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Identification
NameSCV-07
Accession NumberDB05475
TypeSmall Molecule
GroupsInvestigational
Description

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.

Structure
Thumb
SynonymsNot Available
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
CategoriesNot Available
UNIINot Available
CAS numberNot Available
WeightAverage: 333.3392
Monoisotopic: 333.132470733
Chemical FormulaC16H19N3O5
InChI KeyInChIKey=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[[email protected]](CCC(=O)N[C@@H](CC1=CNC2=CC=CC=C12)C(O)=O)C(O)=O
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as gamma-glutamyl amino acids. These are dipeptides consisting of any C-terminal amino acid having a gamma-glutamyl residue attached at the N alpha-position.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentGamma-glutamyl amino acids
Alternative Parents
Substituents
  • Gamma-glutamyl alpha-amino acid
  • N-acyl-aliphatic-alpha amino acid
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-alpha-amino acid
  • N-acyl-l-alpha-amino acid
  • D-alpha-amino acid
  • Alpha-amino acid or derivatives
  • N-substituted-alpha-amino acid
  • Alpha-amino acid
  • Indole or derivatives
  • Indole
  • Amino fatty acid
  • Fatty acyl
  • Benzenoid
  • Substituted pyrrole
  • N-acyl-amine
  • Fatty amide
  • Dicarboxylic acid or derivatives
  • Heteroaromatic compound
  • Pyrrole
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Azacycle
  • Organoheterocyclic compound
  • Carboxylic acid
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationInvestigated for use/treatment in hepatitis (viral, C), infectious and parasitic disease (unspecified), and tuberculosis.
PharmacodynamicsSCV-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 actionSCV-07 (g -D-glutamyl-L-tryptophan) has broad effects on the Toll-like receptor (TLR) pathway.
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNo adverse effects were observed in any patients participating in clinical trials.
Affected organisms
  • Hepatitis C virus, RSV and other RNA/DNA viruses
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.824
Blood Brain Barrier+0.8532
Caco-2 permeable-0.8369
P-glycoprotein substrateNon-substrate0.605
P-glycoprotein inhibitor INon-inhibitor0.9875
P-glycoprotein inhibitor IINon-inhibitor0.9811
Renal organic cation transporterNon-inhibitor0.9088
CYP450 2C9 substrateNon-substrate0.8633
CYP450 2D6 substrateNon-substrate0.8422
CYP450 3A4 substrateNon-substrate0.6654
CYP450 1A2 substrateNon-inhibitor0.9522
CYP450 2C9 inhibitorNon-inhibitor0.9458
CYP450 2D6 inhibitorNon-inhibitor0.9427
CYP450 2C19 inhibitorNon-inhibitor0.9514
CYP450 3A4 inhibitorNon-inhibitor0.9435
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9788
Ames testNon AMES toxic0.9305
CarcinogenicityNon-carcinogens0.9641
BiodegradationNot ready biodegradable0.7093
Rat acute toxicity1.6624 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9896
hERG inhibition (predictor II)Non-inhibitor0.9498
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.347 mg/mLALOGPS
logP-1.4ALOGPS
logP-2ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)1.98ChemAxon
pKa (Strongest Basic)9.31ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area145.51 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity84.29 m3·mol-1ChemAxon
Polarizability33.36 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis ReferenceNot Available
General References
  1. Aspinall RJ, Pockros PJ: SCV-07 (SciClone Pharmaceuticals/Verta). Curr Opin Investig Drugs. 2006 Feb;7(2):180-5. [PubMed:16499289 ]
  2. 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. [PubMed:15246665 ]
  3. Bayes M, Rabasseda X, Prous JR: Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2003 Jun;25(5):387-408. [PubMed:12851663 ]
  4. Orellana C: Immune system stimulator shows promise against tuberculosis. Lancet Infect Dis. 2002 Dec;2(12):711. [PubMed:12467673 ]
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
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 bacterial lipoproteins or lipopeptides (PubMed:17889651). Acts via MYD88 and TRAF6, leading to NF-kappa-B activation, cytokine secretion and the inflammatory response. May also promote apoptosis in re...
Gene Name:
TLR2
Uniprot ID:
O60603
Molecular Weight:
89836.575 Da
Kind
Protein
Organism
Human
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 the inflammatory response (PubMed:9237759, PubMed:10835634). Also involved in LPS-independent inflammatory responses triggered by free fatty acids, such as palmitate, and Ni(2+). Responses triggered b...
Gene Name:
TLR4
Uniprot ID:
O00206
Molecular Weight:
95679.19 Da
Kind
Protein
Organism
Human
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 is a nucleotide-sensing TLR which is activated by single-stranded RNA. Acts via MYD88 and TRAF6, leading to NF-kappa-B activation, cytokine secretion and the inflammatory response (By similarity).
Gene Name:
TLR7
Uniprot ID:
Q9NYK1
Molecular Weight:
120920.8 Da
Kind
Protein
Organism
Human
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 is a nucleotide-sensing TLR which is activated by unmethylated cytidine-phosphate-guanosine (CpG) dinucleotides. Acts via MYD88 and TRAF6, leading to NF-kappa-B activation, cytokine secretion and the i...
Gene Name:
TLR9
Uniprot ID:
Q9NR96
Molecular Weight:
115858.665 Da
Comments
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Drug created on November 18, 2007 11:25 / Updated on August 17, 2016 12:24