Identification
- Generic Name
- Golotimod
- DrugBank Accession Number
- DB05475
- Background
SCV-07 (g -D-glutamyl-L-tryptophan) is a novel synthetic dipeptide that acts broadly on the Toll-like receptor pathway. It has been shown to stimulate T-lymphocyte differentiation, macrocytic phagocytosis, and specific immune responses, and enhance IL-2 and INF-g production. Due to this preferential activation of Th1 cytokine production, SCV-07 may show utility in treatment of tuberculosis. It can be administered orally or subcutaneously. In independent studies, treatment of tuberculosis with SCV-07 improved clearance of mycobacteria, improved cavity healing, improvements in immune parameters and reduced symptoms (fever, weakness, sweating, dry cough, productive cough, dyspnea, chest pain, tachycardia) without any adverse local or general effects. SCV-07 has shown efficacy in treating various viral and bacterial infections.
- Type
- Small Molecule
- Groups
- Investigational
- Structure
Structure for Golotimod (DB05475)
- Weight
- Average: 333.3392
Monoisotopic: 333.132470733 - Chemical Formula
- C16H19N3O5
- Synonyms
- Golotimod
- External IDs
- SCV-07
Pharmacology
- Indication
Investigated for use/treatment in hepatitis (viral, C), infectious and parasitic disease (unspecified), and tuberculosis.
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SCV-07 (g -D-glutamyl-L-tryptophan) is a novel synthetic dipeptide that acts broadly on the Toll-like receptor pathway. It has been shown to stimulate T-lymphocyte differentiation, macrocytic phagocytosis, and specific immune responses, and enhance IL-2 and INF-g production.
- Mechanism of action
SCV-07 (g -D-glutamyl-L-tryptophan) has broad effects on the Toll-like receptor (TLR) pathway.
Target Actions Organism UToll-like receptor 2 Not Available Humans UToll-like receptor 4 Not Available Humans UToll-like receptor 7 Not Available Humans UToll-like receptor 9 Not Available Humans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
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No adverse effects were observed in any patients participating in clinical trials.
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.Not Available
- Food Interactions
- Not Available
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.
- Kingdom
- Organic compounds
- Super Class
- Organic acids and derivatives
- Class
- Carboxylic acids and derivatives
- Sub Class
- Amino acids, peptides, and analogues
- Direct Parent
- Dipeptides
- Alternative Parents
- Gamma-glutamyl amino acids / Glutamine and derivatives / N-acyl-L-alpha-amino acids / 3-alkylindoles / D-alpha-amino acids / Substituted pyrroles / Benzenoids / Dicarboxylic acids and derivatives / N-acyl amines / Heteroaromatic compounds show 9 more
- Substituents
- 3-alkylindole / Alpha-amino acid / Alpha-amino acid or derivatives / Alpha-dipeptide / Amine / Amino acid / Amino acid or derivatives / Aromatic heteropolycyclic compound / Azacycle / Benzenoid show 29 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Hepatitis C virus, RSV and other RNA/DNA viruses
Chemical Identifiers
- UNII
- 637C487Y09
- CAS number
- 229305-39-9
- InChI Key
- CATMPQFFVNKDEY-YPMHNXCESA-N
- InChI
- InChI=1S/C16H19N3O5/c17-11(15(21)22)5-6-14(20)19-13(16(23)24)7-9-8-18-12-4-2-1-3-10(9)12/h1-4,8,11,13,18H,5-7,17H2,(H,19,20)(H,21,22)(H,23,24)/t11-,13+/m1/s1
- IUPAC Name
- (2R)-2-amino-4-{[(1S)-1-carboxy-2-(1H-indol-3-yl)ethyl]carbamoyl}butanoic acid
- SMILES
- N[C@H](CCC(=O)N[C@@H](CC1=CNC2=CC=CC=C12)C(O)=O)C(O)=O
References
- General References
- Aspinall RJ, Pockros PJ: SCV-07 (SciClone Pharmaceuticals/Verta). Curr Opin Investig Drugs. 2006 Feb;7(2):180-5. [Article]
- Suzuki H, Kato K, Kumagai H: Development of an efficient enzymatic production of gamma-D-glutamyl-L-tryptophan (SCV-07), a prospective medicine for tuberculosis, with bacterial gamma-glutamyltranspeptidase. J Biotechnol. 2004 Aug 5;111(3):291-5. [Article]
