Identification

Name
Bleomycin
Accession Number
DB00290
Description

A complex of related glycopeptide antibiotics from Streptomyces verticillus consisting of bleomycin A2 and B2 (B2 CAS # 9060-10-0). It inhibits DNA metabolism and is used as an antineoplastic, especially for solid tumors. Bleomycin A2 is used as the representative structure for Bleomycin.

Type
Small Molecule
Groups
Approved, Investigational
Structure
Thumb
Weight
Average: 1415.552
Monoisotopic: 1414.518979905
Chemical Formula
C55H84N17O21S3
Synonyms
  • Bleocin
  • Bleomicin
  • Bleomicina
  • Bleomycin
  • Bleomycine
  • Bleomycinum

Pharmacology

Indication

For palliative treatment in the management malignant neoplasm (trachea, bronchus, lung), squamous cell carcinoma, and lymphomas.

Associated Conditions
Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
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Pharmacodynamics

Bleomycin is an antibiotic which has been shown to have antitumor activity. Bleomycin selectively inhibits the synthesis of deoxyribonucleic acid (DNA). The guanine and cytosine content correlates with the degree of mitomycin-induced cross-linking. At high concentrations of the drug, cellular RNA and protein synthesis are also suppressed. Bleomycin has been shown in vitro to inhibit B cell, T cell, and macrophage proliferation and impair antigen presentation, as well as the secretion of interferon gamma, TNFa, and IL-2. The antibiotic antitumor drugs are cell cycle-nonspecific except for Bleomycin (which has major effects in G2 and M phases).

Mechanism of action

Although the exact mechanism of action of bleomycin is unknown, available evidence would seem to indicate that the main mode of action is the inhibition of DNA synthesis with some evidence of lesser inhibition of RNA and protein synthesis. As evident in in vitro studies, the DNA-cleaving actions of bleomycin is dependent on oxygen and metal ions. It is believed that bleomycin chelates metal ions (primarily iron) producing a pseudoenzyme that reacts with oxygen to produce superoxide and hydroxide free radicals that cleave DNA.

TargetActionsOrganism
UDNA ligase 1
inhibitor
Humans
ADNA
cleavage
Humans
UDNA ligase 3
inhibitor
Humans
Absorption

Systemic absorption is approximately 45%.

Volume of distribution
Not Available
Protein binding

1%

Metabolism

Hepatic

Route of elimination

It was reported that patients with moderately severe renal failure excreted less than 20% of the dose in the urine.

Half-life

115 minutes

Clearance
Not Available
Adverse Effects
Learn about our commercial Adverse Effects data.
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Toxicity

Excessive exposure may cause fever, chills, nausea, vomiting, mental, confusion, and wheezing. Bleomycin may cause irritation to eyes, skin and respiratory tract. It may also cause a darkening or thickening of the skin. It may cause an allergic reaction.

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Interacting Gene/EnzymeAllele nameGenotype(s)Defining Change(s)Type(s)DescriptionDetails
Bleomycin hydrolase---(G;G)G AlleleEffect Directly StudiedPatients with this genotype have reduced survival time and increased frequency of early relapse when using bleomycin to treat testicular cancer.Details

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
AbacavirBleomycin may decrease the excretion rate of Abacavir which could result in a higher serum level.
AbataceptThe risk or severity of adverse effects can be increased when Bleomycin is combined with Abatacept.
AcarboseAcarbose may decrease the excretion rate of Bleomycin which could result in a higher serum level.
AceclofenacAceclofenac may decrease the excretion rate of Bleomycin which could result in a higher serum level.
AcemetacinAcemetacin may decrease the excretion rate of Bleomycin which could result in a higher serum level.
AcetaminophenBleomycin may decrease the excretion rate of Acetaminophen which could result in a higher serum level.
AcetazolamideAcetazolamide may increase the excretion rate of Bleomycin which could result in a lower serum level and potentially a reduction in efficacy.
AcetyldigitoxinAcetyldigitoxin may decrease the cardiotoxic activities of Bleomycin.
Acetylsalicylic acidAcetylsalicylic acid may decrease the excretion rate of Bleomycin which could result in a higher serum level.
AclidiniumBleomycin may decrease the excretion rate of Aclidinium which could result in a higher serum level.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions
No interactions found.

