Vinblastine sulfate

Iupac Name：methyl (1R,9R,10S,11R,12R,19R)-11-acetyloxy-12-ethyl-4-[(13S,15S,17S)-17-ethyl-17-hydroxy-13-methoxycarbonyl-1,11-diazatetracyclo[13.3.1.04,12.05,10]nonadeca-4(12),5,7,9-tetraen-13-yl]-10-hydroxy-5-methoxy-8-methyl-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2,4,6,13-tetraene-10-carboxylate;sulfuric acid

CAS No.: 143-67-9

Molecular Weight：909.061

Modify Date.: 2023-02-23 18:50

Introduction: Vinblastine sulfate is a cytotoxic alkaloid used against various cancer types. Vinblastine sulfate inhibits the formation of microtubule and suppresses nAChR with an IC50 of 8.9 μM. View more+

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1. Names and Identifiers

1.1 Name: Vinblastine sulfate
1.2 Synonyms: éthoxy-6-méthyl-3a,4,5,5a,6,11,12,13a-octahydro-1H-indolizino[8,1-cd]carbazole-5-carboxylate de méthyle sulfate (salt) (+)-vinblastine (2'Β)-Vincaleukoblastine sulfate (1:1) (2ξ,2'β,3α,4α,5β,19β)-Vincaleukoblastine sulfate (1:1) (3aR,4R,5S,5aR,10bR,13aR)-4-(acétyloxy)-3a-éthyl-9-[(13S,15S,17S)-17-éthyl-17-hydroxy-13-(méthoxycarbonyl)-1,11-diazatétracyclo[13.3.1.0.0]nonadéca-4(12),5,7,9-tétraén-13-yl]-5-hydroxy-8-m (3aR,4R,5S,5aR,10bR,13aR)-4-(acétyloxy)-3a-éthyl-9-[(13S,15S,17S)-17-éthyl-17-hydroxy-13-(méthoxycarbonyl)-1,11-diazatétracyclo[13.3.1.0.0]nonadéca-4(12),5,7,9-tétraén-13-yl]-5-hydroxy-8-méthoxy-6-méthyl-3a,4,5,5a,6,11,12,13a-octahydro-1H-indolizino[8,1-cd]carbazole-5-carboxylate de méthyle sulfate (salt) 29060le EINECS 205-606-0 exal methyl (3aR,4R,5S,5aR,10bR,13aR)-4-(acetyloxy)-3a-ethyl-9-[(13S,15S,17S)-17-ethyl-17-hydroxy-13-(methoxycarbonyl)-1,11-diazatetracyclo[13.3.1.0.0]nonadeca-4(12),5,7,9-tetraen-13-yl]-5-hydr methyl (3aR,4R,5S,5aR,10bR,13aR)-4-(acetyloxy)-3a-ethyl-9-[(13S,15S,17S)-17-ethyl-17-hydroxy-13-(methoxycarbonyl)-1,11-diazatetracyclo[13.3.1.0.0]nonadeca-4(12),5,7,9-tetraen-13-yl]-5-hydroxy-8-methoxy-6-methyl-3a,4,5,5a,6,11,12,13a-octahydro-1H-indolizino[8,1-cd]carbazole-5-carboxylate sulfate (salt) Methyl-(3aR,4R,5S,5aR,10bR,13aR)-4-(acetyloxy)-3a-ethyl-9-[(13S,15S,17S)-17-ethyl-17-hydroxy-13-(methoxycarbonyl)-1,11-diazatetracyclo[13.3.1.0.0]nonadeca-4(12),5,7,9-tetraen-13-yl]-5-hydr Methyl-(3aR,4R,5S,5aR,10bR,13aR)-4-(acetyloxy)-3a-ethyl-9-[(13S,15S,17S)-17-ethyl-17-hydroxy-13-(methoxycarbonyl)-1,11-diazatetracyclo[13.3.1.0.0]nonadeca-4(12),5,7,9-tetraen-13-yl]-5-hydroxy-8-methoxy-6-methyl-3a,4,5,5a,6,11,12,13a-octahydro-1H-indolizino[8,1-cd]carbazol-5-carboxylatsulfat(salt) MFCD00082457 nsc49842 oxy-8-methoxy-6-methyl-3a,4,5,5a,6,11,12,13a-octahydro-1H-indolizino[8,1-cd]carbazol-5-carboxylatsulfat(salt) oxy-8-methoxy-6-methyl-3a,4,5,5a,6,11,12,13a-octahydro-1H-indolizino[8,1-cd]carbazole-5-carboxylate sulfate (salt) Periblastine rozevinsulfate velban velbe Velsar vinbalastine Vinblastine (sulfate) Vinblastine, sulphate salt Vinblastine-d3 Vincaleukoblastine sulfate salt Vincaleukoblastine, (2'Β)-, sulfate (1:1) Vincaleukoblastine, (2ξ,2'β,3α,4α,5β,19β)-, sulfate (1:1) vincaleukoblastine, (3Β,4'Β)-, sulfate (1:1) vincaleukoblastine,sulfate(1:1)(salt) VLB VLB Vincaleukoblastine sulfate salt

