Belumosudil

Identification

Summary

Belumosudil is an oral inhibitor of rho-associated coiled-coil-containing protein kinases (ROCK) used in the treatment of chronic graft-versus-host disease (GVHD).

Brand Names
Rezurock
Generic Name
Belumosudil
DrugBank Accession Number
DB16703
Background

Belumosudil is used in the treatment of chronic graft-versus-host disease (GVHD) and has been investigated for the treatment of pulmonary arterial hypertension.4 It is an inhibitor of rho-associated coiled-coil-containing protein kinases (ROCK), with significantly more selectivity for ROCK2 as compared to ROCK1 (IC50 100 nM vs. 3 μM, respectively).5 In the treatment of GVHD, a condition in which donor T-cells begin to attack recipient tissues following allogeneic hematopoeitic stem cell transplantation (HSCT), belumosudil helps to resolve immune dysregulation by shifting the balance between Th17 cells and T-regulatory cells, thereby dampening the inflammatory cascade that can occasionally be fatal.3,7

Belumosudil was first approved by the FDA in July 2021, under the brand name Rezurock, for the treatment of chronic GVHD in patients who have tried and failed at least two prior lines of systemic therapy.6 In July 2022, Belumosudil was approved by Health Canada under the brand name RHOLISTIQ to treat the same condition in adult and pediatric patients 12 years or older.10

Type
Small Molecule
Groups
Approved, Investigational
Structure
Weight
Average: 452.518
Monoisotopic: 452.196074037
Chemical Formula
C26H24N6O2
Synonyms
  • Belumosudil
External IDs
  • BN101
  • KD-025
  • KD025
  • SLx-2119
  • WHO 11343

Pharmacology

Indication

Belumosudil is indicated for the treatment of chronic graft-versus-host disease (GVHD) in adult and pediatric patients 12 years of age and older following failure of at least two other lines of systemic therapy.5

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Treatment ofChronic graft-versus-host disease•••••••••••••••••• •••••••••••• ••••• •••••••• •••••••••••••••
Treatment ofChronic graft-versus-host disease•••••••••••••• ••••• ••• ••••• •••••••• •••••••••••••••
Contraindications & Blackbox Warnings
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Pharmacodynamics

Belumosudil appears to inhibit several pro-fibrotic and pro-inflammatory processes in order to prevent and treat the damage incurred by graft-versus-host disease. Given its mechanism of action and findings in animal trials, belumosudil is considered to carry embryo-fetal toxicity and may cause significant harm to a developing fetus should a pregnant mother be exposed.5 Female patients of reproductive potential, or male patients with female partners of reproductive potential, should be advised to use effective contraception during treatment with belumosudil and for one week after the last dose.5

Mechanism of action

Chronic graft-versus-host disease (GVHD) is a life-threatening complication of allogeneic hematopoietic stem cell transplantation in which the transplanted donor T-cells recognize the recipient's tissues as foreign and mount an immune response.2 During the conditioning regimen prior to stem cell transplantation (e.g. involving irradiation or chemotherapy) the host tissues can become damaged which results in downstream inflammatory responses and the generation of inflammatory mediators like TNF-alpha and IL-1. These cytokines increase the expression of host major histocompatibility (MHC) antigens and adhesion molecules which enhances the ability of mature donor T-cells to recognize these molecules. The activation of these donor T-cells results in the activation of mononuclear phagocytes, whose effector functions are triggered by stimulatory molecules generated by the damage incurred during the conditioning phase of treatment. Activated macrophages and cytotoxic T-lymphocytes begin to directly lyse target cells and/or cause their apoptosis, which eventually leads to local tissue damage and further inflammatory responses.3

Belumosudil is an inhibitor of Rho-associated coiled-coil kinase 2 (ROCK2), a protein that plays a vital role in the pathogenesis of immune and fibrotic diseases. The inhibition of ROCK2 has been shown to resolve immune dysregulation by down-regulating pro-inflammatory Th17 cells and up-regulating regulatory T-cells by manipulating the phosphorylation of STAT3 and STAT5.5,7

TargetActionsOrganism
ARho-associated protein kinase 2
inhibitor
Humans
ARho-associated protein kinase 1
inhibitor
Humans
Absorption

Following oral administration, the mean bioavailability of belumosudil is 64% and the median Tmax at steady-state is 1.26 to 2.53 hours.5 As compared to administration in a fasted state, belumosudil Cmax and AUC increased by 2.2 and 2 times, respectively, when administered with a high-fat, high-calorie meal.5

Volume of distribution

Following a single oral dose of belumosudil in healthy subjects, the mean geometric volume of distribution was 184 L.5

Protein binding

Belumosudil appears to be extensively protein-bound in plasma - in vitro protein binding to serum albumin and alpha-1-acid glycoprotein was found to be 99.9% and 98.6%, respectively.5

Metabolism

The in vitro metabolism of belumosudil occurs primarily via CYP3A4 and to a lesser extent by CYP2C8, CYP2D6, and UGT1A9.5 The specific metabolites generated by belumosudil metabolism remain unclear.

