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865-21-4

865-21-4 structure
865-21-4 structure
  • Name: Vinblastine
  • Chemical Name: vincaleukoblastine
  • CAS Number: 865-21-4
  • Molecular Formula: C46H58N4O9
  • Molecular Weight: 810.974
  • Catalog: Biochemical Plant extracts
  • Create Date: 2018-03-26 08:00:00
  • Modify Date: 2024-01-03 06:31:43
  • 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.
Name vincaleukoblastine
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
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
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.

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
Storage condition -20C

CHEMICAL IDENTIFICATION

RTECS NUMBER :
YY8050000
CHEMICAL NAME :
Vincaleukoblastine
CAS REGISTRY NUMBER :
865-21-4
LAST UPDATED :
199612
DATA ITEMS CITED :
44
MOLECULAR FORMULA :
C46-H58-N4-O9
MOLECULAR WEIGHT :
811.08
WISWESSER LINE NOTATION :
T C6 B5665 2AB S BX IN QN NU JH&&TTTTJ FO1 I KVO1 KQ LOV1 M2 E- NT F6 E596 A BN LM&&TTJ

HEALTH HAZARD DATA

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)
RIDADR UN 1544
Packaging Group II
Hazard Class 6.1(a)

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title: CAS No. 865-21-4 | Chemsrc address: https://m.chemsrc.com/en/baike/314490.html

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