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MedKoo Cat#: 200841 | Name: CUDC-101
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Description:

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

CUDC-101 is a multi-targeted, small-molecule inhibitor of histone deacetylase (HDAC), epidermal growth factor receptor tyrosine kinase (EGFR/ErbB1), and human epidermal growth factor receptor 2 tyrosine kinase (HER2/neu or ErbB2) with potential antineoplastic activity. HDAC/EGFR/HER2 inhibitor CUDC-101 inhibits the activity of these three enzymes but the exact mechanism of action is presently unknown. This agent may help overcome resistance to inhibition of EGFR and Her2 through a simultaneous, synergistic inhibition of EGFR, Her2, and HDAC.

Chemical Structure

CUDC-101
CUDC-101
CAS#1012054-59-9

Theoretical Analysis

MedKoo Cat#: 200841

Name: CUDC-101

CAS#: 1012054-59-9

Chemical Formula: C24H26N4O4

Exact Mass: 434.1954

Molecular Weight: 434.49

Elemental Analysis: C, 66.34; H, 6.03; N, 12.89; O, 14.73

Price and Availability

Size Price Availability Quantity
10mg USD 90.00 Ready to ship
25mg USD 150.00 Ready to ship
50mg USD 250.00 Ready to ship
100mg USD 450.00 Ready to ship
200mg USD 750.00 Ready to ship
500mg USD 1,350.00 Ready to ship
1g USD 2,350.00 Ready to Ship
2g USD 4,250.00 Ready to Ship
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Synonym
CUDC101; CUDC 101; CUDC-101
IUPAC/Chemical Name
7-(4-(3-ethynylphenylamino)-7-methoxyquinazolin-6-yloxy)-N-hydroxyheptanamide
InChi Key
PLIVFNIUGLLCEK-UHFFFAOYSA-N
InChi Code
InChI=1S/C24H26N4O4/c1-3-17-9-8-10-18(13-17)27-24-19-14-22(21(31-2)15-20(19)25-16-26-24)32-12-7-5-4-6-11-23(29)28-30/h1,8-10,13-16,30H,4-7,11-12H2,2H3,(H,28,29)(H,25,26,27)
SMILES Code
O=C(NO)CCCCCCOC1=CC2=C(NC3=CC=CC(C#C)=C3)N=CN=C2C=C1OC
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, not in water
Shelf Life
>2 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
   
