4-Desacetylvinblastine
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MedKoo CAT#: 581541

CAS#: 3352-69-0

Description: 4-Desacetylvinblastine is a a pro-drug of Vinblastine. An anti-tumor agent used in the treatment of prostate cancer.


Chemical Structure

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4-Desacetylvinblastine
CAS# 3352-69-0

Theoretical Analysis

MedKoo Cat#: 581541
Name: 4-Desacetylvinblastine
CAS#: 3352-69-0
Chemical Formula: C44H56N4O8
Exact Mass: 768.4098
Molecular Weight: 768.95
Elemental Analysis: C, 68.73; H, 7.34; N, 7.29; O, 16.64

Price and Availability

Size Price Availability Quantity
5.0mg USD 740.0 2 Weeks
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Synonym: 4-Desacetylvinblastine; Deacetylvinblastine; Desacetylvinblastine; 4-Desacetyl Vinblastine

IUPAC/Chemical Name: methyl (3aR,3a1R,4R,5S,5aR)-3a-ethyl-9-((5S,7S,9S)-5-ethyl-5-hydroxy-9-(methoxycarbonyl)-1,4,5,6,7,8,9,10-octahydro-2H-3,7-methano[1]azacycloundecino[5,4-b]indol-9-yl)-4,5-dihydroxy-8-methoxy-6-methyl-3a,3a1,4,5,5a,6,11,12-octahydro-1H-indolizino[8,1-cd]carbazole-5-carboxylate

InChi Key: NDMPLJNOPCLANR-SAYSVMKTSA-N

InChi Code: 1S/C44H56N4O8/c1-7-40(52)22-26-23-43(38(50)55-5,34-28(14-18-47(24-26)25-40)27-12-9-10-13-31(27)45-34)30-20-29-32(21-33(30)54-4)46(3)36-42(29)16-19-48-17-11-15-41(8-2,35(42)48)37(49)44(36,53)39(51)56-6/h9-13,15,20-21,26,35-37,45,49,52-53H,7-8,14,16-19,22-25H2,1-6H3/t26-,35+,36-,37-,40+,41-,42?,43+,44+/m1/s1

SMILES Code: CC[C@@]1(C[C@@H]2C[C@@](c3c(c4ccccc4[nH]3)CCN(C2)C1)(c5cc6c(cc5OC)N([C@@H]7C68CCN9[C@H]8[C@@](C=CC9)([C@H]([C@@]7(C(=O)OC)O)O)CC)C)C(=O)OC)O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >3 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.03.00

Preparing Stock Solutions

The following data is based on the product molecular weight 768.95 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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1: Zhao R, Diop-Bove N, Goldman ID. Enhanced receptor-mediated endocytosis and cytotoxicity of a folic acid-desacetylvinblastine monohydrazide conjugate in a pemetrexed-resistant cell line lacking folate-specific facilitative carriers but with increased folate receptor expression. Mol Pharmacol. 2014 Feb;85(2):310-21. doi: 10.1124/mol.113.089110. Epub 2013 Nov 18. PubMed PMID: 24249723; PubMed Central PMCID: PMC3913358.

2: Li J, Sausville EA, Klein PJ, Morgenstern D, Leamon CP, Messmann RA, LoRusso P. Clinical pharmacokinetics and exposure-toxicity relationship of a folate-Vinca alkaloid conjugate EC145 in cancer patients. J Clin Pharmacol. 2009 Dec;49(12):1467-76. doi: 10.1177/0091270009339740. Epub 2009 Oct 16. PubMed PMID: 19837906; PubMed Central PMCID: PMC3807256.

3: Vlahov IR, Santhapuram HK, Kleindl PJ, Howard SJ, Stanford KM, Leamon CP. Design and regioselective synthesis of a new generation of targeted chemotherapeutics. Part 1: EC145, a folic acid conjugate of desacetylvinblastine monohydrazide. Bioorg Med Chem Lett. 2006 Oct 1;16(19):5093-6. Epub 2006 Jul 25. PubMed PMID: 16870437.

4: Gutowski MC, Fix DV, Corvalan JR, Johnson DA. Reduction of toxicity of a vinca alkaloid by an anti-vinca alkaloid antibody. Cancer Invest. 1995;13(4):370-4. PubMed PMID: 7627723.

5: Hilselberger Kanitz M, Mastro JM, Moore RE, Starling JJ. In vivo expression of P-glycoprotein in a human colon carcinoma xenograft is modulated by therapy with free and monoclonal antibody-conjugated vinca alkaloids. Anticancer Res. 1994 May-Jun;14(3A):857-68. PubMed PMID: 7915508.

6: Meyer DL, Jungheim LN, Law KL, Mikolajczyk SD, Shepherd TA, Mackensen DG, Briggs SL, Starling JJ. Site-specific prodrug activation by antibody-beta-lactamase conjugates: regression and long-term growth inhibition of human colon carcinoma xenograft models. Cancer Res. 1993 Sep 1;53(17):3956-63. PubMed PMID: 8358723.

