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Identification
- Summary
Artesunate is artesunate is an artemesinin derivative indicated for the initial treatment of severe malaria.
- Generic Name
- Artesunate
- DrugBank Accession Number
- DB09274
- Background
Artesunate is indicated for the initial treatment of severe malaria.8 The World Health Organization recommends artesunate as first line treatment for severe malaria.6 Artesunate was developed out of a need for a more hydrophilic derivative of artemisinin.5
Artesunate was granted FDA approval on 26 May 2020.8
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
Structure for Artesunate (DB09274)
- Weight
- Average: 384.425
Monoisotopic: 384.178417862 - Chemical Formula
- C19H28O8
- Synonyms
- Artesunate
- Artesunato
- Artesunatum
- Artesunic acid
- AS
- butanedioic acid, 1-[(3R,5aS,6R,8aS,9R,10S,12R,12aR)-decahydro-3,6,9-trimethyl-3,12-epoxy-12H-pyrano[4,3-j]-1,2-benzodioxepin-10-yl] ester
- dihydroqinghasu hemsuccinate
- Succinyl dihydroartemisinin
- External IDs
- 182824-33-5
- NSC-712571
Pharmacology
- Indication
Artesunate is indicated for the initial treatment of severe malaria in adult and pediatric patients.8
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Used in combination to treat Acute uncomplicated plasmodium falciparum malaria Combination Product in combination with: Mefloquine (DB00358) •••••••••••• •••••• Treatment of Malaria, cerebral •••••••••••• •••••••••• ••••••• ••• •••••••• Treatment of Severe malaria •••••••••••• •••••• Treatment of Severe malaria •••••••••••• •••••• ••••••••• ••••••••• - Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Artesunate is an artemisinin derivative that is metabolized to DHA, which generates free radicals to inhibit normal function of Plasmodium parasites.1,7,8 It has a short duration of action due to its short half life, and a moderate therapeutic index.7,8 Patients should be counselled regarding the risk of post treatment hemolytic anemia and hypersenstivity.8
- Mechanism of action
Artesunate is metabolized to the active DHA.8 the endoperoxide bridge of DHA reacts with heme, generating free radicals which inhibit protein and nucleic acid synthesis of the Plasmodium parasites during all erythrocytic stages.8,7 Reactions with these free radicals can also lead to alkylation of parasitic proteins such as a calcium adenosine triphosphatase and EXP1, a glutathione S-transferase.1,7
Target Actions Organism AMalaria protein EXP-1 inhibitorPlasmodium falciparum - Absorption
The Cmax of artesunate is 3.3µg/mL while the Cmax of the active metabolite DHA is 3.1µg/mL.8 The AUC of artesunate is 0.7µg*h/mL while the AUC of DHA is 3.5µg*h/mL.8 After intravenous artesunate, DHA has a Tmax of 0.5-15 minutes in adult patients and 21-64 minutes in pediatric patients.7 Intramuscular artesunate has a Tmax of 8-12 minutes.7 Infants less than 6 months old will have a higher AUC due to an undeveloped UGT metabolic pathway.8
- Volume of distribution
The volume of distribution of artesunate is 68.5L while the volume of distribution of DHA is 59.7L.8
- Protein binding
Artesunate and its metabolite DHA are approximately 93% protein bound in plasma.8 Artesunate can bind to serum albumin.4
- Metabolism
Artesunate is rapidly metabolized to dihydroartemisinin (DHA) by plasma esterases.8 DHA is glucuronidated by UGT1A9 and UGT2B7 to DHA-glucuronide.2,8 DHA-glucuronide can undergo a minor metabolic pathway to for a furano acetate derivative of DHA-glucuronide.2 CYP2A6 may minorly contribute to the metabolism of artesunate.7
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- Route of elimination
The main route of elimination in humans is unknown.8 In rats, a dose of artesunate is 56.1% eliminated in the urine and 38.5% in the feces.3
- Half-life
The elimination half life of artesunate is 0.3h with a range of 0.1-1.8h.8 The elimination half life of DHA is 1.3h with a range of 0.9-2.9h.8 Half life after intramuscular administration is 48 min in children and 41 min in adults.7
- Clearance
The clearance of artesunate is 180L/h while the clearance of DHA is 32.3L/h.8
- 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