1.3 CAS No.: 143-67-9

1.4 CID: 241902

1.5 EINECS(EC#): 205-606-0

1.6 Molecular Formula: C46H60N4O13S (isomer)

1.7 Inchi: InChI=1S/C46H58N4O9.H2O4S/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;1-5(2,3)4/h10-14,16,21-22,28,37-39,47,54-55H,8-9,15,17-20,23-26H2,1-7H3;(H2,1,2,3,4)/t28-,37+,38-,39-,42+,43-,44-,45+,46+;/m1./s1

1.8 InChkey: KDQAABAKXDWYSZ-JKDPCDLQSA-N

1.9 Canonical Smiles: CCC1(CC2CC(C3=C(CCN(C2)C1)C4=CC=CC=C4N3)(C5=C(C=C6C(=C5)C78CCN9C7C(C=CC9)(C(C(C8N6C)(C(=O)OC)O)OC(=O)C)CC)OC)C(=O)OC)O.OS(=O)(=O)O

1.10 Isomers Smiles: CC[C@@]1(C[C@@H]2C[C@@](C3=C(CCN(C2)C1)C4=CC=CC=C4N3)(C5=C(C=C6C(=C5)[C@]78CCN9[C@H]7[C@@](C=CC9)([C@H]([C@@]([C@@H]8N6C)(C(=O)OC)O)OC(=O)C)CC)OC)C(=O)OC)O.OS(=O)(=O)O

2. Properties

2.1 Density: 1.37

2.1 Melting point: 267℃

2.1 Precise Quality: 908.38800

2.1 PSA: 237.08000

2.1 logP: 4.35970

2.1 Solubility: H2O: 10?mg/mL

2.2 Appearance: white powder

2.3 Storage: Keep Cold.

2.4 Chemical Properties: Crystalline Solid

2.5 Color/Form: Powder

2.6 PH: 3.5～5.0 (1g/l, 25℃)

2.7 Water Solubility: >=1 g/100 mL at 24.5 oC

2.8 StorageTemp: 2-8°C

3. Use and Manufacturing

3.1 Usage: An antineoplastic

4. Safety and Handling

4.1 Symbol: GHS05, GHS07

4.1 Hazard Codes: T

4.1 Signal Word: Danger

4.1 Risk Statements: R22;R36/37/38;R41;R61

4.1 Safety Statements: S26;S37/39;S45;S53

4.1 Packing Group: II

4.1 Fire Hazard: Flash point data for Vinblastine sulfate are not available; however Vinblastine sulfate is probably combustible.

4.2 Hazard Class: 6.1(a)

4.2 Hazard Declaration: H302-H315-H318-H335

4.2 RIDADR: OTH

4.2 Safety Profile: Poison by ingestion,intraperitoneal, and intravenous routes. Anexperimental teratogen. Human systemiceffects by intravenous route: bloodleukopenia and hair changes. Experimentalreproductive effects. Questionablecarcinogen. Human mutation data reported. When heated to decomposition it emits verytoxic fumes of NOx and SOx. See alsoVINCALEUKOBLASTINE andSULFATES.

4.3 Caution Statement: P280-P301 + P312 + P330-P305 + P351 + P338 + P310

4.3 WGK Germany: 3

4.3 RTECS: YY8400000

4.3 Report: 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.

4.4 Safety: 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:?Xn,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

4.5 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.

4.6 Toxicity

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.

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5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Acute toxicity - Oral, Category 4

Skin irritation, Category 2

Serious eye damage, Category 1

Specific target organ toxicity \u2013 single exposure, Category 3

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Danger
Hazard statement(s)	H302 Harmful if swallowed H315 Causes skin irritation H318 Causes serious eye damage H335 May cause respiratory irritation
Precautionary statement(s)
Prevention	P264 Wash ... thoroughly after handling. P270 Do not eat, drink or smoke when using this product. P280 Wear protective gloves/protective clothing/eye protection/face protection. P261 Avoid breathing dust/fume/gas/mist/vapours/spray. P271 Use only outdoors or in a well-ventilated area.
Response	P301+P312 IF SWALLOWED: Call a POISON CENTER/doctor/\u2026if you feel unwell. P330 Rinse mouth. P302+P352 IF ON SKIN: Wash with plenty of water/... P321 Specific treatment (see ... on this label). P332+P313 If skin irritation occurs: Get medical advice/attention. P362+P364 Take off contaminated clothing and wash it before reuse. P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. P310 Immediately call a POISON CENTER/doctor/\u2026 P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing. P312 Call a POISON CENTER/doctor/\u2026if you feel unwell.
Storage	P403+P233 Store in a well-ventilated place. Keep container tightly closed. P405 Store locked up.
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

