Identification
- Generic Name
- Andrographolide
- DrugBank Accession Number
- DB05767
- Background
Andrographolide (HMPL-004) is a botanical product extracted from a herb that occurs naturally in China. The herb has an extensive history of use in TCM for the treatment of upper respiratory tract infections and other inflammatory and infectious diseases.
- Type
- Small Molecule
- Groups
- Investigational
- Structure
Structure for Andrographolide (DB05767)
- Weight
- Average: 350.455
Monoisotopic: 350.209324066 - Chemical Formula
- C20H30O5
- Synonyms
- 3α,14,15,18-tetrahydroxy-5b,9bH,10a-labda-8(20),12-dien-16-oic acid γ-Lactone
- External IDs
- HMPL-004
- HMPL004
Pharmacology
- Indication
Investigated for use/treatment in ulcerative colitis.
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Not Available
- Mechanism of action
HMPL-004 acts on multiple cellular targets in the inflammatory signal transduction pathways resulting in suppressed inflammation cytokine expression including TNF-α, IL-1β and IL-6. HMPL-004 was demonstrated to inhibit TNF-α and IL-1β production in cell-based assays. HMPL-004 is also able to inhibit NF-kB activation. NF-kB is a family of transcriptional factors that regulate a wide spectrum of genes critically involved in host defence and inflammation. The mechanism of action of HMPL-004 was further supported in laboratory IBD animal models. Treatment of IBD rats with HMPL-004 caused a significant drop in plasma cytokine concentrations, including TNF-α and IL-1β.
Target Actions Organism UTumor necrosis factor Not Available Humans UInterleukin-1 beta Not Available Humans UInterleukin-6 Not Available Humans UNuclear factor NF-kappa-B p100 subunit Not Available Humans UNuclear factor NF-kappa-B p105 subunit 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
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
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.
Drug Interaction Integrate drug-drug
interactions in your softwareAbciximab The risk or severity of bleeding can be increased when Andrographolide is combined with Abciximab. Abrocitinib The risk or severity of bleeding and thrombocytopenia can be increased when Andrographolide is combined with Abrocitinib. Aceclofenac The risk or severity of bleeding can be increased when Aceclofenac is combined with Andrographolide. Acemetacin The risk or severity of bleeding can be increased when Acemetacin is combined with Andrographolide. Acenocoumarol The risk or severity of bleeding can be increased when Andrographolide is combined with Acenocoumarol. Acetylsalicylic acid Acetylsalicylic acid may increase the antiplatelet activities of Andrographolide. Alclofenac The risk or severity of bleeding can be increased when Alclofenac is combined with Andrographolide. Aldesleukin The risk or severity of bleeding can be increased when Andrographolide is combined with Aldesleukin. Alemtuzumab The risk or severity of bleeding can be increased when Andrographolide is combined with Alemtuzumab. Alteplase The risk or severity of bleeding can be increased when Andrographolide is combined with Alteplase. 
Identify potential medication risksEasily compare up to 40 drugs with our drug interaction checker.Get severity rating, description, and management advice.Learn more - Food Interactions
- Not Available
Categories
- Drug Categories
- Acanthaceae
- Analgesics
- Analgesics, Non-Narcotic
- Andrographis
- Angiosperms
- Anti-Infective Agents
- Anti-Inflammatory Agents
- Antiparasitic Agents
- Antiplatelet agents
- Antiprotozoals
- Antirheumatic Agents
- Biological Products
- Colitis, Ulcerative
- Colitis, Ulcerative, drug therapy
- Complex Mixtures
- Embryophyta
- Eukaryota
- Hematologic Agents
- Lamiales
- Peripheral Nervous System Agents
- Pharmaceutical Preparations
- Plant Preparations
- Sensory System Agents
- Stereoisomerism
- Streptophyta
- Terpenes
- Tracheophyta
- Viridiplantae
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as gamma butyrolactones. These are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Lactones
- Sub Class
- Gamma butyrolactones
- Direct Parent
- Gamma butyrolactones
- Alternative Parents
- Tetrahydrofurans / Enoate esters / Secondary alcohols / Cyclic alcohols and derivatives / Oxacyclic compounds / Monocarboxylic acids and derivatives / Primary alcohols / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
- Substituents
- Alcohol / Aliphatic heteropolycyclic compound / Alpha,beta-unsaturated carboxylic ester / Carbonyl group / Carboxylic acid derivative / Carboxylic acid ester / Cyclic alcohol / Enoate ester / Gamma butyrolactone / Hydrocarbon derivative