Data regarding overdoses of artesunate are rare.8 Patients experiencing an overdose may present with pancytopenia, melena, seizures, multiorgan failure, and death.8 Treat overdose with symptomatic and supportive measures.8
- 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 softwareAcetophenazine The risk or severity of QTc prolongation can be increased when Artesunate is combined with Acetophenazine. Alimemazine The risk or severity of QTc prolongation can be increased when Artesunate is combined with Alimemazine. Ambroxol The risk or severity of methemoglobinemia can be increased when Artesunate is combined with Ambroxol. Artemether The risk or severity of QTc prolongation can be increased when Artesunate is combined with Artemether. Articaine The risk or severity of methemoglobinemia can be increased when Artesunate is combined with Articaine. - Food Interactions
- No interactions found.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Artesunate sodium CN5E49Z611 82864-68-4 ZISJLHQNEVGTIU-RFEYTNPVSA-M - Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Artesunate Injection, powder, for solution; Kit 110 mg/1 Parenteral Amivas, Inc 2020-12-11 Not applicable US 
Artesunate - Amivas Injection, powder, for solution 110 mg Intravenous Amivas Ireland Ltd 2022-01-21 Not applicable EU 
Artesunate - Amivas Injection, powder, for solution 110 mg Intravenous Amivas Ireland Ltd 2022-01-21 Not applicable EU - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Artesunate Artesunate (110 mg/1) + Artesunate (110 mg/1) Injection; Kit Parenteral Amivas, LLC 2020-12-11 Not applicable US Artesunate Artesunate (110 mg/1) + Artesunate (110 mg/1) Injection; Kit Parenteral Amivas, LLC 2020-12-11 Not applicable US PYRAMAX TABLETS Artesunate (60 MG) + Pyronaridine tetraphosphate (180 MG) Tablet, film coated บริษัท ดีซีเอฟ เฮลท์แคร์ จำกัด 2017-10-10 Not applicable Thailand 
อาร์ทีซูเนทและเมฟลอควินไฮโดรคลอไรด์ 100/220 มก. Artesunate (100 MG) + Mefloquine hydrochloride (220 MG) Tablet, film coated บริษัท ฮีลลอล ฟาร์มาซูติคอล จำกัด จำกัด 2019-04-10 Not applicable Thailand อาร์ทีซูเนทและเมฟลอควินไฮโดรคลอไรด์ 25/55 มก. Artesunate (25 MG) + Mefloquine hydrochloride (55 MG) Tablet, film coated บริษัท ฮีลลอล ฟาร์มาซูติคอล จำกัด จำกัด 2019-04-10 Not applicable Thailand
Categories
- ATC Codes
- P01BE03 — Artesunate
- P01BE — Artemisinin and derivatives, plain
- P01B — ANTIMALARIALS
- P01 — ANTIPROTOZOALS
- P — ANTIPARASITIC PRODUCTS, INSECTICIDES AND REPELLENTS
- P01BF — Artemisinin and derivatives, combinations
- P01B — ANTIMALARIALS
- P01 — ANTIPROTOZOALS
- P — ANTIPARASITIC PRODUCTS, INSECTICIDES AND REPELLENTS
- P01BF — Artemisinin and derivatives, combinations
- P01B — ANTIMALARIALS
- P01 — ANTIPROTOZOALS
- P — ANTIPARASITIC PRODUCTS, INSECTICIDES AND REPELLENTS
- P01BF — Artemisinin and derivatives, combinations
- P01B — ANTIMALARIALS
- P01 — ANTIPROTOZOALS
- P — ANTIPARASITIC PRODUCTS, INSECTICIDES AND REPELLENTS
- P01BF — Artemisinin and derivatives, combinations
- P01B — ANTIMALARIALS
- P01 — ANTIPROTOZOALS
- P — ANTIPARASITIC PRODUCTS, INSECTICIDES AND REPELLENTS
- Drug Categories
- Acids, Acyclic
- Anions
- Anthelmintics
- Anti-Infective Agents
- Antimalarials
- Antineoplastic Agents
- Antiparasitic Agents
- Antiparasitic Products, Insecticides and Repellents
- Antiplatyhelmintic Agents
- Antiprotozoals
- Antiviral Agents
- Artemisinin and derivatives
- Artemisinins
- BCRP/ABCG2 Substrates
- Cytochrome P-450 CYP2A6 Substrates
- Cytochrome P-450 Substrates
- Dicarboxylic Acids
- Electrolytes
- Free Radicals
- Ions
- OAT3/SLC22A8 Inhibitors
- OATP1B1/SLCO1B1 Inhibitors
- Oxides
- Oxygen Compounds
- P-glycoprotein substrates
- Peroxides
- Reactive Oxygen Species
- Schistosomicides
- Terpenes
- UGT1A9 Substrates
- UGT2B7 substrates
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as artemisinins. These are sesquiterpenoids originally isolated from the herb Artemisia annua. Their structure is based on artemisinin, a tetracyclic compound that contains a 1,2-dioxepane fused to an octahydrobenzopyran moiety. The internal peroxide bridge is believed to be a key to the mode of action of artemisinins.