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6. Other Information

6.0 Merck: 13,10044

6.1 BRN: 3659812

6.2 Description: Vinblastine, derived from C. roseus, also known as V. rosea, a Madagascar periwinkle, is an antimicrotubule drug used to treat certain cancers, including Hodgkin’s lymphoma, non-small cell lung, breast, head and neck, and testicular cancer. Like its chemical analog vincristine, vinblastine binds tubulin, inhibiting the assembly of microtubules and causing M phase-specific cell cycle arrest by disrupting microtubule assembly and proper formation of the mitotic spindle. It has been shown to inhibit steady-state tubulin addition to microtubules with a K_i value of 0.18 μM, inhibit B16 melanoma cell proliferation with an IC₅₀ value of 1 nM, and produce complete inhibition of L-cell proliferation at 40 nM. Vinblastine is reported to be an effective component of certain chemotherapy regimens, particularly when used with bleomycin and methotrexate in vinblastine, bleomycin, and methotrexate combination chemotherapy for Stage IA or IIA Hodgkin lymphomas.

6.3 Chemical Properties: Vinblastine sulfate is a white to off-white crystalline powder that is freely soluble in water, soluble in methane, and slightly soluble in ethanol. Its empiric formula is C46H58N4O9.H2SO4 , and it has a molecular weight of 909.07.

6.4 Originator: Velban ,Lilly ,US ,1961

6.5 Uses: Vinblastin sulfate USP (Velban) is used to treat Hodgkin’s disease; lymphosarcoma; reticulum cell sarcoma; neuroblastoma; choriocarcinoma; carcinoma of breast, lung, oral cavity, testis, bladder; acute and chronic leukemia; histiocytosis; mycosis fungoides.

6.6 Brand name: Velban (Lilly).

6.7 Therapeutic Function: Cancer chemotherapy

6.8 General Description: Vinblastine sulfate is available as a powder in 10-mg vials and as a solution in 10- and 25-mL vials for IV administrationin the treatment of various cancers including Hodgkin’sdisease, lymphocytic lymphoma, histiocytic lymphoma, advancedmycosis fungoides, advanced testicular carcinoma,and Kaposi sarcoma. It has also been used in treating choriocarcinomaand breast cancer when other therapies havefailed. Vinblastine is part of the ABVD (adriamycin,bleomycin, vinblastine, and dacarbazine) regimen used inthe treatment of Hodgkin’s lymphoma. This may be alternatedwith the MOPP regimen. Extravasation is a concernwith the vincas and is treated by administration ofhyaluronidase and application of heat. Hyaluronidase hydrolyzeshyaluronic acid, a polysaccharide component of theconnective tissue. In so doing, the drug may increase diffusionout of the area of extravasation more quickly, preventingthe buildup of toxic levels. Vinblastine is highly proteinbound and metabolized by CYP to the 4-O-desacetylmetabolite, which has been shown to be active although onlysmall amounts have been recovered in the bile and feces. Themetabolism of the vinca alkaloids has not been well characterized.Vinblastine is eliminated primarily in the feces;however, little of the unchanged drug has been recovered.Metabolism appears to involve CYP3A but other than thedesacetyl derivative, other metabolites have not been characterized.The elimination half-life for vinblastine is 25 hours.Like vinorelbine, myelosuppression is commonly seen withvinblastine and is dose limiting. Inflammation of the GI tractis more commonly seen with vinblastine than vincristine.Nausea and vomiting may also occur. Other adverse effectsinclude alopecia, secretion of antidiuretic hormone,headache, and depression. Neurotoxicity is mild comparedwith vincristine, but peripheral neuropathy may be seen. Anadditional manifestation of this neurotoxicity.

6.9 General Description: An anticancer drug. White to slightly yellow crystalline powder.

6.10 Air & Water Reactions: Water soluble..Rapidly hydrolyzes.

6.11 Reactivity Profile: Vinblastine sulfate is sensitive to light, hydrolysis, oxidation, and heat. Vinblastine sulfate is very hygroscopic. .

