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Basic Information

Molecular Structure:
CAS No.:	143-67-9
Name:	Vinblastine sulfate
Article Data:	3

Formula:	C₄₆H₅₈N₄O₉
Molecular Weight:	810.988
Synonyms:	Alkaban-AQ;Exal;VLBmonosulfate;Velban;Velbe;Velsar;Vincaleukoblastine derivative;vincaleukoblastine, (2'beta)-;(2'beta)-Vincaleukoblastine;Vincaleukoblastine sulfate (1:1) (salt);Vinblastine 5;Rozevin sulfate;
EINECS:	205-606-0
Density:	1.37 g/cm³
Melting Point:	267°C (dec.)(lit.)
Solubility:	water: 10 mg/mL
Appearance:	crystalline solid
Hazard Symbols:	Xn,T
Risk Codes:	22-37/38-41-61-36/37/38-63-23/24/25
Safety:	26-36/39-53-45-37/39-36/37/39
PSA:	237.08000
LogP:	4.35970

Synthetic route

: C46H54N4O9

: 143-67-9
vinblastine

Conditions

Conditions	Yield
With hydrogen; palladium on activated charcoal In ethanol at 20℃; for 0.75h;	89%

: exo-catharanthine

: 2182-14-1
vindoline

: 143-67-9
vinblastine

Conditions

Conditions	Yield
Stage #1: exo-catharanthine; vindoline With hydrogenchloride; iron(III) chloride; 2,2,2-trifluoroethanol for 2h; Stage #2: With sodium tetrahydroborate; oxygen at 0℃; for 0.5h;	50%

: 124096-76-0
(+)-(9R)-3-oxo-9-methoxycarbonylindolizino<8,7-b>indole

: 143-67-9
vinblastine

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1.1: triethylamine; dmap / dichloromethane / 14 h / 20 °C 2.1: lithium diisopropyl amide / tetrahydrofuran / 12 h 3.1: trifluoroacetic acid / dichloromethane / 16 h 4.1: trimethoxonium tetrafluoroborate; 2,6-di-tert-butyl-pyridine / dichloromethane / 12 h 4.2: 0.5 h 5.1: [bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold(I); 2-bromopyridine-N-oxide; methanesulfonic acid; silver trifluoromethanesulfonate / 5 h / 20 °C 5.2: 3 h / 20 °C 6.1: potassium tert-butylate / tetrahydrofuran / 2 h 7.1: hydrogenchloride; 2,2,2-trifluoroethanol; iron(III) chloride / 2 h 7.2: 0.5 h / 0 °C View Scheme

Yield

Multi-step reaction with 7 steps
1.1: triethylamine; dmap / dichloromethane / 14 h / 20 °C
2.1: lithium diisopropyl amide / tetrahydrofuran / 12 h
3.1: trifluoroacetic acid / dichloromethane / 16 h
4.1: trimethoxonium tetrafluoroborate; 2,6-di-tert-butyl-pyridine / dichloromethane / 12 h
4.2: 0.5 h
5.1: [bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold(I); 2-bromopyridine-N-oxide; methanesulfonic acid; silver trifluoromethanesulfonate / 5 h / 20 °C
5.2: 3 h / 20 °C
6.1: potassium tert-butylate / tetrahydrofuran / 2 h
7.1: hydrogenchloride; 2,2,2-trifluoroethanol; iron(III) chloride / 2 h
7.2: 0.5 h / 0 °C
View Scheme

: C19H18N2O3

: 143-67-9
vinblastine

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: trimethoxonium tetrafluoroborate; 2,6-di-tert-butyl-pyridine / dichloromethane / 12 h 1.2: 0.5 h 2.1: [bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold(I); 2-bromopyridine-N-oxide; methanesulfonic acid; silver trifluoromethanesulfonate / 5 h / 20 °C 2.2: 3 h / 20 °C 3.1: potassium tert-butylate / tetrahydrofuran / 2 h 4.1: hydrogenchloride; 2,2,2-trifluoroethanol; iron(III) chloride / 2 h 4.2: 0.5 h / 0 °C View Scheme

Yield

Multi-step reaction with 4 steps
1.1: trimethoxonium tetrafluoroborate; 2,6-di-tert-butyl-pyridine / dichloromethane / 12 h
1.2: 0.5 h
2.1: [bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold(I); 2-bromopyridine-N-oxide; methanesulfonic acid; silver trifluoromethanesulfonate / 5 h / 20 °C
2.2: 3 h / 20 °C
3.1: potassium tert-butylate / tetrahydrofuran / 2 h
4.1: hydrogenchloride; 2,2,2-trifluoroethanol; iron(III) chloride / 2 h
4.2: 0.5 h / 0 °C
View Scheme