- Kingdom
- Organic compounds
- Super Class
- Lipids and lipid-like molecules
- Class
- Prenol lipids
- Sub Class
- Sesquiterpenoids
- Direct Parent
- Artemisinins
- Alternative Parents
- Oxepanes / Heterocyclic fatty acids / Fatty acid esters / Trioxanes / Oxanes / Dicarboxylic acids and derivatives / Dialkyl peroxides / Carboxylic acid esters / Oxacyclic compounds / Carboxylic acids show 3 more
- Substituents
- 1,2,4-trioxane / Acetal / Aliphatic heteropolycyclic compound / Artemisinin skeleton / Carbonyl group / Carboxylic acid / Carboxylic acid derivative / Carboxylic acid ester / Dialkyl peroxide / Dicarboxylic acid or derivatives show 11 more
- Molecular Framework
- Aliphatic heteropolycyclic compounds
- External Descriptors
- dicarboxylic acid monoester, semisynthetic derivative, sesquiterpenoid, artemisinin derivative, cyclic acetal (CHEBI:63918)
- Affected organisms
- Plasmodium
Chemical Identifiers
- UNII
- 60W3249T9M
- CAS number
- 88495-63-0
- InChI Key
- FIHJKUPKCHIPAT-AHIGJZGOSA-N
- InChI
- InChI=1S/C19H28O8/c1-10-4-5-13-11(2)16(23-15(22)7-6-14(20)21)24-17-19(13)12(10)8-9-18(3,25-17)26-27-19/h10-13,16-17H,4-9H2,1-3H3,(H,20,21)/t10-,11-,12+,13+,16-,17-,18-,19-/m1/s1
- IUPAC Name
- 4-oxo-4-{[(1R,4S,5R,8S,9R,10S,12R,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0⁴,¹³.0⁸,¹³]hexadecan-10-yl]oxy}butanoic acid
- SMILES
- [H][C@@]12CC[C@@H](C)[C@]3([H])CC[C@@]4(C)OO[C@@]13[C@]([H])(O[C@@H](OC(=O)CCC(O)=O)[C@@H]2C)O4
References
- General References
- Lisewski AM, Quiros JP, Ng CL, Adikesavan AK, Miura K, Putluri N, Eastman RT, Scanfeld D, Regenbogen SJ, Altenhofen L, Llinas M, Sreekumar A, Long C, Fidock DA, Lichtarge O: Supergenomic network compression and the discovery of EXP1 as a glutathione transferase inhibited by artesunate. Cell. 2014 Aug 14;158(4):916-28. doi: 10.1016/j.cell.2014.07.011. [Article]
- Ilett KF, Ethell BT, Maggs JL, Davis TM, Batty KT, Burchell B, Binh TQ, Thu le TA, Hung NC, Pirmohamed M, Park BK, Edwards G: Glucuronidation of dihydroartemisinin in vivo and by human liver microsomes and expressed UDP-glucuronosyltransferases. Drug Metab Dispos. 2002 Sep;30(9):1005-12. doi: 10.1124/dmd.30.9.1005. [Article]
- Li Q, Xie LH, Haeberle A, Zhang J, Weina P: The evaluation of radiolabeled artesunate on tissue distribution in rats and protein binding in humans. Am J Trop Med Hyg. 2006 Nov;75(5):817-26. [Article]
- Veerappan A, Eichhorn T, Zeino M, Efferth T, Schneider D: Differential interactions of the broad spectrum drugs artemisinin, dihydroartemisinin and artesunate with serum albumin. Phytomedicine. 2013 Aug 15;20(11):969-74. doi: 10.1016/j.phymed.2013.04.003. Epub 2013 May 16. [Article]
- White NJ, Hien TT, Nosten FH: A Brief History of Qinghaosu. Trends Parasitol. 2015 Dec;31(12):607-610. doi: 10.1016/j.pt.2015.10.010. [Article]
- CDC: Artesunate [Link]
- Artesunate Product Information [Link]
- FDA Approved Drug Products: Artesunate Intravenous Injection [Link]
- External Links
- Human Metabolome Database
- HMDB0240267
- KEGG Drug
- D02482
- PubChem Compound
- 6917864
- PubChem Substance
- 310265169
- ChemSpider
- 5293084
- 18346
- ChEBI
- 63918
- ChEMBL
- CHEMBL361497
- ZINC
- ZINC000014096305
- PDBe Ligand
- D95
- Wikipedia
- Artesunate
- PDB Entries
- 6fgc / 6yk1
- FDA label
- Download (360 KB)
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample dataNot Available Completed Treatment Malaria 1 somestatus stop reason just information to hide Not Available Not Yet Recruiting Not Available Malaria 1 somestatus stop reason just information to hide 4 Active Not Recruiting Prevention Malaria / Parasitic Diseases 1 somestatus stop reason just information to hide 4 Active Not Recruiting Treatment Malaria 2 somestatus stop reason just information to hide 4 Completed Not Available Healthy Volunteers (HV) 1 somestatus stop reason just information to hide