Route of elimination

Belumosudil is eliminated primarily in the feces. Following the administration of a radiolabeled oral dose of belumosudil in healthy subjects, approximately 85% of the radioactivity was recovered in the feces, 30% of which was unchanged parent drug, with less than 5% recovered in the urine.5

Half-life

The mean elimination half-life of belumosudil following oral administration is 19 hours.5

Clearance

The mean clearance of belumosudil is 9.83 L/h.5

Adverse Effects
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Toxicity

There are no data regarding overdosage with belumosudil.

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.
DrugInteraction
AbametapirThe serum concentration of Belumosudil can be increased when it is combined with Abametapir.
AbataceptThe risk or severity of adverse effects can be increased when Abatacept is combined with Belumosudil.
AbemaciclibThe serum concentration of Abemaciclib can be increased when it is combined with Belumosudil.
AdalimumabThe risk or severity of adverse effects can be increased when Adalimumab is combined with Belumosudil.
Adenovirus type 7 vaccine liveThe risk or severity of infection can be increased when Adenovirus type 7 vaccine live is combined with Belumosudil.
Food Interactions
  • Take at the same time every day. Belumosudil should be taken with a meal at approximately the same time each day.
  • Take with food. The co-administration of food increases the absorption of belumosudil.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Belumosudil mesylate6MX7XE1M0U2109704-99-4BGNMZPDNJWWQCU-UHFFFAOYSA-N
Belumosudil trifluoroacetateLL4OG4RZ5D1243152-02-4PBWWPJDQYJXRII-UHFFFAOYSA-N
International/Other Brands
Rezurock (Kadmon Holdings, Inc.)
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
RezurockTablet200 mg/1OralPharma Packaging Solutions, LLC dba Tjoapack LLC2021-07-16Not applicableUS flag
RezurockTablet200 mgOralSanofi Aventis2023-03-08Not applicableCanada flag
RezurockTablet200 mg/1OralKadmon Pharmaceuticals, LLC2021-07-16Not applicableUS flag

Categories

ATC Codes
L04AA48 — Belumosudil
Drug Categories
Classification
Not classified
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
834YJF89WO
CAS number
911417-87-3
InChI Key
GKHIVNAUVKXIIY-UHFFFAOYSA-N
InChI
InChI=1S/C26H24N6O2/c1-16(2)28-24(33)15-34-20-7-5-6-17(13-20)25-30-23-9-4-3-8-21(23)26(31-25)29-19-10-11-22-18(12-19)14-27-32-22/h3-14,16H,15H2,1-2H3,(H,27,32)(H,28,33)(H,29,30,31)
IUPAC Name
2-(3-{4-[(1H-indazol-5-yl)amino]quinazolin-2-yl}phenoxy)-N-(propan-2-yl)acetamide
SMILES
CC(C)NC(=O)COC1=CC=CC(=C1)C1=NC2=C(C=CC=C2)C(NC2=CC=C3NN=CC3=C2)=N1

References

Synthesis Reference

殷燕, 孙玉星, 张华, 孙国峰, 陶瑞衡, 段永斌, 孙越, and 江沁楠. The Synthetic Method of SLx 2119. SHANGHAI SCIENPHARM BIOTECHNOLOGY Co.,Ltd., assignee. Patent CN106916145A. 4 June 2019.

