ADH-1

DCTPepD ID  DCTPepD0030

Active Ingredients   ADH-1

Description  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.

Synonyms  Exherin; ADH-1

Disease  Cancer/Tumor

Classification

  

Peptide and derivative Cyclic Antiangiogenesis agent

Structure Information


Molecular Formula  C22H34N8O6S2

Molecular Weight  570.7

Active Sequence  CHAVC

Sequence Length  5

Modification  C-terminal Ac, N-terminal NH2

Structure

 

Show IUPAC/InChI/SMILES

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

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

InChI_Key FQVLRGLGWNWPSS-BXBUPLCLSA-N

SMILES  O=C(C)N[C@H](C(N[C@H](C(N[C@H](C(N[C@H](C(N1)=O)C(C)C)=O)C)=O)CC2=CN=CN2)=O)CSSC[C@H]1C(N)=O

External Codes


PubChem CID  9916058

DrugBank Accession Number  DB05485

NCI Thesaurus Code  C53399  

UNII  B058ME29VU   GSRS

CAS  229971-81-7



Drug approval


Drug indication
    Investigated for use/treatment in breast cancer, cancer/tumors (unspecified), melanoma, ovarian cancer, and solid tumors.

    The drug is not approved.

ClinicalTrials.gov Identifier Title Condition or disease Phase Purpose
NCT00421811 An Open-Label, Multicenter, Phase 1/2 Dose Escalation Study to Evaluate Safety, Tolerability and Anti-tumor Activity of Systemic ADH-1 in Combination With Normothermic Isolated Limb Infusion of Melphalan in Subjects With Locally Advanced In-Transit Malignant Melanoma (Adherex Protocol Number AHX-01-007). Neoplasms Phase 1/2 Treatment
NCT00265057 Dose Finding, Safety, Pharmacokinetic and Pharmacodynamic Study of the Vascular Targeting Agent Exherin™ (ADH-1) Administered Once Weekly in 3 Week Cycles by Intravenous Infusion in Patients With N-Cadherin Expressing, Incurable, Solid Tumors (Adherex Protocol Number AHX-01-004) Neoplasms Phase 1/2 Treatment
NCT00264433 An Open-Label Phase 2a Study in Subjects With N-Cadherin Positive, Advanced or Recurrent Solid Tumors to Investigate the Safety and Efficacy of ADH-1 Administered Intravenously as a Single Agent (Adherex Protocol Number AHX-01-201) Neoplasms Phase 2 Treatment
NCT00390676 A Phase 1, Multicenter, Dose-Escalation Study to Investigate the Safety and Tolerability of ADH-1 in Combination With 1) Carboplatin or 2) Docetaxel or 3) Capecitabine in Subjects With N-Cadherin Positive, Advanced Solid Tumors (Adherex Protocol Number AHX-01-006) Neoplasms Phase 1 Treatment
NCT00225550 Dose Finding, Safety, Pharmacokinetic and Pharmacodynamic Study of the Vascular Targeting Agent Exherin™ (ADH-1) Administered Once Daily for 5 Consecutive Days by Intravenous Infusion in Subjects With N-Cadherin Expressing, Incurable, Solid Tumors (Adherex Protocol Number AHX 01 003) Neoplasms Phase 1/2 Treatment

    More clinical information is obtained from ClinicalTrials.gov.





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