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MedKoo Cat#: 201530 | Name: Indibulin
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Indibulin is a synthetic small molecule with antimitotic and potential antineoplastic activities. Indibulin binds to a site on tubulin that is different from taxane- or Vinca alkaloid-binding sites, destabilizing tubulin polymerization and inducing tumor cell cycle arrest and apoptosis. This agent has been shown to be active against multidrug-resistant (MDR) and taxane- resistant tumor cell lines. Check for active clinical trials or closed clinical trials using this agent. (NCI Thesaurus).

Chemical Structure

Indibulin
Indibulin
CAS#204205-90-3

Theoretical Analysis

MedKoo Cat#: 201530

Name: Indibulin

CAS#: 204205-90-3

Chemical Formula: C22H16ClN3O2

Exact Mass: 389.0931

Molecular Weight: 389.84

Elemental Analysis: C, 67.78; H, 4.14; Cl, 9.09; N, 10.78; O, 8.21

Price and Availability

Size Price Availability Quantity
10mg USD 350.00
25mg USD 600.00 2 Weeks
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Related CAS #
No Data
Synonym
ZIO-301；ZERO/005632；ZINC01996564；d-24851; D-24851；NCGC00160428-01.
IUPAC/Chemical Name
2-(1-(4-chlorobenzyl)-1H-indol-3-yl)-2-oxo-N-(pyridin-4-yl)acetamide
InChi Key
SOLIIYNRSAWTSQ-UHFFFAOYSA-N
InChi Code
InChI=1S/C22H16ClN3O2/c23-16-7-5-15(6-8-16)13-26-14-19(18-3-1-2-4-20(18)26)21(27)22(28)25-17-9-11-24-12-10-17/h1-12,14H,13H2,(H,24,25,28)
SMILES Code
O=C(NC1=CC=NC=C1)C(C2=CN(CC3=CC=C(Cl)C=C3)C4=C2C=CC=C4)=O
Appearance
Solid powder
Purity
>98%
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, not in water
Shelf Life
>5 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
2934.99.9001
More Info
Indibulin (ZIO-301) is a novel anti-cancer agent that binds to tubulin, one of the essential proteins for chromosomal segregation, and targets mitosis like the taxanes and Vinca alkaloids. It is available as both an oral and an intravenous form. Indibulin has a pharmacologic profile that is different from other tubulin inhibitors currently on the market. Indibulin binds to a site on tubulin that is different from the taxanes or Vinca alkaloid binding sites. In contrast to taxanes, which stabilize tubulin polymers, indibulin destabilizes tubulin polymerization. Indibulin has demonstrated significant and broad anti-tumor activity in many types of cancer cells. These include multi drug resistant tumor cell lines and taxane resistant tumor cell lines. In animal tumor models it was active at non-toxic levels in rat sarcoma AH13, MDR-1 leukemia mouse models and other xenograft models. No neurotoxicity or bone marrow suppression was detected at curative levels in animals. (Source:  http://www.ziopharm.com/clinical_zio301.php ).      
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Indibulin (ZIO 301), an orally applicable inhibitor of tubulin assembly, shows potent anticancer activity with a minimal neurotoxicity. Indibulin reduces inter-kinetochoric tension, produces aberrant spindles, activates mitotic checkpoint proteins Mad2 and BubR1, and induces mitotic arrest and apoptosis.
In vitro activity:
Indibulin inhibited the proliferation of MCF-7 cells with a half-maximal inhibitory concentration of 150 ± 13 nM (Fig. 1B). A flow cytometric analysis using propidium iodide staining suggested that indibulin treatment blocked the cells in the G2/M phase of the cell cycle (Fig. 1C). Furthermore, the percentage of phosphohistone H3 (S10) (a mitotic marker) positive cells increased from 4.1 ± 0.6% in control to 61 ± 5.3% in 600 nM indibulin treated cells indicating that indibulin blocked the progression of the cell cycle at mitosis (Fig. 1D,E). Reference: Sci Rep. 2018 Aug 17;8(1):12363. https://pubmed.ncbi.nlm.nih.gov/30120268/
In vivo activity:
TBD
Solvent mg/mL mM
Solubility
DMSO 33.3 85.29
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 389.84 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
Formulation protocol:
1. Kapoor S, Srivastava S, Panda D. Indibulin dampens microtubule dynamics and produces synergistic antiproliferative effect with vinblastine in MCF-7 cells: Implications in cancer chemotherapy. Sci Rep. 2018 Aug 17;8(1):12363. doi: 10.1038/s41598-018-30376-y. PMID: 30120268; PMCID: PMC6098095. 2. Yu PF, Chen H, Wang J, He CX, Cao B, Li M, Yang N, Lei ZY, Cheng MS. Design, synthesis and cytotoxicity of novel podophyllotoxin derivatives. Chem Pharm Bull (Tokyo). 2008 Jun;56(6):831-4. doi: 10.1248/cpb.56.831. PMID: 18520089.
In vitro protocol:
1. Kapoor S, Srivastava S, Panda D. Indibulin dampens microtubule dynamics and produces synergistic antiproliferative effect with vinblastine in MCF-7 cells: Implications in cancer chemotherapy. Sci Rep. 2018 Aug 17;8(1):12363. doi: 10.1038/s41598-018-30376-y. PMID: 30120268; PMCID: PMC6098095. 2. Yu PF, Chen H, Wang J, He CX, Cao B, Li M, Yang N, Lei ZY, Cheng MS. Design, synthesis and cytotoxicity of novel podophyllotoxin derivatives. Chem Pharm Bull (Tokyo). 2008 Jun;56(6):831-4. doi: 10.1248/cpb.56.831. PMID: 18520089.
In vivo protocol:
TBD
1: Putey A, Popowycz F, Do QT, Bernard P, Talapatra SK, Kozielski F, Galmarini CM, Joseph B. Indolobenzazepin-7-ones and 6-, 8-, and 9-membered ring derivatives as tubulin polymerization inhibitors: synthesis and structure--activity relationship studies. J Med Chem. 2009 Oct 8;52(19):5916-25. PubMed PMID: 19743863.