Explore a selection of our essential drug information below, or:
Overview
- DrugBank ID
- DB05479
- Type
- Small Molecule
- Clinical Trials
- Phase 0
- 0
- Phase 1
- 0
- Phase 2
- 0
- Phase 3
- 0
- Phase 4
- 0
Identification
- Generic Name
- CZEN 002
- DrugBank Accession Number
- DB05479
- Background
CZEN-002 is a novel, non-azole anti-fungal synthetic octapeptide, derived from alpha-Melanocyte-Stimulating Hormone (a-MSH). CZEN-002 modulates inflammatory and immune responses. It has also been shown to kill Candida albicans (C. albicans), a single-celled fungal organism that causes a variety of infections, including vaginitis. This organism can invade tissues and produce fatal infections in individuals with compromised immune systems such as those suffering from HIV/AIDS or undergoing organ or bone transplants. The antimicrobial activity of CZEN-002 is unique in that it does not depend on direct damage to the microbial membrane. It appears that CZEN-002 works on a receptor in yeast that has yet to be identified.
Studies attempting to understand the candidacidal activity of derivatives of alpha-MSH have focused on the alpha-MSH amino acid sequence (6-13), which contains the invariant core sequence His-Phe-Arg-Trp (6-9) that is important for binding to the known melanocortin receptors. A second focus was on the sequence Lys-Pro-Val (11-13) that is known to be important for antimicrobial activity.
- Type
- Small Molecule
- Groups
- Investigational
- Structure
Structure for CZEN 002 (DB05479)
- Weight
- Average: 1664.884
Monoisotopic: 1663.792931101 - Chemical Formula
- C77H109N21O19S
- Synonyms
- Not Available
Pharmacology
- Indication
Investigated for use/treatment in candidiasis and vaginitis.
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CZEN-002 is a novel, non-azole anti-fungal synthetic octapeptide, derived from alpha-Melanocyte-Stimulating Hormone (a-MSH). CZEN-002 modulates inflammatory and immune responses. It has also been shown to kill Candida albicans (C. albicans). The antimicrobial activity of CZEN-002 is unique in that it does not depend on direct damage to the microbial membrane. It appears that CZEN-002 works on a receptor in yeast that has yet to be identified.
- Mechanism of action
The antimicrobial activity of CZEN-002 is unique in that it does not depend on direct damage to the microbial membrane. It appears that CZEN-002 works on a receptor in yeast that has yet to be identified.
Studies attempting to understand the candidacidal activity of derivatives of alpha-MSH have focused on the alpha-MSH amino acid sequence (6-13), which contains the invariant core sequence His-Phe-Arg-Trp (6-9) that is important for binding to the known melanocortin receptors. A second focus was on the sequence Lys-Pro-Val (11-13) that is known to be important for antimicrobial activity.
Target Actions Organism UMelanocyte-stimulating hormone receptor 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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Not Available
- 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
- Not Available
- Classification
- Not classified
- Affected organisms
- Fungi
- Yeast and other fungi
Chemical Identifiers
- UNII
- Not Available
- CAS number
- Not Available
- InChI Key
- WHNFPRLDDSXQCL-PDEGJNOBSA-N
- InChI
- InChI=1S/C77H109N21O19S/c1-42(2)64(65(79)106)97-75(116)61-20-13-30-98(61)76(117)54(18-10-11-28-78)88-62(103)38-85-66(107)57(34-46-36-84-50-17-9-8-16-49(46)50)94-67(108)51(19-12-29-83-77(80)81)89-70(111)55(32-44-14-6-5-7-15-44)92-72(113)58(35-47-37-82-41-86-47)95-68(109)52(25-26-63(104)105)90-69(110)53(27-31-118-4)91-74(115)60(40-100)96-71(112)56(33-45-21-23-48(102)24-22-45)93-73(114)59(39-99)87-43(3)101/h5-9,14-17,21-24,36-37,41-42,51-61,64,84,99-100,102H,10-13,18-20,25-35,38-40,78H2,1-4H3,(H2,79,106)(H,82,86)(H,85,107)(H,87,101)(H,88,103)(H,89,111)(H,90,110)(H,91,115)(H,92,113)(H,93,114)(H,94,108)(H,95,109)(H,96,112)(H,97,116)(H,104,105)(H4,80,81,83)/t51-,52-,53-,54-,55-,56-,57-,58?,59-,60-,61-,64-/m0/s1
