Alvespimycin HCl
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MedKoo CAT#: 200170

CAS#:  467214-21-7(HCl)

Description: Alvespimycin is an analogue of the antineoplastic benzoquinone antibiotic geldanamycin. Alvespimycin binds to HSP90, a chaperone protein that aids in the assembly, maturation and folding of proteins. Subsequently, the function of Hsp90 is inhibited, leading to the degradation and depletion of its client proteins such as kinases and transcription factors involved with cell cycle regulation and signal transduction. Check for active clinical trials or closed clinical trials using this agent.


Chemical Structure

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Alvespimycin HCl
CAS#  467214-21-7(HCl)

Theoretical Analysis

MedKoo Cat#: 200170
Name: Alvespimycin HCl
CAS#:  467214-21-7(HCl)
Chemical Formula: C32H48ClN3O9
Exact Mass:
Molecular Weight: 654.19
Elemental Analysis: C, 58.75; H, 7.40; Cl, 5.42; N, 6.42; O, 22.01

Size Price Shipping out time Quantity
100mg USD 250 2 Weeks
200mg USD 450 2 Weeks
500mg USD 850 2 Weeks
1g USD 1250 2 Weeks
2g USD 1950 2 Weeks
5g USD 2950 2 Weeks
10g USD 4950 2 Weeks
Inquire bulk and customized quantity

Pricing updated 2021-02-27. Prices are subject to change without notice.

Alvespimycin (HCl salt), purity > 98%, is in stock .Current shipping out time is about 2 weeks after order is received.

Related CAS #:  467214-21-7(HCl)   467214-20-6 (free base)    

Synonym: 17-DMAG HCl; KOS1022; KO-S1022; KOS 1022; Alvespimycin; Alvespimycin HCl.

IUPAC/Chemical Name: (4E,6Z,8S,9S,10E,12S,13R,14S,16R)-19-(2-(dimethylamino)ethoxy)-13-hydroxy-8,14-dimethoxy-4,10,12,16-tetramethyl-3,20,22-trioxo-2-azabicyclo[16.3.1]docosa-1(21),4,6,10,18-pentaen-9-yl carbamate hydrochloride

InChi Key: BXRBNELYISPBKT-BJGZLATJSA-N

InChi Code: InChI=1S/C32H47N3O9.ClH/c1-18-14-22-28(38)23(17-24(36)30(22)43-13-12-35(5)6)34-31(39)19(2)10-9-11-25(41-7)29(44-32(33)40)21(4)16-20(3)27(37)26(15-18)42-8;/h9-11,16-18,20,25-27,29,37H,12-15H2,1-8H3,(H2,33,40)(H,34,39);1H/b11-9-,19-10+,21-16+;/t18-,20+,25+,26+,27-,29+;/m1./s1

SMILES Code: NC(O[C@@H](/C(C)=C/[C@H](C)[C@@H](O)[C@@H](OC)C[C@H](C)CC1=C2OCCN(C)C)[C@@H](OC)/C=C\C=C(C)\C(NC(C1=O)=CC2=O)=O)=O.[H]Cl

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:
>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

Handling Instructions:

Preparing Stock Solutions

The following data is based on the product molecular weight 654.19 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.

Select a batch to recalculate based on the batch molecular weight:
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: Kobayashi N, Toyooka S, Soh J, Yamamoto H, Dote H, Kawasaki K, Otani H, Kubo T, Jida M, Ueno T, Ando M, Ogino A, Kiura K, Miyoshi S. The anti-proliferative effect of heat shock protein 90 inhibitor, 17-DMAG, on non-small-cell lung cancers being resistant to EGFR tyrosine kinase inhibitor. Lung Cancer. 2012 Feb;75(2):161-6. Epub 2011 Jul 20. PubMed PMID: 21767894.

2: Kiang JG, Agravante NG, Smith JT, Bowman PD. 17-DMAG diminishes hemorrhage-induced small intestine injury by elevating Bcl-2 protein and inhibiting iNOS pathway, TNF-α increase, and caspase-3 activation. Cell Biosci. 2011 Jun 3;1(1):21. PubMed PMID: 21711488; PubMed Central PMCID: PMC3135504.

