Pingyangmycin

Pingyangmycin

Clinical data
Pregnancy category	D
Routes of administration	intravenous, intraarterial, intramuscular, intratumoral
Legal status
Legal status	In general: ℞ (Prescription only)
Pharmacokinetic data
Metabolism	amidase
Biological half-life	1.3 hours
Excretion	renal (25-50%)
Identifiers
IUPAC name (2R,3S,4S,5R,6R)-2-{[(2R,3S,4S,5S,6S)-2-{[(1R,2S)-2-[({6-Amino-2-[(1S)-3-amino-1-{[(2S)-2,3-diamino-3-oxopropyl]amino}-3-oxopropyl]-5-methyl-4-pyrimidinyl}carbonyl)amino]-3-{[(2R,3S,4S)-5-{[(2S,3R)-1- ({2-[4-({3-[(4-aminobutyl)amino]propyl}carbamoyl)-2,4'-bi-1,3-thiazol-2'-yl]ethyl}amino)-3-hydroxy-1-oxo-2-butanyl]amino}-3-hydroxy-4-methyl-5-oxo-2-pentanyl]amino}-1-(1H-imidazol-5-yl)-3-oxopropyl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-4-yl carbamate
Synonyms	Bleomycin A5
CAS Number	11116-32-8 Y
PubChem CID	84046
ChemSpider	8232875 Y
UNII	5DY91Y7601
ECHA InfoCard	100.031.221
Chemical and physical data
Formula	C57H89N19O21S2
Molar mass	1440.56126
3D model (Jmol)	Interactive image
SMILES O=C(N)[C@@H](N)CN[C@H](c1nc(N)c(c(n1)C(=O)N[C@H](C(=O)N[C@H](C)[C@@H](O)[C@@H](C(=O)N[C@H](C(=O)NCCc2nc(cs2)c3nc(C(=O)NCCCNCCCCN)cs3)[C@H](O)C)C)[C@@H](O[C@@H]5O[C@@H](CO)[C@@H](O)[C@H](O)[C@@H]5O[C@H]4O[C@H](CO)[C@@H](O)[C@H](OC(=O)N)[C@@H]4O)c6cncn6)C)CC(=O)N
InChI InChI=1S/C57H89N19O21S2/c1-22-35(73-48(76-46(22)61)27(14-33(60)80)68-15-26(59)47(62)86)52(90)75-37(43(28-16-65-21-69-28)95-56-45(41(84)39(82)31(17-77)94-56)96-55-42(85)44(97-57(63)92)40(83)32(18-78)93-55)53(91)70-24(3)38(81)23(2)49(87)74-36(25(4)79)51(89)67-13-8-34-71-30(20-98-34)54-72-29(19-99-54)50(88)66-12-7-11-64-10-6-5-9-58/h16,19-21,23-27,31-32,36-45,55-56,64,68,77-79,81-85H,5-15,17-18,58-59H2,1-4H3,(H2,60,80)(H2,62,86)(H2,63,92)(H,65,69)(H,66,88)(H,67,89)(H,70,91)(H,74,87)(H,75,90)(H2,61,73,76)/t23-,24+,25+,26-,27-,31-,32+,36-,37-,38-,39+,40+,41-,42-,43-,44-,45-,55+,56-/m0/s1 Y Key:QYOAUOAXCQAEMW-UTXKDXHTSA-N Y

Pingyangmycin (also known as bleomycin A₅) is an antitumor glycopeptide antibiotic belonging to the bleomycin family, which is produced by Streptomyces verticillus var. pingyangensis n.sp., a variety of Streptomyces verticillus. It was discovered in 1969 at Pingyang County of Zhejiang Province in China, and was brought into clinical use in 1978.

In China, pingyangmycin has largely superseded bleomycin A₂ (commonly known as "bleomycin"), since it is more effective, costs less, is easier to get, can treat a larger variety of cancers (such as breast cancer and liver cancer) and causes less lung injury. Though it also results in pulmonary fibrosis, unlike bleomycin, its most serious side effect is anaphylactic shock, which is rare, but may happen even in a low dose, and can be fatal. In addition, it causes a higher incidence of fever than bleomycin; the occurrence of this complication in patients is between 20 and 50%.