Products

Product Ingredients
IngredientUNIICASInChI Key
Bleomycin sulfate7DP3NTV15T9041-93-4WUIABRMSWOKTOF-OCBSMOPSSA-N
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
BlenoxaneInjection, powder, for solution30 [USP'U]/1Intramuscular; Intrapleural; Intravenous; SubcutaneousE.R. Squibb & Sons, L.L.C.2009-06-012010-02-28Us
BlenoxaneInjection, powder, for solution15 [USP'U]/1Intramuscular; Intrapleural; Intravenous; SubcutaneousE.R. Squibb & Sons, L.L.C.2009-06-012010-01-31Us
Blenoxane Pws 15unitPowder, for solutionIntramuscular; IntravenousBristol Labs Division Of Bristol Myers Squibb1973-12-312011-10-19Canada
BleomycinInjection, powder, lyophilized, for solution15000 [iU]/1Intra-arterial; Intramuscular; IntravenousAmneal Pharmaceuticals LLC2016-06-20Not applicableUs
Bleomycin for InjectionPowder, for solutionIntramuscular; Intrapleural; Intravenous; SubcutaneousFresenius Kabi2009-03-20Not applicableCanada
Bleomycin for Injection USPPowder, for solutionIntramuscular; Intrapleural; Intravenous; SubcutaneousSandoz Canada IncorporatedNot applicableNot applicableCanada
Bleomycin for Injection USPPowder, for solutionIntra-arterial; Intracavitary; Intramuscular; Intravenous; SubcutaneousPfizer Canada Ulc1998-03-12Not applicableCanada
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

    Learn more
  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
BleomycinInjection, powder, lyophilized, for solution30 [USP'U]/1Intramuscular; Intrapleural; Intravenous; SubcutaneousBedford Pharmaceuticals2003-03-102009-02-28Us
BleomycinInjection, powder, lyophilized, for solution15 [USP'U]/1Intramuscular; Intrapleural; Intravenous; SubcutaneousHospira, Inc.2015-04-25Not applicableUs
BleomycinInjection, powder, lyophilized, for solution30 [USP'U]/1Intramuscular; Intrapleural; Intravenous; SubcutaneousHospira, Inc.2000-04-10Not applicableUs
BleomycinInjection, powder, lyophilized, for solution30 [USP'U]/1Intramuscular; Intrapleural; Intravenous; SubcutaneousTeva Parenteral Medicines, Inc.2000-06-30Not applicableUs
BleomycinInjection, powder, lyophilized, for solution30 [USP'U]/1Intramuscular; Intrapleural; Intravenous; SubcutaneousFresenius Kabi USA, LLC2009-02-13Not applicableUs
BleomycinPowder, for solution30 [USP'U]/1Intramuscular; Intrapleural; Intravenous; SubcutaneousNorthStar Rx LLC2018-12-01Not applicableUs
BleomycinPowder, for solution30 [USP'U]/1Intramuscular; Intrapleural; Intravenous; SubcutaneousMeitheal Pharmaceuticals Inc.2018-08-31Not applicableUs
BleomycinInjection, powder, lyophilized, for solution15 [USP'U]/1Intramuscular; Intrapleural; Intravenous; SubcutaneousBedford Pharmaceuticals2003-03-102009-02-28Us
BleomycinInjection, powder, lyophilized, for solution30 [USP'U]/1Intramuscular; Intrapleural; Intravenous; SubcutaneousHospira, Inc.2018-04-25Not applicableUs
BleomycinInjection, powder, lyophilized, for solution15 [USP'U]/1Intramuscular; Intrapleural; Intravenous; SubcutaneousTeva Parenteral Medicines, Inc.2000-06-30Not applicableUs
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

    Learn more
  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

    Learn more
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
BleomycinBleomycin sulfate (15000 [iU]/1)Injection, powder, lyophilized, for solutionIntra-arterial; Intramuscular; IntravenousAmneal Pharmaceuticals LLC2016-06-20Not applicableUs