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Injection, powder, for solution Intravenous 60 mg Injection, powder, for solution; kit Parenteral 110 mg/1 Injection; kit Parenteral Injection, powder, for solution Intravenous 110 mg Powder 60 mg/1vial Tablet 50 mg Tablet, film coated Oral 50 mg Tablet, film coated Oral 200 mg Capsule, liquid filled Rectal 200 mg Tablet, film coated - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 131-135 MSDS - Predicted Properties
Property Value Source Water Solubility 0.678 mg/mL ALOGPS logP 2.35 ALOGPS logP 3.1 Chemaxon logS -2.8 ALOGPS pKa (Strongest Acidic) 3.77 Chemaxon pKa (Strongest Basic) -4.2 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 7 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 100.52 Å2 Chemaxon Rotatable Bond Count 5 Chemaxon Refractivity 89.95 m3·mol-1 Chemaxon Polarizability 39.46 Å3 Chemaxon Number of Rings 4 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 splash10-000i-0096000000-2a4fa36d13ab900a06f4 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-001i-1091000000-9fdcf05d1d9031635640 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-00kr-1094000000-e7218ed1e326d4796ed5 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-00e9-9021000000-151b8724a431ab0c3349 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0ab9-9041000000-bbc2a82c8786fe62ed22 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-05n3-9043000000-17f7c108d09e594861fd Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 197.9901793 predictedDarkChem Lite v0.1.0 [M-H]- 187.40324 predictedDeepCCS 1.0 (2019) [M+H]+ 198.0526793 predictedDarkChem Lite v0.1.0 [M+H]+ 189.22813 predictedDeepCCS 1.0 (2019) [M+Na]+ 197.9538793 predictedDarkChem Lite v0.1.0 [M+Na]+ 194.83395 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Plasmodium falciparum
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Not Available
- Specific Function
- Not Available
- Gene Name
- EXP-1
- Uniprot ID
- P04926
- Uniprot Name
- Malaria protein EXP-1
- Molecular Weight
- 17449.565 Da
References
- Lisewski AM, Quiros JP, Ng CL, Adikesavan AK, Miura K, Putluri N, Eastman RT, Scanfeld D, Regenbogen SJ, Altenhofen L, Llinas M, Sreekumar A, Long C, Fidock DA, Lichtarge O: Supergenomic network compression and the discovery of EXP1 as a glutathione transferase inhibited by artesunate. Cell. 2014 Aug 14;158(4):916-28. doi: 10.1016/j.cell.2014.07.011. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- UDP-glucuronosyltransferase (UGT) that catalyzes phase II biotransformation reactions in which lipophilic substrates are conjugated with glucuronic acid to increase the metabolite's water solubility, thereby facilitating excretion into either the urine or bile (PubMed:10702251, PubMed:15470161, PubMed:15472229, PubMed:17442341, PubMed:18674515, PubMed:18719240, PubMed:19022937, PubMed:23288867, PubMed:23756265, PubMed:26220143). Essential for the elimination and detoxification of drugs, xenobiotics and endogenous compounds (PubMed:15470161, PubMed:18674515, PubMed:23756265). Catalyzes the glucuronidation of endogenous steroid hormones such as androgens (epitestosterone, androsterone) and estrogens (estradiol, epiestradiol, estriol, catechol estrogens) (PubMed:15472229, PubMed:17442341, PubMed:18719240, PubMed:19022937, PubMed:2159463, PubMed:23288867, PubMed:26220143). Also regulates the levels of retinoic acid, a major metabolite of vitamin A involved in apoptosis, cellular growth and differentiation, and embryonic development (PubMed:10702251). Contributes to bile acid (BA) detoxification by catalyzing the glucuronidation of BA substrates, which are natural detergents for dietary lipids absorption (PubMed:23756265). Involved in the glucuronidation of the AGTR1 angiotensin receptor antagonist losartan, caderastan and zolarsatan, drugs which can inhibit the effect of angiotensin II (PubMed:18674515). Also metabolizes mycophenolate, an immunosuppressive agent (PubMed:15470161)