- Bayes M, Rabasseda X, Prous JR: Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2003 Jun;25(5):387-408. [Article]
- Orellana C: Immune system stimulator shows promise against tuberculosis. Lancet Infect Dis. 2002 Dec;2(12):711. [Article]
- External Links
- PubChem Compound
- 6992140
- PubChem Substance
- 175427014
- ChemSpider
- 5360288
- 2367440
- ChEMBL
- CHEMBL2103812
- ZINC
- ZINC000001549362
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 2 Completed Health Services Research Chronic Hepatitis C Virus (HCV) Infection 1 2 Completed Health Services Research Head And Neck Cancer / Oral Mucositis 1 2 Unknown Status Prevention Oral Mucositis 1 Not Available Completed Not Available Chronic Hepatitis C Virus (HCV) Infection 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.347 mg/mL ALOGPS logP -1.4 ALOGPS logP -2 Chemaxon logS -3 ALOGPS pKa (Strongest Acidic) 1.98 Chemaxon pKa (Strongest Basic) 9.31 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 6 Chemaxon Hydrogen Donor Count 5 Chemaxon Polar Surface Area 145.51 Å2 Chemaxon Rotatable Bond Count 8 Chemaxon Refractivity 84.29 m3·mol-1 Chemaxon Polarizability 33.36 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.824 Blood Brain Barrier + 0.8532 Caco-2 permeable - 0.8369 P-glycoprotein substrate Non-substrate 0.605 P-glycoprotein inhibitor I Non-inhibitor 0.9875 P-glycoprotein inhibitor II Non-inhibitor 0.9811 Renal organic cation transporter Non-inhibitor 0.9088 CYP450 2C9 substrate Non-substrate 0.8633 CYP450 2D6 substrate Non-substrate 0.8422 CYP450 3A4 substrate Non-substrate 0.6654 CYP450 1A2 substrate Non-inhibitor 0.9522 CYP450 2C9 inhibitor Non-inhibitor 0.9458 CYP450 2D6 inhibitor Non-inhibitor 0.9427 CYP450 2C19 inhibitor Non-inhibitor 0.9514 CYP450 3A4 inhibitor Non-inhibitor 0.9435 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9788 Ames test Non AMES toxic 0.9305 Carcinogenicity Non-carcinogens 0.9641 Biodegradation Not ready biodegradable 0.7093 Rat acute toxicity 1.6624 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9896 hERG inhibition (predictor II) Non-inhibitor 0.9498
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Triacyl lipopeptide binding
- Specific Function
- Cooperates with LY96 to mediate the innate immune response to bacterial lipoproteins and other microbial cell wall components. Cooperates with TLR1 or TLR6 to mediate the innate immune response to ...
- Gene Name
- TLR2
- Uniprot ID
- O60603
- Uniprot Name
- Toll-like receptor 2
- Molecular Weight
- 89836.575 Da
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Transmembrane signaling receptor activity
- Specific Function
- Cooperates with LY96 and CD14 to mediate the innate immune response to bacterial lipopolysaccharide (LPS). Acts via MYD88, TIRAP and TRAF6, leading to NF-kappa-B activation, cytokine secretion and ...
- Gene Name
- TLR4
- Uniprot ID
- O00206
- Uniprot Name
- Toll-like receptor 4
- Molecular Weight
- 95679.19 Da
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Transmembrane signaling receptor activity
- Specific Function
- Key component of innate and adaptive immunity. TLRs (Toll-like receptors) control host immune response against pathogens through recognition of molecular patterns specific to microorganisms. TLR7 i...
- Gene Name
- TLR7
- Uniprot ID
- Q9NYK1
- Uniprot Name
- Toll-like receptor 7
- Molecular Weight
- 120920.8 Da
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Transmembrane signaling receptor activity
- Specific Function
- Key component of innate and adaptive immunity. TLRs (Toll-like receptors) control host immune response against pathogens through recognition of molecular patterns specific to microorganisms. TLR9 i...
- Gene Name
- TLR9
- Uniprot ID
- Q9NR96
- Uniprot Name
- Toll-like receptor 9
- Molecular Weight
- 115858.665 Da
Drug created at November 18, 2007 18:25 / Updated at February 21, 2021 18:51