Categories

ATC Codes
L01DC01 — Bleomycin
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as hybrid glycopeptides. These are compounds containing a carbohydrate component linked to a hybrid peptide component.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Peptidomimetics
Sub Class
Hybrid peptides
Direct Parent
Hybrid glycopeptides
Alternative Parents
Histidine and derivatives / Fatty acyl glycosides of mono- and disaccharides / N-acyl-alpha amino acids and derivatives / Gamma amino acids and derivatives / Alpha amino acid amides / Beta amino acids and derivatives / Disaccharides / O-glycosyl compounds / Pyrimidinecarboxylic acids and derivatives / 2-heteroaryl carboxamides
show 26 more
Substituents
2,4-disubstituted 1,3-thiazole / 2-heteroaryl carboxamide / Acetal / Alcohol / Alpha-amino acid amide / Alpha-amino acid or derivatives / Amine / Amino acid or derivatives / Aminopyrimidine / Aralkylamine
show 50 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Non-ribosomal peptide/polyketide hybrids (LMPK14000006)

Chemical Identifiers

UNII
40S1VHN69B
CAS number
11056-06-7
InChI Key
OYVAGSVQBOHSSS-WXFSZRTFSA-O
InChI
InChI=1S/C55H83N17O21S3/c1-20-33(69-46(72-44(20)58)25(12-31(57)76)64-13-24(56)45(59)82)50(86)71-35(41(26-14-61-19-65-26)91-54-43(39(80)37(78)29(15-73)90-54)92-53-40(81)42(93-55(60)88)38(79)30(16-74)89-53)51(87)66-22(3)36(77)21(2)47(83)70-34(23(4)75)49(85)63-10-8-32-67-28(18-94-32)52-68-27(17-95-52)48(84)62-9-7-11-96(5)6/h14,17-19,21-25,29-30,34-43,53-54,64,73-75,77-81H,7-13,15-16,56H2,1-6H3,(H13-,57,58,59,60,61,62,63,65,66,69,70,71,72,76,82,83,84,85,86,87,88)/p+1/t21-,22+,23+,24-,25-,29?,30?,34-,35-,36-,37?,38?,39?,40?,41-,42?,43?,53?,54?/m0/s1
IUPAC Name
(3-{[2-(2-{2-[(2S,3R)-2-[(2S,3S,4R)-4-[(2S,3R)-2-({6-amino-2-[(1S)-1-{[(2S)-2-amino-2-carbamoylethyl]amino}-2-carbamoylethyl]-5-methylpyrimidin-4-yl}formamido)-3-[(3-{[4-(carbamoyloxy)-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy]-3-(1H-imidazol-4-yl)propanamido]-3-hydroxy-2-methylpentanamido]-3-hydroxybutanamido]ethyl}-1,3-thiazol-4-yl)-1,3-thiazol-4-yl]formamido}propyl)dimethylsulfanium
SMILES
[H][C@](C)(NC(=O)[C@@]([H])(NC(=O)C1=NC(=NC(N)=C1C)[C@H](CC(N)=O)NC[C@H](N)C(N)=O)[C@@]([H])(OC1OC(CO)C(O)C(O)C1OC1OC(CO)C(O)C(OC(N)=O)C1O)C1=CNC=N1)[C@@H](O)[C@H](C)C(=O)N[C@]([H])(C(=O)NCCC1=NC(=CS1)C1=NC(=CS1)C(=O)NCCC[S+](C)C)[C@@]([H])(C)O

References

Synthesis Reference

Hamao Umezawa, Kenji Maeda, Tomohisa Takita, Yuya Nakayama, Akio Fujii, Nobuyoshi Shimada, Hideo Chimura, "Novel process for producing antibiotics bleomycin." U.S. Patent USRE0304514, issued October, 1970.

USRE0304514
General References
  1. Claussen CA, Long EC: Nucleic Acid recognition by metal complexes of bleomycin. Chem Rev. 1999 Sep 8;99(9):2797-816. [PubMed:11749501]
Human Metabolome Database
HMDB0014435
KEGG Compound
C06854
PubChem Compound
5360373
PubChem Substance
46509116
ChemSpider
4514492
BindingDB
50122169
RxNav
1622
ChEBI
22907
ChEMBL
CHEMBL403664
Therapeutic Targets Database
DAP000531
PharmGKB
PA448645
PDBe Ligand
BLM
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Bleomycin
AHFS Codes
  • 10:00.00 — Antineoplastic Agents
FDA label
Download (46.3 KB)
MSDS
Download (34.4 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedTreatmentHead and Neck Carcinoma1
4CompletedTreatmentMalignancies1
4RecruitingTreatmentNon-Hodgkin's Lymphoma (NHL)1
4RecruitingTreatmentPediatric Hodgkin's Disease1
4RecruitingTreatmentVenous Malformations1
3Active Not RecruitingTreatmentAnn Arbor Stage IIB Hodgkin Lymphoma / Ann Arbor Stage IIIB Hodgkin Lymphoma / Ann Arbor Stage IV Hodgkin Lymphoma / Ann Arbor Stage IVA Hodgkin Lymphoma / Ann Arbor Stage IVB Hodgkin Lymphoma / Childhood Hodgkin Lymphoma / Classic Hodgkin Lymphoma1
3Active Not RecruitingTreatmentExtragonadal Germ Cell Tumor / Teratoma / Testicular germ cell tumour1
3Active Not RecruitingTreatmentHuman Immunodeficiency Virus Type 1 (HIV-1) Infection1
3Active Not RecruitingTreatmentLymphoma, Hodgkins3
3Active Not RecruitingTreatmentMalignant Lymphomas5