- Specific Function
- Glucuronosyltransferase activity
- Gene Name
- UGT2B7
- Uniprot ID
- P16662
- Uniprot Name
- UDP-glucuronosyltransferase 2B7
- Molecular Weight
- 60720.15 Da
References
- Ilett KF, Ethell BT, Maggs JL, Davis TM, Batty KT, Burchell B, Binh TQ, Thu le TA, Hung NC, Pirmohamed M, Park BK, Edwards G: Glucuronidation of dihydroartemisinin in vivo and by human liver microsomes and expressed UDP-glucuronosyltransferases. Drug Metab Dispos. 2002 Sep;30(9):1005-12. doi: 10.1124/dmd.30.9.1005. [Article]
- FDA Approved Drug Products: Artesunate Intravenous Injection [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- UDP-glucuronosyltransferase (UGT) that catalyzes phase II biotransformation reactions in which lipophilic substrates are conjugated with glucuronic acid to increase the metabolite's water solubility, thereby facilitating excretion into either the urine or bile (PubMed:12181437, PubMed:15470161, PubMed:15472229, PubMed:18004212, PubMed:18052087, PubMed:18674515, PubMed:19545173). Essential for the elimination and detoxification of drugs, xenobiotics and endogenous compounds (PubMed:12181437, PubMed:18004212). Catalyzes the glucuronidation of endogenous estrogen hormones such as estradiol and estrone (PubMed:15472229). Also catalyzes the glucuronidation of the isoflavones genistein, daidzein, glycitein, formononetin, biochanin A and prunetin, which are phytoestrogens with anticancer and cardiovascular properties (PubMed:18052087, PubMed:19545173). Involved in the glucuronidation of the AGTR1 angiotensin receptor antagonist caderastan, a drug which can inhibit the effect of angiotensin II (PubMed:18674515). Involved in the biotransformation of 7-ethyl-10-hydroxycamptothecin (SN-38), the pharmacologically active metabolite of the anticancer drug irinotecan (PubMed:12181437, PubMed:20610558). Also metabolizes mycophenolate, an immunosuppressive agent (PubMed:15470161, PubMed:18004212)
- Specific Function
- Enzyme binding
- Gene Name
- UGT1A9
- Uniprot ID
- O60656
- Uniprot Name
- UDP-glucuronosyltransferase 1A9
- Molecular Weight
- 59940.495 Da
References
- Ilett KF, Ethell BT, Maggs JL, Davis TM, Batty KT, Burchell B, Binh TQ, Thu le TA, Hung NC, Pirmohamed M, Park BK, Edwards G: Glucuronidation of dihydroartemisinin in vivo and by human liver microsomes and expressed UDP-glucuronosyltransferases. Drug Metab Dispos. 2002 Sep;30(9):1005-12. doi: 10.1124/dmd.30.9.1005. [Article]
- FDA Approved Drug Products: Artesunate Intravenous Injection [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Exhibits a high coumarin 7-hydroxylase activity. Can act in the hydroxylation of the anti-cancer drugs cyclophosphamide and ifosphamide. Competent in the metabolic activation of aflatoxin B1. Constitutes the major nicotine C-oxidase. Acts as a 1,4-cineole 2-exo-monooxygenase. Possesses low phenacetin O-deethylation activity
- Specific Function
- Arachidonic acid epoxygenase activity
- Gene Name
- CYP2A6
- Uniprot ID
- P11509
- Uniprot Name
- Cytochrome P450 2A6
- Molecular Weight
- 56517.005 Da
References
- Phompradit P, Muhamad P, Cheoymang A, Na-Bangchang K: Preliminary investigation of the contribution of CYP2A6, CYP2B6, and UGT1A9 polymorphisms on artesunate-mefloquine treatment response in Burmese patients with Plasmodium falciparum malaria. Am J Trop Med Hyg. 2014 Aug;91(2):361-6. doi: 10.4269/ajtmh.13-0531. Epub 2014 Jun 2. [Article]
