Umifenovir

Identification

Summary

Umifenovir is a dual direct-acting antiviral/host-targeting agent used in the treatment and prophylaxis of influenza and other respiratory viruses.

Generic Name

Umifenovir

DrugBank Accession Number

DB13609

Background

Umifenovir is an indole-based, hydrophobic, dual-acting direct antiviral/host-targeting agent used for the treatment and prophylaxis of influenza and other respiratory infections.¹³ It has been in use in Russia for approximately 25 years and in China since 2006. Its invention is credited to a collaboration between Russian scientists from several research institutes 40-50 years ago, and reports of its chemical synthesis date back to 1993.¹³ Umifenovir's ability to exert antiviral effects through multiple pathways has resulted in considerable investigation into its use for a variety of enveloped and non-enveloped RNA and DNA viruses, including Flavivirus,² Zika virus,³ foot-and-mouth disease,⁴ Lassa virus,⁶ Ebola virus,⁶ herpes simplex,⁸, hepatitis B and C viruses, chikungunya virus, reovirus, Hantaan virus, and coxsackie virus B5.^13,9 This dual activity may also confer additional protection against viral resistance, as the development of resistance to umifenovir does not appear to be significant.¹³

Umifenovir is currently being investigated as a potential treatment and prophylactic agent for COVID-19 caused by SARS-CoV2 infections in combination with both currently available and investigational HIV therapies.^1,16,18

Type

Small Molecule

Groups

Investigational

Structure

3D

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MOLSDF3D-SDFPDBSMILESInChI

Similar Structures

Structure for Umifenovir (DB13609)

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Weight

Average: 477.42
Monoisotopic: 476.076927

Chemical Formula

C₂₂H₂₅BrN₂O₃S

Synonyms

• Umifenovir

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Pharmacology

Indication

Umifenovir is currently licensed in China and Russia for the prophylaxis and treatment of influenza and other respiratory viral infections.¹³ It has demonstrated activity against a number of viruses and has been investigated in the treatment of Flavivirus,² Zika virus,³ foot-and-mouth disease,⁴ Lassa virus,⁶ Ebola virus,⁶ and herpes simplex.⁸ In addition, it has shown in vitro activity against hepatitis B and C viruses, chikungunya virus, reovirus, Hantaan virus, and coxsackie virus B5.^13,9

Umifenovir is currently being investigated as a potential treatment and prophylactic agent for the prevention of COVID-19 caused by SARS-CoV-2 infections.^1,16

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Contraindications & Blackbox Warnings

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Pharmacodynamics

Umifenovir exerts its antiviral effects via both direct-acting virucidal activity and by inhibiting one (or several) stage(s) of the viral life cycle.¹³ Its broad-spectrum of activity covers both enveloped and non-enveloped RNA and DNA viruses. It is relatively well-tolerated and possesses a large therapeutic window - weight-based doses up to 100-fold greater than those used in humans failed to produce any pathological changes in test animals.¹³

Umifenovir does not appear to result in significant viral resistance. Instances of umifenovir-resistant influenza virus demonstrated a single mutation in the HA2 subunit of influenza hemagglutinin, suggesting resistance is conferred by prevention of umifenovir’s activity related to membrane fusion. The mechanism through which other viruses may become resistant to umifenovir requires further study.¹³

Mechanism of action

Umifenovir is considered both a direct-acting antiviral (DAA) due to direct virucidal effects and a host-targeting agent (HTA) due to effects on one or multiple stages of viral life cycle (e.g. attachment, internalization), and its broad-spectrum antiviral activity is thought to be due to this dual activity.¹³ It is a hydrophobic molecule capable of forming aromatic stacking interactions with certain amino acid residues (e.g. tyrosine, tryptophan), which contributes to its ability to directly act against viruses. Antiviral activity may also be due to interactions with aromatic residues within the viral glycoproteins involved in fusion and cellular recognition,^5,7 with the plasma membrane to interfere with clathrin-mediated exocytosis and intracellular trafficking,¹⁰ or directly with the viral lipid envelope itself (in enveloped viruses).^13,12 Interactions at the plasma membrane may also serve to stabilize it and prevent viral entry (e.g. stabilizing influenza hemagglutinin inhibits the fusion step necessary for viral entry).¹³

Due to umifenovir’s ability to interact with both viral proteins and lipids, it may also interfere with later stages of the viral life cycle. Some virus families, such as Flaviviridae, replicate in a subcellular compartment called the membranous web - this web requires lipid-protein interactions that may be hindered by umifenovir. Similarly, viral assembly of hepatitis C viruses is contingent upon the assembly of lipoproteins, presenting another potential target.¹³

Absorption

Umifenovir is rapidly absorbed following oral administration, with an estimated T_max between 0.65-1.8 hours.^14,15,13 The C_max has been estimated as 415 - 467 ng/mL and appears to increase linearly with dose,^14,15 and the AUC_0-inf following oral administration has been estimated to be approximately 2200 ng/mL/h.^14,15

Volume of distribution

Data regarding the volume of distribution of umifenovir are currently unavailable.