3: Fukumoto R, Kiang JG. Geldanamycin analog 17-DMAG limits apoptosis in human peripheral blood cells by inhibition of p53 activation and its interaction with heat-shock protein 90 kDa after exposure to ionizing radiation. Radiat Res. 2011 Sep;176(3):333-45. Epub 2011 Jun 10. PubMed PMID: 21663398.

4: Pacey S, Wilson RH, Walton M, Eatock MM, Hardcastle A, Zetterlund A, Arkenau HT, Moreno-Farre J, Banerji U, Roels B, Peachey H, Aherne W, de Bono JS, Raynaud F, Workman P, Judson I. A phase I study of the heat shock protein 90 inhibitor alvespimycin (17-DMAG) given intravenously to patients with advanced solid tumors. Clin Cancer Res. 2011 Mar 15;17(6):1561-70. Epub 2011 Jan 28. PubMed PMID: 21278242; PubMed Central PMCID: PMC3060938.

5: Hertlein E, Wagner AJ, Jones J, Lin TS, Maddocks KJ, Towns WH 3rd, Goettl VM, Zhang X, Jarjoura D, Raymond CA, West DA, Croce CM, Byrd JC, Johnson AJ. 17-DMAG targets the nuclear factor-kappaB family of proteins to induce apoptosis in chronic lymphocytic leukemia: clinical implications of HSP90 inhibition. Blood. 2010 Jul 8;116(1):45-53. Epub 2010 Mar 29. PubMed PMID: 20351313; PubMed Central PMCID: PMC2904580.

6: Lancet JE, Gojo I, Burton M, Quinn M, Tighe SM, Kersey K, Zhong Z, Albitar MX, Bhalla K, Hannah AL, Baer MR. Phase I study of the heat shock protein 90 inhibitor alvespimycin (KOS-1022, 17-DMAG) administered intravenously twice weekly to patients with acute myeloid leukemia. Leukemia. 2010 Apr;24(4):699-705. Epub 2010 Jan 28. PubMed PMID: 20111068.

7: Ghoshal S, Rao I, Earp JC, Jusko WJ, Wetzler M. Down-regulation of heat shock protein 70 improves arsenic trioxide and 17-DMAG effects on constitutive signal transducer and activator of transcription 3 activity. Cancer Chemother Pharmacol. 2010 Sep;66(4):681-9. Epub 2009 Dec 25. PubMed PMID: 20035426; PubMed Central PMCID: PMC3152797.

8: Kummar S, Gutierrez ME, Gardner ER, Chen X, Figg WD, Zajac-Kaye M, Chen M, Steinberg SM, Muir CA, Yancey MA, Horneffer YR, Juwara L, Melillo G, Ivy SP, Merino M, Neckers L, Steeg PS, Conley BA, Giaccone G, Doroshow JH, Murgo AJ. Phase I trial of 17-dimethylaminoethylamino-17-demethoxygeldanamycin (17-DMAG), a heat shock protein inhibitor, administered twice weekly in patients with advanced malignancies. Eur J Cancer. 2010 Jan;46(2):340-7. Epub 2009 Nov 27. PubMed PMID: 19945858; PubMed Central PMCID: PMC2818572.

9: Ayrault O, Godeny MD, Dillon C, Zindy F, Fitzgerald P, Roussel MF, Beere HM. Inhibition of Hsp90 via 17-DMAG induces apoptosis in a p53-dependent manner to prevent medulloblastoma. Proc Natl Acad Sci U S A. 2009 Oct 6;106(40):17037-42. Epub 2009 Sep 23. PubMed PMID: 19805107; PubMed Central PMCID: PMC2761355.

10: Kiang JG, Smith JT, Agravante NG. Geldanamycin analog 17-DMAG inhibits iNOS and caspases in gamma-irradiated human T cells. Radiat Res. 2009 Sep;172(3):321-30. PubMed PMID: 19708781.