Pharmacoeconomics

Manufacturers
  • Bristol myers squibb co pharmaceutical research institute
  • App pharmaceuticals llc
  • Bedford laboratories div ben venue laboratories inc
  • Hospira inc
  • Pharmachemie bv
  • Teva parenteral medicines inc
Packagers
  • APP Pharmaceuticals
  • Bedford Labs
  • Bristol-Myers Squibb Co.
  • Hospira Inc.
  • Mead Johnson and Co.
  • Nippon Kayaku Co. Ltd.
  • Sicor Pharmaceuticals
  • Teva Pharmaceutical Industries Ltd.
Dosage Forms
FormRouteStrength
Injection, powder, for solutionIntramuscular; Intrapleural; Intravenous; Subcutaneous15 [USP'U]/1
Injection, powder, for solutionIntramuscular; Intrapleural; Intravenous; Subcutaneous30 [USP'U]/1
Powder, for solutionIntramuscular; Intravenous
InjectionIntramuscular; Intrapleural; Intravenous; Subcutaneous15 [USP'U]/1
Injection, powder, lyophilized, for solutionIntra-arterial; Intramuscular; Intravenous15000 [iU]/1
Injection, powder, lyophilized, for solutionIntramuscular; Intrapleural; Intravenous; Subcutaneous15 [USP'U]/1
Injection, powder, lyophilized, for solutionIntramuscular; Intrapleural; Intravenous; Subcutaneous30 [USP'U]/1
Powder, for solutionIntramuscular; Intrapleural; Intravenous; Subcutaneous15 [USP'U]/1
Powder, for solutionIntramuscular; Intrapleural; Intravenous; Subcutaneous30 [USP'U]/1
Powder, for solutionIntra-arterial; Intracavitary; Intramuscular; Intravenous; Subcutaneous
Powder, for solutionIntramuscular; Intrapleural; Intravenous; Subcutaneous
Prices
Unit descriptionCostUnit
Blenoxane 30 unit vial584.83USD vial
Blenoxane 15 unit vial292.42USD vial
Bleomycin sulfate 30 unit vial120.0USD vial
Bleomycin sulfate 15 unit vial81.6USD vial
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)71 °CNot Available
water solubilitySolubleNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0277 mg/mLALOGPS
logP-0.41ALOGPS
logP-9.3ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)11.39ChemAxon
pKa (Strongest Basic)7.65ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count28ChemAxon
Hydrogen Donor Count20ChemAxon
Polar Surface Area627.07 Å2ChemAxon
Rotatable Bond Count36ChemAxon
Refractivity343.83 m3·mol-1ChemAxon
Polarizability139.19 Å3ChemAxon
Number of Rings6ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.8877
Blood Brain Barrier-0.9732
Caco-2 permeable-0.6551
P-glycoprotein substrateSubstrate0.853
P-glycoprotein inhibitor INon-inhibitor0.8781
P-glycoprotein inhibitor IINon-inhibitor0.8454
Renal organic cation transporterNon-inhibitor0.9331
CYP450 2C9 substrateNon-substrate0.7773
CYP450 2D6 substrateNon-substrate0.7966
CYP450 3A4 substrateSubstrate0.6154
CYP450 1A2 substrateNon-inhibitor0.7423
CYP450 2C9 inhibitorNon-inhibitor0.7035
CYP450 2D6 inhibitorNon-inhibitor0.8678
CYP450 2C19 inhibitorNon-inhibitor0.6794
CYP450 3A4 inhibitorNon-inhibitor0.67
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8609
Ames testAMES toxic0.772
CarcinogenicityNon-carcinogens0.8957
BiodegradationNot ready biodegradable0.8863
Rat acute toxicity2.6132 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.991
hERG inhibition (predictor II)Inhibitor0.6172
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Metal ion binding
Specific Function
DNA ligase that seals nicks in double-stranded DNA during DNA replication, DNA recombination and DNA repair.
Gene Name
LIG1
Uniprot ID
P18858
Uniprot Name
DNA ligase 1
Molecular Weight
