Bleomycin

Bleomycin
	Bleomycin A2
Clinical data
Trade names	Blenoxane
AHFS/Drugs.com	Monograph
MedlinePlus	a682125
License data	US DailyMed: Bleomycin;
Pregnancy; category	AU: D;
Routes of; administration	intravenous, intramuscular, subcutaneous, intrapleural
Drug class	Glycopeptide antibiotic
ATC code	L01DC01 (WHO) ;
Legal status
Legal status	UK: POM (Prescription only); US: WARNINGRx-only; EU: Rx-only;
Pharmacokinetic data
Bioavailability	100% and 70% following intramuscular and subcutaneous administrations, respectively, and 45% following both intraperitoneal and intrapleural administrations
Elimination half-life	two hours
Excretion	Kidney (60–70%)
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	11056-06-7 ; sulfate: 9041-93-4 ;
PubChem CID	5460769;
DrugBank	DB00290 ;
ChemSpider	4574226 ;
UNII	40S1VHN69B; sulfate: 7DP3NTV15T ;
KEGG	D07535 ; sulfate: C15773 ;
ChEBI	CHEBI:22907 ;
ChEMBL	ChEMBL403664 ;
CompTox Dashboard (EPA)	DTXSID1030862 ;
Chemical and physical data
Formula	C55H84N17O21S3
Molar mass	1415.56 g·mol−1
3D model (JSmol)	Interactive image;
	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 ; Key:OYVAGSVQBOHSSS-UAPAGMARSA-O ;
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Bleomycin is a medication used to treat cancer. This includes Hodgkin's lymphoma, non-Hodgkin's lymphoma, testicular cancer, ovarian cancer, and cervical cancer among others. Typically used with other cancer medications, it can be given intravenously, by injection into a muscle or under the skin. 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.

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

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

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