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Exherin

CAT: 0013-GTR19162713-08Size: 50 mgDry Ice: NoHazardous: No
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CAT#:0013-GTR19162713-08Size:50 mg
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Description
Exherin (ADH-1) is a small, cyclic pentapeptide vascular-targeting agent with potential antineoplastic and antiangiogenic activities; selectively and competitively binds to and blocks N-cadherin.
CAS Number
229971-81-7
Product Name Alternative
ADH-1
Purity
>98% (HPLC)
Solubility
DMSO: 10 mM
Smiles
C[C@H]1C (=O) N[C@H] (C (=O) N[C@@H] (CSSC[C@@H] (C (=O) N[C@H] (C (=O) N1) CC2=CN=CN2) NC (=O) C) C (=O) N) C (C) C
Molecular Formula
C22H34N8O6S2
Molecular Weight
570.69
Storage Conditions
Storage temperature: -20°C. Stability: ≥ 2 years
Notes
For research use only.

Chemical Information

Adh-1

Adherex's biotechnology compound, ADH-1, targets N-cadherin, a protein present on certain tumor cells and established tumor blood vessels. ADH-1 is currently in clinical development in a combination program with a range of chemotherapeutic agents to investigate the synergistic effects noted in our preclinical models. At the end of 2006, the Company also completed patient enrollment in our single-agent Phase Ib/II and Phase II trials of ADH-1. Cadherins are cell adhesion and cell signaling molecules crucial to the development of tissues, organs and organisms. Agents that target and inhibit cadherin function have the potential to attack the progression of cancer at two distinct points: * Direct targeting of cadherins expressed on cancer cells may disturb cadherin-mediated signaling, leading to apoptosis (death) of cancer cells. * Cadherin inhibitors may exploit the inherent structural weaknesses of the tumor vasculature, causing angiolysis (disruption of blood vessels) and tumor damage. As many tumors become more aggressive, invasive, and malignant, researchers have found that N-cadherin is expressed in greater amounts, making it an important target for developing anti-cancer treatments. Poorly differentiated, highly invasive carcinomas are characterized by over-expression of N-cadherin (as opposed to E-cadherin). This change in primary cadherin expression causes the epithelial cells to lose their tightly adherent, polarized and well-defined shape and become loosely adherent, flattened and migratory. Such cadherin switching promotes properties such as dedifferentiation, local invasion and metastasis, leading to poor prognosis. ADH-1 may have utility in a wide variety of cancers as N-cadherin is overexpressed in a variety of tumors. As tumors progress to become higher grade, invasive and more metastatic, the frequency of N-cadherin expression generally rises.

CAS Number229971-81-7
PubChem CID9916058
IUPAC Name(4R,7S,10S,13S,16R)-16-acetamido-13-(1H-imidazol-5-ylmethyl)-10-methyl-6,9,12,15-tetraoxo-7-propan-2-yl-1,2-dithia-5,8,11,14-tetrazacycloheptadecane-4-carboxamide
Molecular FormulaC22H34N8O6S2
Molecular Weight570.7
XLogP-1.7
Topological Polar Surface Area268
Hydrogen Bond Donor Count7
Hydrogen Bond Acceptor Count9
Rotatable Bond Count5
Heavy Atom Count38
Formal Charge0
Complexity907
SMILES
C[C@H]1C(=O)N[C@H](C(=O)N[C@@H](CSSC[C@@H](C(=O)N[C@H](C(=O)N1)CC2=CN=CN2)NC(=O)C)C(=O)N)C(C)C
InChI
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
InChIKey
FQVLRGLGWNWPSS-BXBUPLCLSA-N
Chemical Structure
2D Structure
2D structure of Adh-1
CAS: 229971-81-7
CID: 9916058
Formula: C22H34N8O6S2
MW: 570.7
Interactive 3D Structure
Loading 3D structure...
Computed Properties
PropertyValue
Molecular Weight570.7
XLogP3-1.7
Hydrogen Bond Donor Count7
Hydrogen Bond Acceptor Count9
Rotatable Bond Count5
Exact Mass570.20427318
Monoisotopic Mass570.20427318
Topological Polar Surface Area268 Ų
Heavy Atom Count38
Formal Charge0
Complexity907
Isotope Atom Count0
Defined Atom Stereocenter Count5
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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