6.12 Health Hazard: SYMPTOMS: Symptoms of exposure to Vinblastine sulfate include temporary mental depression, paresthesias, loss of deep-tendon reflexes, headache, convulsions, psychoses; dysfunction of the autonomic nervous system, with marked constipation, paralytic ileus, urinary retention, bilateral pain and tenderness of the parotid glands associated with dryness of the mouth, sinus tachycardia; nausea, vomiting, anorexia, diarrhea; loss of hair, vesicular mucositis of the mouth, and dermatitis.

6.13 Fire Hazard: Flash point data for Vinblastine sulfate are not available; however Vinblastine sulfate is probably combustible.

6.14 Biological Activity: Anticancer agent; microtubule disrupter. Induces apoptosis in cultured hepatocytes and human lymphoma cells.

6.15 Biochem/physiol Actions: Primary TargetInteraction of tubulin with microtubule-associated proteins, specifically Tau and MAP2

6.16 Side effects: The major toxic effect of vinblastine is a dose-related bone marrow depression. This is more frequent and severe than with the close structural analog, vincristine. Dose-related leukopenia occurs with a nadir of 4 to 10 days and with recovery occurring over another 7 to 14 days. Because of the relatively predictable nadir, it may be possible to administer vinblastine cautiously as often as every 7 to 10 days. Thrombocytopenia typically occurs; however, with standard dosing regimens, serious platelet depressions are infrequent. Erythrocytes are usually only slightly depressed.

6.17 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 NOx and SOx. See also VINCALEUKOBLASTINE and SULFATES.

6.18 Veterinary Drugs and Treatments: Vinblastine may be employed in the treatment of lymphomas, carcinomas, mastocytomas, and splenic tumors in small animals. It is more effective than vincristine in the treatment of canine mast cell tumors.

6.19 Purification Methods: Crystallise the sulfate from MeOH or EtOH and dry it in vacuo over conc H2SO4. The free base crystallises from EtOH or MeOH m 211-216o (+ 2MeOH .1 H2O) and forms a stable etherate from Et2O with m 201-211o, and [] D +42o (CHCl3), and UV max at 214 and 259nm (log 4.73 and 4.21). The dihydrochloride has m 244-246o(dec)(MeOH). It is a monoamine oxidase B inhibitor and induces microtubule aggregation. It is an antineoplastic drug for Hodgkin’s lymphoma. [Neuss et al. J Am Chem Soc 81 4754 1959, Jong-KeunSon et al. J Med Chem 33 1845 1990, Warfield & Bouck Science 186 1219 1974, Beilstein 26 III/IV 3167.]

6.20 Mode of action: Vinblastine binds to tubulin and inhibits microtubule assembly. This inhibition prevents mitotic spindle formation and results in an accumulation of cells in metaphase.
Vinblastine is considered cell cycle phase specic for mitosis; however, the cytotoxic effect probably occurs in S phase and is expressed only in M phase. At high doses, direct effects may be expressed in S and G1 phases. Vinblastine is assumed to have stathmokinetic (cell cycle arrest) effects similar to vincristine.

6.21 Usage: Anticancer agent; microtubule disrupter; Induces apoptosis.Vinblastine sulfate is therapeutically used as an antineoplastic. It is also used in the treatment of Hodgkin disease, choriocarcinoma, acute and chronic leukemias.

7. Computational chemical data

Molecular Weight: 909.061g/mol
Molecular Formula: C₄₆H₆₀N₄O₁₃S
Compound Is Canonicalized: True
XLogP3-AA: null
Exact Mass: 908.38775915
Monoisotopic Mass: 908.38775915
Complexity: 1780
Rotatable Bond Count: 10
Hydrogen Bond Donor Count: 5
Hydrogen Bond Acceptor Count: 16
Topological Polar Surface Area: 237
Heavy Atom Count: 64
Defined Atom Stereocenter Count: 9
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 2
CACTVS Substructure Key Fingerprint: AAADcfB/vABAAAAAAAAAAAAAAAAAAWLFgAA8YMECAAAAAFiB9AAAHgAQCAAAD3zhngYyzvPJloCoAyTyTDKCiCAhIiAImSF+bJgPJv7E9ZuGcChn8Bnb6Af62fOfqAACAgAKAABQgAYECBSgAAAAAAAAAA==

8. Question & Answer

About Vinblastine sulfate May 18 2021
Uses Vinblastine is used to treat cancer. It works by slowing or stopping the growth of cancer cells. How to use Vinblastine SULFATE Vial This medication is given by injection into a vein by a health care professional. It is usually given once a week or as directed by your doctor. To prevent leakag...

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