Protein binding

Data regarding protein-binding of umifenovir are currently unavailable.

Metabolism

Umifenovir is highly metabolized in the body, primarily in hepatic and intestinal microsomess, with approximately 33 metabolites having been observed in human plasma, urine, and feces.¹⁴ The principal phase I metabolic pathways include sulfoxidation, N-demethylation, and hydroxylation, followed by phase II sulfate and glucuronide conjugation. In the urine, the major metabolites were sulfate and glucuronide conjugates, while the major species in the feces was unchanged parent drug (~40%) and the M10 metabolite (~3.0%). In the plasma, the principal metabolites are M6-1, M5, and M8 - of these, M6-1 appears of most importance given its high plasma exposure and long elimination half-life (~25h), making it a potentially important player in the safety and efficacy of umifenovir.¹⁴

Enzymes involved in the metabolism of umifenovir include members of the cytochrome P450 family (primarily CYP3A4), flavin-containing monooxygenase (FMO) family, and UDP-glucuronosyltransferase (UGT) family (specifically UGT1A9 and UGT2B7).^14,11,17

Hover over products below to view reaction partners

• Umifenovir
  • Arbidol M1 metabolite
    • Arbidol M13-2 metabolite
    • Arbidol M13-1 metabolite
    • Arbidol M4 metabolite
  • Arbidol M10 metabolite
  • Arbidol M18 metabolite
  • Arbidol M3-2 metabolite
    • Arbidol M9-2 metabolite
    • Arbidol M17-2 metabolite
  • Arbidol M5 metabolite
    • Arbidol M11-2 metabolite
    • Arbidol M19 metabolite
  • Arbidol M6-1 metabolite
    • Arbidol M14-1 metabolite
    • Arbidol M20 metabolite
  • Arbidol M7 metabolite
    • Arbidol M15 metabolite
    • Arbidol M21 metabolite
  • Arbidol M8 metabolite
    • Arbidol M16 metabolite
    • Arbidol M22 metabolite
  • Arbidol M3-1 metabolite
    • Arbidol M9-1 metabolite
  • Arbidol M6-2 metabolite

Route of elimination

The major route of elimination is via the feces. Approximately 40% of an ingested dose is excreted unchanged, of which 38.9% is excreted in the bile and 0.12% excreted through the kidneys.¹⁵ The total recovery of parent drug and metabolites in the urine accounts for less than 1% of an ingested dose.¹⁴

Half-life

The half-life of umifenovir following oral administration has been estimated to be between 17-21 hours.^13,14 Serum half-lives of the M5, M6-1, and M8 metabolites were found to be 26.3 ± 5.9, 25.0 ± 5.4, and 25.7 ± 8.8, respectively.¹⁴

Clearance

In a study involving healthy male Chinese volunteers, the oral clearance of umifenovir was found to be 99 ± 34 L/h.¹⁴

Adverse Effects

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Toxicity

The oral LD₅₀ of umifenovir in mice and rats has been reported as 340-400 mg/kg and >3000 mg/kg, respectively.¹³ Chronic administration of doses 10-50 times the therapeutic human dose resulted in no pathological changes to animal subjects.

Further information regarding the management of umifenovir overdose is unavailable.

Pathways

Not Available

Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">

Not Available

Interactions

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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.

• Approved
• Vet approved
• Nutraceutical
• Illicit
• Withdrawn
• Investigational
• Experimental
• All Drugs

Drug	Interaction
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Abametapir	The serum concentration of Umifenovir can be increased when it is combined with Abametapir.
Acetaminophen	The metabolism of Acetaminophen can be decreased when combined with Umifenovir.
Adenovirus type 7 vaccine live	The therapeutic efficacy of Adenovirus type 7 vaccine live can be decreased when used in combination with Umifenovir.
Ambrisentan	The metabolism of Ambrisentan can be decreased when combined with Umifenovir.
Amiodarone	The metabolism of Umifenovir can be decreased when combined with Amiodarone.