- Molecular Framework
- Aliphatic heteropolycyclic compounds
- External Descriptors
- secondary alcohol, primary alcohol, gamma-lactone, carbobicyclic compound, labdane diterpenoid (CHEBI:65408)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 410105JHGR
- CAS number
- 5508-58-7
- InChI Key
- BOJKULTULYSRAS-OTESTREVSA-N
- InChI
- InChI=1S/C20H30O5/c1-12-4-7-16-19(2,9-8-17(23)20(16,3)11-21)14(12)6-5-13-15(22)10-25-18(13)24/h5,14-17,21-23H,1,4,6-11H2,2-3H3/b13-5+/t14-,15-,16+,17-,19+,20+/m1/s1
- IUPAC Name
- (3E,4S)-3-{2-[(1R,4aS,5R,6R,8aS)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-decahydronaphthalen-1-yl]ethylidene}-4-hydroxyoxolan-2-one
- SMILES
- [H][C@]12CCC(=C)[C@@H](C\C=C3/[C@H](O)COC3=O)[C@]1(C)CC[C@@H](O)[C@@]2(C)CO
References
- General References
- Not Available
- External Links
- PubChem Compound
- 5318517
- PubChem Substance
- 347827741
- ChemSpider
- 4477067
- BindingDB
- 50084419
- ChEBI
- 65408
- ChEMBL
- CHEMBL186141
- ZINC
- ZINC000003881797
- Wikipedia
- Andrographolide
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Unknown Status Treatment Acute Exacerbation of Chronic Bronchitis (AECB) 1 4 Unknown Status Treatment Acute Tonsillitis 1 4 Unknown Status Treatment Acute Tracheobronchitis 1 3 Terminated Treatment Ulcerative Colitis 2 2 Completed Treatment Crohn's Disease (CD) 1 2 Completed Treatment Ulcerative Colitis 1 1 Terminated Treatment Crohn's Disease (CD) / Ulcerative Colitis 1 1, 2 Completed Treatment Relapsing Remitting Multiple Sclerosis (RRMS) 1 1, 2 Unknown Status Treatment Primary Progressive Multiple Sclerosis (PPMS) / Secondary Progressive Multiple Sclerosis (SPMS) 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 0.284 mg/mL ALOGPS logP 1.57 ALOGPS logP 1.66 Chemaxon logS -3.1 ALOGPS pKa (Strongest Acidic) 13.48 Chemaxon pKa (Strongest Basic) -2.8 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 3 Chemaxon Polar Surface Area 86.99 Å2 Chemaxon Rotatable Bond Count 3 Chemaxon Refractivity 94.93 m3·mol-1 Chemaxon Polarizability 38.27 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
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
- Tumor necrosis factor receptor binding
- Specific Function
- Cytokine that binds to TNFRSF1A/TNFR1 and TNFRSF1B/TNFBR. It is mainly secreted by macrophages and can induce cell death of certain tumor cell lines. It is potent pyrogen causing fever by direct ac...
- Gene Name
- TNF
- Uniprot ID
- P01375
- Uniprot Name
- Tumor necrosis factor
- Molecular Weight
- 25644.15 Da
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Protein domain specific binding
- Specific Function
- Potent proinflammatory cytokine. Initially discovered as the major endogenous pyrogen, induces prostaglandin synthesis, neutrophil influx and activation, T-cell activation and cytokine production, ...
- Gene Name
- IL1B
- Uniprot ID
- P01584
- Uniprot Name
- Interleukin-1 beta
- Molecular Weight
- 30747.7 Da
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Interleukin-6 receptor binding
- Specific Function
- Cytokine with a wide variety of biological functions. It is a potent inducer of the acute phase response. Plays an essential role in the final differentiation of B-cells into Ig-secreting cells Inv...
- Gene Name
- IL6
- Uniprot ID
- P05231
- Uniprot Name
- Interleukin-6
- Molecular Weight
- 23717.965 Da
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Transcriptional activator activity, rna polymerase ii core promoter proximal region sequence-specific binding
- Specific Function
- NF-kappa-B is a pleiotropic transcription factor present in almost all cell types and is the endpoint of a series of signal transduction events that are initiated by a vast array of stimuli related...
- Gene Name
- NFKB2
- Uniprot ID
- Q00653
- Uniprot Name
- Nuclear factor NF-kappa-B p100 subunit
- Molecular Weight
- 96748.355 Da
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Transcriptional repressor activity, rna polymerase ii transcription regulatory region sequence-specific binding
- Specific Function
- NF-kappa-B is a pleiotropic transcription factor present in almost all cell types and is the endpoint of a series of signal transduction events that are initiated by a vast array of stimuli related...
- Gene Name
- NFKB1
- Uniprot ID
- P19838
- Uniprot Name
- Nuclear factor NF-kappa-B p105 subunit
- Molecular Weight
- 105355.175 Da
Drug created at November 18, 2007 18:27 / Updated at June 12, 2020 16:52