101735.11 Da
References
  1. Rose JL, Reeves KC, Likhotvorik RI, Hoyt DG: Base excision repair proteins are required for integrin-mediated suppression of bleomycin-induced DNA breakage in murine lung endothelial cells. J Pharmacol Exp Ther. 2007 Apr;321(1):318-26. Epub 2007 Jan 3. [PubMed:17202402]
Kind
Nucleotide
Organism
Humans
Pharmacological action
Yes
Actions
Cleavage
DNA is the molecule of heredity, as it is responsible for the genetic propagation of most inherited traits. It is a polynucleic acid that carries genetic information on cell growth, division, and function. DNA consists of two long strands of nucleotides twisted into a double helix and held together by hydrogen bonds. The sequence of nucleotides determines hereditary characteristics. Each strand serves as the template for subsequent DNA replication and as a template for mRNA production, leading to protein synthesis via ribosomes.
References
  1. Ma Q, Akiyama Y, Xu Z, Konishi K, Hecht SM: Identification and cleavage site analysis of DNA sequences bound strongly by bleomycin. J Am Chem Soc. 2009 Feb 11;131(5):2013-22. doi: 10.1021/ja808629s. [PubMed:19146404]
  2. Chow MS, Liu LV, Solomon EI: Further insights into the mechanism of the reaction of activated bleomycin with DNA. Proc Natl Acad Sci U S A. 2008 Sep 9;105(36):13241-5. doi: 10.1073/pnas.0806378105. Epub 2008 Aug 29. [PubMed:18757754]
  3. Akiyama Y, Ma Q, Edgar E, Laikhter A, Hecht SM: Identification of strong DNA binding motifs for bleomycin. J Am Chem Soc. 2008 Jul 30;130(30):9650-1. doi: 10.1021/ja802905g. Epub 2008 Jul 3. [PubMed:18597467]
  4. Mirabelli CK, Ting A, Huang CH, Mong S, Crooke ST: Bleomycin and talisomycin sequence-specific strand scission of DNA: a mechanism of double-strand cleavage. Cancer Res. 1982 Jul;42(7):2779-85. [PubMed:6177398]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Zinc ion binding
Specific Function
Isoform 3 functions as heterodimer with DNA-repair protein XRCC1 in the nucleus and can correct defective DNA strand-break repair and sister chromatid exchange following treatment with ionizing rad...
Gene Name
LIG3
Uniprot ID
P49916
Uniprot Name
DNA ligase 3
Molecular Weight
112905.96 Da
References
  1. Rose JL, Reeves KC, Likhotvorik RI, Hoyt DG: Base excision repair proteins are required for integrin-mediated suppression of bleomycin-induced DNA breakage in murine lung endothelial cells. J Pharmacol Exp Ther. 2007 Apr;321(1):318-26. Epub 2007 Jan 3. [PubMed:17202402]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Cysteine-type peptidase activity
Specific Function
The normal physiological role of BLM hydrolase is unknown, but it catalyzes the inactivation of the antitumor drug BLM (a glycopeptide) by hydrolyzing the carboxamide bond of its B-aminoalaninamide...
Gene Name
BLMH
Uniprot ID
Q13867
Uniprot Name
Bleomycin hydrolase
Molecular Weight
52561.93 Da
References
  1. Lazo JS, Boland CJ, Schwartz PE: Bleomycin hydrolase activity and cytotoxicity in human tumors. Cancer Res. 1982 Oct;42(10):4026-31. [PubMed:6179595]
  2. Lefterov IM, Koldamova RP, King J, Lazo JS: The C-terminus of human bleomycin hydrolase is required for protection against bleomycin-induced chromosomal damage. Mutat Res. 1998 Oct 12;421(1):1-7. [PubMed:9748474]

Drug created on June 13, 2005 07:24 / Updated on August 10, 2020 08:11

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