: C19H20N2O2

: 143-67-9
vinblastine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: [bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold(I); 2-bromopyridine-N-oxide; methanesulfonic acid; silver trifluoromethanesulfonate / 5 h / 20 °C 1.2: 3 h / 20 °C 2.1: potassium tert-butylate / tetrahydrofuran / 2 h 3.1: hydrogenchloride; 2,2,2-trifluoroethanol; iron(III) chloride / 2 h 3.2: 0.5 h / 0 °C View Scheme

: C19H20N2O3

: 143-67-9
vinblastine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: potassium tert-butylate / tetrahydrofuran / 2 h 2.1: hydrogenchloride; 2,2,2-trifluoroethanol; iron(III) chloride / 2 h 2.2: 0.5 h / 0 °C View Scheme

: C21H24N2O5

: 143-67-9
vinblastine

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1.1: lithium diisopropyl amide / tetrahydrofuran / 12 h 2.1: trifluoroacetic acid / dichloromethane / 16 h 3.1: trimethoxonium tetrafluoroborate; 2,6-di-tert-butyl-pyridine / dichloromethane / 12 h 3.2: 0.5 h 4.1: [bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold(I); 2-bromopyridine-N-oxide; methanesulfonic acid; silver trifluoromethanesulfonate / 5 h / 20 °C 4.2: 3 h / 20 °C 5.1: potassium tert-butylate / tetrahydrofuran / 2 h 6.1: hydrogenchloride; 2,2,2-trifluoroethanol; iron(III) chloride / 2 h 6.2: 0.5 h / 0 °C View Scheme

Yield

Multi-step reaction with 6 steps
1.1: lithium diisopropyl amide / tetrahydrofuran / 12 h
2.1: trifluoroacetic acid / dichloromethane / 16 h
3.1: trimethoxonium tetrafluoroborate; 2,6-di-tert-butyl-pyridine / dichloromethane / 12 h
3.2: 0.5 h
4.1: [bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold(I); 2-bromopyridine-N-oxide; methanesulfonic acid; silver trifluoromethanesulfonate / 5 h / 20 °C
4.2: 3 h / 20 °C
5.1: potassium tert-butylate / tetrahydrofuran / 2 h
6.1: hydrogenchloride; 2,2,2-trifluoroethanol; iron(III) chloride / 2 h
6.2: 0.5 h / 0 °C
View Scheme

: C24H26N2O5

: 143-67-9
vinblastine

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: trifluoroacetic acid / dichloromethane / 16 h 2.1: trimethoxonium tetrafluoroborate; 2,6-di-tert-butyl-pyridine / dichloromethane / 12 h 2.2: 0.5 h 3.1: [bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold(I); 2-bromopyridine-N-oxide; methanesulfonic acid; silver trifluoromethanesulfonate / 5 h / 20 °C 3.2: 3 h / 20 °C 4.1: potassium tert-butylate / tetrahydrofuran / 2 h 5.1: hydrogenchloride; 2,2,2-trifluoroethanol; iron(III) chloride / 2 h 5.2: 0.5 h / 0 °C View Scheme

Yield

Multi-step reaction with 5 steps
1.1: trifluoroacetic acid / dichloromethane / 16 h
2.1: trimethoxonium tetrafluoroborate; 2,6-di-tert-butyl-pyridine / dichloromethane / 12 h
2.2: 0.5 h
3.1: [bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold(I); 2-bromopyridine-N-oxide; methanesulfonic acid; silver trifluoromethanesulfonate / 5 h / 20 °C
3.2: 3 h / 20 °C
4.1: potassium tert-butylate / tetrahydrofuran / 2 h
5.1: hydrogenchloride; 2,2,2-trifluoroethanol; iron(III) chloride / 2 h
5.2: 0.5 h / 0 °C
View Scheme

: 75-11-6
diiodomethane

: 143-67-9
vinblastine

A: C47H61N4O9(1+)*I(1-)

B: vinamidine

C: cyclovinblastine

Conditions

Conditions	Yield
With diethylzinc In hexane; dichloromethane at 0 - 20℃; Inert atmosphere;	A 18% B n/a C n/a

...Expand

: 143-67-9
vinblastine

: 55383-37-4
desacetylvinblastine monohydrazide

Conditions

Conditions	Yield
With hydrogenchloride; sodium nitrite In methanol; water at 0℃; for 0.2h; pH=7.6;

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Chemistry

Molecular Structure of Vinblastine sulfate (CAS NO.143-67-9):

