Bleomycin

Bleomycin
Bleomycin A2
Clinical data
Trade namesBlenoxane
AHFS/Drugs.comMonograph
MedlinePlusa682125
License data
Pregnancy
category
Routes of
administration		intravenous, intramuscular, subcutaneous, intrapleural[2]
Drug classGlycopeptide antibiotic
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability100% and 70% following intramuscular and subcutaneous administrations, respectively, and 45% following both intraperitoneal and intrapleural administrations[2]
Elimination half-lifetwo hours[2]
ExcretionKidney (60–70%)[2]
Identifiers
IUPAC name
  • (3-{[(2'-{(5S,8S,9S,10R,13S)-15-{6-amino-2- [(1S)-3-amino-1-{[(2S)-2,3-diamino-3-oxopropyl]amino}-3-oxopropyl] -5-methylpyrimidin-4-yl}-13-[{[(2R,3S,4S,5S,6S)-3- {[(2R,3S,4S,5R,6R)-4-(carbamoyloxy)-3,5-dihydroxy-6- (hydroxymethyl)tetrahydro-2H-pyran-2-yl]oxy} -4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl]oxy} (1H-imidazol-5-yl)methyl]-9-hydroxy-5-[(1R)-1-hydroxyethyl]-8,10-dimethyl-4,7,12,15-tetraoxo-3,6,11,14-tetraazapentadec-1-yl}-2,4'-bi-1,3-thiazol-4-yl)carbonyl]amino}propyl)(dimethyl)sulfonium
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC55H84N17O21S3
Molar mass1415.56 g·mol−1
3D model (JSmol)
SMILES
  • CC1=C(N=C(N=C1N)[C@H](CC(=O)N)NC[C@@H](C(=O)N)N)C(=O)N[C@@H](C(C2=CN=CN2)O[C@H]3[C@H]([C@H]([C@@H]([C@@H](O3)CO)O)O)O[C@@H]4[C@H]([C@H]([C@@H]([C@H](O4)CO)O)OC(=O)N)O)C(=O)N[C@H](C)[C@H]([C@H](C)C(=O)N[C@@H]([C@@H](C)O)C(=O)NCCC5=NC(=CS5)C6=NC(=CS6)C(=O)NCCC[S+](C)C)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 N
  • Key:OYVAGSVQBOHSSS-UAPAGMARSA-O N
 NY (what is this?)  (verify)

Bleomycin is a medication primarily used to treat cancer.[5] This includes Hodgkin's lymphoma, non-Hodgkin's lymphoma, testicular cancer, ovarian cancer, and cervical cancer among others.[5] Typically used with other cancer medications,[5] it can be given intravenously, by injection into a muscle or under the skin.[5] It may also be administered inside the chest to help prevent the recurrence of a pleural effusion due to cancer; however talc is better for this.[5][6] It may sometimes be used to treat other difficult-to-treat skin lesions such as plantar warts in immunocompromised patients.

Common side effects include fever, weight loss, vomiting, and rash.[5] A severe type of anaphylaxis may occur.[5] It may also cause inflammation of the lungs that can result in lung scarring.[5] Chest X-rays every couple of weeks are recommended to check for this.[5] Bleomycin may cause harm to the baby if used during pregnancy.[5] It is believed to primarily work by preventing the synthesis of DNA.[5]

Bleomycin was discovered in 1962.[7][8] It is on the World Health Organization's List of Essential Medicines.[9] It is available as a generic medication.[5] It is made by the bacterium Streptomyces verticillus.[5]

  1. ^ "Bleomycin Use During Pregnancy". Drugs.com. 9 August 2019. Retrieved 16 February 2020.
  2. ^ a b c d "Bleomycin- bleomycin sulfate injection, powder, lyophilized, for solution". DailyMed. 31 December 2019. Retrieved 16 February 2020.
  3. ^ "Bleo-Kyowa Powder for solution for injection - Summary of Product Characteristics (SmPC)". (emc). 31 August 2018. Archived from the original on 16 February 2020. Retrieved 16 February 2020.
  4. ^ "Bleomycin". European Medicines Agency (EMA). 18 March 2009.
  5. ^ a b c d e f g h i j k l m "Bleomycin Sulfate". The American Society of Health-System Pharmacists. Archived from the original on 8 September 2015. Retrieved 1 August 2015.
  6. ^ Dipper A, Jones HE, Bhatnagar R, Preston NJ, Maskell N, Clive AO (April 2020). "Interventions for the management of malignant pleural effusions: a network meta-analysis". The Cochrane Database of Systematic Reviews. 2020 (4): CD010529. doi:10.1002/14651858.CD010529.pub3. PMC 7173736. PMID 32315458.
  7. ^ Sneader W (2005). Drug discovery : a history (Rev. and updated ed.). Chichester: Wiley. p. 312. ISBN 9780471899792. Archived from the original on 5 March 2016.
  8. ^ Phillips GO (2018). Innovation and Technology Transfer in Japan and Europe: Industry-Academic Interactions. Routledge. p. PT155. ISBN 9780429774546.
  9. ^ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
This article is issued from Wikipedia. The text is available under Creative Commons Attribution-Share Alike 4.0 unless otherwise noted. Additional terms may apply for the media files.