern of cytotoxic alkaloid vinblastine with multiple targets. J Mol Graph Model. 2014 Nov;54:1-9. [3]. Calviño E, et al. JNK and NFκB dependence of apoptosis induced by vinblastine in human acute promyelocytic leukaemia cells. Cell Biochem Funct. 2015 Jun;33(4):211-9. [4]. Selimovic D, et al. Vinblastine-induced apoptosis of melanoma cells is mediated by Ras homologous A protein (Rho A) via mitochondrial and non-mitochondrial-dependent mechanisms. Apoptosis. 2013 Aug;18(8):980-97. [5]. Bánóczi Z, et al. Synthesis and in vitro antitumor effect of vinblastine derivative-oligoarginine conjugates. Bioconjug Chem. 2010 Nov 17;21(11):1948-55. |
Chemical & Physical Properties
| Density | 1.4±0.1 g/cm3 |
|---|---|
| Melting Point | 211 - 216ºC |
| Molecular Formula | C46H58N4O9 |
| Molecular Weight | 810.974 |
| Exact Mass | 810.420349 |
| PSA | 154.10000 |
| LogP | 4.18 |
| Index of Refraction | 1.671 |
| InChIKey | JXLYSJRDGCGARV-JQQWJEIDSA-N |
| SMILES | CCC1(O)CC2CN(CCc3c([nH]c4ccccc34)C(C(=O)OC)(c3cc4c(cc3OC)N(C)C3C(O)(C(=O)OC)C(OC(C)=O)C5(CC)C=CCN6CCC43C65)C2)C1 |
| Storage condition | -20C |
Toxicological Information
CHEMICAL IDENTIFICATION |
ACUTE TOXICITY DATA - TYPE OF TEST :
- LDLo - Lowest published lethal dose
- ROUTE OF EXPOSURE :
- Intravenous
- SPECIES OBSERVED :
- Human - man
- DOSE/DURATION :
- 2319 ug/kg/38W-I
- TOXIC EFFECTS :
- Cardiac - cardiomyopathy including infarction
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Ocular
- SPECIES OBSERVED :
- Human
- DOSE/DURATION :
- 14 ug/kg
- TOXIC EFFECTS :
- Sense Organs and Special Senses (Eye) - visual field changes Sense Organs and Special Senses (Eye) - conjunctive irritation Sense Organs and Special Senses (Eye) - effect, not otherwise specified
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Unreported
- SPECIES OBSERVED :
- Human - man
- DOSE/DURATION :
- 80 ug/kg
- TOXIC EFFECTS :
- Blood - changes in bone marrow (not otherwise specified)
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Intravenous
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- 2 mg/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 :
- Intraperitoneal
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 3120 ug/kg
- TOXIC EFFECTS :
- Blood - changes in bone marrow (not otherwise specified) Immunological Including Allergic - decreased immune response
- TYPE OF TEST :
- LD10 - Lethal Dose
- ROUTE OF EXPOSURE :
- Subcutaneous
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 20 mg/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Intravenous
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- 5120 ug/kg/4W-I
- TOXIC EFFECTS :
- Endocrine - other changes Blood - changes in leukocyte (WBC) count Nutritional and Gross Metabolic - weight loss or decreased weight gain
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Intraperitoneal
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- 2 mg/kg/7W-I
- TOXIC EFFECTS :
- Tumorigenic - equivocal tumorigenic agent by RTECS criteria Endocrine - tumors Skin and Appendages - tumors
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Intraperitoneal
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 7 mg/kg/26W-I
- TOXIC EFFECTS :
- Tumorigenic - equivocal tumorigenic agent by RTECS criteria Lungs, Thorax, or Respiration - tumors Kidney, Ureter, Bladder - tumors
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Intravenous
- DOSE :
- 62500 ug/kg
- SEX/DURATION :
- female 10-11 day(s) after conception
- TOXIC EFFECTS :
- Reproductive - Effects on Newborn - behavioral
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Intravenous
- DOSE :
- 7 mg/kg
- SEX/DURATION :
- male 1 day(s) pre-mating
- TOXIC EFFECTS :
- Reproductive - Paternal Effects - spermatogenesis (incl. genetic material, sperm morphology, motility, and count)
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Intravenous
- DOSE :
- 500 ug/kg
- SEX/DURATION :
- female 1 day(s) after conception
- TOXIC EFFECTS :
- Reproductive - Fertility - pre-implantation mortality (e.g. reduction in number of implants per female; total number of implants per corpora lutea)