- Artesunate Product Information [Link]
- Artesunate and Amiodiquine FDA Label [File]
Carriers
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Binder
- General Function
- Binds water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs (Probable). Its main function is the regulation of the colloidal osmotic pressure of blood (Probable). Major zinc transporter in plasma, typically binds about 80% of all plasma zinc (PubMed:19021548). Major calcium and magnesium transporter in plasma, binds approximately 45% of circulating calcium and magnesium in plasma (By similarity). Potentially has more than two calcium-binding sites and might additionally bind calcium in a non-specific manner (By similarity). The shared binding site between zinc and calcium at residue Asp-273 suggests a crosstalk between zinc and calcium transport in the blood (By similarity). The rank order of affinity is zinc > calcium > magnesium (By similarity). Binds to the bacterial siderophore enterobactin and inhibits enterobactin-mediated iron uptake of E.coli from ferric transferrin, and may thereby limit the utilization of iron and growth of enteric bacteria such as E.coli (PubMed:6234017). Does not prevent iron uptake by the bacterial siderophore aerobactin (PubMed:6234017)
- Specific Function
- Antioxidant activity
- Gene Name
- ALB
- Uniprot ID
- P02768
- Uniprot Name
- Albumin
- Molecular Weight
- 69365.94 Da
References
- Veerappan A, Eichhorn T, Zeino M, Efferth T, Schneider D: Differential interactions of the broad spectrum drugs artemisinin, dihydroartemisinin and artesunate with serum albumin. Phytomedicine. 2013 Aug 15;20(11):969-74. doi: 10.1016/j.phymed.2013.04.003. Epub 2013 May 16. [Article]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Broad substrate specificity ATP-dependent transporter of the ATP-binding cassette (ABC) family that actively extrudes a wide variety of physiological compounds, dietary toxins and xenobiotics from cells (PubMed:11306452, PubMed:12958161, PubMed:19506252, PubMed:20705604, PubMed:28554189, PubMed:30405239, PubMed:31003562). Involved in porphyrin homeostasis, mediating the export of protoporphyrin IX (PPIX) from both mitochondria to cytosol and cytosol to extracellular space, it also functions in the cellular export of heme (PubMed:20705604, PubMed:23189181). Also mediates the efflux of sphingosine-1-P from cells (PubMed:20110355). Acts as a urate exporter functioning in both renal and extrarenal urate excretion (PubMed:19506252, PubMed:20368174, PubMed:22132962, PubMed:31003562, PubMed:36749388). In kidney, it also functions as a physiological exporter of the uremic toxin indoxyl sulfate (By similarity). Also involved in the excretion of steroids like estrone 3-sulfate/E1S, 3beta-sulfooxy-androst-5-en-17-one/DHEAS, and other sulfate conjugates (PubMed:12682043, PubMed:28554189, PubMed:30405239). Mediates the secretion of the riboflavin and biotin vitamins into milk (By similarity). Extrudes pheophorbide a, a phototoxic porphyrin catabolite of chlorophyll, reducing its bioavailability (By similarity). Plays an important role in the exclusion of xenobiotics from the brain (Probable). It confers to cells a resistance to multiple drugs and other xenobiotics including mitoxantrone, pheophorbide, camptothecin, methotrexate, azidothymidine, and the anthracyclines daunorubicin and doxorubicin, through the control of their efflux (PubMed:11306452, PubMed:12477054, PubMed:15670731, PubMed:18056989, PubMed:31254042). In placenta, it limits the penetration of drugs from the maternal plasma into the fetus (By similarity). May play a role in early stem cell self-renewal by blocking differentiation (By similarity)