- IUPAC Name
- (4S)-4-[(1-{[(1S)-1-{[(1S)-1-{[(1S)-1-[({[(2S)-6-amino-1-[(2S)-2-{[(1S)-1-carbamoyl-2-methylpropyl]carbamoyl}pyrrolidin-1-yl]-1-oxohexan-2-yl]carbamoyl}methyl)carbamoyl]-2-(1H-indol-3-yl)ethyl]carbamoyl}-4-carbamimidamidobutyl]carbamoyl}-2-phenylethyl]carbamoyl}-2-(1H-imidazol-5-yl)ethyl)carbamoyl]-4-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-acetamido-3-hydroxypropanamido]-3-(4-hydroxyphenyl)propanamido]-3-hydroxypropanamido]-4-(methylsulfanyl)butanamido]butanoic acid
- SMILES
- CSCC[C@H](NC(=O)[C@H](CO)NC(=O)[C@H](CC1=CC=C(O)C=C1)NC(=O)[C@H](CO)NC(C)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)NC(CC1=CN=CN1)C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC1=CNC2=CC=CC=C12)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N1CCC[C@H]1C(=O)N[C@@H](C(C)C)C(N)=O
References
- General References
- Csato M, Kenderessy AS, Dobozy A: Enhancement of Candida albicans killing activity of separated human epidermal cells by alpha-melanocyte stimulating hormone. Br J Dermatol. 1989 Jul;121(1):145-7. [Article]
- External Links
Clinical Trials
- Clinical Trials
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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 0.0261 mg/mL ALOGPS logP -1.6 ALOGPS logP -8.9 Chemaxon logS -4.8 ALOGPS pKa (Strongest Acidic) 3.47 Chemaxon pKa (Strongest Basic) 11.57 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 24 Chemaxon Hydrogen Donor Count 23 Chemaxon Polar Surface Area 642.98 Å2 Chemaxon Rotatable Bond Count 50 Chemaxon Refractivity 437.71 m3·mol-1 Chemaxon Polarizability 171.95 Å3 Chemaxon Number of Rings 6 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.932 Blood Brain Barrier - 0.9902 Caco-2 permeable - 0.8409 P-glycoprotein substrate Substrate 0.8961 P-glycoprotein inhibitor I Non-inhibitor 0.8369 P-glycoprotein inhibitor II Non-inhibitor 0.7796 Renal organic cation transporter Non-inhibitor 0.7295 CYP450 2C9 substrate Non-substrate 0.7581 CYP450 2D6 substrate Non-substrate 0.7956 CYP450 3A4 substrate Substrate 0.6508 CYP450 1A2 substrate Non-inhibitor 0.8291 CYP450 2C9 inhibitor Non-inhibitor 0.7953 CYP450 2D6 inhibitor Non-inhibitor 0.8856 CYP450 2C19 inhibitor Non-inhibitor 0.7936 CYP450 3A4 inhibitor Non-inhibitor 0.6388 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9465 Ames test Non AMES toxic 0.725 Carcinogenicity Non-carcinogens 0.8491 Biodegradation Not ready biodegradable 0.9938 Rat acute toxicity 2.9852 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9219 hERG inhibition (predictor II) Inhibitor 0.5748
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Not Available
Targets
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Receptor for MSH (alpha, beta and gamma) and ACTH (PubMed:11442765, PubMed:11707265, PubMed:1325670, PubMed:1516719, PubMed:8463333). The activity of this receptor is mediated by G proteins which activate adenylate cyclase (PubMed:11707265, PubMed:1325670, PubMed:16463023, PubMed:19737927). Mediates melanogenesis, the production of eumelanin (black/brown) and phaeomelanin (red/yellow), via regulation of cAMP signaling in melanocytes (PubMed:31097585)
- Specific Function
- G protein-coupled peptide receptor activity
- Gene Name
- MC1R
- Uniprot ID
- Q01726
- Uniprot Name
- Melanocyte-stimulating hormone receptor
- Molecular Weight
- 34705.04 Da
Drug created at November 18, 2007 18:25 / Updated at June 12, 2020 16:52