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Intravenous
- DOSE :
- 300 ug/kg
- SEX/DURATION :
- female 1 day(s) pre-mating
- TOXIC EFFECTS :
- Reproductive - Specific Developmental Abnormalities - Central Nervous System
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Unreported
- DOSE :
- 7500 ug/kg
- SEX/DURATION :
- female 4-28 day(s) after conception
- TOXIC EFFECTS :
- Reproductive - Fertility - pre-implantation mortality (e.g. reduction in number of implants per female; total number of implants per corpora lutea) Reproductive - Specific Developmental Abnormalities - other developmental abnormalities
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Intravenous
- DOSE :
- 100 ug/kg
- SEX/DURATION :
- female 8 day(s) after conception
- TOXIC EFFECTS :
- Reproductive - Effects on Embryo or Fetus - fetal death Reproductive - Specific Developmental Abnormalities - eye/ear Reproductive - Specific Developmental Abnormalities - musculoskeletal system
- TYPE OF TEST :
- Specific locus test
- TYPE OF TEST :
- Heritable translocation test
- TYPE OF TEST :
- Micronucleus test
- TYPE OF TEST :
- Cytogenetic analysis
- TYPE OF TEST :
- Sex chromosome loss and nondisjunction
- TYPE OF TEST :
- Dominant lethal test
- TYPE OF TEST :
- Sperm Morphology
MUTATION DATA - TYPE OF TEST :
- Sex chromosome loss and nondisjunction
- TEST SYSTEM :
- Rodent - hamster Lung
- DOSE/DURATION :
- 5 ug/L
- REFERENCE :
- MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 287,29,1993 *** REVIEWS *** TOXICOLOGY REVIEW 32XPAD "Teratology," Berry, C.L., and D.E. Poswillo, eds., New York, Springer, 1975 Volume(issue)/page/year: -,49,1975 TOXICOLOGY REVIEW ARVPAX Annual Review of Pharmacology. (Palo Alto, CA) V.1-15, 1961-75. For publisher information, see ARPTDI. Volume(issue)/page/year: 5,447,1965 TOXICOLOGY REVIEW CRTXB2 CRC Critical Reviews in Toxicology. (CRC Press, Inc., 2000 Corporate Blvd., NW, Boca Raton, FL 33431) V.1- 1971- Volume(issue)/page/year: 2,159,1973 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X3898 No. of Facilities: 161 (estimated) No. of Industries: 1 No. of Occupations: 5 No. of Employees: 2136 (estimated) No. of Female Employees: 1159 (estimated)
- TYPE OF TEST :
- Sex chromosome loss and nondisjunction
- TEST SYSTEM :
- Rodent - hamster Lung
- DOSE/DURATION :
- 5 ug/L
- REFERENCE :
- MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 287,29,1993 *** REVIEWS *** TOXICOLOGY REVIEW 32XPAD "Teratology," Berry, C.L., and D.E. Poswillo, eds., New York, Springer, 1975 Volume(issue)/page/year: -,49,1975 TOXICOLOGY REVIEW ARVPAX Annual Review of Pharmacology. (Palo Alto, CA) V.1-15, 1961-75. For publisher information, see ARPTDI. Volume(issue)/page/year: 5,447,1965 TOXICOLOGY REVIEW CRTXB2 CRC Critical Reviews in Toxicology. (CRC Press, Inc., 2000 Corporate Blvd., NW, Boca Raton, FL 33431) V.1- 1971- Volume(issue)/page/year: 2,159,1973 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X3898 No. of Facilities: 161 (estimated) No. of Industries: 1 No. of Occupations: 5 No. of Employees: 2136 (estimated) No. of Female Employees: 1159 (estimated)
Safety Information
| RIDADR | UN 1544 |
|---|---|
| Packaging Group | II |
| Hazard Class | 6.1(a) |
Synonyms
| UNII-5V9KLZ54CY |
| vinblastine sulfuric acid salt |
| Vincoblastine |
| (3aR-(3aα,4β,5β,5aβ,9(3R*,5S*,7R*,9S*),10bR*,13aα))-methyl 4-(acetyloxy)-3a-ethyl-9-(5-ethyl-1,4,5,6,7,8,9,10-octahydro-5-hydroxy-9-(methoxycarbonyl)-2H-3,7-methanoazacycloundecino(5,4-b)indol-9-yl)-3a,4,5,5a,6,11,12,13a-octahydro-5-hydroxy-8-methoxy-6-methyl-1H-indolizino(8,1-cd)carbazole-5-carboxylate |
| Vinblastine |
| Vincaleucoblastin |
| 1H-Indolizino(8,1-cd)carbazole-5-carboxylic acid, 4-(acetyloxy)-3a-ethyl-9-(5-ethyl-1,4,5,6,7,8,9,10-octahydro-5-hydroxy-9-(methoxycarbonyl)-2H-3,7-methanoazacycloundecino(5,4-b)indol-9-yl)-3a,4,5,5a,6,11,12,13a-octahydro-5-hydroxy-8-methoxy-6-methyl-, methyl ester, (3aR-(3aα,4β,5β,5aβ,9(3R*,5S*,7R*,9S*),10bR*,13aα))- |
| Vincaleukoblastine |
| Vinblastine,Vincaleukoblastine |
| Rozevin |
| Vincaleucoblastine |
| Vinblastine sulphate |
| EINECS 212-734-0 |