Biological target:
CUDC-101 is a potent inhibitor of HDAC, EGFR, and HER2 with IC50s of 4.4, 2.4, and 15.7 nM, respectively.
In vitro activity:
Further mechanistic studies show that CUDC-101 triggers caspase-dependent degradation of the promyelocytic leukemia-retinoic acid receptor alpha fusion protein. As a result, APL and ATO-resistant APL cells undergo apoptosis upon CUDC-101 treatment and this apoptosis-inducing effect is even stronger than that of ATO. Reference: Anticancer Drugs. 2020 Feb;31(2):158-168. https://pubmed.ncbi.nlm.nih.gov/31584454/
In vivo activity:
This study first evaluated if pretreatment could reduce the rate of metastasis to assess the possible effects of CUDC-101 as an adjuvant therapy, and found that pre-treatment with CUDC-101 significantly reduced ATC metastasis in the mice (Figure 6A–6B). Reference: Oncotarget. 2015 Apr 20; 6(11): 9073–9085. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4496203/
Solvent mg/mL mM
Solubility
DMSO 15.7 36.07
DMF 10.0 23.02
DMF:PBS (pH 7.2) (1:9) 0.1 0.23
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 434.49 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. Zhang T, Ma D, Wei D, Lu T, Yu K, Zhang Z, Wang W, Fang Q, Wang J. CUDC-101 overcomes arsenic trioxide resistance via caspase-dependent promyelocytic leukemia-retinoic acid receptor alpha degradation in acute promyelocytic leukemia. Anticancer Drugs. 2020 Feb;31(2):158-168. doi: 10.1097/CAD.0000000000000847. PMID: 31584454. 2. Jin JX, Li S, Hong Y, Jin L, Zhu HY, Guo Q, Gao QS, Yan CG, Kang JD, Yin XJ. CUDC-101, a histone deacetylase inhibitor, improves the in vitro and in vivo developmental competence of somatic cell nuclear transfer pig embryos. Theriogenology. 2014 Mar 1;81(4):572-8. doi: 10.1016/j.theriogenology.2013.11.011. Epub 2013 Nov 21. PMID: 24342668. 3. Sun H, Mediwala SN, Szafran AT, Mancini MA, Marcelli M. CUDC-101, a Novel Inhibitor of Full-Length Androgen Receptor (flAR) and Androgen Receptor Variant 7 (AR-V7) Activity: Mechanism of Action and In Vivo Efficacy. Horm Cancer. 2016 Jun;7(3):196-210. doi: 10.1007/s12672-016-0257-2. Epub 2016 Mar 8. PMID: 26957440; PMCID: PMC4896833. 4. Zhang L, Zhang Y, Mehta A, Boufraqech M, Davis S, Wang J, Tian Z, Yu Z, Boxer MB, Kiefer JA, Copland JA, Smallridge RC, Li Z, Shen M, Kebebew E. Dual inhibition of HDAC and EGFR signaling with CUDC-101 induces potent suppression of tumor growth and metastasis in anaplastic thyroid cancer. Oncotarget. 2015 Apr 20;6(11):9073-85. doi: 10.18632/oncotarget.3268. PMID: 25940539; PMCID: PMC4496203.
In vitro protocol:
1. Zhang T, Ma D, Wei D, Lu T, Yu K, Zhang Z, Wang W, Fang Q, Wang J. CUDC-101 overcomes arsenic trioxide resistance via caspase-dependent promyelocytic leukemia-retinoic acid receptor alpha degradation in acute promyelocytic leukemia. Anticancer Drugs. 2020 Feb;31(2):158-168. doi: 10.1097/CAD.0000000000000847. PMID: 31584454. 2. Jin JX, Li S, Hong Y, Jin L, Zhu HY, Guo Q, Gao QS, Yan CG, Kang JD, Yin XJ. CUDC-101, a histone deacetylase inhibitor, improves the in vitro and in vivo developmental competence of somatic cell nuclear transfer pig embryos. Theriogenology. 2014 Mar 1;81(4):572-8. doi: 10.1016/j.theriogenology.2013.11.011. Epub 2013 Nov 21. PMID: 24342668.
In vivo protocol:
1. Sun H, Mediwala SN, Szafran AT, Mancini MA, Marcelli M. CUDC-101, a Novel Inhibitor of Full-Length Androgen Receptor (flAR) and Androgen Receptor Variant 7 (AR-V7) Activity: Mechanism of Action and In Vivo Efficacy. Horm Cancer. 2016 Jun;7(3):196-210. doi: 10.1007/s12672-016-0257-2. Epub 2016 Mar 8. PMID: 26957440; PMCID: PMC4896833. 2. Zhang L, Zhang Y, Mehta A, Boufraqech M, Davis S, Wang J, Tian Z, Yu Z, Boxer MB, Kiefer JA, Copland JA, Smallridge RC, Li Z, Shen M, Kebebew E. Dual inhibition of HDAC and EGFR signaling with CUDC-101 induces potent suppression of tumor growth and metastasis in anaplastic thyroid cancer. Oncotarget. 2015 Apr 20;6(11):9073-85. doi: 10.18632/oncotarget.3268. PMID: 25940539; PMCID: PMC4496203.
1. Cai, Xiong; Zhai, Hai-Xiao; Wang, Jing; Forrester, Jeffrey; Qu, Hui; Yin, Ling; Lai, Cheng-Jung; Bao, Rudi; Qian, Changgeng. Discovery of 7-(4-(3-Ethynylphenylamino)-7-methoxyquinazolin-6-yloxy)-N-hydroxyheptanamide (CUDC-101) as a Potent Multi-Acting HDAC, EGFR, and HER2 Inhibitor for the Treatment of Cancer. Journal of Medicinal Chemistry (2010), 53(5), 2000-2009. CODEN: JMCMAR ISSN:0022-2623. CAN 152:326271 AN 2010:170333 2. Morphy, Richard. Selectively Nonselective Kinase Inhibition: Striking the Right Balance. Journal of Medicinal Chemistry (2010), 53(4), 1413-1437. CODEN: JMCMAR ISSN:0022-2623. CAN 152:183130 AN 2009:1315799 3. Cai, Xiong; Qian, Changgeng; Zhai, Haixiao; Bao, Rudi. Preparation of 4-phenylaminoquinazoline derivatives as epidermal growth factor receptor tyrosine kinase (EGFR-TK) inhibitors containing a zinc binding moiety and formulation containing them. U.S. Pat. Appl. Publ. (2009), 116 pp. CODEN: USXXCO US 2009111772 A1 20090430 CAN 150:472748 AN 2009:524181 4. Cai, Xiong; Qian, Changgeng; Zhai, Haixiao. Preparation of tartaric acid salts or complexes of quinazoline compounds containing a zinc binding moiety as EGFR tyrosine kinase inhibitors. PCT Int. Appl. (2009), 169pp. CODEN: PIXXD2 WO 2009035718 A1 20090319 CAN 150:352185 AN 2009:336937 5. Cai, Xiong; Qian, Changgeng; Gould, Stephen; Zhai, Haixiao. Multi-functional small molecules as anti-proliferative agents and their preparation. PCT Int. Appl. (2008), 494pp. CODEN: PIXXD2 WO 2008033747 A2 20080320 CAN 148:355828 AN 2008:353001 6. Qian, Changgeng; Cai, Xiong; Gould, Stephen; Zhai, Haixiao. Preparation of quinazoline based EGFR inhibitors containing a zinc binding moiety. PCT Int. Appl. (2008), 210 pp. CODEN: PIXXD2 WO 2008033749 A2 20080320 CAN 148:355813 AN 2008:351417