- Specific Function
- Abc-type xenobiotic transporter activity
- Gene Name
- ABCG2
- Uniprot ID
- Q9UNQ0
- Uniprot Name
- Broad substrate specificity ATP-binding cassette transporter ABCG2
- Molecular Weight
- 72313.47 Da
References
- FDA Approved Drug Products: Artesunate Intravenous Injection [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Translocates drugs and phospholipids across the membrane (PubMed:2897240, PubMed:35970996, PubMed:8898203, PubMed:9038218). Catalyzes the flop of phospholipids from the cytoplasmic to the exoplasmic leaflet of the apical membrane. Participates mainly to the flop of phosphatidylcholine, phosphatidylethanolamine, beta-D-glucosylceramides and sphingomyelins (PubMed:8898203). Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells (PubMed:2897240, PubMed:35970996, PubMed:9038218)
- Specific Function
- Abc-type xenobiotic transporter activity
- Gene Name
- ABCB1
- Uniprot ID
- P08183
- Uniprot Name
- ATP-dependent translocase ABCB1
- Molecular Weight
- 141477.255 Da
References
- FDA Approved Drug Products: Artesunate Intravenous Injection [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Mediates the Na(+)-independent uptake of organic anions (PubMed:10358072, PubMed:15159445, PubMed:17412826). Shows broad substrate specificity, can transport both organic anions such as bile acid taurocholate (cholyltaurine) and conjugated steroids (dehydroepiandrosterone 3-sulfate, 17-beta-glucuronosyl estradiol, and estrone 3-sulfate), as well as eicosanoids (prostaglandin E2, thromboxane B2, leukotriene C4, and leukotriene E4), and thyroid hormones (T4/L-thyroxine, and T3/3,3',5'-triiodo-L-thyronine) (PubMed:10358072, PubMed:10601278, PubMed:10873595, PubMed:11159893, PubMed:12196548, PubMed:12568656, PubMed:15159445, PubMed:15970799, PubMed:16627748, PubMed:17412826, PubMed:19129463, PubMed:26979622). Can take up bilirubin glucuronides from plasma into the liver, contributing to the detoxification-enhancing liver-blood shuttling loop (PubMed:22232210). Involved in the clearance of endogenous and exogenous substrates from the liver (PubMed:10358072, PubMed:10601278). Transports coproporphyrin I and III, by-products of heme synthesis, and may be involved in their hepatic disposition (PubMed:26383540). May contribute to regulate the transport of organic compounds in testes across the blood-testis-barrier (Probable). Can transport HMG-CoA reductase inhibitors (also known as statins), such as pravastatin and pitavastatin, a clinically important class of hypolipidemic drugs (PubMed:10601278, PubMed:15159445, PubMed:15970799). May play an important role in plasma and tissue distribution of the structurally diverse chemotherapeutic drug methotrexate (PubMed:23243220). May also transport antihypertension agents, such as the angiotensin-converting enzyme (ACE) inhibitor prodrug enalapril, and the highly selective angiotensin II AT1-receptor antagonist valsartan, in the liver (PubMed:16624871, PubMed:16627748). Shows a pH-sensitive substrate specificity towards prostaglandin E2 and T4 which may be ascribed to the protonation state of the binding site and leads to a stimulation of substrate transport in an acidic microenvironment (PubMed:19129463). Hydrogencarbonate/HCO3(-) acts as the probable counteranion that exchanges for organic anions (PubMed:19129463)
- Specific Function
- Bile acid transmembrane transporter activity
- Gene Name
- SLCO1B1
- Uniprot ID
- Q9Y6L6
- Uniprot Name
- Solute carrier organic anion transporter family member 1B1
- Molecular Weight
- 76447.99 Da
