Exherin free base

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MedKoo CAT#: 201350

CAS#: 229971-81-7 (free base)

Description: Exherin, also known as ADH-1, is a small, cyclic pentapeptide vascular-targeting agent with potential antineoplastic and antiangiogenic activities. ADH-1 selectively and competitively binds to and blocks N-cadherin, which may result in disruption of tumor vasculature, inhibition of tumor cell growth, and the induction of tumor cell and endothelial cell apoptosis. N-cadherin, a cell- surface transmembrane glycoprotein of the cadherin superfamily of proteins involved in calcium-mediated cell-cell adhesion and signaling mechanisms; may be upregulated in some aggressive tumors and the endothelial cells and pericytes of some tumor blood vessels. Note: The old CAT# for this product was 201350A

Chemical Structure

Exherin free base
CAS# 229971-81-7 (free base)

Theoretical Analysis

MedKoo Cat#: 201350
Name: Exherin free base
CAS#: 229971-81-7 (free base)
Chemical Formula: C22H34N8O6S2
Exact Mass: 570.20427
Molecular Weight: 570.68
Elemental Analysis: C, 46.30; H, 6.01; N, 19.63; O, 16.82; S, 11.24

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Size Price Availability Quantity
5.0mg USD 120.0 Same day
10.0mg USD 190.0 Same day
25.0mg USD 250.0 Same day
50.0mg USD 450.0 Same day
100.0mg USD 750.0 Same day
200.0mg USD 1250.0 Same day
500.0mg USD 1950.0 Same day
1.0g USD 2950.0 Same day
5.0g USD 8650.0 Same day
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Related CAS #: 1135237-88-5 (TFA)   229971-81-7 (free base)    

Synonym: NSC729477; ADH1; ADH-1; ADH 1. Brand name: Exherin; Exherin free base

IUPAC/Chemical Name: (4R,7S,10S,13S,16R)-13-((1H-imidazol-5-yl)methyl)-16-acetamido-7-isopropyl-10-methyl-6,9,12,15-tetraoxo-1,2-dithia-5,8,11,14-tetraazacycloheptadecane-4-carboxamide


InChi Code: InChI=1S/C22H34N8O6S2/c1-10(2)17-22(36)29-15(18(23)32)7-37-38-8-16(27-12(4)31)21(35)28-14(5-13-6-24-9-25-13)20(34)26-11(3)19(33)30-17/h6,9-11,14-17H,5,7-8H2,1-4H3,(H2,23,32)(H,24,25)(H,26,34)(H,27,31)(H,28,35)(H,29,36)(H,30,33)/t11-,14-,15-,16-,17-/m0/s1

SMILES Code: O=C([C@@H](NC([C@H](C(C)C)NC([C@H](C)NC([C@H](CC1=CN=CN1)N2)=O)=O)=O)CSSC[C@H](NC(C)=O)C2=O)N

Appearance: white 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 5% HCl aqueous solution, slightly soluble in water at room temperature, not soluble in water at low temperature.

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in 5% HCl solution or 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

Preparing Stock Solutions

The following data is based on the product molecular weight 570.68 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: Leitsch D, Williams CF, Lloyd D, Duchêne M. Unexpected properties of NADP-dependent secondary alcohol dehydrogenase (ADH-1) in Trichomonas vaginalis and other microaerophilic parasites. Exp Parasitol. 2013 Jul;134(3):374-80. doi: 10.1016/j.exppara.2013.03.034. Epub 2013 Apr 8. PubMed PMID: 23578856; PubMed Central PMCID: PMC3682184.

2: Yarom N, Stewart D, Malik R, Wells J, Avruch L, Jonker DJ. Phase I clinical trial of Exherin (ADH-1) in patients with advanced solid tumors. Curr Clin Pharmacol. 2013 Feb 1;8(1):81-8. PubMed PMID: 22280327.

3: Haseba T, Kameyama K, Mashimo K, Ohno Y. Dose-Dependent Change in Elimination Kinetics of Ethanol due to Shift of Dominant Metabolizing Enzyme from ADH 1 (Class I) to ADH 3 (Class III) in Mouse. Int J Hepatol. 2012;2012:408190. doi: 10.1155/2012/408190. Epub 2011 Nov 22. PubMed PMID: 22164338; PubMed Central PMCID: PMC3227458.

4: Yarom N, Stewart D, Avruch L, Malik R, Wells J, Jonker DJ. ADH-1 in the treatment of metastatic adrenocortical carcinoma--case report. Anticancer Res. 2011 Nov;31(11):3921-5. PubMed PMID: 22110220.

5: Beasley GM, Riboh JC, Augustine CK, Zager JS, Hochwald SN, Grobmyer SR, Peterson B, Royal R, Ross MI, Tyler DS. Prospective multicenter phase II trial of systemic ADH-1 in combination with melphalan via isolated limb infusion in patients with advanced extremity melanoma. J Clin Oncol. 2011 Mar 20;29(9):1210-5. doi: 10.1200/JCO.2010.32.1224. Epub 2011 Feb 22. PubMed PMID: 21343562.

6: Beasley GM, McMahon N, Sanders G, Augustine CK, Selim MA, Peterson B, Norris R, Peters WP, Ross MI, Tyler DS. A phase 1 study of systemic ADH-1 in combination with melphalan via isolated limb infusion in patients with locally advanced in-transit malignant melanoma. Cancer. 2009 Oct 15;115(20):4766-74. doi: 10.1002/cncr.24509. PubMed PMID: 19637344.

7: Perotti A, Sessa C, Mancuso A, Noberasco C, Cresta S, Locatelli A, Carcangiu ML, Passera K, Braghetti A, Scaramuzza D, Zanaboni F, Fasolo A, Capri G, Miani M, Peters WP, Gianni L. Clinical and pharmacological phase I evaluation of Exherin (ADH-1), a selective anti-N-cadherin peptide in patients with N-cadherin-expressing solid tumours. Ann Oncol. 2009 Apr;20(4):741-5. doi: 10.1093/annonc/mdn695. Epub 2009 Feb 3. PubMed PMID: 19190075.

8: Shintani Y, Fukumoto Y, Chaika N, Grandgenett PM, Hollingsworth MA, Wheelock MJ, Johnson KR. ADH-1 suppresses N-cadherin-dependent pancreatic cancer progression. Int J Cancer. 2008 Jan 1;122(1):71-7. PubMed PMID: 17721921.

9: Kelland L. Drug evaluation: ADH-1, an N-cadherin antagonist targeting cancer vascularization. Curr Opin Mol Ther. 2007 Feb;9(1):86-91. PubMed PMID: 17330406.

10: Gomulski LM, Brogna S, Babaratsas A, Gasperi G, Zacharopoulou A, Savakis C, Bourtzis K. Molecular basis of the size polymorphism of the first intron of the Adh-1 gene of the mediterranean fruit fly, Ceratitis capitata. J Mol Evol. 2004 Jun;58(6):732-42. PubMed PMID: 15461430.

Additional Information

   Note: The old CAT# for this product was 201350A