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Vinblastine

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Name

Vinblastine

EINECS 212-734-0
CAS No. 865-21-4 Density 1.37 g/cm3
PSA 154.10000 LogP 3.93170
Solubility N/A Melting Point 211 - 216oC
Formula C46H58N4O9 Boiling Point 755.65°C (rough estimate)
Molecular Weight 810.988 Flash Point N/A
Transport Information N/A Appearance POWDER
Safety Risk Codes N/A
Molecular Structure Molecular Structure of 865-21-4 (Vinblastine) Hazard Symbols N/A
Synonyms

Vinblastine(7CI);(+)-Vinblastine;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-[3aa,4b,5b,5ab,9(3R*,5S*,7R*,9S*),10bR*,13aa]]-;Rozevin;VLB;Valban;Vinblastin;Vincaleucoblastin;Vincaleucoblastine;[3aR-[3aa,4b,5b,5ab,9(3R*,5S*,7R*,9S*),10bR*,13aa]]-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;

Article Data 5

Vinblastine History

 Vinblastine (865-21-4) was first isolated by Robert Noble and Charles Thomas Beer from the Madagascar periwinkle plant. Vinblastine's utility as a chemotherapeutic agent was first discovered when it was crushed into a tea. Consumption of the tea led to a decreased number of white blood cells; therefore, it was hypothesized that vinblastine might be effective against cancers of the white blood cells such as lymphoma.

Vinblastine Consensus Reports

NCI Carcinogenesis Studies (ipr); No Evidence: mouse CANCAR    Cancer. 40 (1977),1935. ; (ipr); Clear Evidence: rat CANCAR    Cancer. 40 (1977),1935. . EPA Genetic Toxicology Program.

Vinblastine Specification

The CAS registry number of Vinblastine is 865-21-4. Its EINECS registry number is 212-734-0. The systematic name is (2α,3α,4α,5β,19β)-vincaleukoblastine. In addition, the molecular formula is C46H58N4O9 and the molecular weight is 810.97. It is also called Vincaleukoblastine. What's more, it is a vinca alkaloid and a chemical analogue of vincristine.

Physical properties about this chemical are: (1)ACD/LogP: 4.18; (2)# of Rule of 5 Violations: 2; (3)ACD/LogD (pH 5.5): 1.73; (4)ACD/LogD (pH 7.4): 3.69; (5)ACD/BCF (pH 5.5): 3.16; (6)ACD/BCF (pH 7.4): 284.81; (7)ACD/KOC (pH 5.5): 16; (8)ACD/KOC (pH 7.4): 1440.47; (9)#H bond acceptors: 13; (10)#H bond donors: 3; (11)#Freely Rotating Bonds: 12; (12)Polar Surface Area: 121.24 Å2; (13)Index of Refraction: 1.671; (14)Molar Refractivity: 220.74 cm3; (15)Molar Volume: 590 cm3; (16)Polarizability: 87.5 ×10-24cm3; (17)Surface Tension: 70.9 dyne/cm; (18)Density: 1.37 g/cm3.

Preparation of Vinblastine: it can be prepared by C54H63N5O14. This reaction will need reagent H2, catalyst 10percent Pd/C and solvent methanol. The reaction time is 2 hours at reaction temperature of 25 °C. The yield is about 89%.

Vinblastine can be prepared by C54H63N5O14

Uses of Vinblastine: it can used to treat some kinds of cancer, including Hodgkin's lymphoma, non-small cell lung cancer, breast cancer, head and neck cancer, and testicular cancer. It is also used to treat Langerhan cell histiocytosis. In addition, it can be used to get C46H56ClFN4O8 and C46H56F2N4O8. This reaction will need reagents HF, SbF5 and CHCl3.

Vinblastine can be used to get C46H56ClFN4O8 and C46H56F2N4O8

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(OC)[C@]4(c2c(c1ccccc1n2)CCN3C[C@](O)(CC)C[C@H](C3)C4)c5c(OC)cc6c(c5)[C@@]89[C@@H](N6C)[C@@](O)(C(=O)OC)[C@H](OC(=O)C)[C@@]7(/C=C\CN([C@@H]78)CC9)CC
(2)InChI: InChI=1/C46H58N4O9/c1-8-42(54)23-28-24-45(40(52)57-6,36-30(15-19-49(25-28)26-42)29-13-10-11-14-33(29)47-36)32-21-31-34(22-35(32)56-5)48(4)38-44(31)17-20-50-18-12-16-43(9-2,37(44)50)39(59-27(3)51)46(38,55)41(53)58-7/h10-14,16,21-22,28,37-39,47,54-55H,8-9,15,17-20,23-26H2,1-7H3/t28-,37-,38+,39+,42-,43+,44+,45-,46-/m0/s1
(3)InChIKey: JXLYSJRDGCGARV-CFWMRBGOBT

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
human TDLo ocular 14ug/kg (0.014mg/kg) SENSE ORGANS AND SPECIAL SENSES: VISUAL FIELD CHANGES: EYE

SENSE ORGANS AND SPECIAL SENSES: CONJUNCTIVE IRRITATION: EYE

SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE
British Journal of Ophthalmology. Vol. 62, Pg. 97, 1978.
man LDLo intravenous 2319ug/kg/38W (2.319mg/kg) CARDIAC: CARDIOMYOPATHY INCLUDING INFARCTION Lancet. Vol. 2, Pg. 692, 1980.
man TDLo unreported 80ug/kg (0.08mg/kg) BLOOD: CHANGES IN BONE MARROW NOT INCLUDED ABOVE Cancer Chemotherapy Reports. Vol. 50, Pg. 219, 1966.
mouse LD10 subcutaneous 20mg/kg (20mg/kg)   European Journal of Cancer. Vol. 10, Pg. 667, 1974.
mouse LD50 intraperitoneal 3120ug/kg (3.12mg/kg) BLOOD: CHANGES IN BONE MARROW NOT INCLUDED ABOVE

IMMUNOLOGICAL INCLUDING ALLERGIC: DECREASED IMMUNE RESPONSE
Cancer Treatment Reports. Vol. 61, Pg. 103, 1977.
mouse LD50 intravenous 15mg/kg (15mg/kg)   United States Patent Document. Vol. #4279915,
rat LD50 intravenous 2mg/kg (2mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 20, Pg. 1467, 1970.

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