General References
  1. Cutler CS, Lee SJ, Arai S, Rotta M, Zoghi B, Lazaryan A, Ramakrishnan A, DeFilipp Z, Salhotra A, Chai-Ho W, Mehta RS, Wang T, Arora M, Pusic I, Saad A, Shah NN, Abhyankar S, Bachier C, Galvin JP, Im A, Langston A, Liesveld JL, Juckett M, Logan A, Schachter L, Alavi A, Howard DS, Waksal H, Ryan J, Eiznhamer D, Aggarwal SK, Ieyoub J, Schueller O, Green LS, Yang Z, Krenz H, Jagasia M, Blazar BR, Pavletic SZ: Belumosudil for Chronic Graft-versus-Host Disease (cGVHD) After 2 or More Prior Lines of Therapy: The ROCKstar Study. Blood. 2021 Jul 15. pii: 476399. doi: 10.1182/blood.2021012021. [Article]
  2. Braun LM, Zeiser R: Immunomodulatory Therapies for the Treatment of Graft-versus-host Disease. Hemasphere. 2021 Jun 1;5(6):e581. doi: 10.1097/HS9.0000000000000581. eCollection 2021 Jun. [Article]
  3. Ferrara JL, Reddy P: Pathophysiology of graft-versus-host disease. Semin Hematol. 2006 Jan;43(1):3-10. doi: 10.1053/j.seminhematol.2005.09.001. [Article]
  4. Yamamura A, Nayeem MJ, Sato M: The Rho kinase 2 (ROCK2)-specific inhibitor KD025 ameliorates the development of pulmonary arterial hypertension. Biochem Biophys Res Commun. 2021 Jan 1;534:795-801. doi: 10.1016/j.bbrc.2020.10.106. Epub 2020 Nov 5. [Article]
  5. FDA Approved Drug Products: Rezurock (belumosudil) tablets for oral use [Link]
  6. FDA News Release: FDA approves belumosudil for chronic graft-versus-host disease [Link]
  7. Kadmon: Belumosudil Mechanism of Action [Link]
  8. MedChemExpress: Belumosudil Safety Data Sheet [Link]
  9. Health Canada Approved Drug Proucts: RHOLISTIQ (Belumosudil) tablet for oral use [Link]
  10. Health Canada News Release: Health Canada approves belumosudil for chronic graft-versus-host disease [Link]
Human Metabolome Database
HMDB0247641
KEGG Drug
D11815
ChemSpider
10124479
BindingDB
322155
RxNav
2564025
ChEMBL
CHEMBL2005186
ZINC
ZINC000063298464
PDBe Ligand
ICQ
Wikipedia
Belumosudil
PDB Entries
7z39

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
3RecruitingTreatmentChronic Graft-Versus-Host Disease1
3RecruitingTreatmentLung Transplant Rejection1
2Active Not RecruitingTreatmentChronic Graft-Versus-Host Disease1
2CompletedTreatmentChronic Graft-Versus-Host Disease1
2CompletedTreatmentChronic Plaque Psoriasis1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
TabletOral200 mg
TabletOral200 mg/1
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US10696660No2020-06-302033-10-07US flag
US10183931No2019-01-222033-10-07US flag
US9815820No2017-11-142033-10-07US flag
US8357693No2013-01-222029-10-30US flag
US11311541No2015-04-092035-04-09US flag

Properties

State
Solid
Experimental Properties
PropertyValueSource
boiling point (°C)682.6±55.0https://file.medchemexpress.com/batch_PDF/HY-15307/Belumosudil-SDS-MedChemExpress.pdf
water solubilityPractically insolublehttps://www.accessdata.fda.gov/drugsatfda_docs/label/2021/214783s000lbl.pdf
Predicted Properties
PropertyValueSource
Water Solubility0.00289 mg/mLALOGPS
logP4.65ALOGPS
logP4.65Chemaxon
logS-5.2ALOGPS
pKa (Strongest Acidic)13.08Chemaxon
pKa (Strongest Basic)4.11Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count6Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area104.82 Å2Chemaxon
Rotatable Bond Count7Chemaxon
Refractivity141.46 m3·mol-1Chemaxon
Polarizability49.55 Å3Chemaxon
Number of Rings5Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udi-3202900000-4bf7c16e5a8dff9c735f
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udl-9008200000-604c6acda59190e36777
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udl-1009400000-9726f355b56f1083e69e
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-6009100000-9f41f132a348f00f26c6
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0f6x-8009200000-052993a792c017ec4d34
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-2049000000-8002047d898435abd8ba
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-241.63022
predicted
DarkChem Lite v0.1.0
[M+H]+241.32422
predicted
DarkChem Lite v0.1.0
[M+Na]+241.29102
predicted
DarkChem Lite v0.1.0