Food Interactions

No interactions found.

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International/Other Brands

Arbidol / Arbidole

Categories

ATC Codes

J05AX13 — Umifenovir

• J05AX — Other antivirals
• J05A — DIRECT ACTING ANTIVIRALS
• J05 — ANTIVIRALS FOR SYSTEMIC USE
• J — ANTIINFECTIVES FOR SYSTEMIC USE

Drug Categories

• Anions
• Antiinfectives for Systemic Use
• Antiviral Agents
• Antivirals for Systemic Use
• Cytochrome P-450 CYP1A2 Substrates
• Cytochrome P-450 CYP2C9 Substrates
• Cytochrome P-450 CYP2D6 Substrates
• Cytochrome P-450 CYP2E1 Substrates
• Cytochrome P-450 CYP3A Substrates
• Cytochrome P-450 CYP3A4 Substrates
• Cytochrome P-450 CYP3A5 Substrates
• Cytochrome P-450 Substrates
• Direct Acting Antivirals
• Electrolytes
• Experimental Unapproved Treatments for COVID-19
• Heterocyclic Compounds, Fused-Ring
• Hydrogen Sulfide
• Ions
• Sulfur Compounds
• UGT1A9 Inhibitors
• UGT1A9 Substrates
• UGT2B7 Inhibitors

Chemical TaxonomyProvided by Classyfire

Description

This compound belongs to the class of organic compounds known as indolecarboxylic acids and derivatives. These are compounds containing a carboxylic acid group (or a derivative thereof) linked to an indole.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indolecarboxylic acids and derivatives

Direct Parent

Indolecarboxylic acids and derivatives

Alternative Parents

Hydroxyindoles / N-alkylindoles / Indoles / Thiophenol ethers / Pyrrole carboxylic acids and derivatives / O-bromophenols / Alkylarylthioethers / Aralkylamines / Aryl bromides / Benzene and substituted derivatives / N-methylpyrroles / Vinylogous amides / Heteroaromatic compounds / Trialkylamines / Amino acids and derivatives / Carboxylic acid esters / Sulfenyl compounds / Azacyclic compounds / Monocarboxylic acids and derivatives / Organobromides / Organooxygen compounds / Organopnictogen compounds / Hydrocarbon derivatives / Organic oxides

show 14 more

Substituents

2-bromophenol / Alkylarylthioether / Amine / Amino acid or derivatives / Aralkylamine / Aromatic heteropolycyclic compound / Aryl bromide / Aryl halide / Aryl thioether / Azacycle / Benzenoid / Carboxylic acid derivative / Carboxylic acid ester / Heteroaromatic compound / Hydrocarbon derivative / Hydroxyindole / Indole / Indolecarboxylic acid derivative / Monocarboxylic acid or derivatives / Monocyclic benzene moiety / N-alkylindole / N-methylpyrrole / Organic nitrogen compound / Organic oxide / Organic oxygen compound / Organobromide / Organohalogen compound / Organonitrogen compound / Organooxygen compound / Organopnictogen compound / Organosulfur compound / Pyrrole / Pyrrole-3-carboxylic acid or derivatives / Substituted pyrrole / Sulfenyl compound / Tertiary aliphatic amine / Tertiary amine / Thioether / Thiophenol ether / Vinylogous amide

show 30 more

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Affected organisms

• Herpes simplex virus
• Hepatitis B virus
• Hepatitis C Virus (HCV)
• SARS-CoV-2
• Zika virus
• Lassa mammarenavirus
• Chikungunya virus
• Coxsackievirus B5
• Reovirus spp.
• Hantaan orthohantavirus
• Ebolavirus

Chemical Identifiers

UNII

93M09WW4RU

CAS number

131707-25-0

InChI Key

KCFYEAOKVJSACF-UHFFFAOYSA-N

InChI

InChI=1S/C22H25BrN2O3S/c1-5-28-22(27)20-18(13-29-14-9-7-6-8-10-14)25(4)17-11-16(23)21(26)15(19(17)20)12-24(2)3/h6-11,26H,5,12-13H2,1-4H3

IUPAC Name

ethyl 6-bromo-4-[(dimethylamino)methyl]-5-hydroxy-1-methyl-2-[(phenylsulfanyl)methyl]-1H-indole-3-carboxylate

SMILES

CCOC(=O)C1=C(CSC2=CC=CC=C2)N(C)C2=CC(Br)=C(O)C(CN(C)C)=C12

References

Synthesis Reference

Trofimov, F.A., Tsyshkova, N.G., Zotova, S.A., Grinev, A.N., 1993. Synthesis of a new antiviral agent, arbidole. Pharm Chem J 27, 75–76.

