Pingyangmycin

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.

Pingyangmycin
Clinical data
Other namesBleomycin A5
Pregnancy
category
  • D
Routes of
administration		intravenous, intra-arterial, intramuscular, intratumoral
Legal status
Legal status
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Metabolismamidase
Elimination half-life1.3 hours
Excretionrenal (25-50%)
Identifiers
  • (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
CAS Number
PubChem CID
ChemSpider
UNII
ECHA InfoCard100.031.221
Chemical and physical data
FormulaC57H89N19O21S2
Molar mass1440.56126 g·mol−1
3D model (JSmol)
  • C[C@@H](O)[C@H](NC(=O)[C@@H](C)[C@H](O)[C@@H](C)NC(=O)[C@@H](NC(=O)c1nc(nc(N)c1C)[C@H](CC(N)=O)NC[C@H](N)C(N)=O)[C@@H](O[C@@H]1O[C@@H](CO)[C@@H](O)[C@H](O)[C@@H]1O[C@H]1O[C@H](CO)[C@@H](O)[C@H](OC(N)=O)[C@@H]1O)c1c[nH]cn1)C(=O)NCCc1nc(cs1)-c1nc(cs1)C(=O)NCCCNCCCCN
  • 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

In China, pingyangmycin has largely superseded bleomycin A2 (commonly known as "bleomycin"), since according to Chinese sources it is more effective, costs less, is easier to get, can treat a larger variety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 pingyangmycin and bleomycin can each cause pulmonary fibrosis, pingyangmycin's most serious side effect - which it does not share with bleomycin - 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%.

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