References
- FDA Approved Drug Products: Artesunate Intravenous Injection [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Functions as an organic anion/dicarboxylate exchanger that couples organic anion uptake indirectly to the sodium gradient (PubMed:14586168, PubMed:15644426, PubMed:15846473, PubMed:16455804, PubMed:31553721). Transports organic anions such as estrone 3-sulfate (E1S) and urate in exchange for dicarboxylates such as glutarate or ketoglutarate (2-oxoglutarate) (PubMed:14586168, PubMed:15846473, PubMed:15864504, PubMed:22108572, PubMed:23832370). Plays an important role in the excretion of endogenous and exogenous organic anions, especially from the kidney and the brain (PubMed:11306713, PubMed:14586168, PubMed:15846473). E1S transport is pH- and chloride-dependent and may also involve E1S/cGMP exchange (PubMed:26377792). Responsible for the transport of prostaglandin E2 (PGE2) and prostaglandin F2(alpha) (PGF2(alpha)) in the basolateral side of the renal tubule (PubMed:11907186). Involved in the transport of neuroactive tryptophan metabolites kynurenate and xanthurenate (PubMed:22108572, PubMed:23832370). Functions as a biopterin transporters involved in the uptake and the secretion of coenzymes tetrahydrobiopterin (BH4), dihydrobiopterin (BH2) and sepiapterin to urine, thereby determining baseline levels of blood biopterins (PubMed:28534121). May be involved in the basolateral transport of steviol, a metabolite of the popular sugar substitute stevioside (PubMed:15644426). May participate in the detoxification/ renal excretion of drugs and xenobiotics, such as the histamine H(2)-receptor antagonists fexofenadine and cimetidine, the antibiotic benzylpenicillin (PCG), the anionic herbicide 2,4-dichloro-phenoxyacetate (2,4-D), the diagnostic agent p-aminohippurate (PAH), the antiviral acyclovir (ACV), and the mycotoxin ochratoxin (OTA), by transporting these exogenous organic anions across the cell membrane in exchange for dicarboxylates such as 2-oxoglutarate (PubMed:11669456, PubMed:15846473, PubMed:16455804). Contributes to the renal uptake of potent uremic toxins (indoxyl sulfate (IS), indole acetate (IA), hippurate/N-benzoylglycine (HA) and 3-carboxy-4-methyl-5-propyl-2-furanpropionate (CMPF)), pravastatin, PCG, E1S and dehydroepiandrosterone sulfate (DHEAS), and is partly involved in the renal uptake of temocaprilat (an angiotensin-converting enzyme (ACE) inhibitor) (PubMed:14675047). May contribute to the release of cortisol in the adrenals (PubMed:15864504). Involved in one of the detoxification systems on the choroid plexus (CP), removes substrates such as E1S or taurocholate (TC), PCG, 2,4-D and PAH, from the cerebrospinal fluid (CSF) to the blood for eventual excretion in urine and bile (By similarity). Also contributes to the uptake of several other organic compounds such as the prostanoids prostaglandin E(2) and prostaglandin F(2-alpha), L-carnitine, and the therapeutic drugs allopurinol, 6-mercaptopurine (6-MP) and 5-fluorouracil (5-FU) (By similarity). Mediates the transport of PAH, PCG, and the statins pravastatin and pitavastatin, from the cerebrum into the blood circulation across the blood-brain barrier (BBB). In summary, plays a role in the efflux of drugs and xenobiotics, helping reduce their undesired toxicological effects on the body (By similarity)
- Specific Function
- Organic anion transmembrane transporter activity
- Gene Name
- SLC22A8
- Uniprot ID
- Q8TCC7
- Uniprot Name
- Organic anion transporter 3
- Molecular Weight
- 59855.585 Da
References
- FDA Approved Drug Products: Artesunate Intravenous Injection [Link]
Drug created at October 28, 2015 21:21 / Updated at June 02, 2024 21:55