General References

1. Lu H: Drug treatment options for the 2019-new coronavirus (2019-nCoV). Biosci Trends. 2020 Jan 28. doi: 10.5582/bst.2020.01020. [Article]
2. Haviernik J, Stefanik M, Fojtikova M, Kali S, Tordo N, Rudolf I, Hubalek Z, Eyer L, Ruzek D: Arbidol (Umifenovir): A Broad-Spectrum Antiviral Drug That Inhibits Medically Important Arthropod-Borne Flaviviruses. Viruses. 2018 Apr 10;10(4). pii: v10040184. doi: 10.3390/v10040184. [Article]
3. Fink SL, Vojtech L, Wagoner J, Slivinski NSJ, Jackson KJ, Wang R, Khadka S, Luthra P, Basler CF, Polyak SJ: The Antiviral Drug Arbidol Inhibits Zika Virus. Sci Rep. 2018 Jun 12;8(1):8989. doi: 10.1038/s41598-018-27224-4. [Article]
4. Herod MR, Adeyemi OO, Ward J, Bentley K, Harris M, Stonehouse NJ, Polyak SJ: The broad-spectrum antiviral drug arbidol inhibits foot-and-mouth disease virus genome replication. J Gen Virol. 2019 Sep;100(9):1293-1302. doi: 10.1099/jgv.0.001283. Epub 2019 Jun 4. [Article]
5. Kadam RU, Wilson IA: Structural basis of influenza virus fusion inhibition by the antiviral drug Arbidol. Proc Natl Acad Sci U S A. 2017 Jan 10;114(2):206-214. doi: 10.1073/pnas.1617020114. Epub 2016 Dec 21. [Article]
6. Hulseberg CE, Feneant L, Szymanska-de Wijs KM, Kessler NP, Nelson EA, Shoemaker CJ, Schmaljohn CS, Polyak SJ, White JM: Arbidol and Other Low-Molecular-Weight Drugs That Inhibit Lassa and Ebola Viruses. J Virol. 2019 Apr 3;93(8). pii: JVI.02185-18. doi: 10.1128/JVI.02185-18. Print 2019 Apr 15. [Article]
7. Zeng LY, Yang J, Liu S: Investigational hemagglutinin-targeted influenza virus inhibitors. Expert Opin Investig Drugs. 2017 Jan;26(1):63-73. doi: 10.1080/13543784.2017.1269170. Epub 2016 Dec 14. [Article]
8. Li MK, Liu YY, Wei F, Shen MX, Zhong Y, Li S, Chen LJ, Ma N, Liu BY, Mao YD, Li N, Hou W, Xiong HR, Yang ZQ: Antiviral activity of arbidol hydrochloride against herpes simplex virus I in vitro and in vivo. Int J Antimicrob Agents. 2018 Jan;51(1):98-106. doi: 10.1016/j.ijantimicag.2017.09.001. Epub 2017 Sep 7. [Article]
9. Pecheur EI, Borisevich V, Halfmann P, Morrey JD, Smee DF, Prichard M, Mire CE, Kawaoka Y, Geisbert TW, Polyak SJ: The Synthetic Antiviral Drug Arbidol Inhibits Globally Prevalent Pathogenic Viruses. J Virol. 2016 Jan 6;90(6):3086-92. doi: 10.1128/JVI.02077-15. [Article]
10. Blaising J, Levy PL, Polyak SJ, Stanifer M, Boulant S, Pecheur EI: Arbidol inhibits viral entry by interfering with clathrin-dependent trafficking. Antiviral Res. 2013 Oct;100(1):215-9. doi: 10.1016/j.antiviral.2013.08.008. Epub 2013 Aug 25. [Article]
11. Song JH, Fang ZZ, Zhu LL, Cao YF, Hu CM, Ge GB, Zhao DW: Glucuronidation of the broad-spectrum antiviral drug arbidol by UGT isoforms. J Pharm Pharmacol. 2013 Apr;65(4):521-7. doi: 10.1111/jphp.12014. Epub 2012 Dec 24. [Article]
12. Teissier E, Zandomeneghi G, Loquet A, Lavillette D, Lavergne JP, Montserret R, Cosset FL, Bockmann A, Meier BH, Penin F, Pecheur EI: Mechanism of inhibition of enveloped virus membrane fusion by the antiviral drug arbidol. PLoS One. 2011 Jan 25;6(1):e15874. doi: 10.1371/journal.pone.0015874. [Article]
13. Blaising J, Polyak SJ, Pecheur EI: Arbidol as a broad-spectrum antiviral: an update. Antiviral Res. 2014 Jul;107:84-94. doi: 10.1016/j.antiviral.2014.04.006. Epub 2014 Apr 24. [Article]
14. Deng P, Zhong D, Yu K, Zhang Y, Wang T, Chen X: Pharmacokinetics, metabolism, and excretion of the antiviral drug arbidol in humans. Antimicrob Agents Chemother. 2013 Apr;57(4):1743-55. doi: 10.1128/AAC.02282-12. Epub 2013 Jan 28. [Article]
15. Liu MY, Wang S, Yao WF, Wu HZ, Meng SN, Wei MJ: Pharmacokinetic properties and bioequivalence of two formulations of arbidol: an open-label, single-dose, randomized-sequence, two-period crossover study in healthy Chinese male volunteers. Clin Ther. 2009 Apr;31(4):784-92. doi: 10.1016/j.clinthera.2009.04.016. [Article]
16. Wang Z, Chen X, Lu Y, Chen F, Zhang W: Clinical characteristics and therapeutic procedure for four cases with 2019 novel coronavirus pneumonia receiving combined Chinese and Western medicine treatment. Biosci Trends. 2020 Feb 9. doi: 10.5582/bst.2020.01030. [Article]
17. Liu X, Huang T, Chen JX, Zeng J, Fan XR, Xu-Zhu, Yu ZW, Sun XY, Hong M, Sun HZ: Arbidol exhibits strong inhibition towards UDP-glucuronosyltransferase (UGT) 1A9 and 2B7. Pharmazie. 2013 Dec;68(12):945-50. [Article]
18. Nature Biotechnology: Coronavirus puts drug repurposing on the fast track [Link]