Targets

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Use our structured and evidence-based datasets to unlock new
insights and accelerate drug research.
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Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Structural molecule activity
Specific Function
Protein kinase which is a key regulator of actin cytoskeleton and cell polarity. Involved in regulation of smooth muscle contraction, actin cytoskeleton organization, stress fiber and focal adhesio...
Gene Name
ROCK2
Uniprot ID
O75116
Uniprot Name
Rho-associated protein kinase 2
Molecular Weight
160898.555 Da
References
  1. Cutler CS, Lee SJ, Arai S, Rotta M, Zoghi B, Lazaryan A, Ramakrishnan A, DeFilipp Z, Salhotra A, Chai-Ho W, Mehta RS, Wang T, Arora M, Pusic I, Saad A, Shah NN, Abhyankar S, Bachier C, Galvin JP, Im A, Langston A, Liesveld JL, Juckett M, Logan A, Schachter L, Alavi A, Howard DS, Waksal H, Ryan J, Eiznhamer D, Aggarwal SK, Ieyoub J, Schueller O, Green LS, Yang Z, Krenz H, Jagasia M, Blazar BR, Pavletic SZ: Belumosudil for Chronic Graft-versus-Host Disease (cGVHD) After 2 or More Prior Lines of Therapy: The ROCKstar Study. Blood. 2021 Jul 15. pii: 476399. doi: 10.1182/blood.2021012021. [Article]
  2. FDA Approved Drug Products: Rezurock (belumosudil) tablets for oral use [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Protein serine/threonine kinase activity
Specific Function
Protein kinase which is a key regulator of actin cytoskeleton and cell polarity. Involved in regulation of smooth muscle contraction, actin cytoskeleton organization, stress fiber and focal adhesio...
Gene Name
ROCK1
Uniprot ID
Q13464
Uniprot Name
Rho-associated protein kinase 1
Molecular Weight
158173.545 Da
References
  1. FDA Approved Drug Products: Rezurock (belumosudil) tablets for oral use [Link]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. FDA Approved Drug Products: Rezurock (belumosudil) tablets for oral use [Link]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C8
Uniprot ID
P10632
Uniprot Name
Cytochrome P450 2C8
Molecular Weight
55824.275 Da
References
  1. FDA Approved Drug Products: Rezurock (belumosudil) tablets for oral use [Link]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
Gene Name
CYP2D6
Uniprot ID
P10635
Uniprot Name
Cytochrome P450 2D6
Molecular Weight
55768.94 Da
References
  1. FDA Approved Drug Products: Rezurock (belumosudil) tablets for oral use [Link]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
Inhibitor
General Function
Retinoic acid binding
Specific Function
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform has specificity for phenols. Isoform 2 lacks trans...
Gene Name
UGT1A9
Uniprot ID
O60656
Uniprot Name
UDP-glucuronosyltransferase 1-9
Molecular Weight
59940.495 Da
References
  1. FDA Approved Drug Products: Rezurock (belumosudil) tablets for oral use [Link]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Inhibitor
General Function
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP1A2
Uniprot ID
P05177
Uniprot Name
Cytochrome P450 1A2
Molecular Weight
58293.76 Da
References
  1. FDA Approved Drug Products: Rezurock (belumosudil) tablets for oral use [Link]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and im...
Gene Name
CYP2C19
Uniprot ID
P33261
Uniprot Name
Cytochrome P450 2C19
Molecular Weight
55930.545 Da
References
  1. FDA Approved Drug Products: Rezurock (belumosudil) tablets for oral use [Link]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Inhibitor
General Function
Steroid binding
Specific Function
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the...
Gene Name
UGT1A1
Uniprot ID
P22309
Uniprot Name
UDP-glucuronosyltransferase 1-1
Molecular Weight
59590.91 Da
References
  1. FDA Approved Drug Products: Rezurock (belumosudil) tablets for oral use [Link]

Carriers

Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Binder
General Function
Toxic substance binding
Specific Function
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
Molecular Weight
69365.94 Da
References
  1. FDA Approved Drug Products: Rezurock (belumosudil) tablets for oral use [Link]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Binder
General Function
Not Available
Specific Function
Functions as transport protein in the blood stream. Binds various ligands in the interior of its beta-barrel domain. Also binds synthetic drugs and influences their distribution and availability in...
Gene Name
ORM1
Uniprot ID
P02763
Uniprot Name
Alpha-1-acid glycoprotein 1
Molecular Weight
23511.38 Da
References
  1. FDA Approved Drug Products: Rezurock (belumosudil) tablets for oral use [Link]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
Inhibitor
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da
References
  1. FDA Approved Drug Products: Rezurock (belumosudil) tablets for oral use [Link]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Inhibitor
General Function
Xenobiotic-transporting atpase activity
Specific Function
High-capacity urate exporter functioning in both renal and extrarenal urate excretion. Plays a role in porphyrin homeostasis as it is able to mediates the export of protoporhyrin IX (PPIX) both fro...
Gene Name
ABCG2
Uniprot ID
Q9UNQ0
Uniprot Name
ATP-binding cassette sub-family G member 2
Molecular Weight
72313.47 Da
References
  1. FDA Approved Drug Products: Rezurock (belumosudil) tablets for oral use [Link]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Inhibitor
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Mediates the Na(+)-independent uptake of organic anions such as pravastatin, taurocholate, methotrexate, dehydroepiandrosterone sulfate, 17-beta-glucuronosyl estradiol, estrone sulfate, prostagland...
Gene Name
SLCO1B1
Uniprot ID
Q9Y6L6
Uniprot Name
Solute carrier organic anion transporter family member 1B1
Molecular Weight
76447.99 Da
References
  1. FDA Approved Drug Products: Rezurock (belumosudil) tablets for oral use [Link]

Drug created at July 19, 2021 06:02 / Updated at December 01, 2022 11:30