Molecular formula: C₄₆H₆₀N₄O₁₃S
Molecular Weight: 909.05
Index of Refraction: 1.671
Molar Refractivity: 220.74 cm³
Molar Volume: 590 cm³
Surface Tension: 70.9 dyne/cm
Density: 1.37 g/cm³
NECS: 205-606-0
Melting point: 267 °C (dec.)(lit.)
Alpha: -21.7 o (c=2, CH₃OH 21 oC)
Storage temp: 2-8°C
Solubility: H₂O: 10 mg/mL
Water Solubility: >=1 g/100 mL at 24.5 ^oC
Appearance: white powder

Toxicity Data With Reference

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
dog	LDLo	intravenous	500ug/kg (0.5mg/kg)	BEHAVIORAL: FOOD INTAKE (ANIMAL) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"	Vsesoyuznyi Institut Nauchnoi i Tekhnicheskoi Informatsii Vol. #3713-83,
hamster	LD50	intraperitoneal	4300ug/kg (4.3mg/kg)		Cancer Letters Vol. 2, Pg. 267, 1977.
human	TDLo	intravenous	557ug/kg (0.557mg/kg)	BLOOD: LEUKOPENIA SKIN AND APPENDAGES (SKIN): HAIR: OTHER	Cancer Chemotherapy Reports. Vol. 29, Pg. 111, 1963.
mouse	LD50	intraperitoneal	2700ug/kg (2.7mg/kg)		Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 21, Pg. 359, 1979.
mouse	LD50	intravenous	9500ug/kg (9.5mg/kg)		Cancer Research. Vol. 39, Pg. 3575, 1979.
mouse	LD50	oral	423mg/kg (423mg/kg)		Oyo Yakuri. Pharmacometrics. Vol. 3, Pg. 68, 1969.
mouse	LD50	subcutaneous	324mg/kg (324mg/kg)		Oyo Yakuri. Pharmacometrics. Vol. 3, Pg. 68, 1969.
rat	LD50	intraperitoneal	1mg/kg (1mg/kg)	BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"	Vsesoyuznyi Institut Nauchnoi i Tekhnicheskoi Informatsii Vol. #3713-83,
rat	LD50	intravenous	37mg/kg (37mg/kg)		Oyo Yakuri. Pharmacometrics. Vol. 3, Pg. 68, 1969.
rat	LD50	oral	305mg/kg (305mg/kg)		Oyo Yakuri. Pharmacometrics. Vol. 3, Pg. 68, 1969.
rat	LD50	subcutaneous	355mg/kg (355mg/kg)		Oyo Yakuri. Pharmacometrics. Vol. 3, Pg. 68, 1969.

Consensus Reports

IARC Cancer Review: Group 3 IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of chemicals to Man . 7 ,1987,p. 371.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Animal Inadequate Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of chemicals to Man . 26 ,1981,p. 349.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Human Inadequate Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of chemicals to Man . 26 ,1981,p. 349.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) . EPA Genetic Toxicology Program.

Safety Profile

Poison by ingestion, intraperitoneal, and intravenous routes. An experimental teratogen. Human systemic effects by intravenous route: blood leukopenia and hair changes. Experimental reproductive effects. Questionable carcinogen. Human mutation data reported. When heated to decomposition it emits very toxic fumes of NO_x and SO_x. See also vincaleukoblastine and sulfates.
Hazard Codes: Harmful Xn, Toxic T
Risk Statements: 22-37/38-41-61-36/37/38-63-23/24/25
R22:Harmful if swallowed.
R37/38:Irritating to respiratory system and skin.
R41:Risk of serious damage to the eyes.
R61:May cause harm to the unborn child.
R36/37/38:Irritating to eyes, respiratory system and skin.
R63:Possible risk of harm to the unborn child.
R23/24/25:Toxic by inhalation, in contact with skin and if swallowed.
Safety Statements: 26-36/39-53-45-37/39-36/37/39
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S53:Avoid exposure - obtain special instructions before use.
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
S37/39:Wear suitable gloves and eye/face protection.
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection.
RIDADR: 1544
WGK Germany: 3
RTECS: YY8400000
F: 8-10
HazardClass: 6.1(a)
PackingGroup: II

Specification

Vinblastine sulfate , with CAS number of 143-67-9, can be called Vincaleukoblastine derivative ; vincaleukoblastine, (2'beta)- ; Vincaleukoblastine derivative ; Vincaleukoblastine sulfate (1:1) (salt) ; Vinblastine 5 ; Rozevin sulfate . It is an antineoplastic agents for the treatment of Hodgkin's disease, choriocarcinoma and lymphosarcoma, it also has some effect on acute leukemia, breast cancer.

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