7: Apelgren LD, Bailey DL, Briggs SL, Barton RL, Guttman-Carlisle D, Koppel GA, Nichols CL, Scott WL, Lindstrom TD, Baker AL, et al. Chemoimmunoconjugate development for ovarian carcinoma therapy: preclinical studies with vinca alkaloid-monoclonal antibody constructs. Bioconjug Chem. 1993 Mar-Apr;4(2):121-6. PubMed PMID: 7873643.

8: van Tellingen O, Beijnen JH, Nooijen WJ, Bult A. Tissue disposition, excretion and metabolism of vinblastine in mice as determined by high-performance liquid chromatography. Cancer Chemother Pharmacol. 1993;32(4):286-92. PubMed PMID: 8324870.

9: Schrappe M, Bumol TF, Apelgren LD, Briggs SL, Koppel GA, Markowitz DD, Mueller BM, Reisfeld RA. Long-term growth suppression of human glioma xenografts by chemoimmunoconjugates of 4-desacetylvinblastine-3-carboxyhydrazide and monoclonal antibody 9.2.27. Cancer Res. 1992 Jul 15;52(14):3838-44. PubMed PMID: 1617657.

10: Starling JJ, Maciak RS, Hinson NA, Nichols CL, Briggs SL, Laguzza BC, Smith W, Corvalan JR. In vivo antitumor activity of a panel of four monoclonal antibody-vinca alkaloid immunoconjugates which bind to three distinct epitopes of carcinoembryonic antigen. Bioconjug Chem. 1992 Jul-Aug;3(4):315-22. PubMed PMID: 1382618.

11: Meyer DL, Jungheim LN, Mikolajczyk SD, Shepherd TA, Starling JJ, Ahlem CN. Preparation and characterization of a beta-lactamase-Fab' conjugate for the site-specific activation of oncolytic agents. Bioconjug Chem. 1992 Jan-Feb;3(1):42-8. PubMed PMID: 1616948.

12: Roy ML, Pikal MJ, Rickard EC, Maloney AM. The effects of formulation and moisture on the stability of a freeze-dried monoclonal antibody-vinca conjugate: a test of the WLF glass transition theory. Dev Biol Stand. 1992;74:323-39; discussion 340. PubMed PMID: 1592182.

13: Labus JM, Petersen BH. Quantitation of human anti-mouse antibody in serum by flow cytometry. Cytometry. 1992;13(3):275-81. PubMed PMID: 1576893.

14: Johnson DA, Barton RL, Fix DV, Scott WL, Gutowski MC. Induction of immunogenicity of monoclonal antibodies by conjugation with drugs. Cancer Res. 1991 Oct 15;51(20):5774-6. PubMed PMID: 1913696.

15: Gutowski MC, Briggs SL, Johnson DA. Epidermal growth factor receptor-reactive monoclonal antibodies: xenograft antitumor activity alone and as drug immunoconjugates. Cancer Res. 1991 Oct 15;51(20):5471-5. PubMed PMID: 1913667.

16: van Tellingen O, Beijnen JH, Baurain R, ten Bokkel Huinink WW, van der Woude HR, Nooyen WJ. High-performance liquid chromatographic determination of vinblastine, 4-O-deacetylvinblastine and the potential metabolite 4-O-deacetylvinblastine-3-oic acid in biological fluids. J Chromatogr. 1991 Aug 16;553(1-2):47-53. PubMed PMID: 1787167.

17: Starling JJ, Maciak RS, Law KL, Hinson NA, Briggs SL, Laguzza BC, Johnson DA. In vivo antitumor activity of a monoclonal antibody-Vinca alkaloid immunoconjugate directed against a solid tumor membrane antigen characterized by heterogeneous expression and noninternalization of antibody-antigen complexes. Cancer Res. 1991 Jun 1;51(11):2965-72. PubMed PMID: 2032233.

18: Petersen BH, DeHerdt SV, Schneck DW, Bumol TF. The human immune response to KS1/4-desacetylvinblastine (LY256787) and KS1/4-desacetylvinblastine hydrazide (LY203728) in single and multiple dose clinical studies. Cancer Res. 1991 May 1;51(9):2286-90. PubMed PMID: 2015593.

19: Apelgren LD, Zimmerman DL, Briggs SL, Bumol TF. Antitumor activity of the monoclonal antibody-Vinca alkaloid immunoconjugate LY203725 (KS1/4-4-desacetylvinblastine-3-carboxhydrazide) in a nude mouse model of human ovarian cancer. Cancer Res. 1990 Jun 15;50(12):3540-4. PubMed PMID: 2340502.

20: Johnson DA, Baker AL, Laguzza BC, Fix DV, Gutowski MC. Antitumor activity of L/1C2-4-desacetylvinblastine-3-carboxhydrazide immunoconjugate in xenografts. Cancer Res. 1990 Mar 15;50(6):1790-4. PubMed PMID: 2306731.