External Links

ChemSpider

116151

BindingDB

83797

ChEBI

134730

ChEMBL

CHEMBL1214598

ZINC

ZINC000019907652

PDBe Ligand

75U

Wikipedia

Umifenovir

PDB Entries

5t6n / 5t6s

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">

Phase	Status	Purpose	Conditions	Count
4	Completed	Treatment	Coronavirus Disease 2019 (COVID‑19)	1
4	Completed	Treatment	Infections, Coronavirus	1
4	Enrolling by Invitation	Treatment	COPD Patients	1
4	Not Yet Recruiting	Treatment	Coronavirus Disease 2019 (COVID‑19)	1
4	Unknown Status	Treatment	Coronavirus Disease 2019 (COVID‑19)	2

Pharmacoeconomics

Manufacturers

Not Available

Packagers

Not Available

Dosage Forms

Not Available

Prices

Not Available

Patents

Not Available

Properties

State

Solid

Experimental Properties

Property	Value	Source
water solubility	"Expected to be poorly soluble"	Blaising, J. et. al.

Predicted Properties

Property	Value	Source
Water Solubility	0.00678 mg/mL	ALOGPS
logP	4.97	ALOGPS
logP	3.75	Chemaxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	6.01	Chemaxon
pKa (Strongest Basic)	9.87	Chemaxon
Physiological Charge	0	Chemaxon
Hydrogen Acceptor Count	3	Chemaxon
Hydrogen Donor Count	1	Chemaxon
Polar Surface Area	54.7 Å2	Chemaxon
Rotatable Bond Count	8	Chemaxon
Refractivity	124.41 m3·mol-1	Chemaxon
Polarizability	48.17 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	Yes	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	splash10-00o0-0007900000-1a1da9dfaf1423bee564
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0699-1009200000-b99b6a6d1c88f51c97c3
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	splash10-005i-0207900000-5b83e56456081982772f
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0a4i-0903100000-259edee7382d789b281f
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	splash10-03di-8915100000-c9e8438dff42f526f19f
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0a6s-2229000000-ad1ff2b3e325f7f70ba6
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]-	192.84248	predicted	DeepCCS 1.0 (2019)
[M+H]+	195.20049	predicted	DeepCCS 1.0 (2019)
[M+Na]+	201.57095	predicted	DeepCCS 1.0 (2019)

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Drug created at June 23, 2017 20:45 / Updated at February 03, 2022 06:26